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Elegant Mediterranean estate, masterfully crafted by Akers Custom Homes and set within the heart of the Vias. Privately tucked behind a gated drive, the approach unfolds to a grand circular motor court framed by lush, manicured grounds spanning over two acres with impressive sunset views across Lake Maitland. Every element of the estate is thoughtfully connected by covered walkways, including five garages (three-car and two-car) and two motor courts, a detached office or seventh bedroom suite, and a lakeside pool cabana, creating a seamless blend of function, elegance and architectural harmony in this one-owner Lake Maitland residence. A dramatic arrival sets the tone as a flowing water feature guides guests along the walkway to the front entry. Inside, the grand foyer opens to a breathtaking gathering room, anchored by soaring two-story windows that frame panoramic lake views, the expansive terrace and terraced outdoor space. A dedicated space for a grand piano enhances the home’s capacity for elegant entertainment and memorable gatherings. The spacious kitchen overlooks the family room and is positioned alongside a dedicated bar, breakfast room and dining room. The family room, warmed by a gas fireplace, is filled with natural light and opens through a wall of French doors to the open terrace, blurring the line between indoor and outdoor living. The first-floor primary suite is a serene retreat with French doors to a covered outdoor space, a fireside sitting area wrapped in custom bookshelves, and a spa-inspired bath featuring a large glass shower, soaking tub, expansive walk-in closet, and a versatile flex room ideal for yoga, massage or expanded wardrobe space. A full guest suite with en-suite bath and walk-in closet is also on the main level. Upstairs, a grand mezzanine overlooks the gathering room, offering a dramatic extension of the living areas. French doors open to a front balcony, while the west wing features two bedrooms with a shared private living room and full bath. The east wing hosts two additional bedroom suites, each with walk-in closets and en-suite baths, one enhanced by a private sitting area and access to a spacious rear balcony. Off the kitchen, a wrought-iron gate leads to the basement level, where a refrigerated wine cellar, theater room, and generous storage space await. Outdoors, the stunning terrace showcases a heated spa, sparkling lakeside pool, expansive gas fire pit and an extraordinary 700-square-foot pool cabana that offers a wraparound screened porch with summer kitchen, a full bar, gaming area and full bath, ideal for lakeside entertaining. Elevated above the water for commanding views and shielded from the main road for complete privacy, this remarkable estate is a masterpiece, designed for multi-generational living and destined to create lasting memories for generations to come.

6 Beds ⋅ 9 Baths ⋅ --- SubDv. ⋅ 32789 Zip Code

Elegant Mediterranean estate, masterfully crafted by Akers Custom Homes and set within the heart of the Vias. Privately tucked behind a gated drive, the approach unfolds to a grand circular motor court framed by lush, manicured grounds spanning over two acres with impressive sunset views across Lake Maitland. Every element of the estate is thoughtfully connected by covered walkways, including five garages (three-car and two-car) and two motor courts, a detached office or seventh bedroom suite, and a lakeside pool cabana, creating a seamless blend of function, elegance and architectural harmony in this one-owner Lake Maitland residence. A dramatic arrival sets the tone as a flowing water feature guides guests along the walkway to the front entry. Inside, the grand foyer opens to a breathtaking gathering room, anchored by soaring two-story windows that frame panoramic lake views, the expansive terrace and terraced outdoor space. A dedicated space for a grand piano enhances the home’s capacity for elegant entertainment and memorable gatherings. The spacious kitchen overlooks the family room and is positioned alongside a dedicated bar, breakfast room and dining room. The family room, warmed by a gas fireplace, is filled with natural light and opens through a wall of French doors to the open terrace, blurring the line between indoor and outdoor living. The first-floor primary suite is a serene retreat with French doors to a covered outdoor space, a fireside sitting area wrapped in custom bookshelves, and a spa-inspired bath featuring a large glass shower, soaking tub, expansive walk-in closet, and a versatile flex room ideal for yoga, massage or expanded wardrobe space. A full guest suite with en-suite bath and walk-in closet is also on the main level. Upstairs, a grand mezzanine overlooks the gathering room, offering a dramatic extension of the living areas. French doors open to a front balcony, while the west wing features two bedrooms with a shared private living room and full bath. The east wing hosts two additional bedroom suites, each with walk-in closets and en-suite baths, one enhanced by a private sitting area and access to a spacious rear balcony. Off the kitchen, a wrought-iron gate leads to the basement level, where a refrigerated wine cellar, theater room, and generous storage space await. Outdoors, the stunning terrace showcases a heated spa, sparkling lakeside pool, expansive gas fire pit and an extraordinary 700-square-foot pool cabana that offers a wraparound screened porch with summer kitchen, a full bar, gaming area and full bath, ideal for lakeside entertaining. Elevated above the water for commanding views and shielded from the main road for complete privacy, this remarkable estate is a masterpiece, designed for multi-generational living and destined to create lasting memories for generations to come.

2203 Via Tuscany, Winter Park

$7,164,000

Set on over half an acre along the shores of Lake Maitland in the heart of the coveted Vias, this exceptional residence by Modish Homes is both a former 2018 Parade of Homes winner and a standout example of Winter Park luxury living. From the moment you enter, a dramatic two-story foyer sets the tone, drawing your eye through to the main living space where a statement wood-burning fireplace anchors the room and expansive glass frames breathtaking views of the water beyond. Every space has been thoughtfully designed to maximize both scale and sightlines, creating an effortless connection between indoors and the natural beauty outside. The home features touches of Walnut floors, detailing and doors, bringing warmth throughout. At the center of the home, the chef’s kitchen is both refined and functional, featuring custom cabinetry, a full suite of Dacor appliances, and an oversized walk-in pantry. A striking wet bar with a glass wine wall adds a layer of sophistication, ideal for entertaining. The dining room is equally impressive, offering panoramic lake views and seamless access to the outdoor living areas. The main-level primary suite is a true private retreat, highlighted by chevron-pattern tile flooring and a spa-inspired bath complete with dual vanities, designer lighting, a freestanding soaking tub, and an expansive walk-in shower. The main level also includes two additional guest suites and a glass-enclosed office, offering both comfort and flexibility. Upstairs, two more bedrooms are complemented by a spacious loft and a large balcony that captures sweeping views of the lake. Designed to rival a private resort, the outdoor living experience is nothing short of exceptional. A fully equipped summer kitchen, resort-style pool and spa, two outdoor showers, and expansive green space create a setting that is both functional and visually stunning. A private viewing dock overlooks the water or reconfigure it to a boat dock, allowing you to fully embrace life on the lake while enjoying views of the iconic Isle of Sicily. Beyond the property, the lifestyle is equally compelling. Additional features include a full Control4 home automation system, sauna, and an expansive double-entry driveway providing ample parking. Located just minutes from the boutiques, dining, and cafés of Park Avenue, and within close proximity to Kraft Azalea Garden and the Winter Park Racquet Ball Club, this home offers the perfect balance of privacy and convenience. This is truly a one-of-a-kind opportunity to own a true showpiece on the Winter Park Chain of Lakes.

5 Beds ⋅ 7 Baths ⋅ Sicilian Shores SubDv. ⋅ 32789 Zip Code

Set on over half an acre along the shores of Lake Maitland in the heart of the coveted Vias, this exceptional residence by Modish Homes is both a former 2018 Parade of Homes winner and a standout example of Winter Park luxury living. From the moment you enter, a dramatic two-story foyer sets the tone, drawing your eye through to the main living space where a statement wood-burning fireplace anchors the room and expansive glass frames breathtaking views of the water beyond. Every space has been thoughtfully designed to maximize both scale and sightlines, creating an effortless connection between indoors and the natural beauty outside. The home features touches of Walnut floors, detailing and doors, bringing warmth throughout. At the center of the home, the chef’s kitchen is both refined and functional, featuring custom cabinetry, a full suite of Dacor appliances, and an oversized walk-in pantry. A striking wet bar with a glass wine wall adds a layer of sophistication, ideal for entertaining. The dining room is equally impressive, offering panoramic lake views and seamless access to the outdoor living areas. The main-level primary suite is a true private retreat, highlighted by chevron-pattern tile flooring and a spa-inspired bath complete with dual vanities, designer lighting, a freestanding soaking tub, and an expansive walk-in shower. The main level also includes two additional guest suites and a glass-enclosed office, offering both comfort and flexibility. Upstairs, two more bedrooms are complemented by a spacious loft and a large balcony that captures sweeping views of the lake. Designed to rival a private resort, the outdoor living experience is nothing short of exceptional. A fully equipped summer kitchen, resort-style pool and spa, two outdoor showers, and expansive green space create a setting that is both functional and visually stunning. A private viewing dock overlooks the water or reconfigure it to a boat dock, allowing you to fully embrace life on the lake while enjoying views of the iconic Isle of Sicily. Beyond the property, the lifestyle is equally compelling. Additional features include a full Control4 home automation system, sauna, and an expansive double-entry driveway providing ample parking. Located just minutes from the boutiques, dining, and cafés of Park Avenue, and within close proximity to Kraft Azalea Garden and the Winter Park Racquet Ball Club, this home offers the perfect balance of privacy and convenience. This is truly a one-of-a-kind opportunity to own a true showpiece on the Winter Park Chain of Lakes.

1821 Pinetree Road, Winter Park

$7,000,000

In the exclusive community of Windsong on Lake Berry, this magnificent 1.6-acre gated Mediterranean estate is a private oasis. With over 11,000 square feet of living area and a beautifully landscaped lakefront lot, this residence offers an exceptional blend of elegance, charm and privacy rarely found in Winter Park. The home features seven spacious bedrooms and nine full and two half baths. Entertain in the all-glass conservatory, dedicated theater room with motorized seating and a fully equipped game room. Modern conveniences throughout including gas-powered generators, an elevator and dumbwaiter. Two above-garage apartments provide ideal accommodations for guests and family. Outdoors, enjoy an expansive covered lanai, infinity edge pool and spa, boat dock with jet ski lift, and a summer kitchen complete with wood-burning fireplace, gas grill, refrigerator and icemaker, all overlooking the beautifully landscaped yard and lake. With its private gated entrance, this home is a one-of-a-kind opportunity to enjoy all the amenities Winter Park and Windsong have to offer.

7 Beds ⋅ 11 Baths ⋅ Windsong-Preserve Point SubDv. ⋅ 32789 Zip Code

In the exclusive community of Windsong on Lake Berry, this magnificent 1.6-acre gated Mediterranean estate is a private oasis. With over 11,000 square feet of living area and a beautifully landscaped lakefront lot, this residence offers an exceptional blend of elegance, charm and privacy rarely found in Winter Park. The home features seven spacious bedrooms and nine full and two half baths. Entertain in the all-glass conservatory, dedicated theater room with motorized seating and a fully equipped game room. Modern conveniences throughout including gas-powered generators, an elevator and dumbwaiter. Two above-garage apartments provide ideal accommodations for guests and family. Outdoors, enjoy an expansive covered lanai, infinity edge pool and spa, boat dock with jet ski lift, and a summer kitchen complete with wood-burning fireplace, gas grill, refrigerator and icemaker, all overlooking the beautifully landscaped yard and lake. With its private gated entrance, this home is a one-of-a-kind opportunity to enjoy all the amenities Winter Park and Windsong have to offer.

1120 Preserve Point Drive, Winter Park

$6,500,000

Stunning Custom Estate on the Shores of Lake Osceola

4 Beds ⋅ 3 Baths ⋅ Osceola Shores Sec 03 SubDv. ⋅ 32789 Zip Code

Stunning Custom Estate on the Shores of Lake Osceola

405 Lakewood Drive, Winter Park

$6,300,000

Quintisential Lake Maitland Estate - first time available. Classic architecture with incredible and thoughtful details throughout. Private setting on over an acre captures sweeping views of Lake Maitland. Sought after location close to Park Avenue. This legacy property embodies the best of Winter Park Lakefront Living.

4 Beds ⋅ 6 Baths ⋅ Camwood SubDv. ⋅ 32789 Zip Code

Quintisential Lake Maitland Estate - first time available. Classic architecture with incredible and thoughtful details throughout. Private setting on over an acre captures sweeping views of Lake Maitland. Sought after location close to Park Avenue. This legacy property embodies the best of Winter Park Lakefront Living.

1308 Green Cove, Winter Park

$6,200,000

Exquisite new construction with 5 Bedrooms 6.5 Baths and a 3 car garage, in the Heart of Winter Park perfectly positioned on an oversized lot just steps from Park Avenue’s renowned shops, fine dining, and the iconic Winter Park 9-hole golf course, this extraordinary custom residence is a showcase of timeless design and modern luxury. Conceived by acclaimed architect Dan Delong of Origins Residential Design and brought to life by Sean Wulff of Native Homes, every detail has been thoughtfully curated to impress even the most discerning buyer. The expansive floor plan encompasses 5 bedrooms, 6 full baths, and 1 half bath, blending sophistication and comfort across multiple living spaces. Highlights include a dramatic great room, inviting family room, private study, downstairs guest suite, a full bar featuring a 56-bottle wine refrigerator, and an upstairs game room ideal for both everyday living and elegant entertaining. A grand entry reveals the great room with soaring floor-to-ceiling windows and elegant Italian porcelain tile, all overlooking the serene pool and patio. The chef’s kitchen seamlessly connects to the family room and features Canadian-crafted European-style cabinetry, Wolf, Sub-Zero & Fisher & Paykel appliances (dual ovens, dual dishwashers, built-in coffee maker, wine cooler, and beverage center), quartzite countertops, a large island with bar seating, hidden walk-in pantry, plus whole house water softener and filtration systems for premium convenience. The first-floor primary suite is a true retreat with spa-inspired amenities and a custom-built walk-in closet complete with cabinetry and a spacious island. Also on the main level: a private guest suite and dedicated home office/study. Upstairs, a generous game room and three additional en suite bedrooms provide comfort and privacy for family and guests alike. Designed for seamless indoor-outdoor living, the residence boasts two covered lanais finished in Turkish Marble, disappearing screens, a summer kitchen with Urban Bonfire Cabinetry, refrigerator, and ice maker, along with a freestanding fire pit and lush tropical landscaping. The saltwater pool with sun shelf and heated gas spa ensures year-round enjoyment. Built to the highest standards, the home features R-14 block walls with core 500 insulation, open cell foam insulation in attic, Andersen windows, a flat concrete tile roof, and tongue-and-groove ceilings on all lanais. Additional luxuries include: Select European white oak wood floors and Italian porcelain flooring throughout 12’ ceilings on the main level, 10’ ceilings upstairs Cutting-edge construction for efficiency and durability

5 Beds ⋅ 7 Baths ⋅ Osceola Place SubDv. ⋅ 32789 Zip Code

Exquisite new construction with 5 Bedrooms 6.5 Baths and a 3 car garage, in the Heart of Winter Park perfectly positioned on an oversized lot just steps from Park Avenue’s renowned shops, fine dining, and the iconic Winter Park 9-hole golf course, this extraordinary custom residence is a showcase of timeless design and modern luxury. Conceived by acclaimed architect Dan Delong of Origins Residential Design and brought to life by Sean Wulff of Native Homes, every detail has been thoughtfully curated to impress even the most discerning buyer. The expansive floor plan encompasses 5 bedrooms, 6 full baths, and 1 half bath, blending sophistication and comfort across multiple living spaces. Highlights include a dramatic great room, inviting family room, private study, downstairs guest suite, a full bar featuring a 56-bottle wine refrigerator, and an upstairs game room ideal for both everyday living and elegant entertaining. A grand entry reveals the great room with soaring floor-to-ceiling windows and elegant Italian porcelain tile, all overlooking the serene pool and patio. The chef’s kitchen seamlessly connects to the family room and features Canadian-crafted European-style cabinetry, Wolf, Sub-Zero & Fisher & Paykel appliances (dual ovens, dual dishwashers, built-in coffee maker, wine cooler, and beverage center), quartzite countertops, a large island with bar seating, hidden walk-in pantry, plus whole house water softener and filtration systems for premium convenience. The first-floor primary suite is a true retreat with spa-inspired amenities and a custom-built walk-in closet complete with cabinetry and a spacious island. Also on the main level: a private guest suite and dedicated home office/study. Upstairs, a generous game room and three additional en suite bedrooms provide comfort and privacy for family and guests alike. Designed for seamless indoor-outdoor living, the residence boasts two covered lanais finished in Turkish Marble, disappearing screens, a summer kitchen with Urban Bonfire Cabinetry, refrigerator, and ice maker, along with a freestanding fire pit and lush tropical landscaping. The saltwater pool with sun shelf and heated gas spa ensures year-round enjoyment. Built to the highest standards, the home features R-14 block walls with core 500 insulation, open cell foam insulation in attic, Andersen windows, a flat concrete tile roof, and tongue-and-groove ceilings on all lanais. Additional luxuries include: Select European white oak wood floors and Italian porcelain flooring throughout 12’ ceilings on the main level, 10’ ceilings upstairs Cutting-edge construction for efficiency and durability

550 Palmer Avenue, Winter Park

$6,111,000

Tucked away on a quiet and beautiful Lake Maitland lot in the highly desirable Green Oaks neighborhood, this stunning French Provincial residence offers magnificent water views from nearly every room. With one of the most private entrances and lots in all of Winter Park, this timeless home blends European charm with modern comfort. The light-filled, open floor plan features a downstairs primary suite and a gorgeous family room with gas fireplace, opening to the pool and lake. The gourmet kitchen, also facing the backyard, is the heart of the home. Featuring granite countertops, light cabinetry and gas cooktop. The open layout includes the eat-in breakfast area and family room. Multiple French doors to the pool and lakefront for everyday indoor-outdoor living and enjoy breathtaking views that make every moment feel like a getaway. Upstairs, two generously sized bedrooms-each with en-suite baths are joined by a cozy conversation area with lake views, a large bonus room and a private office/study that could easily be an additional bedroom. A connecting guesthouse offers a true retreat with two bedrooms, a full bath, living area and kitchen, perfect for hosting friends or family. Sparkling pool, lush landscaping, and private dock on Lake Maitland, enjoy awe-inspiring sunrise views over the Isle of Sicily. Craftsmanship is showcased throughout, from the millwork to the 4-car garage, with extensive updates: roof (2021), multiple A/C systems with UV lights (2020–2025), new flooring throughout downstairs and all bedrooms (2020), updated upstairs windows (2020), rebuilt balcony with Trex decking, new pool equipment (2020) and pool converted to salt (filter 2024), Generac whole-house generator, Trex deck and dock with new cables and 7,500-lb lift (2022), new primary, upstairs guest suites and powder baths (2025), marble porcelain fireplace surround, remote shades in the primary suite, and new lighting fixtures throughout. Surrounded by manicured grounds and minutes from downtown Winter Park, Park Avenue shopping and restaurants, Enzian Theater, library, bike paths, and top-rated schools, (Dommerich, Maitland Middle and Winter Park High School). Just around the corner from Park Maitland and near Lake Highland and Trinity Preparatory Schools. This lakeside masterpiece offers unmatched privacy, luxury, and timeless sophistication-a truly exceptional home. Ski, wakeboard, pontoon or cruise around Dog Island and Isle of Sicily on the chain of lakes. Enjoy the magic of the holiday season- festive boat parade and holiday light displays. 121 ft of lakefront on the Winter Park Chain of Lakes.

5 Beds ⋅ 6 Baths ⋅ Green Oaks Rep SubDv. ⋅ 32789 Zip Code

Tucked away on a quiet and beautiful Lake Maitland lot in the highly desirable Green Oaks neighborhood, this stunning French Provincial residence offers magnificent water views from nearly every room. With one of the most private entrances and lots in all of Winter Park, this timeless home blends European charm with modern comfort. The light-filled, open floor plan features a downstairs primary suite and a gorgeous family room with gas fireplace, opening to the pool and lake. The gourmet kitchen, also facing the backyard, is the heart of the home. Featuring granite countertops, light cabinetry and gas cooktop. The open layout includes the eat-in breakfast area and family room. Multiple French doors to the pool and lakefront for everyday indoor-outdoor living and enjoy breathtaking views that make every moment feel like a getaway. Upstairs, two generously sized bedrooms-each with en-suite baths are joined by a cozy conversation area with lake views, a large bonus room and a private office/study that could easily be an additional bedroom. A connecting guesthouse offers a true retreat with two bedrooms, a full bath, living area and kitchen, perfect for hosting friends or family. Sparkling pool, lush landscaping, and private dock on Lake Maitland, enjoy awe-inspiring sunrise views over the Isle of Sicily. Craftsmanship is showcased throughout, from the millwork to the 4-car garage, with extensive updates: roof (2021), multiple A/C systems with UV lights (2020–2025), new flooring throughout downstairs and all bedrooms (2020), updated upstairs windows (2020), rebuilt balcony with Trex decking, new pool equipment (2020) and pool converted to salt (filter 2024), Generac whole-house generator, Trex deck and dock with new cables and 7,500-lb lift (2022), new primary, upstairs guest suites and powder baths (2025), marble porcelain fireplace surround, remote shades in the primary suite, and new lighting fixtures throughout. Surrounded by manicured grounds and minutes from downtown Winter Park, Park Avenue shopping and restaurants, Enzian Theater, library, bike paths, and top-rated schools, (Dommerich, Maitland Middle and Winter Park High School). Just around the corner from Park Maitland and near Lake Highland and Trinity Preparatory Schools. This lakeside masterpiece offers unmatched privacy, luxury, and timeless sophistication-a truly exceptional home. Ski, wakeboard, pontoon or cruise around Dog Island and Isle of Sicily on the chain of lakes. Enjoy the magic of the holiday season- festive boat parade and holiday light displays. 121 ft of lakefront on the Winter Park Chain of Lakes.

1860 Summerland Avenue, Winter Park

$5,700,000

SOLD DATA ENTRY.. Welcome to this timeless lakefront estate located on the shores of Lake Virginia, offering approximately 143 feet of private waterfront along the highly sought-after Winter Park Chain of Lakes. Situated on over an acre, this beautifully updated residence blends classic architecture with modern luxury and an exceptional indoor-outdoor lifestyle. Thoughtfully renovated in 2016, the home features spacious formal and informal living areas, high ceilings, custom millwork, and stunning lake views throughout.The chef’s kitchen is equipped with Wolf and Sub-Zero appliances, double ovens, built-in Miele coffee system, wine refrigeration, and additional refrigerator/freezer drawers. The kitchen opens to the main living space and flows seamlessly to the outdoor entertaining areas. The primary suite offers a serene lakefront setting with a spa-inspired bath and generous closets. Additional bedrooms are well-appointed and offer both privacy and flexible living arrangements.Step outside to a resort-style waterfront setting, complete with a large pool and spa, expansive terrace, summer kitchen, gas fire pit, and private boat dock with lift. Enjoy boating, paddleboarding, or sunset cruises right from your backyard. The property’s elevation provides exceptional views stretching across Lake Virginia toward downtown Orlando and Rollins College.Located on a quiet, private street just moments from Park Avenue dining, shops, and Winter Park’s most desirable amenities, this is a rare opportunity to enjoy lakefront living in one of Central Florida’s most distinguished neighborhoods.

5 Beds ⋅ 6 Baths ⋅ Thomas M Henkels Add SubDv. ⋅ 32789 Zip Code

SOLD DATA ENTRY.. Welcome to this timeless lakefront estate located on the shores of Lake Virginia, offering approximately 143 feet of private waterfront along the highly sought-after Winter Park Chain of Lakes. Situated on over an acre, this beautifully updated residence blends classic architecture with modern luxury and an exceptional indoor-outdoor lifestyle. Thoughtfully renovated in 2016, the home features spacious formal and informal living areas, high ceilings, custom millwork, and stunning lake views throughout.The chef’s kitchen is equipped with Wolf and Sub-Zero appliances, double ovens, built-in Miele coffee system, wine refrigeration, and additional refrigerator/freezer drawers. The kitchen opens to the main living space and flows seamlessly to the outdoor entertaining areas. The primary suite offers a serene lakefront setting with a spa-inspired bath and generous closets. Additional bedrooms are well-appointed and offer both privacy and flexible living arrangements.Step outside to a resort-style waterfront setting, complete with a large pool and spa, expansive terrace, summer kitchen, gas fire pit, and private boat dock with lift. Enjoy boating, paddleboarding, or sunset cruises right from your backyard. The property’s elevation provides exceptional views stretching across Lake Virginia toward downtown Orlando and Rollins College.Located on a quiet, private street just moments from Park Avenue dining, shops, and Winter Park’s most desirable amenities, this is a rare opportunity to enjoy lakefront living in one of Central Florida’s most distinguished neighborhoods.

374 Henkel Circle, Winter Park

$5,600,000

Have you been waiting for a home on the Winter Park Chain of Lakes? Here is your chance!! Discover an unparalleled living experience on the prestigious Winter Park Chain of Lakes! Nestled on highly sought-after Alabama Drive, this exquisite two-story residence invites you to embrace a lifestyle of comfort and elegance. With 3,680 square feet of meticulously designed space, this home offers five bedrooms and three and a half baths, including a charming guest suite above the garage complete with a private bath and kitchenette – perfect for visitors or extended family. A covered front porch and a welcoming circular driveway, framed by mature trees, greet you with incredible, sweeping views of Lake Maitland, promising serene mornings and breathtaking sunsets. Step inside and feel instantly at home as original hardwood floors guide you through a spacious foyer, where a grand staircase sets a tone of refined sophistication. The heart of this home, the kitchen, is a captivating blend of functionality and style, ready for culinary adventures. It features a generous central island with a stovetop, complemented by crisp white countertops, warm wooden cabinetry, and stainless steel appliances. A built-in oven, microwave, and a charming terracotta wine rack enhance the culinary experience. Spacious, open and roomy. Thoughtfully designed living spaces beckon, perfect for grand entertaining or cozy, intimate gatherings. An elegant living room offers a warm ambiance with a fireplace and captivating lake views that will enchant you all day long! Another expansive living area off the kitchen showcases exposed wooden beams and rich brick tile flooring, exuding rustic charm. Large windows throughout the front of the home frame picturesque lake views, creating a serene backdrop for daily life. With a total of four fireplaces—three gas and one wood-burning—you'll find inviting focal points throughout. A sunroom, bathed in natural light from its expansive windows and finished with cheerful brick tile flooring, provides a tranquil retreat, further enhanced by the endless windows. Enjoy casual meals in the eat-in dining room, or host memorable dinners in the formal dining room, which boasts amazing custom shelving, detailed molding, a beautiful gas fireplace, original hardwood floors and of course view of the lake. The primary suite is a luxurious sanctuary, generously sized and anchored by stunning views of Lake Maitland and a cozy fireplace, creating an inviting sitting area within the bedroom itself. The spacious primary bathroom offers a double vanity, an updated shower, and a separate soaking tub for ultimate relaxation. In the main home, you'll find three additional bedrooms, each offering spacious comfort and ample storage. A truly distinctive feature of this property is the private guest suite, thoughtfully designed with one bedroom, one bath, a kitchenette, and a cozy wood-burning stove, offering comfort and privacy. This versatile space serves as the home's fifth bedroom, providing a wonderful haven for guests. Beyond the inviting interior, the property extends its allure to the outdoors. A private wooden dock extends onto Lake Maitland, part of the prestigious Winter Park Chain of Lakes, offering direct access to shimmering waters and endless aquatic adventures. A boathouse further enhances lakeside enjoyment. A charming patio area provides an ideal setting for outdoor leisure and entertaining amidst the verdant surroundings. Welcome home!

5 Beds ⋅ 4 Baths ⋅ Alabama Oaks SubDv. ⋅ 32789 Zip Code

Have you been waiting for a home on the Winter Park Chain of Lakes? Here is your chance!! Discover an unparalleled living experience on the prestigious Winter Park Chain of Lakes! Nestled on highly sought-after Alabama Drive, this exquisite two-story residence invites you to embrace a lifestyle of comfort and elegance. With 3,680 square feet of meticulously designed space, this home offers five bedrooms and three and a half baths, including a charming guest suite above the garage complete with a private bath and kitchenette – perfect for visitors or extended family. A covered front porch and a welcoming circular driveway, framed by mature trees, greet you with incredible, sweeping views of Lake Maitland, promising serene mornings and breathtaking sunsets. Step inside and feel instantly at home as original hardwood floors guide you through a spacious foyer, where a grand staircase sets a tone of refined sophistication. The heart of this home, the kitchen, is a captivating blend of functionality and style, ready for culinary adventures. It features a generous central island with a stovetop, complemented by crisp white countertops, warm wooden cabinetry, and stainless steel appliances. A built-in oven, microwave, and a charming terracotta wine rack enhance the culinary experience. Spacious, open and roomy. Thoughtfully designed living spaces beckon, perfect for grand entertaining or cozy, intimate gatherings. An elegant living room offers a warm ambiance with a fireplace and captivating lake views that will enchant you all day long! Another expansive living area off the kitchen showcases exposed wooden beams and rich brick tile flooring, exuding rustic charm. Large windows throughout the front of the home frame picturesque lake views, creating a serene backdrop for daily life. With a total of four fireplaces—three gas and one wood-burning—you'll find inviting focal points throughout. A sunroom, bathed in natural light from its expansive windows and finished with cheerful brick tile flooring, provides a tranquil retreat, further enhanced by the endless windows. Enjoy casual meals in the eat-in dining room, or host memorable dinners in the formal dining room, which boasts amazing custom shelving, detailed molding, a beautiful gas fireplace, original hardwood floors and of course view of the lake. The primary suite is a luxurious sanctuary, generously sized and anchored by stunning views of Lake Maitland and a cozy fireplace, creating an inviting sitting area within the bedroom itself. The spacious primary bathroom offers a double vanity, an updated shower, and a separate soaking tub for ultimate relaxation. In the main home, you'll find three additional bedrooms, each offering spacious comfort and ample storage. A truly distinctive feature of this property is the private guest suite, thoughtfully designed with one bedroom, one bath, a kitchenette, and a cozy wood-burning stove, offering comfort and privacy. This versatile space serves as the home's fifth bedroom, providing a wonderful haven for guests. Beyond the inviting interior, the property extends its allure to the outdoors. A private wooden dock extends onto Lake Maitland, part of the prestigious Winter Park Chain of Lakes, offering direct access to shimmering waters and endless aquatic adventures. A boathouse further enhances lakeside enjoyment. A charming patio area provides an ideal setting for outdoor leisure and entertaining amidst the verdant surroundings. Welcome home!

1530 Alabama Drive, Winter Park

$5,410,000

On the beautiful shores of Lake Maitland, the largest and most desired lake on the Winter Park Chain of Lakes, this beautifully designed home captures the essence of luxury waterfront living with breathtaking views that can be enjoyed throughout the home. Offering five bedrooms and 4.5 baths in the desirable Green Oaks neighborhood, this home is surely a must-see! The heart of the home is the spacious kitchen, ideally positioned to overlook the sparkling waters of Lake Maitland, making meal preparation and entertaining a spectacular experience. Expansive windows fill the living spaces with natural light while framing picturesque lake views that create a seamless connection between the indoors and beautiful waterfront beyond. Retreat to the private primary suite, where you'll wake each morning to sweeping panoramic views of the lake. Thoughtfully designed for comfort and relaxation, it provides the ideal sanctuary to enjoy spectacular sunrises and the peaceful beauty of this remarkable setting. This home features a split plan with the primary suite, two bedrooms and a bath in one wing. The other wing has two bedrooms, two baths, and a bonus/flex area. Whether entertaining family and friends or enjoying a quiet evening by the water, the outdoor living spaces invite you to embrace the desired Chain of Lakes lifestyle. Spend your days boating, paddleboarding, skiing, fishing or simply relaxing while taking in the tranquil surroundings. Just minutes from renowned shops and restaurants of Park Avenue, Rollins College and top-rated Winter Park schools, this extraordinary waterfront property offers a balance of luxury, convenience and recreation. Rarely does an opportunity arise to own a home on Lake Maitland that combines stunning views, spacious living and one of Central Florida's most desirable addresses.

5 Beds ⋅ 5 Baths ⋅ Green Oaks Rep 02 SubDv. ⋅ 32789 Zip Code

On the beautiful shores of Lake Maitland, the largest and most desired lake on the Winter Park Chain of Lakes, this beautifully designed home captures the essence of luxury waterfront living with breathtaking views that can be enjoyed throughout the home. Offering five bedrooms and 4.5 baths in the desirable Green Oaks neighborhood, this home is surely a must-see! The heart of the home is the spacious kitchen, ideally positioned to overlook the sparkling waters of Lake Maitland, making meal preparation and entertaining a spectacular experience. Expansive windows fill the living spaces with natural light while framing picturesque lake views that create a seamless connection between the indoors and beautiful waterfront beyond. Retreat to the private primary suite, where you'll wake each morning to sweeping panoramic views of the lake. Thoughtfully designed for comfort and relaxation, it provides the ideal sanctuary to enjoy spectacular sunrises and the peaceful beauty of this remarkable setting. This home features a split plan with the primary suite, two bedrooms and a bath in one wing. The other wing has two bedrooms, two baths, and a bonus/flex area. Whether entertaining family and friends or enjoying a quiet evening by the water, the outdoor living spaces invite you to embrace the desired Chain of Lakes lifestyle. Spend your days boating, paddleboarding, skiing, fishing or simply relaxing while taking in the tranquil surroundings. Just minutes from renowned shops and restaurants of Park Avenue, Rollins College and top-rated Winter Park schools, this extraordinary waterfront property offers a balance of luxury, convenience and recreation. Rarely does an opportunity arise to own a home on Lake Maitland that combines stunning views, spacious living and one of Central Florida's most desirable addresses.

2025 Summerland Avenue, Winter Park

$5,400,000

Extraordinary Waterfront Neoclassical Italian Estate situated on a prime .72-acre corner lot in one of Winter Park's most sought-after locations. This 7,916 SF property includes a main residence of over 7,100 SF, a detached guest house, and a poolside catering suite. The private covered boat dock is located just steps away, across the street, in the historic Kraft Azalea Garden, providing direct lake access with boat and personal watercraft storage on Lake Maitland, without the upkeep of a waterfront backyard. Inside, fresh neutral interiors and beautiful landscaping frame elegant arrival and living spaces. The thoughtful layout offers 5 bedrooms and 5 full plus 4 half baths, including a 550 SF guest house. Expansive entertaining areas flow seamlessly into a private courtyard with a heated pool and spa, covered dining, an outdoor grill, a wood-burning fireplace, and multiple terraces. Highlights include a grand primary suite with dual bathrooms and closets, a two-story wardrobe with an office in one of the primary closets, an impressive entertainment room, and a gourmet kitchen outfitted with Viking appliances, a newly replaced double oven, and a trash compactor. For large-scale entertaining, the detached pool house doubles as a catering suite with prep sink, refrigerator, and wall-to-wall storage. Built by renowned builder Charles Clayton and designed by Marc-Michaels, the home is a masterpiece of solid block construction and timeless detail featuring imported Parisian fireplaces, solid marble columns, both marble and travertine floors, and Venetian plaster walls. A new barrel tile roof (2023) adds lasting value and peace of mind. Ideally located across from Kraft Azalea Garden and near Rollins College, the estate offers a rare combination of waterfront tranquility and walkable access to Park Avenue’s world-class dining, boutiques, and museums. The Winter Park Racquet Club is also just a short golf cart ride away. A rare opportunity to acquire a legacy property with major aesthetic updates already completed and future equity positioned for growth.

5 Beds ⋅ 9 Baths ⋅ J Kronenberger Sub SubDv. ⋅ 32789 Zip Code

Extraordinary Waterfront Neoclassical Italian Estate situated on a prime .72-acre corner lot in one of Winter Park's most sought-after locations. This 7,916 SF property includes a main residence of over 7,100 SF, a detached guest house, and a poolside catering suite. The private covered boat dock is located just steps away, across the street, in the historic Kraft Azalea Garden, providing direct lake access with boat and personal watercraft storage on Lake Maitland, without the upkeep of a waterfront backyard. Inside, fresh neutral interiors and beautiful landscaping frame elegant arrival and living spaces. The thoughtful layout offers 5 bedrooms and 5 full plus 4 half baths, including a 550 SF guest house. Expansive entertaining areas flow seamlessly into a private courtyard with a heated pool and spa, covered dining, an outdoor grill, a wood-burning fireplace, and multiple terraces. Highlights include a grand primary suite with dual bathrooms and closets, a two-story wardrobe with an office in one of the primary closets, an impressive entertainment room, and a gourmet kitchen outfitted with Viking appliances, a newly replaced double oven, and a trash compactor. For large-scale entertaining, the detached pool house doubles as a catering suite with prep sink, refrigerator, and wall-to-wall storage. Built by renowned builder Charles Clayton and designed by Marc-Michaels, the home is a masterpiece of solid block construction and timeless detail featuring imported Parisian fireplaces, solid marble columns, both marble and travertine floors, and Venetian plaster walls. A new barrel tile roof (2023) adds lasting value and peace of mind. Ideally located across from Kraft Azalea Garden and near Rollins College, the estate offers a rare combination of waterfront tranquility and walkable access to Park Avenue’s world-class dining, boutiques, and museums. The Winter Park Racquet Club is also just a short golf cart ride away. A rare opportunity to acquire a legacy property with major aesthetic updates already completed and future equity positioned for growth.

1400 Alabama Drive, Winter Park

$5,125,000

Owner/Agent - Properties of this caliber are exceptionally rare in Winter Park — in a neighborhood defined by its walkability to Park Avenue, top-rated schools, and exclusive deeded access to the Winter Park Chain of Lakes. While new construction continues to emerge throughout Winter Park, few can approach the level of intention, artistry and personal investment found here. Named best custom home in the entire Southeast, this grand award-winning residence was conceived and executed by Master Custom Homebuilder Chris Salhab of Valdara Custom Homes as his own family home. Every element of this home reflects a standard of craftsmanship and care that is immediately felt upon entry and discovered anew in every room. The open-concept floor plan flows effortlessly between interior and exterior living spaces, where a summer kitchen, covered entertaining areas and a signature rain curtain that doubles as an outdoor movie screen create an experience unlike anything else on the market. Intelligent design, smart home integration and refined finishes complete a residence that is as functional as it is extraordinary. Offered with the added benefit of premium lease income through early 2027, this is a rare chance to secure one of Winter Park's finest homes as both a trophy asset and an immediate income-producing investment. Private showings by appointment only.

5 Beds ⋅ 6 Baths ⋅ Virginia Heights Rep SubDv. ⋅ 32789 Zip Code

Owner/Agent - Properties of this caliber are exceptionally rare in Winter Park — in a neighborhood defined by its walkability to Park Avenue, top-rated schools, and exclusive deeded access to the Winter Park Chain of Lakes. While new construction continues to emerge throughout Winter Park, few can approach the level of intention, artistry and personal investment found here. Named best custom home in the entire Southeast, this grand award-winning residence was conceived and executed by Master Custom Homebuilder Chris Salhab of Valdara Custom Homes as his own family home. Every element of this home reflects a standard of craftsmanship and care that is immediately felt upon entry and discovered anew in every room. The open-concept floor plan flows effortlessly between interior and exterior living spaces, where a summer kitchen, covered entertaining areas and a signature rain curtain that doubles as an outdoor movie screen create an experience unlike anything else on the market. Intelligent design, smart home integration and refined finishes complete a residence that is as functional as it is extraordinary. Offered with the added benefit of premium lease income through early 2027, this is a rare chance to secure one of Winter Park's finest homes as both a trophy asset and an immediate income-producing investment. Private showings by appointment only.

1221 Richmond Road, Winter Park

$5,125,000

This stunning private residence is on an oversized lot featuring a private sports pad, kids playground and sparkling pool. Encompassing over 6,700 square feet of expansive .55-acre lot, this home boast five spacious bedrooms, one office, 5.5 baths and a dedicated movie room, recording studio and a fully equipped gym with a private sauna. Ideally just moments from serene Lake Maitland and the charming Azalea Park, this home offers natural beauty and prime location. The chef's kitchen is designed for function and style with dual oversized islands, ideal for entertaining and everyday living. Spacious, inviting and thoughtfully designed, this oversized family room is the heart of the home-ideal for everything from cozy movie nights to lively holiday parties featuring expansive square footage, the room comfortably accommodates large groups, with plenty of space for multiple seating areas and a bar area. Oversized windows flood the space with natural light while the high ceilings and an open layout enhance the airy welcoming feel. Whether you are hosting extended family or entertaining friends, this room is built for connection, comfort and lasting memories. The private recording studio can be turned into a private mother-in-law suite or a kids playroom. The luxurious primary suite retreat to your own private oasis featuring a cozy fireplace, direct access to a serene private porch and a one-of-a-kind walk-in closet designed for style and functionality. The oversized en-suite bath boasts a steam shower, creating a spa-like experience right at home. Two additional en-suite bedrooms upstairs, each with walk in closets. Thoughtfully designed for convenience, this home features a spacious mud room off the garage which is ideal for busy households. Enjoy the ultimate convenience with two separate laundry rooms, one’s downstairs for easy access and a second upstairs near the bedrooms, making laundry day effortless and efficient. Ideally near Winter Park Racquet Club, Interlachen Country Club and accessible to Park Avenue, this exceptional residence also offers an extraordinary residence with a luxurious functionality and a premier location.

5 Beds ⋅ 6 Baths ⋅ J Kronenberger Sub SubDv. ⋅ 32789 Zip Code

This stunning private residence is on an oversized lot featuring a private sports pad, kids playground and sparkling pool. Encompassing over 6,700 square feet of expansive .55-acre lot, this home boast five spacious bedrooms, one office, 5.5 baths and a dedicated movie room, recording studio and a fully equipped gym with a private sauna. Ideally just moments from serene Lake Maitland and the charming Azalea Park, this home offers natural beauty and prime location. The chef's kitchen is designed for function and style with dual oversized islands, ideal for entertaining and everyday living. Spacious, inviting and thoughtfully designed, this oversized family room is the heart of the home-ideal for everything from cozy movie nights to lively holiday parties featuring expansive square footage, the room comfortably accommodates large groups, with plenty of space for multiple seating areas and a bar area. Oversized windows flood the space with natural light while the high ceilings and an open layout enhance the airy welcoming feel. Whether you are hosting extended family or entertaining friends, this room is built for connection, comfort and lasting memories. The private recording studio can be turned into a private mother-in-law suite or a kids playroom. The luxurious primary suite retreat to your own private oasis featuring a cozy fireplace, direct access to a serene private porch and a one-of-a-kind walk-in closet designed for style and functionality. The oversized en-suite bath boasts a steam shower, creating a spa-like experience right at home. Two additional en-suite bedrooms upstairs, each with walk in closets. Thoughtfully designed for convenience, this home features a spacious mud room off the garage which is ideal for busy households. Enjoy the ultimate convenience with two separate laundry rooms, one’s downstairs for easy access and a second upstairs near the bedrooms, making laundry day effortless and efficient. Ideally near Winter Park Racquet Club, Interlachen Country Club and accessible to Park Avenue, this exceptional residence also offers an extraordinary residence with a luxurious functionality and a premier location.

1240 Harding Street, Winter Park

$4,950,000

New Hamptons-style residence offering a seamless blend of elegance and modern sophistication. A gated entrance opening to a circular driveway and motor court, set the stage for enjoying this exceptional estate. As you enter home, an impressive 2-story foyer with a glass-paneled staircase wraps around a temperature-controlled wine room and a transparent glass elevator, effortlessly connecting all levels including an expansive third-floor multi-purpose space. Designed for contemporary living, the thoughtfully curated floor plan features a spacious open concept kitchen/gathering room along with the dining area enjoy a wall of glass doors and picture window overlooking an expansive lanai, and serene backyard with a sparkling pool and spa. The main residence offers 4 bedrooms, private home office, and multiple flex spaces, complemented by a detached pool cabana that serves as a 5th guest retreat or versatile use building. The gourmet kitchen is an entertainer’s dream, featuring dual 10-foot stone islands, a 60-inch Wolf range, dual 36-inch Sub-Zero refrigerator and freezer columns, a warming drawer, beverage center and a 146-bottle Sub-Zero dual-zone wine cooler. A separate pantry kitchen is equipped with a Dacor induction cooktop, convection oven, additional refrigerator, microwave, dishwasher and ample cabinetry, ideal for catering and meal preparation. The 1st-level primary suite is a tranquil retreat, offering a sitting area, an all-marble bath with a glass-enclosed shower, multiple body sprays, a soaking tub, and French doors leading to a secluded Zen garden with an outdoor shower and fountain. There is also a hidden private home office near the front of home. The second level hosts 3 additional en-suite bedrooms, a generous lounge area, bar, and a well-appointed laundry room with extra storage cabinetry. As noted previously, there is also a unique 3rd level accessible by a staircase or elevator. The outdoor living is elevated with a spacious lanai featuring motorized screens, a gas fireplace, dining space, and a summer kitchen with a 54-inch Coyote wood and gas grill, plus a separate burner beneath a remote-controlled louvered roof. There is also a detached cabana perfectly suited for a guest suite, fitness studio, additional office or game room, complete with a full bath, mini kitchen, and washer/dryer. Crafted with meticulous attention to detail, this home showcases Anderson windows, 10-foot solid doors, high-end lighting, plumbing and electrical fixtures, custom cabinetry built-ins, as well as Trane HVAC systems, ensuring quality and comfort... Lush landscaping, including magnolia trees, bamboo and cypress, surrounds the property, creating a private sanctuary. An attached side-entry garage features a powered car lift providing space for up to three vehicles. Ideally near Interlachen Country Club, Winter Park Racquet Club, Phelps Park/YMCA, and renowned Park Avenue. Note: Partial staging by RH and the furniture package can be purchased separately...

5 Beds ⋅ 7 Baths ⋅ Comstock Park SubDv. ⋅ 32789 Zip Code

New Hamptons-style residence offering a seamless blend of elegance and modern sophistication. A gated entrance opening to a circular driveway and motor court, set the stage for enjoying this exceptional estate. As you enter home, an impressive 2-story foyer with a glass-paneled staircase wraps around a temperature-controlled wine room and a transparent glass elevator, effortlessly connecting all levels including an expansive third-floor multi-purpose space. Designed for contemporary living, the thoughtfully curated floor plan features a spacious open concept kitchen/gathering room along with the dining area enjoy a wall of glass doors and picture window overlooking an expansive lanai, and serene backyard with a sparkling pool and spa. The main residence offers 4 bedrooms, private home office, and multiple flex spaces, complemented by a detached pool cabana that serves as a 5th guest retreat or versatile use building. The gourmet kitchen is an entertainer’s dream, featuring dual 10-foot stone islands, a 60-inch Wolf range, dual 36-inch Sub-Zero refrigerator and freezer columns, a warming drawer, beverage center and a 146-bottle Sub-Zero dual-zone wine cooler. A separate pantry kitchen is equipped with a Dacor induction cooktop, convection oven, additional refrigerator, microwave, dishwasher and ample cabinetry, ideal for catering and meal preparation. The 1st-level primary suite is a tranquil retreat, offering a sitting area, an all-marble bath with a glass-enclosed shower, multiple body sprays, a soaking tub, and French doors leading to a secluded Zen garden with an outdoor shower and fountain. There is also a hidden private home office near the front of home. The second level hosts 3 additional en-suite bedrooms, a generous lounge area, bar, and a well-appointed laundry room with extra storage cabinetry. As noted previously, there is also a unique 3rd level accessible by a staircase or elevator. The outdoor living is elevated with a spacious lanai featuring motorized screens, a gas fireplace, dining space, and a summer kitchen with a 54-inch Coyote wood and gas grill, plus a separate burner beneath a remote-controlled louvered roof. There is also a detached cabana perfectly suited for a guest suite, fitness studio, additional office or game room, complete with a full bath, mini kitchen, and washer/dryer. Crafted with meticulous attention to detail, this home showcases Anderson windows, 10-foot solid doors, high-end lighting, plumbing and electrical fixtures, custom cabinetry built-ins, as well as Trane HVAC systems, ensuring quality and comfort... Lush landscaping, including magnolia trees, bamboo and cypress, surrounds the property, creating a private sanctuary. An attached side-entry garage features a powered car lift providing space for up to three vehicles. Ideally near Interlachen Country Club, Winter Park Racquet Club, Phelps Park/YMCA, and renowned Park Avenue. Note: Partial staging by RH and the furniture package can be purchased separately...

1660 Palmer Avenue, Winter Park

$4,800,000

An extraordinary opportunity on the shores of Lake Osceola on one of Winter Park's most charming streets. This architecturally interesting lakefront estate offers breathtaking panoramic sunset views and an irreplaceable setting. Thoughtfully designed with the beautiful finishes. First time available in over three decades, this is rare chance to own a legacy property!

5 Beds ⋅ 6 Baths ⋅ Comstock Park SubDv. ⋅ 32789 Zip Code

An extraordinary opportunity on the shores of Lake Osceola on one of Winter Park's most charming streets. This architecturally interesting lakefront estate offers breathtaking panoramic sunset views and an irreplaceable setting. Thoughtfully designed with the beautiful finishes. First time available in over three decades, this is rare chance to own a legacy property!

641 Bonita Drive, Winter Park

$4,720,000

*Under Contract - Accepting Backup Offers* An expression of modern luxury by SMRS Design and Cole Homes, The Maybourne masterfully blends Neoclassical elegance with Art Deco sophistication—all just steps from Winter Park’s iconic Park Avenue. A curved, manicured driveway leads to a grand entrance featuring bespoke double doors with electromagnetic privacy glass, setting the tone for the artistry within. Inside, a European hotel–inspired foyer greets guests with precast stone-clad walls, inlaid marble flooring, and a Murano-style polyhedral chandelier. Two first-floor guest suites, each with its own bath, are adorned with rift-cut white oak millwork, curved ceilings, and crystal chandeliers. At the heart of the home lies the main salon, where oak detailing and a deco-style stone fireplace with a holographic insert create an atmosphere of understated grandeur. The two-tone oak kitchen, wrapped in natural quartzite and anchored by a curved island and custom hood, features a curated suite of professional-grade appliances: • ILVE range • Miele refrigerator, freezer, and dishwasher • Sub-Zero wine and beverage preservation systems Adjacent, a dining area glows under a custom chandelier, while the powder bath impresses with wood and marble accents, an integrated stone sink, and a Saint Louis crystal faucet by Kallista. A scullery expands the culinary capability with a chef’s sink, Samsung Bespoke laundry and refrigeration, Wolf microwave drawer, and additional Miele dishwasher—ideal for both entertaining and daily ease. The first floor primary suite, discreetly hidden behind millwork, offers a serene retreat with an opulent closet system and a marble mosaic-clad bathing suite featuring Kohler digital shower technology and MTI tub. Upstairs, two additional ensuite bedrooms, a bonus room with walk-in closet, and a secondary laundry continue the home’s standard of refined luxury. Outdoors, the residence embraces resort-style living with a natural gas summer kitchen, infinity-edge pool, and 360-degree raised glass-tile spa. A two-car garage and porte cochere, both EV-ready, provide elegant utility. Modern conveniences include Lutron HomeWorks lighting and shade prewire, built-in SONOS audio zones, pre-installed speakers, and a commercial-grade Ubiquiti WiFi network ensuring flawless connectivity throughout. A feast for the senses, The Maybourne is more than a home—it’s a statement of artistry and craftsmanship, conceived for the most discerning Winter Park resident.

5 Beds ⋅ 6 Baths ⋅ Camwood Sub SubDv. ⋅ 32789 Zip Code

*Under Contract - Accepting Backup Offers* An expression of modern luxury by SMRS Design and Cole Homes, The Maybourne masterfully blends Neoclassical elegance with Art Deco sophistication—all just steps from Winter Park’s iconic Park Avenue. A curved, manicured driveway leads to a grand entrance featuring bespoke double doors with electromagnetic privacy glass, setting the tone for the artistry within. Inside, a European hotel–inspired foyer greets guests with precast stone-clad walls, inlaid marble flooring, and a Murano-style polyhedral chandelier. Two first-floor guest suites, each with its own bath, are adorned with rift-cut white oak millwork, curved ceilings, and crystal chandeliers. At the heart of the home lies the main salon, where oak detailing and a deco-style stone fireplace with a holographic insert create an atmosphere of understated grandeur. The two-tone oak kitchen, wrapped in natural quartzite and anchored by a curved island and custom hood, features a curated suite of professional-grade appliances: • ILVE range • Miele refrigerator, freezer, and dishwasher • Sub-Zero wine and beverage preservation systems Adjacent, a dining area glows under a custom chandelier, while the powder bath impresses with wood and marble accents, an integrated stone sink, and a Saint Louis crystal faucet by Kallista. A scullery expands the culinary capability with a chef’s sink, Samsung Bespoke laundry and refrigeration, Wolf microwave drawer, and additional Miele dishwasher—ideal for both entertaining and daily ease. The first floor primary suite, discreetly hidden behind millwork, offers a serene retreat with an opulent closet system and a marble mosaic-clad bathing suite featuring Kohler digital shower technology and MTI tub. Upstairs, two additional ensuite bedrooms, a bonus room with walk-in closet, and a secondary laundry continue the home’s standard of refined luxury. Outdoors, the residence embraces resort-style living with a natural gas summer kitchen, infinity-edge pool, and 360-degree raised glass-tile spa. A two-car garage and porte cochere, both EV-ready, provide elegant utility. Modern conveniences include Lutron HomeWorks lighting and shade prewire, built-in SONOS audio zones, pre-installed speakers, and a commercial-grade Ubiquiti WiFi network ensuring flawless connectivity throughout. A feast for the senses, The Maybourne is more than a home—it’s a statement of artistry and craftsmanship, conceived for the most discerning Winter Park resident.

1302 Raintree Place, Winter Park

$4,650,000

Privately nestled on 1.32 acres (1.1+ acres HIGH & DRY) along the tranquil shores of Lake Temple, this remarkable residence is a true compound where architecture, craftsmanship, and nature exist in perfect balance. Completed in 2019 by Gallimore Homes and enhanced with more than $300K in upgrades, this home was designed to feel secluded and private while serving as the ultimate destination for entertaining. This unique property offers a 4,060+ SF main residence (4 beds / 3.5 baths plus bonus room for a future 5th bedroom), a detached 480+ SF guest house (1 bed / 1 bath), and resort-style outdoor living overlooking peaceful water views and a rolling backyard. Designed for exceptional privacy, the home is positioned well back from the street and buffered by mature landscaping, a private courtyard wall with a security gate, and hurricane-impact windows and doors throughout. Additional highlights include an oversized three-car garage, parking for 15+ vehicles, and space to park a boat or RV next to the conservation area. Inside, soaring ceilings and premium finishes create an immediate sense of warmth and sophistication. Ten-foot-tall EuroWall folding glass doors span 15 feet across the great room, seamlessly blending indoor and outdoor living while framing beautiful backyard and water views. The chef's kitchen showcases professional-grade Sub-Zero and Wolf appliances, an oversized gathering island with prep sink, ice maker, waterfall countertops, a 48-inch Wolf six-burner dual-fuel range, dry bar with refrigerated drawers, and a spacious walk-in pantry. The open-concept design flows effortlessly into the great room and dining area, making everyday living and entertaining equally inviting. The split-bedroom floor plan offers exceptional privacy, highlighted by a spacious first-floor primary suite with 2 walk-in closets (totaling 175+ SF) and a spa-inspired bath. The first floor also includes a guest suite, two additional bedrooms with a Jack-and-Jill bath, and a powder/pool bath with access to the lania. Upstairs, the bonus room provides flexibility for a media room, game room, home office, and pre-plumed for a bath and kitchenette for a future 5th bedroom. Equally impressive is the detached guest house, complete with its own covered front porch, full kitchen, living room, bedroom, full bath, and beautiful backyard views…ideal for multigenerational living, extended guests, a private office, or long-term visitors. The covered lanai was designed for year-round outdoor living with three Phantom Screens spanning nearly 45 feet, an authentic Argentine wood-fired grill, and a built-in wet bar. The heated saltwater infinity-edge pool features a sun shelf, LED lighting, and a composite wood sun deck overlooking the water. The expansive lawn gently slopes to the shoreline beneath a magnificent 100+ year-old oak tree, enhanced by mature landscaping and landscape lighting that creates an unforgettable setting for intimate evenings and large-scale gatherings too. Located less than three miles from Interlachen Country Club and a few blocks from the Winter Park Racquet Club, this property offers a rare combination of privacy, flexibility, and estate-style living on more than an acre of waterfront in Winter Park.

5 Beds ⋅ 5 Baths ⋅ Lake Maitland SubDv. ⋅ 32789 Zip Code

Privately nestled on 1.32 acres (1.1+ acres HIGH & DRY) along the tranquil shores of Lake Temple, this remarkable residence is a true compound where architecture, craftsmanship, and nature exist in perfect balance. Completed in 2019 by Gallimore Homes and enhanced with more than $300K in upgrades, this home was designed to feel secluded and private while serving as the ultimate destination for entertaining. This unique property offers a 4,060+ SF main residence (4 beds / 3.5 baths plus bonus room for a future 5th bedroom), a detached 480+ SF guest house (1 bed / 1 bath), and resort-style outdoor living overlooking peaceful water views and a rolling backyard. Designed for exceptional privacy, the home is positioned well back from the street and buffered by mature landscaping, a private courtyard wall with a security gate, and hurricane-impact windows and doors throughout. Additional highlights include an oversized three-car garage, parking for 15+ vehicles, and space to park a boat or RV next to the conservation area. Inside, soaring ceilings and premium finishes create an immediate sense of warmth and sophistication. Ten-foot-tall EuroWall folding glass doors span 15 feet across the great room, seamlessly blending indoor and outdoor living while framing beautiful backyard and water views. The chef's kitchen showcases professional-grade Sub-Zero and Wolf appliances, an oversized gathering island with prep sink, ice maker, waterfall countertops, a 48-inch Wolf six-burner dual-fuel range, dry bar with refrigerated drawers, and a spacious walk-in pantry. The open-concept design flows effortlessly into the great room and dining area, making everyday living and entertaining equally inviting. The split-bedroom floor plan offers exceptional privacy, highlighted by a spacious first-floor primary suite with 2 walk-in closets (totaling 175+ SF) and a spa-inspired bath. The first floor also includes a guest suite, two additional bedrooms with a Jack-and-Jill bath, and a powder/pool bath with access to the lania. Upstairs, the bonus room provides flexibility for a media room, game room, home office, and pre-plumed for a bath and kitchenette for a future 5th bedroom. Equally impressive is the detached guest house, complete with its own covered front porch, full kitchen, living room, bedroom, full bath, and beautiful backyard views…ideal for multigenerational living, extended guests, a private office, or long-term visitors. The covered lanai was designed for year-round outdoor living with three Phantom Screens spanning nearly 45 feet, an authentic Argentine wood-fired grill, and a built-in wet bar. The heated saltwater infinity-edge pool features a sun shelf, LED lighting, and a composite wood sun deck overlooking the water. The expansive lawn gently slopes to the shoreline beneath a magnificent 100+ year-old oak tree, enhanced by mature landscaping and landscape lighting that creates an unforgettable setting for intimate evenings and large-scale gatherings too. Located less than three miles from Interlachen Country Club and a few blocks from the Winter Park Racquet Club, this property offers a rare combination of privacy, flexibility, and estate-style living on more than an acre of waterfront in Winter Park.

2525 Temple Drive, Winter Park

$4,550,000

Under Construction. Stunning Winter Park new build by Vimaro Homes in Park Grove.

5 Beds ⋅ 6 Baths ⋅ Green Oaks Rep SubDv. ⋅ 32789 Zip Code

Under Construction. Stunning Winter Park new build by Vimaro Homes in Park Grove.

1701 Summerland Avenue, Winter Park

$4,500,000

Wonderfully executed remodel of a classic mid-century modern residence with an elevated view overlooking scenic Lake Sylvan. This home was restored beautifully and now with up-to-date amenities including provisions for home automation, current kitchen and baths, pool, outdoor living, and finished off with Signature Landscape Contractors hardscape and landscape to complete the vision well executed by Floridian Homes! Completely remodeled with effective year built of 2026 and original year built of 1962.

4 Beds ⋅ 5 Baths ⋅ Sylvan Lake Shores SubDv. ⋅ 32789 Zip Code

Wonderfully executed remodel of a classic mid-century modern residence with an elevated view overlooking scenic Lake Sylvan. This home was restored beautifully and now with up-to-date amenities including provisions for home automation, current kitchen and baths, pool, outdoor living, and finished off with Signature Landscape Contractors hardscape and landscape to complete the vision well executed by Floridian Homes! Completely remodeled with effective year built of 2026 and original year built of 1962.

1521 Harris Circle, Winter Park

$4,500,000

Offered for the first time in over 50 years, this distinguished Winter Park estate is a true traditional gem, nestled on a picturesque brick street and situated on a full 1-acre lot. Exuding timeless charm with a subtle New England ambiance, this residence represents the best of historic Winter Park living—all within walking distance to Park Avenue. This stately 6-bedroom, 5.5-bathroom home offers 5,759 square feet of thoughtfully designed living space, plus an additional 1,859-square-foot unfinished basement that spans the entire length of the home, offering endless possibilities for expansion or customization. Upon entry, you'll be welcomed by coffered ceilings in the spacious formal living room, rich dark oak floors, and one of the home’s three gas fireplaces. This elegant yet inviting room overlooks the lush gardens, making it an ideal setting for both entertaining and quiet relaxation. Adjacent to the living room is a cozy, beautifully appointed den featuring another gas fireplace and natural jute flooring—undoubtedly one of the most beloved spaces in the home. The kitchen is filled with natural light and includes a large casual dining area, a charming butler’s pantry, and direct access to both the laundry room—complete with a full-size refrigerator and half-bath—and the oversized 2-car garage. The formal dining room showcases lattice-framed bay windows with views of the back garden and pool area, creating a warm and elegant space perfect for holiday dinners and family gatherings. The home features two primary bedroom suites on the main level, including one expansive L-shaped suite with its own gas fireplace and views of the pool, gardens, and outdoor terrace. The primary bathroom includes a dressing area and marble finishes throughout. Upstairs, the south wing includes two generous bedrooms with a shared full bathroom, while the north wing—located above the kitchen—offers two additional bedrooms and a charming full bath. The expansive backyard is a private sanctuary, framed by majestic oak trees, bamboo, and thoughtfully designed gardens, with several inviting sitting areas for outdoor relaxation. An extra-large swimming pool completes the setting—perfect for warm Florida days or evening gatherings under the stars.

6 Beds ⋅ 6 Baths ⋅ Dyer Susan Resub SubDv. ⋅ 32789 Zip Code

Offered for the first time in over 50 years, this distinguished Winter Park estate is a true traditional gem, nestled on a picturesque brick street and situated on a full 1-acre lot. Exuding timeless charm with a subtle New England ambiance, this residence represents the best of historic Winter Park living—all within walking distance to Park Avenue. This stately 6-bedroom, 5.5-bathroom home offers 5,759 square feet of thoughtfully designed living space, plus an additional 1,859-square-foot unfinished basement that spans the entire length of the home, offering endless possibilities for expansion or customization. Upon entry, you'll be welcomed by coffered ceilings in the spacious formal living room, rich dark oak floors, and one of the home’s three gas fireplaces. This elegant yet inviting room overlooks the lush gardens, making it an ideal setting for both entertaining and quiet relaxation. Adjacent to the living room is a cozy, beautifully appointed den featuring another gas fireplace and natural jute flooring—undoubtedly one of the most beloved spaces in the home. The kitchen is filled with natural light and includes a large casual dining area, a charming butler’s pantry, and direct access to both the laundry room—complete with a full-size refrigerator and half-bath—and the oversized 2-car garage. The formal dining room showcases lattice-framed bay windows with views of the back garden and pool area, creating a warm and elegant space perfect for holiday dinners and family gatherings. The home features two primary bedroom suites on the main level, including one expansive L-shaped suite with its own gas fireplace and views of the pool, gardens, and outdoor terrace. The primary bathroom includes a dressing area and marble finishes throughout. Upstairs, the south wing includes two generous bedrooms with a shared full bathroom, while the north wing—located above the kitchen—offers two additional bedrooms and a charming full bath. The expansive backyard is a private sanctuary, framed by majestic oak trees, bamboo, and thoughtfully designed gardens, with several inviting sitting areas for outdoor relaxation. An extra-large swimming pool completes the setting—perfect for warm Florida days or evening gatherings under the stars.

887 Georgia Avenue, Winter Park

$4,450,000

SOLD DATA ENTRY ONLY Welcome to this exceptional custom residence located on one of Winter Park’s most desirable streets. Built in 2017 and impeccably maintained, this like-new home offers timeless architecture, modern luxury, and thoughtful design throughout. Offering 6 bedrooms, 6 full bathrooms, and 1 half bath, the home encompasses over 5,100 square feet of living space on a generous half-acre lot, providing both privacy and an impressive sense of scale. Upon entry, engineered hardwood flooring, high ceilings, and abundant natural light set the tone for the refined interiors.The open-concept floor plan seamlessly connects the main living areas, making the home ideal for both everyday living and entertaining. The kitchen is equipped with custom solid-wood cabinetry, premium Wolf and Sub-Zero appliances, a large center island, and ample storage, all opening to the family and dining spaces for effortless flow.The primary suite is located on the main level and offers a peaceful retreat with a spacious walk-in closet and a spa-inspired bathroom. Each additional bedroom is generously sized and features its own en-suite bath, ensuring comfort and privacy for family and guests. Multiple flex spaces throughout the home provide versatility for a home office, gym, or media room.Additional features include a Crestron lighting and sound system, a four-car garage with built-in cabinetry, a cement tile roof, and built-in closet systems throughout. The expansive backyard offers ample room for outdoor living and future enhancements. Ideally situated just minutes from Park Avenue, top-rated schools, dining, and shopping, this move-in-ready home presents a rare opportunity to own a nearly new estate in the heart of Winter Park.

5 Beds ⋅ 7 Baths ⋅ Stonehurst Estates SubDv. ⋅ 32789 Zip Code

SOLD DATA ENTRY ONLY Welcome to this exceptional custom residence located on one of Winter Park’s most desirable streets. Built in 2017 and impeccably maintained, this like-new home offers timeless architecture, modern luxury, and thoughtful design throughout. Offering 6 bedrooms, 6 full bathrooms, and 1 half bath, the home encompasses over 5,100 square feet of living space on a generous half-acre lot, providing both privacy and an impressive sense of scale. Upon entry, engineered hardwood flooring, high ceilings, and abundant natural light set the tone for the refined interiors.The open-concept floor plan seamlessly connects the main living areas, making the home ideal for both everyday living and entertaining. The kitchen is equipped with custom solid-wood cabinetry, premium Wolf and Sub-Zero appliances, a large center island, and ample storage, all opening to the family and dining spaces for effortless flow.The primary suite is located on the main level and offers a peaceful retreat with a spacious walk-in closet and a spa-inspired bathroom. Each additional bedroom is generously sized and features its own en-suite bath, ensuring comfort and privacy for family and guests. Multiple flex spaces throughout the home provide versatility for a home office, gym, or media room.Additional features include a Crestron lighting and sound system, a four-car garage with built-in cabinetry, a cement tile roof, and built-in closet systems throughout. The expansive backyard offers ample room for outdoor living and future enhancements. Ideally situated just minutes from Park Avenue, top-rated schools, dining, and shopping, this move-in-ready home presents a rare opportunity to own a nearly new estate in the heart of Winter Park.

1812 Stonehurst Road, Winter Park

$4,300,000

Presenting an extraordinary southern traditional estate in the heart of the coveted Vias of Winter Park, a residence that effortlessly blends timeless architecture with exceptional craftsmanship. This stunning home, designed by acclaimed architect Gary Hancock, made its debut as the Southeast Builder’s Conference Showhouse for two consecutive years, a testament to its design and quality. From the moment you arrive, the home’s presence is both elegant and inviting. A circular drive leads to a charming porte-cochère and an extended driveway, culminating in a three-car garage. The façade is defined by classic columns, a welcoming second-floor balcony, and eleven glowing Bevolo gas lanterns from New Orleans, while nineteen matching electric lanterns illuminate the backyard, casting a warm, timeless ambiance across the property. Inside, every detail tells a story. Reclaimed Chinese Elm wood floors, rich with character and history, flow throughout the main living spaces, perfectly complemented by soaring ceilings adorned with striking wood beams. The kitchen is both a showpiece and a workspace, outfitted with premium Thermador appliances, including a six-burner range, steam oven, warming drawer and dual integrated refrigerators. Antique ceiling tiles form a distinctive backsplash, while custom cabinetry with replicated antique float glass adds a layer of understated sophistication. A hidden walk-in pantry enhances both form and function. The kitchen opens into a grand great room anchored by a fireplace and custom built-ins, creating an ideal setting for both everyday living and entertaining. Beyond, a versatile billiards room shares a dramatic two-sided fireplace and features a full wet bar, wine refrigeration, dishwasher and an adjacent full bath, perfectly suited as a pool bath. The dining room, framed by French doors, offers serene views of the covered lanai and lush backyard. The first-floor primary suite is a private retreat designed for comfort and convenience. A fireplace anchors the space, while thoughtful amenities include a private laundry room, custom walk-in closet and a well-appointed wet bar with leathered granite counters, a Thermador fridge and a dishwasher. The primary bath serves as the main spa-like experience, featuring a marble walk-in shower, a soaking tub, and dual vanities. A second, separate full bath within the suite provides additional functionality. Upstairs, accessible by a sweeping curved staircase or elevator, you’ll find three generously sized ensuite bedrooms and a bonus room complete with a wet bar and access to the rear covered balcony while two bedrooms have access to the front covered balcony, perfect for enjoying morning light or evening breezes. A third-floor retreat, currently used as a playroom, offers endless possibilities for a home office or studio. Outdoor living is equally compelling, with a large, covered lanai overlooking a resort-style pool and expansive backyard designed for relaxation and entertaining. Ideally just minutes from the boutiques and dining of Park Avenue and within walking or biking distance to the Winter Park Racquet Club, this exceptional home is set among the tree-lined streets and distinguished estates that define the Vias, one of Winter Park’s most sought-after neighborhoods. A rare offering where classic elegance, thoughtful design and modern livability come together beautifully.

4 Beds ⋅ 7 Baths ⋅ Sicilian Shores Rep 02 SubDv. ⋅ 32789 Zip Code

Presenting an extraordinary southern traditional estate in the heart of the coveted Vias of Winter Park, a residence that effortlessly blends timeless architecture with exceptional craftsmanship. This stunning home, designed by acclaimed architect Gary Hancock, made its debut as the Southeast Builder’s Conference Showhouse for two consecutive years, a testament to its design and quality. From the moment you arrive, the home’s presence is both elegant and inviting. A circular drive leads to a charming porte-cochère and an extended driveway, culminating in a three-car garage. The façade is defined by classic columns, a welcoming second-floor balcony, and eleven glowing Bevolo gas lanterns from New Orleans, while nineteen matching electric lanterns illuminate the backyard, casting a warm, timeless ambiance across the property. Inside, every detail tells a story. Reclaimed Chinese Elm wood floors, rich with character and history, flow throughout the main living spaces, perfectly complemented by soaring ceilings adorned with striking wood beams. The kitchen is both a showpiece and a workspace, outfitted with premium Thermador appliances, including a six-burner range, steam oven, warming drawer and dual integrated refrigerators. Antique ceiling tiles form a distinctive backsplash, while custom cabinetry with replicated antique float glass adds a layer of understated sophistication. A hidden walk-in pantry enhances both form and function. The kitchen opens into a grand great room anchored by a fireplace and custom built-ins, creating an ideal setting for both everyday living and entertaining. Beyond, a versatile billiards room shares a dramatic two-sided fireplace and features a full wet bar, wine refrigeration, dishwasher and an adjacent full bath, perfectly suited as a pool bath. The dining room, framed by French doors, offers serene views of the covered lanai and lush backyard. The first-floor primary suite is a private retreat designed for comfort and convenience. A fireplace anchors the space, while thoughtful amenities include a private laundry room, custom walk-in closet and a well-appointed wet bar with leathered granite counters, a Thermador fridge and a dishwasher. The primary bath serves as the main spa-like experience, featuring a marble walk-in shower, a soaking tub, and dual vanities. A second, separate full bath within the suite provides additional functionality. Upstairs, accessible by a sweeping curved staircase or elevator, you’ll find three generously sized ensuite bedrooms and a bonus room complete with a wet bar and access to the rear covered balcony while two bedrooms have access to the front covered balcony, perfect for enjoying morning light or evening breezes. A third-floor retreat, currently used as a playroom, offers endless possibilities for a home office or studio. Outdoor living is equally compelling, with a large, covered lanai overlooking a resort-style pool and expansive backyard designed for relaxation and entertaining. Ideally just minutes from the boutiques and dining of Park Avenue and within walking or biking distance to the Winter Park Racquet Club, this exceptional home is set among the tree-lined streets and distinguished estates that define the Vias, one of Winter Park’s most sought-after neighborhoods. A rare offering where classic elegance, thoughtful design and modern livability come together beautifully.

1760 Via Venetia, Winter Park

$4,250,000

Introducing one of Winter Park's most extraordinary offerings — a meticulously designed transitional masterpiece by the acclaimed Winter Park Custom Homes, set on a rare 0.34-acre corner lot in one of the city's most coveted neighborhoods. From the moment you arrive at the circular front drive and step onto the marble-tiled covered front porch, it's clear this home is in a class of its own. Inside, soaring beamed ceilings and wide-plank engineered wood floors set an elevated tone throughout. The grand living room features a gas fireplace and dramatic accordion glass doors that dissolve the boundary between indoors and out, opening to the resort-style backyard with ease. The chef's kitchen is a true work of art: anchored by a massive island with wraparound seating, Thermador gas range and oven, built-in refrigerator and microwave, marble countertops, and a generous walk-in pantry — all complemented by stunning herringbone hardwood floors that make this space feel straight out of the pages of a design magazine. A butler's hallway and charming brick-floored cozy reading room add warmth and character to the everyday. Also on the main level, a full en-suite office — easily serving as a 6th bedroom — offers flexible living for guests or multi-generational needs, while a separate powder room is thoughtfully reserved for guest use. The primary suite is a sanctuary unto itself: a private vestibule entry leads to a spacious bedroom retreat with accordion-style doors that open directly to stepping stones leading into your personal spa. The spa-inspired primary bath showcases marble countertops and inlay floors, separate sink vanities, a freestanding soaking tub, a walk-in shower, and a custom-built walk-in closet that rivals any boutique. Upstairs, four generously sized en-suite bedrooms — each with walk-in closets — surround a spectacular bonus room complete with a wet bar, perfect for entertaining or movie nights. The third floor is a true Winter Park rarity — an expansive additional living level with a dedicated gym area and playroom ideal for home theater, creative pursuits, or whatever your lifestyle demands. Built-in speakers complete the experience. Step outside to your own private resort. A heated pool and spa with a sun shelf, fire bowl, and serene stepping stones are framed by lush artificial turf and elegant marble-inlaid pavers. The covered back patio with tongue-and-groove ceiling and fireplace creates an al fresco living room, while the outdoor grill with prep sink makes entertaining effortless. Natural gas throughout, a full-house generator, sauna, and an epoxy-floored two-car side garage round out this exceptional property — all seamlessly controlled through a whole-home Control4 automation system that puts lighting, climate, audio, security, and more at your fingertips. Zoned for A-rated Winter Park schools and just minutes from Park Maitland School (K–6), Park Avenue's world-class dining and boutiques, and all that Central Florida has to offer. Homes of this caliber, at this scale, in this location simply do not come available often. This is not just a home — it's a lifestyle.

6 Beds ⋅ 7 Baths ⋅ Winflor Court Pt Rep SubDv. ⋅ 32789 Zip Code

Introducing one of Winter Park's most extraordinary offerings — a meticulously designed transitional masterpiece by the acclaimed Winter Park Custom Homes, set on a rare 0.34-acre corner lot in one of the city's most coveted neighborhoods. From the moment you arrive at the circular front drive and step onto the marble-tiled covered front porch, it's clear this home is in a class of its own. Inside, soaring beamed ceilings and wide-plank engineered wood floors set an elevated tone throughout. The grand living room features a gas fireplace and dramatic accordion glass doors that dissolve the boundary between indoors and out, opening to the resort-style backyard with ease. The chef's kitchen is a true work of art: anchored by a massive island with wraparound seating, Thermador gas range and oven, built-in refrigerator and microwave, marble countertops, and a generous walk-in pantry — all complemented by stunning herringbone hardwood floors that make this space feel straight out of the pages of a design magazine. A butler's hallway and charming brick-floored cozy reading room add warmth and character to the everyday. Also on the main level, a full en-suite office — easily serving as a 6th bedroom — offers flexible living for guests or multi-generational needs, while a separate powder room is thoughtfully reserved for guest use. The primary suite is a sanctuary unto itself: a private vestibule entry leads to a spacious bedroom retreat with accordion-style doors that open directly to stepping stones leading into your personal spa. The spa-inspired primary bath showcases marble countertops and inlay floors, separate sink vanities, a freestanding soaking tub, a walk-in shower, and a custom-built walk-in closet that rivals any boutique. Upstairs, four generously sized en-suite bedrooms — each with walk-in closets — surround a spectacular bonus room complete with a wet bar, perfect for entertaining or movie nights. The third floor is a true Winter Park rarity — an expansive additional living level with a dedicated gym area and playroom ideal for home theater, creative pursuits, or whatever your lifestyle demands. Built-in speakers complete the experience. Step outside to your own private resort. A heated pool and spa with a sun shelf, fire bowl, and serene stepping stones are framed by lush artificial turf and elegant marble-inlaid pavers. The covered back patio with tongue-and-groove ceiling and fireplace creates an al fresco living room, while the outdoor grill with prep sink makes entertaining effortless. Natural gas throughout, a full-house generator, sauna, and an epoxy-floored two-car side garage round out this exceptional property — all seamlessly controlled through a whole-home Control4 automation system that puts lighting, climate, audio, security, and more at your fingertips. Zoned for A-rated Winter Park schools and just minutes from Park Maitland School (K–6), Park Avenue's world-class dining and boutiques, and all that Central Florida has to offer. Homes of this caliber, at this scale, in this location simply do not come available often. This is not just a home — it's a lifestyle.

650 Dixie Parkway, Winter Park

$4,250,000

Steeped in history and masterfully reimagined, this 1926 Winter Park estate blends architectural provenance with modern refinement. Thoughtfully restored by E2 Homes, the residence honors its past while offering contemporary sophistication. Unlike many historic properties, it is free from preservation restrictions, allowing for seamless enhancements. On the shores of Lake Virginia along the desirable Winter Park Chain of Lakes, this 3,181-square-foot estate features four bedrooms, three full baths and two half baths, with three bedrooms in the main house plus a detached one-bedroom guest cottage. The second-floor primary suite is a private retreat with a Juliet balcony, dual closets and an elegantly appointed bath with an expansive dual-sink vanity, a separate water closet, and a washroom with a shower-tub combination. A Jack and Jill bath, adorned with Maharam wallpaper, serves the additional upstairs bedrooms. The Poliform Twelve kitchen showcases European craftsmanship with Gaggenau and Sub-Zero appliances, sleek Italian cabinetry and natural basalt countertops. The formal dining room, framed by arched windows and French doors, opens to a vine-covered courtyard, while the sunroom offers uninterrupted lake views. A fireplace in the living room, flanked by custom built-ins, adds warmth to the home’s contemporary aesthetic. Beyond its striking interiors, the estate is an architectural rarity, featuring original woodwork by Gene Leedy, a key figure in the Sarasota School of Architecture. The home is crowned with sought-after Ludowici-Celadon Imperial roof tiles. Poliform built-ins extend throughout, including a dedicated upstairs office/library. An integration of art and architecture, the property features site-specific installations by acclaimed artist Matt Olson. His No Separation project finds a compelling continuation here. The entryway, designed by Olson’s firm OOIEE and inspired by Sol LeWitt, makes a striking first impression. Designed for seamless indoor-outdoor living, the estate’s exterior spaces are as refined as its interiors. A covered deck overlooks a heated saltwater pool. A wood-clad pergola shelters the lanai. The boathouse includes a partial bath, creating a waterfront sanctuary. A Sonos-integrated sound system extends from the main house to the patio, guesthouse and boathouse, ensuring a seamless sensory experience. The detached guesthouse is a private retreat with a full bedroom, bath, kitchenette and Poliform built-ins. Floor-to-ceiling windows frame manicured grounds and lake views, while a private covered porch provides a tranquil space for relaxation. Every detail has been meticulously curated, from designer lighting to motorized roller shades and a wood-burning fireplace anchoring the living room. A private wine library enhances the home’s sophisticated appeal. Meticulously maintained by E2 Concierge services, the residence undergoes routine wellness checks and meticulous upkeep. A distinctive home of this caliber is rarely available, a residence where history, architecture and art converge in harmony. This is a once-in-a-lifetime opportunity to own one of Winter Park’s architecturally and artistically significant properties.

4 Beds ⋅ 5 Baths ⋅ Virginia Heights SubDv. ⋅ 32789 Zip Code

Steeped in history and masterfully reimagined, this 1926 Winter Park estate blends architectural provenance with modern refinement. Thoughtfully restored by E2 Homes, the residence honors its past while offering contemporary sophistication. Unlike many historic properties, it is free from preservation restrictions, allowing for seamless enhancements. On the shores of Lake Virginia along the desirable Winter Park Chain of Lakes, this 3,181-square-foot estate features four bedrooms, three full baths and two half baths, with three bedrooms in the main house plus a detached one-bedroom guest cottage. The second-floor primary suite is a private retreat with a Juliet balcony, dual closets and an elegantly appointed bath with an expansive dual-sink vanity, a separate water closet, and a washroom with a shower-tub combination. A Jack and Jill bath, adorned with Maharam wallpaper, serves the additional upstairs bedrooms. The Poliform Twelve kitchen showcases European craftsmanship with Gaggenau and Sub-Zero appliances, sleek Italian cabinetry and natural basalt countertops. The formal dining room, framed by arched windows and French doors, opens to a vine-covered courtyard, while the sunroom offers uninterrupted lake views. A fireplace in the living room, flanked by custom built-ins, adds warmth to the home’s contemporary aesthetic. Beyond its striking interiors, the estate is an architectural rarity, featuring original woodwork by Gene Leedy, a key figure in the Sarasota School of Architecture. The home is crowned with sought-after Ludowici-Celadon Imperial roof tiles. Poliform built-ins extend throughout, including a dedicated upstairs office/library. An integration of art and architecture, the property features site-specific installations by acclaimed artist Matt Olson. His No Separation project finds a compelling continuation here. The entryway, designed by Olson’s firm OOIEE and inspired by Sol LeWitt, makes a striking first impression. Designed for seamless indoor-outdoor living, the estate’s exterior spaces are as refined as its interiors. A covered deck overlooks a heated saltwater pool. A wood-clad pergola shelters the lanai. The boathouse includes a partial bath, creating a waterfront sanctuary. A Sonos-integrated sound system extends from the main house to the patio, guesthouse and boathouse, ensuring a seamless sensory experience. The detached guesthouse is a private retreat with a full bedroom, bath, kitchenette and Poliform built-ins. Floor-to-ceiling windows frame manicured grounds and lake views, while a private covered porch provides a tranquil space for relaxation. Every detail has been meticulously curated, from designer lighting to motorized roller shades and a wood-burning fireplace anchoring the living room. A private wine library enhances the home’s sophisticated appeal. Meticulously maintained by E2 Concierge services, the residence undergoes routine wellness checks and meticulous upkeep. A distinctive home of this caliber is rarely available, a residence where history, architecture and art converge in harmony. This is a once-in-a-lifetime opportunity to own one of Winter Park’s architecturally and artistically significant properties.

1336 College Point, Winter Park

$4,150,000

Welcome to 702 Via Bella, an impressive 2025 English cottage estate by Floridian Custom Homes that captures the essence of timeless architecture exemplifying elegance and artisan craftsmanship. In one of Winter Park’s desirable residential corridors, warmth and beauty abound in this four-bedroom, six-bath residence spanning 3,720 square feet or air conditioned and 4,535 square feet total under roof, offering layered living, artisanal materials, and a modern infrastructure. Upon entry through a solid mahogany front door, warmth and beauty abounds with Botticino limestone flooring enhanced by a textured finish, extensive custom millwork, and an abundance of open concept living areas. Coffered ceilings and recessed WAC lighting create a gallery-like ambiance, enhanced by natural light from insulated casement windows. The central living space integrates with the dining area and designer kitchen, which features custom cabinetry by Grit & Grain, leathered Taj Mahal quartzite surfaces, and chef-grade appliances: a La Cornue 43-inch gas range with McGurken hood, Thermador 30-inch refrigerator and freezer columns, and Bosch dishwasher. The kitchen transitions into a walk-in pantry with cabinetry, quartzite, dual refrigeration drawers, and a dedicated ice maker. An oversized mudroom, finished with hardwood built-ins, offers expanded storage and functionality. The first-floor primary suite is privately positioned in its own wing and finished with wide-plank European white oak flooring by Forrest Accents, a walk-in closet with textured built-in systems, and a spa bath with natural stone countertops, Rohl polished nickel fixtures, a marble-tiled floor and shower, and a frameless glass enclosure. All doors are solid core with Emtek hardware. The library, near the front of the home, offers a quiet retreat with matching oak floors and custom casements. A solid wood staircase leads to the second level living areas including a lounge flex space. There are three additional bedroom suites, each with en-suite baths, which offer porcelain flooring, frameless glass shower doors, brushed quartz and dolomite vanities, decorative lighting, and built-in closet systems. Additional features include CAT-5/6 wiring, Sonos-integrated speakers, lighting automation via the Lutron RA-3 smart system, and pre-wired home security with digital camera ports at key access points. Thoughtfully placed access points from the primary suite and kitchen wing lead to a fully enclosed backyard retreat, where mature landscape design by Signature Landscape frames a private outdoor living sanctuary. A Roman-inspired cabana with grand ceilings and exposed beams anchors the outdoor entertaining space, flanked by a fully tiled ($50,000 upgrade) saltwater pool featuring therapy jets, LED-lit bubblers, a dual-skimmer system, automated controls via a Jandy heat pump, and a Paramount self-cleaning system. Clay brick pavers and landscape lighting define the walkways as well as front entry driveway. This home was constructed with stem wall foundation, concrete block first-floor exterior walls, and 2-by-6 second-floor framing for structural performance along with spray foam and sound mat insulation between floors ensure comfort and acoustic separation. Finished in a palette of clay brick and hand-troweled stucco, the home is crowned with architectural tile shingles and custom metal accents. Eight-inch half-round gutters, aluminum downspouts and engineered drainage ensure long-term performance.

4 Beds ⋅ 6 Baths ⋅ Palmer Ave Lakeside Prop SubDv. ⋅ 32789 Zip Code

Welcome to 702 Via Bella, an impressive 2025 English cottage estate by Floridian Custom Homes that captures the essence of timeless architecture exemplifying elegance and artisan craftsmanship. In one of Winter Park’s desirable residential corridors, warmth and beauty abound in this four-bedroom, six-bath residence spanning 3,720 square feet or air conditioned and 4,535 square feet total under roof, offering layered living, artisanal materials, and a modern infrastructure. Upon entry through a solid mahogany front door, warmth and beauty abounds with Botticino limestone flooring enhanced by a textured finish, extensive custom millwork, and an abundance of open concept living areas. Coffered ceilings and recessed WAC lighting create a gallery-like ambiance, enhanced by natural light from insulated casement windows. The central living space integrates with the dining area and designer kitchen, which features custom cabinetry by Grit & Grain, leathered Taj Mahal quartzite surfaces, and chef-grade appliances: a La Cornue 43-inch gas range with McGurken hood, Thermador 30-inch refrigerator and freezer columns, and Bosch dishwasher. The kitchen transitions into a walk-in pantry with cabinetry, quartzite, dual refrigeration drawers, and a dedicated ice maker. An oversized mudroom, finished with hardwood built-ins, offers expanded storage and functionality. The first-floor primary suite is privately positioned in its own wing and finished with wide-plank European white oak flooring by Forrest Accents, a walk-in closet with textured built-in systems, and a spa bath with natural stone countertops, Rohl polished nickel fixtures, a marble-tiled floor and shower, and a frameless glass enclosure. All doors are solid core with Emtek hardware. The library, near the front of the home, offers a quiet retreat with matching oak floors and custom casements. A solid wood staircase leads to the second level living areas including a lounge flex space. There are three additional bedroom suites, each with en-suite baths, which offer porcelain flooring, frameless glass shower doors, brushed quartz and dolomite vanities, decorative lighting, and built-in closet systems. Additional features include CAT-5/6 wiring, Sonos-integrated speakers, lighting automation via the Lutron RA-3 smart system, and pre-wired home security with digital camera ports at key access points. Thoughtfully placed access points from the primary suite and kitchen wing lead to a fully enclosed backyard retreat, where mature landscape design by Signature Landscape frames a private outdoor living sanctuary. A Roman-inspired cabana with grand ceilings and exposed beams anchors the outdoor entertaining space, flanked by a fully tiled ($50,000 upgrade) saltwater pool featuring therapy jets, LED-lit bubblers, a dual-skimmer system, automated controls via a Jandy heat pump, and a Paramount self-cleaning system. Clay brick pavers and landscape lighting define the walkways as well as front entry driveway. This home was constructed with stem wall foundation, concrete block first-floor exterior walls, and 2-by-6 second-floor framing for structural performance along with spray foam and sound mat insulation between floors ensure comfort and acoustic separation. Finished in a palette of clay brick and hand-troweled stucco, the home is crowned with architectural tile shingles and custom metal accents. Eight-inch half-round gutters, aluminum downspouts and engineered drainage ensure long-term performance.

702 Via Bella, Winter Park

$4,000,000

Envisioned by acclaimed architect Phil Kean and originally commissioned as the International Showcase Home for the National Association of Home Builders, this award-winning contemporary estate is a masterclass in modern design. Tucked away on a prestigious cul-de-sac between Lake Osceola and the iconic Alfond Inn, the residence offers unparalleled privacy just two blocks from Park Avenue's world-class amenities. A striking entryway with 10-foot mahogany doors reveals a secluded courtyard oasis, featuring a sparkling pool framed by lush Signature landscaping. Inside, expansive living spaces with soaring 14-foot ceilings and a dramatic 40-foot gallery wall flow seamlessly to the outdoors, creating an effortless connection between interior elegance and open-air entertaining. The sleek, state-of-the-art kitchen is curated with premium Monogram, JennAir, and Gaggenau appliances, complemented by a sophisticated wet bar and an intimate media lounge. Ascend the floating staircase or private elevator to the primary sanctuary, which exclusively commands the entire second level. This lavish retreat features a spa-inspired bath with a smart-controlled shower, an oversized marble vanity, and three private terraces. The estate is further elevated by a first-floor guest suite, an executive office, a fitness studio with an en-suite steam shower, and a versatile poolside casita. Integrated smart home technology, automatic Lutron shades, whole-house generator and a three car garage provide ultimate modern convenience. Every element of this residence reflects intentional design, innovation, and timeless elegance, embodying the pinnacle of world-class Winter Park living.

4 Beds ⋅ 6 Baths ⋅ Alexander Place SubDv. ⋅ 32789 Zip Code

Envisioned by acclaimed architect Phil Kean and originally commissioned as the International Showcase Home for the National Association of Home Builders, this award-winning contemporary estate is a masterclass in modern design. Tucked away on a prestigious cul-de-sac between Lake Osceola and the iconic Alfond Inn, the residence offers unparalleled privacy just two blocks from Park Avenue's world-class amenities. A striking entryway with 10-foot mahogany doors reveals a secluded courtyard oasis, featuring a sparkling pool framed by lush Signature landscaping. Inside, expansive living spaces with soaring 14-foot ceilings and a dramatic 40-foot gallery wall flow seamlessly to the outdoors, creating an effortless connection between interior elegance and open-air entertaining. The sleek, state-of-the-art kitchen is curated with premium Monogram, JennAir, and Gaggenau appliances, complemented by a sophisticated wet bar and an intimate media lounge. Ascend the floating staircase or private elevator to the primary sanctuary, which exclusively commands the entire second level. This lavish retreat features a spa-inspired bath with a smart-controlled shower, an oversized marble vanity, and three private terraces. The estate is further elevated by a first-floor guest suite, an executive office, a fitness studio with an en-suite steam shower, and a versatile poolside casita. Integrated smart home technology, automatic Lutron shades, whole-house generator and a three car garage provide ultimate modern convenience. Every element of this residence reflects intentional design, innovation, and timeless elegance, embodying the pinnacle of world-class Winter Park living.

229 Alexander Place, Winter Park

$4,000,000

A pristine location in the Vias of Winter Park, this refined Santa Barbara-inspired Mediterranean estate rests on nearly half an acre — a rare double lot. A 2006 custom build by Maroon Fine Homes and renovated in 2024 by Greg Hardwick, this estate blends timeless architecture with comfortable sophistication and functionality. A stone’s throw to the celebrated shops and dining of Park Avenue, Rollins College, Winter Park Golf Course, and the serene beauty of Kraft Azalea Gardens, the location is simply unrivaled. This extraordinary residence spans nearly 5,000 sf with a flowing floor plan designed for entertaining and everyday living. Solid wood artisan arched doors anchor the inviting foyer with porcelain marble tile, volume ceilings, and a sleek iron circular staircase as a focal point. An open dining and intimate living room layout are flanked by windows and clear view doors, which bring in natural light. The spaces share a unique temperature-controlled wine cellar finished with seamless glass and ambient lighting, adding a dramatic touch for the discerning enthusiast. The main level centers around a spacious kitchen that enjoys a dedicated eat-in space and counter seating, with a family room that overlooks the expansive backyard. A dedicated wet bar and first-floor bonus room make this home ideal for hosting at any scale. The outdoor living rivals a 5-star resort, recently reimagined in 2026 by Signature Landscaping. An immense new pool with a sun shelf anchors the outdoor living experience, surrounded by a lush turf courtyard, sport court, and a covered lanai with generous pavered decking and a summer kitchen. A cozy gas fire pit with casual seating invites you to take in the evening breezes. Privacy abounds with mature Japanese blueberry trees and Podocarpus hedges. A dedicated side yard dog run completes this outdoor haven. The main floor is home to the first-floor primary suite, with privacy doors separating this section of the home. It is a true retreat unto itself, offering a sunlit sitting area with doors leading to the backyard, a beautifully appointed bath, a dedicated home office, and two custom-fitted walk-in closets, one of which includes a secondary laundry area. The spa-inspired bathroom has it all, featuring a generous shower with a soaking tub within the enclosure for the ultimate relaxation experience. A first-floor guest suite, thoughtfully designed with a split-plan layout, provides privacy for visitors, while three additional ensuite bedrooms and a bonus landing are located upstairs. The oversized three-car side-loading garage is air-conditioned and features upgraded flooring, while a generous circular drive and mature front hedge offer a gracious arrival experience and an added layer of privacy. A rare convergence of premier location, architectural distinction, and meticulous renovation — this is Winter Park luxury living at its finest.

5 Beds ⋅ 6 Baths ⋅ Woodmere Terrace Rep SubDv. ⋅ 32789 Zip Code

A pristine location in the Vias of Winter Park, this refined Santa Barbara-inspired Mediterranean estate rests on nearly half an acre — a rare double lot. A 2006 custom build by Maroon Fine Homes and renovated in 2024 by Greg Hardwick, this estate blends timeless architecture with comfortable sophistication and functionality. A stone’s throw to the celebrated shops and dining of Park Avenue, Rollins College, Winter Park Golf Course, and the serene beauty of Kraft Azalea Gardens, the location is simply unrivaled. This extraordinary residence spans nearly 5,000 sf with a flowing floor plan designed for entertaining and everyday living. Solid wood artisan arched doors anchor the inviting foyer with porcelain marble tile, volume ceilings, and a sleek iron circular staircase as a focal point. An open dining and intimate living room layout are flanked by windows and clear view doors, which bring in natural light. The spaces share a unique temperature-controlled wine cellar finished with seamless glass and ambient lighting, adding a dramatic touch for the discerning enthusiast. The main level centers around a spacious kitchen that enjoys a dedicated eat-in space and counter seating, with a family room that overlooks the expansive backyard. A dedicated wet bar and first-floor bonus room make this home ideal for hosting at any scale. The outdoor living rivals a 5-star resort, recently reimagined in 2026 by Signature Landscaping. An immense new pool with a sun shelf anchors the outdoor living experience, surrounded by a lush turf courtyard, sport court, and a covered lanai with generous pavered decking and a summer kitchen. A cozy gas fire pit with casual seating invites you to take in the evening breezes. Privacy abounds with mature Japanese blueberry trees and Podocarpus hedges. A dedicated side yard dog run completes this outdoor haven. The main floor is home to the first-floor primary suite, with privacy doors separating this section of the home. It is a true retreat unto itself, offering a sunlit sitting area with doors leading to the backyard, a beautifully appointed bath, a dedicated home office, and two custom-fitted walk-in closets, one of which includes a secondary laundry area. The spa-inspired bathroom has it all, featuring a generous shower with a soaking tub within the enclosure for the ultimate relaxation experience. A first-floor guest suite, thoughtfully designed with a split-plan layout, provides privacy for visitors, while three additional ensuite bedrooms and a bonus landing are located upstairs. The oversized three-car side-loading garage is air-conditioned and features upgraded flooring, while a generous circular drive and mature front hedge offer a gracious arrival experience and an added layer of privacy. A rare convergence of premier location, architectural distinction, and meticulous renovation — this is Winter Park luxury living at its finest.

1180 Via Lugano, Winter Park

$3,978,550

PRESTIGIOUS VIA TUSCANY NEW CONSTRUCTION. If location was a lottery ticket, you just hit the jackpot!!! Welcome to a masterpiece of modern elegance in the heart of the Winter Park Vias. Crafted by the renowned Element Home Builders, this stunning 4,665 sq. ft. estate offers an unparalleled blend of sophistication and comfort. The expansive open-concept floor plan features 5 generous bedrooms, 4.5 luxurious baths, and a dedicated executive office. At the heart of the home, a gourmet chef's kitchen flows seamlessly into a light-filled great room, perfect for grand-scale entertaining. Step outside to your private sanctuary: a brand-new custom pool and a sprawling covered lanai featuring a cozy outdoor fireplace. Situated on a premier corner lot with a brick-lined street, you are just steps away from the Winter Park Racquet Club and minutes from the world-class dining and shopping of Park Avenue. Experience the pinnacle of Winter Park living in a home designed for the most discerning buyer.

4 Beds ⋅ 5 Baths ⋅ Tuscania SubDv. ⋅ 32789 Zip Code

PRESTIGIOUS VIA TUSCANY NEW CONSTRUCTION. If location was a lottery ticket, you just hit the jackpot!!! Welcome to a masterpiece of modern elegance in the heart of the Winter Park Vias. Crafted by the renowned Element Home Builders, this stunning 4,665 sq. ft. estate offers an unparalleled blend of sophistication and comfort. The expansive open-concept floor plan features 5 generous bedrooms, 4.5 luxurious baths, and a dedicated executive office. At the heart of the home, a gourmet chef's kitchen flows seamlessly into a light-filled great room, perfect for grand-scale entertaining. Step outside to your private sanctuary: a brand-new custom pool and a sprawling covered lanai featuring a cozy outdoor fireplace. Situated on a premier corner lot with a brick-lined street, you are just steps away from the Winter Park Racquet Club and minutes from the world-class dining and shopping of Park Avenue. Experience the pinnacle of Winter Park living in a home designed for the most discerning buyer.

2020 Via Tuscany, Winter Park

$3,965,000

Conveniently situated near the Winter Park Country Club, this contemporary masterpiece, built by premier builder Z Properties, offers the ideal mix of style, comfort, and modern living. Meticulously maintained with great inspection. Completed in 2021, the residence has 4,181 square feet of thoughtfully designed living space, including four bedrooms each with a private ensuite bath and an additional powder room. A 412-square-foot casita with a wet bar and private entrance completes its functionality by providing extra flexibility, perfect for guests, extended family, workspace or workout area. The interiors showcase timeless design with high ceilings, glass walls, and carefully curated finishes. The chef’s kitchen and butler’s pantry pair handcrafted cabinetry and stone surfaces with professional-grade appliances, flowing seamlessly into open living and dining spaces designed for both everyday living and entertaining. Outdoors, a 65-foot lap pool anchors the private backyard retreat, complemented by a covered lanai, marine-grade summer kitchen, fireplace lounge, tree garden and lush landscaping. Solid block construction, advanced state-of-the-art home systems, and a climate-controlled two-car garage with an extended hidden driveway highlight the home’s privacy, quality, and convenience. With a distinct European vibe under canopy trees and cobblestone streets in the desirable Valencia Terrace neighborhood, this home is just moments from Park Avenue’s boutiques, fine dining, Rollins College, the Farmers’ Market, and the Morse Museum. Zoned for top-rated Winter Park schools, it offers both luxury and practicality in one of Central Florida’s most sought-after communities.

4 Beds ⋅ 5 Baths ⋅ Valencia Terrace SubDv. ⋅ 32789 Zip Code

Conveniently situated near the Winter Park Country Club, this contemporary masterpiece, built by premier builder Z Properties, offers the ideal mix of style, comfort, and modern living. Meticulously maintained with great inspection. Completed in 2021, the residence has 4,181 square feet of thoughtfully designed living space, including four bedrooms each with a private ensuite bath and an additional powder room. A 412-square-foot casita with a wet bar and private entrance completes its functionality by providing extra flexibility, perfect for guests, extended family, workspace or workout area. The interiors showcase timeless design with high ceilings, glass walls, and carefully curated finishes. The chef’s kitchen and butler’s pantry pair handcrafted cabinetry and stone surfaces with professional-grade appliances, flowing seamlessly into open living and dining spaces designed for both everyday living and entertaining. Outdoors, a 65-foot lap pool anchors the private backyard retreat, complemented by a covered lanai, marine-grade summer kitchen, fireplace lounge, tree garden and lush landscaping. Solid block construction, advanced state-of-the-art home systems, and a climate-controlled two-car garage with an extended hidden driveway highlight the home’s privacy, quality, and convenience. With a distinct European vibe under canopy trees and cobblestone streets in the desirable Valencia Terrace neighborhood, this home is just moments from Park Avenue’s boutiques, fine dining, Rollins College, the Farmers’ Market, and the Morse Museum. Zoned for top-rated Winter Park schools, it offers both luxury and practicality in one of Central Florida’s most sought-after communities.

1161 Valencia Avenue, Winter Park

$3,925,000

Designed to evoke the timeless architecture of Olde Winter Park, this exceptional modern Tudor home features character, craftsmanship, and presence rarely found in today's market. Perfectly positioned on an expansive 0.37-acre homesite in the highly coveted Park Grove neighborhood, the residence offers the rare privilege of walking to Park Avenue while still having immense privacy. A soaring 20-foot foyer creates an unforgettable first impression and immediately establishes the home's sense of grandeur. Beyond the entry, the expansive great room is defined by dramatic exposed wood beams, a sleek electric fireplace, and a custom-built entertainment wall accented with subtle LED underlighting. At the heart of the home, the chef's kitchen is equal parts statement and workspace. Custom cabinetry is paired with a full Thermador appliance suite, including a paneled built-in refrigerator, while striking Taj Mahal quartzite countertops complete the space. Just beyond, an oversized butler's pantry dramatically expands the kitchen's functionality. Outfitted with extensive cabinetry, generous prep space, a secondary refrigerator, sink, and dishwasher, it is designed to support everything from intimate dinners to large-scale entertaining. The adjacent dining room is equally refined, featuring a custom dry bar complete with a built-in wine refrigerator. One of the home's most exceptional attributes is its floor plan. Offering two luxurious primary suites, a rarity in Winter Park, the residence provides remarkable flexibility for multigenerational living or extended guests. Both suites feature custom Idelli closet systems and spa-inspired baths appointed with marble mosaic tile, expansive walk-in showers, freestanding soaking tubs, and dual vanities. Every additional bedroom is designed as a private ensuite with its own walk-in closet. Two guest suites are conveniently located on the main level, while upstairs you'll find a spacious game room, a dedicated study nook for kids, and a second laundry room to complement the main-level laundry. The outdoor living experience is equally impressive. An expansive backyard, rarely found in Winter Park, creates a private setting for everyday living and entertaining alike. A covered lanai with a fully equipped summer kitchen overlooks the resort-style pool and spa, while upgraded landscaping and generous green space complete the grounds. An oversized motor court and a three-car garage with soaring 12-foot ceilings provide an uncommon level of parking and storage for the car enthusiast. Positioned just moments from Park Avenue, Winter Park Village, and Hannibal Square, this is far more than another luxury home. It is a thoughtfully crafted masterpiece that captures the timeless character of Olde Winter Park while delivering the scale, amenities, and craftsmanship expected of a modern home. Opportunities to own a property of this caliber, in a location this desirable, are exceptionally rare. Don't miss out!

5 Beds ⋅ 6 Baths ⋅ Park Grove SubDv. ⋅ 32789 Zip Code

Designed to evoke the timeless architecture of Olde Winter Park, this exceptional modern Tudor home features character, craftsmanship, and presence rarely found in today's market. Perfectly positioned on an expansive 0.37-acre homesite in the highly coveted Park Grove neighborhood, the residence offers the rare privilege of walking to Park Avenue while still having immense privacy. A soaring 20-foot foyer creates an unforgettable first impression and immediately establishes the home's sense of grandeur. Beyond the entry, the expansive great room is defined by dramatic exposed wood beams, a sleek electric fireplace, and a custom-built entertainment wall accented with subtle LED underlighting. At the heart of the home, the chef's kitchen is equal parts statement and workspace. Custom cabinetry is paired with a full Thermador appliance suite, including a paneled built-in refrigerator, while striking Taj Mahal quartzite countertops complete the space. Just beyond, an oversized butler's pantry dramatically expands the kitchen's functionality. Outfitted with extensive cabinetry, generous prep space, a secondary refrigerator, sink, and dishwasher, it is designed to support everything from intimate dinners to large-scale entertaining. The adjacent dining room is equally refined, featuring a custom dry bar complete with a built-in wine refrigerator. One of the home's most exceptional attributes is its floor plan. Offering two luxurious primary suites, a rarity in Winter Park, the residence provides remarkable flexibility for multigenerational living or extended guests. Both suites feature custom Idelli closet systems and spa-inspired baths appointed with marble mosaic tile, expansive walk-in showers, freestanding soaking tubs, and dual vanities. Every additional bedroom is designed as a private ensuite with its own walk-in closet. Two guest suites are conveniently located on the main level, while upstairs you'll find a spacious game room, a dedicated study nook for kids, and a second laundry room to complement the main-level laundry. The outdoor living experience is equally impressive. An expansive backyard, rarely found in Winter Park, creates a private setting for everyday living and entertaining alike. A covered lanai with a fully equipped summer kitchen overlooks the resort-style pool and spa, while upgraded landscaping and generous green space complete the grounds. An oversized motor court and a three-car garage with soaring 12-foot ceilings provide an uncommon level of parking and storage for the car enthusiast. Positioned just moments from Park Avenue, Winter Park Village, and Hannibal Square, this is far more than another luxury home. It is a thoughtfully crafted masterpiece that captures the timeless character of Olde Winter Park while delivering the scale, amenities, and craftsmanship expected of a modern home. Opportunities to own a property of this caliber, in a location this desirable, are exceptionally rare. Don't miss out!

1417 Williams Drive, Winter Park