Casselberrry/Winter Springs / Tuscawilla Homes with Trees/Woods View

Casselberrry/Winter Springs / Tuscawilla Homes with Trees/Woods View

Welcome to the enchanting region of Casselberry, Winter Springs, and Tuscawilla, nestled in the heart of Seminole County, Florida. This vibrant area is renowned for its lush landscapes, friendly communities, and an abundance of recreational opportunities, making it an ideal place to call home.

Winter Springs, a charming city, is known for its picturesque neighborhoods and family-friendly atmosphere. With its well-maintained parks, scenic walking trails, and a strong sense of community, residents enjoy a suburban lifestyle while being just a short drive from the bustling city of Orlando. The area boasts a rich tapestry of outdoor activities, from serene strolls through nature preserves to engaging community events that bring neighbors together.

Tuscawilla, a hidden gem within Winter Springs, is particularly famous for its stunning homes that overlook tranquil woods and trees. Imagine waking up to the soothing sounds of nature, with views that change with the seasons. Many properties in this area feature spacious backyards and private decks, perfect for sipping morning coffee while surrounded by the beauty of Florida’s natural landscape.

For those who appreciate the serenity of wooded views, the homes in this region offer a unique blend of comfort and tranquility. With a variety of architectural styles, from modern designs to classic Floridian charm, there’s something for everyone. Whether you’re looking for a cozy family home or a luxurious retreat, the Casselberry/Winter Springs/Tuscawilla area has it all.

Explore this delightful region today, and discover why so many choose to make it their forever home!

Newest Casselberrry/Winter Springs / Tuscawilla Homes with Trees/Woods View

2 Beds ⋅ 3 Baths ⋅ Greens At Tuscawilla SubDv. ⋅ 32708 Zip Code

Welcome to the exclusive gated enclave know as The Greens of Tuscawilla. This luxury townhome delivers a rare combination of superior construction, premium finishes, prime location, and a maintenance-free lifestyle. Nestled amongst the trees in the heart of Tuscawilla is The Portofino II Model with Golf, Water and Conservation Views. Level One offers Open Concept Living with the ability for a future Elevator. (Elevator closets are located on both floors and are currently used as walk in storage closets). Level Two allows for privacy with all bedrooms located on this floor. Throughout the unit you will find soaring volume ceilings, crown molding, tall doors, recessed lighting, wood or tiled floors, fresh paint, granite countertops, 42 inch cabinets, designer lighting, fans, fire safety sprinkler system and much more. Start and end each day on your private screened porch where the views are unparralleled. The Greens consists of 15 buildings and 60 units. Residents enjoy lush landscaping, manicured lawns and a private dog park. Partake in the Country Club lifestyle with the private Golf Cart path that leads to Tuscawilla Country Club. Membership provides access to championship golf, Har-Tru clay tennis courts, pickleball court, Jr. Olympic-sized pool, fitness center, private restaurant/bar, and social calendar. The Tuscawilla Community has parks, sports courts and fields, playgrounds, hiking trails and splash pads. Walk, run, or ride while taking in the many natural areas throughout the 3500 acre community.

1541 Corkery Court Unit 1541, Winter Springs

4 Beds ⋅ 3 Baths ⋅ Chestnut Estates Ph 2 SubDv. ⋅ 32708 Zip Code

Elegant conservation retreat in prestigious Chestnut Estates-Tuscawilla. On a quiet cul-de-sac, this impeccably maintained four-bedroom, three-bath residence offers a rare combination of privacy, timeless comfort and everyday luxury. Backing to a serene conservation area with no rear neighbors, the home is surrounded by mature landscaping and picturesque natural views, creating a peaceful retreat, and rear patio has new pavers. Thoughtfully designed with a desirable split-bedroom floor plan, the spacious interior offers functionality and elegance. Generous closet space, large pantry and built-in workspace provide everyday convenience, while the open concept kitchen flows seamlessly into the family room and casual dining area, creating a warm and welcoming atmosphere that's ideal for gathering with family and friends. An oversized bonus room/enclosed Florida room with rich wood flooring expands the living space and offers endless possibilities, including a game room, music room and fitness studio. Enhanced with a mini-split system installed in 2025, this versatile space provides year-round comfort and is the ideal setting for entertaining or enjoying quiet evenings while overlooking the tranquil conservation backdrop. Roof (2023) with secondary barrier, HVAC (2025), plumbing updates and newer water heater. Schedule your private showing today!

223 Blue Creek Drive, Winter Springs

4 Beds ⋅ 3 Baths ⋅ North Orlando Ranches Sec 01 SubDv. ⋅ 32708 Zip Code

Motivated Seller! This custom 4 bedroom, 2.5 bathroom pool home nestled on a gated 2.6 acres in the sought-after Ranchlands Community is a must see! The 40ft long front porch overlooks the nature's paradise with views you must see to appreciate. Oak trees and mature landscaping line the private entrance and make up the bulk of this serene property. An entertainer's paradise features pool with custom waterfall, poolside cabana with fireplace, bar and grill, pergola leading to cabana, romantic gazebo with power, nature trails, tri-level balcony, covered back porch (29x12) overlooking pool and 2 story playhouse/gym. You'll notice the craftmanship and attention to detail throughout the property with custom carpentry and designer touches both inside and out. Kitchen (19x12) with lots of granite counter space boasts solid wood cabinets, modern hardware, stainless steel appliances with range hood, flat top range, stone backsplash, rolling island, and pendant lighting over bar seating while overlooking the beautiful pool oasis. The owner's suite (14x13) offers laminate flooring, walk-in closet, pool views, French doors leading to private balcony and a private study (14x10) perfect for relaxing with a good book. Master bathroom features gorgeous standup shower, waterproof vinyl flooring and lovely tile work. Home features massive family room (39x32) with tile flooring and separate living room (20x13) with wood-exposed cathedral ceilings and gas fireplace. Upstairs you'll find two bedrooms with a shared bathroom in addition to the master bedroom retreat. Laundry room, half bath and fourth bedroom are located on first floor. Upgrades include extending trusses and roof line to add carport, gutters, entire paver driveway, automatic wrought iron gate, sprinklers in front yard, gazebo with power, and a wrought iron fence. Two single car detached garages (20x10) plus additional workshop (20x10) with power, water and exhaust fan, two covered sheds and additional storage space (10x10) located below playhouse/gym provide ample storage to go along with oversized attached carport (33x14). No HOA.

230 E Panama Road, Winter Springs

3 Beds ⋅ 2 Baths ⋅ Country Club Village Unit 3 SubDv. ⋅ 32708 Zip Code

Renovated, remodeled, and reimagined in the highly sought-after Country Club Village at Tuskawilla. This beautifully renovated residence has been thoughtfully transformed with an extraordinary level of quality and attention to detail, delivering a truly turnkey opportunity for today’s discerning buyer - NO EXPENSE SPARED! Extensive recent improvements include a NEW TILE ROOF (July 2025), new gutters, all-new plumbing throughout (2026), fresh interior and exterior paint, and newly textured ceilings throughout, creating a clean, modern aesthetic from top to bottom. Inside, elegance meets functionality with stunning European white oak wood flooring throughout the main living areas, complemented by new carpet in the secondary bedrooms for added comfort. The heart of the home is the beautifully reimagined kitchen, featuring new 42-inch cabinetry, quartz countertops, all-new appliances, and a designer backsplash that adds both sophistication and visual appeal. Entertain effortlessly with a stylish wet bar complete with a beverage refrigerator and matching designer backsplash. Every bathroom has been completely remodeled, showcasing luxurious finishes and quartz surfaces throughout. Additional upgrades include new lighting fixtures inside and out, new door handles and hinges, new plugs and switches, custom roller shades throughout, and a custom closet system in the primary suite. Outside, refreshed landscaping enhances curb appeal and completes this impressive renovation, making this home a rare blend of timeless design, modern luxury, and move-in-ready convenience. The HOA-maintained lawn allows for low-maintenance living, while the location places you just moments from the private Tuscawilla Country Club. Zoned for some of the highest-rated public schools in the state and offers exceptional convenience—just 25 minutes from downtown Orlando, 30 minutes to Orlando International Airport, and less than an hour from Florida’s beautiful beaches and world-renowned theme parks. This property may be under audio/visual surveillance.

1329 Augusta National Boulevard, Winter Springs

7 Beds ⋅ 7 Baths ⋅ Dunmar Estates SubDv. ⋅ 32708 Zip Code

Rare opportunity to own a private estate in the heart of Central Florida. Situated on nearly 6 acres in Dunmar Estates community of Winter Springs, this exceptional property is fully fenced BY METAL FENCE AND SOLID WALL FENCE FROM 6ft to 10 ft and gated, offering outstanding privacy, security, and a true retreat-like setting. The main residence features over 12,000 square feet of living space, including 7 bedrooms, multiple living and entertaining areas, and a unique indoor heated pool that can be enjoyed year-round regardless of weather. Expansive grounds and mature landscaping create a peaceful and secluded environment rarely found in today’s market. A standout feature of the property is its two separate Mother-in-Law Suites, ideal for multigenerational living, extended family, long-term guests, caregivers, private offices, or flexible living arrangements. Additional amenities include a tennis court, circular driveway, 6-car garage, and abundant outdoor space, offering endless opportunities for customization, renovation, and creating a truly one-of-a-kind family compound. Conveniently located just minutes from top-rated schools, shopping, dining, and major highways, this estate combines the tranquility of private country-style living with the convenience of city access. A rare offering with exceptional space, privacy, and unlimited potential.

593 Dunmar Circle, Winter Springs

5 Beds ⋅ 4 Baths ⋅ Seville Chase SubDv. ⋅ 32708 Zip Code

Welcome to Seville Chase, one of Winter Springs' premier gated communities. Situated on a private .41-acre lot, this custom-designed 5-bedroom, 4-bath home offers over 3,000 square feet of thoughtfully designed living space with a functional split floor plan that's perfect for both everyday living and entertaining. From the moment you walk through the double front doors, you'll appreciate the natural light, soaring ceilings, crown molding, and timeless architectural details throughout. The spacious family room flows seamlessly into the kitchen, featuring a large island, abundant cabinet space, breakfast nook, and peaceful backyard views. Step outside to the oversized covered lanai with a gas hookup for a future outdoor kitchen, overlooking a spacious backyard with plenty of room to build your dream pool. The private primary suite offers dual walk-in closets, a spacious bathroom, and direct access to a flexible office or nursery. Three additional bedrooms are located on the main level, while upstairs you'll find a private guest suite with its own full bath plus a large climate-controlled bonus room—perfect for a home gym, media room, playroom, or extra storage. This home has been meticulously maintained with numerous updates, including fresh exterior paint, updated lighting, painted garage floors, professionally cleaned HVAC ducts and carpets, plus an oversized driveway with plenty of parking. Conveniently located near top-rated Seminole County schools, shopping, dining, golf, Winter Springs Town Center, UCF, Research Park, Siemens, and major highways including 417, 434, and I-4. If you're looking for space, privacy, and a home you can truly make your own, this is one you won't want to miss. Schedule your private showing today.

126 Seville Chase Drive, Winter Springs

5 Beds ⋅ 5 Baths ⋅ Reserve At Tuscawilla Ph 1 The SubDv. ⋅ 32708 Zip Code

Privately set within the exclusive gated community of Tuscawilla Reserve, this stunning custom estate delivers over 4,000 square feet of light-filled, designer-inspired living centered around a spectacular kitchen and family room that truly defines the home. With 5 bedrooms, 5 full baths, plus a private office/bonus room, this residence offers exceptional versatility for today’s lifestyle. Sleek wood flooring flows seamlessly throughout the main living areas, complementing the home’s open, modern design. The impressive kitchen and family room feature soaring two-story ceilings and expansive windows, framing views of the outdoors and pool area while filling the space with natural light—creating an inviting setting for both everyday living and elevated entertaining.The chef’s kitchen is a true centerpiece, anchored by JennAir appliances, including double ovens, convection oven, and microwave combo, along with a massive granite-topped island—all coming together to create a stunning focal point that anchors the kitchen and family room. Custom details further enhance the design, including a built-in buffet with integrated wine refrigerator and an oversized walk-in pantry. The thoughtfully designed floor plan offers incredible flexibility, including an upstairs retreat featuring an additional bedroom, full bath, and expansive flex space that can easily function as a media room, playroom, or second private office.Step outside to your private backyard oasis featuring a sparkling pool and spa with a new heater, surrounded by mature landscaping and a fully fenced yard, offering both openness and privacy. Additional highlights include a 3-car side-entry garage, whole house water softener and expansive living areas that support a variety of lifestyle needs. Ideally located near the Seminole Trail and just minutes from Tuscawilla Country Club, residents enjoy golf, tennis, swimming, and vibrant social amenities. Zoned for highly regarded Seminole County schools, this home offers both lifestyle and long-term value. Golf carts are a popular mode of transportation within the community, adding to the charm and convenience. A seamless blend of modern design, natural light, and elevated living—this is Tuscawilla Reserve at its finest. Schedule your private showing today and experience this exceptional home in person.

149 Cherry Creek Circle, Winter Springs

4 Beds ⋅ 3 Baths ⋅ Winding Hollow Unit 2 SubDv. ⋅ 32708 Zip Code

Pride of ownership is evident throughout this beautifully updated, MOVE-IN PERFECT, one-owner home located in the highly sought-after WINDING HOLLOW community of Winter Springs. This ideal two-story floor plan offers 4 BEDROOMS, 3 FULL BATHS, BONUS ROOM, 3-CAR GARAGE, and a LARGE SCREENED LANAI, showcasing timeless style, thoughtful updates, and versatility with TILE FLOORING throughout the first floor and LAMINATE WOOD FLOORING upstairs. The bright, OPEN-CONCEPT floor plan offers exceptional flow and is perfect for entertaining, featuring spacious formal living and dining rooms with soaring ceilings that create an inviting sense of space. The heart of the home is the beautifully designed ISLAND KITCHEN, perfectly positioned between the breakfast nook and impressive family room with 18-FOOT CEILINGS and dramatic upper windows that flood the home with natural light. The kitchen features GRANITE COUNTERTOPS, ABUNDANT WOOD CABINETRY with PULL-OUT DRAWERS, STAINLESS STEEL APPLIANCES, PANTRY, and convenient access to the garage and laundry room with additional storage. The spacious FIRST-FLOOR PRIMARY SUITE offers a sitting area, TWO WALK-IN CLOSETS, and an updated spa-inspired bath featuring a SOAKING TUB, GLASS SHOWER, and DUAL QUARTZ VANITIES, creating the perfect private retreat. A SPLIT FIRST-FLOOR GUEST SUITE with a full bath provides ideal accommodations for visitors or MULTI-GENERATIONAL LIVING. Upstairs you’ll find BEDROOMS 3 & 4, a full hallway bath, and a versatile BONUS ROOM/FLEX SPACE with a walk-in closet overlooking the family room below. Easily used as a 5TH BEDROOM, MEDIA ROOM, PLAYROOM, HOME OFFICE, or HOME GYM, this flexible space adapts to your family’s needs. Enjoy Florida living year-round from the expansive TILED SCREENED LANAI, accessible from the formal living room, family room, and primary suite while overlooking the PRIVATE, LUSHLY TREED BACKYARD. Additional highlights include PLANTATION SHUTTERS THROUGHOUT, a spacious 3-CAR GARAGE with overhead storage, an EXPANDED BRICK-PAVER DRIVEWAY, 2018 ROOF, TWO ZONED A/C SYSTEMS (2022 & 2019), 2019 WATER HEATER, and COMPLETE PLUMBING REPIPE (2025). Ideally located WITHIN WALKING DISTANCE TO THE CROSS SEMINOLE TRAIL & CENTRAL WINDS PARK, and just minutes from TOP-RATED WINTER SPRINGS SCHOOLS, shopping, dining, SR 417, and US 17-92, this exceptional home truly offers the perfect combination of LOCATION, LIFESTYLE, AND VALUE. WELCOME HOME!

525 Saddlewood Lane, Winter Springs

3 Beds ⋅ 2 Baths ⋅ Amherst SubDv. ⋅ 32708 Zip Code

Beautiful pool home located in the highly desirable Amherst community of Winter Springs! Situated on an oversized .34-acre lot, this well-maintained 3-bedroom, 2-bath home offers a spacious split-bedroom floor plan with vaulted ceilings, abundant natural light, and a cozy wood-burning fireplace in the oversized family room. Updated bathrooms and ceramic wood looking flooring in main living areas. The screened with an large pool and covered lanai create the perfect setting for year-round outdoor living and entertaining, and no rear neighbors for privacy. Property has fiber optics, 50 amp car charger in garage, and nest thermostat for A/C. The primary suite features a walk-in closet and spacious bath with dual sinks newly remodeled. Additional highlights include a 2-car garage, irrigation system, rain gutters, public utilities, and low annual HOA dues. New Roof (2025), New Water Heater & A/C (2024). Conveniently located near top-rated Seminole County schools, parks, shopping, dining, major roadways, and the 417.

1055 Chesterfield Circle, Winter Springs

4 Beds ⋅ 3 Baths ⋅ Tuscawilla Unit 14b SubDv. ⋅ 32708 Zip Code

Rare opportunity to own a spacious pool home on a private 2.1-acre conservation homesite in the highly desirable Chelsea Woods section of Tuscawilla. Offering 4 bedrooms, 3 bathrooms and over 3,100 square feet of living space, this home features a dedicated office with custom built-ins, formal living and dining areas, a wood-burning fireplace, and a large upstairs loft that provides flexible space for a media room, game room, home gym, or additional living area. The kitchen overlooks the main living spaces and pool area, while French doors open to an expansive covered lanai and screened pool enclosure designed for year-round Florida living. Step outside and enjoy your own backyard retreat featuring a large pool and spa with waterfall features, outdoor grilling area, generous deck space, mature landscaping, and peaceful conservation views with no rear neighbors. Major improvements include a roof replaced approximately 3 years ago and HVAC systems replaced approximately 3 years ago, providing peace of mind for years to come. Conveniently located near top-rated Seminole County schools, parks, golf, shopping, dining, and major commuter routes. Optional HOA membership available. Homes offering this combination of acreage, privacy, pool, location, and living space rarely become available.

1838 Seneca Blvd, Winter Springs

3 Beds ⋅ 2 Baths ⋅ Highland Village 1 SubDv. ⋅ 32708 Zip Code

Welcome home to this cozy 3-bedroom, 2-bath bungalow-style home located in the resort-like Highlands community, offering 1,178 sq. ft. of living space. This home features vaulted ceilings, ceramic tile throughout, fresh interior paint, and a newly renovated kitchen with granite countertops, solid wood shaker-style cabinets, and black appliances. Major updates include a 2025 water heater and a new electrical panel inside and outside. The generously sized primary bedroom includes a built-in California Closets system, providing stylish and highly functional custom storage. The secondary and third bedrooms are also well-sized—perfect for guests, family, or easily converted into a home office. Washer and dryer are included in the sale. Enjoy the covered and screened lanai overlooking a charming New Orleans-style courtyard with pavers, a firepit, and a lamp post. The oversized, fully fenced, and cleared backyard offers plenty of space to relax, entertain, or garden, providing a strong sense of privacy. The Highlands is a highly sought-after, established community with low HOA fees and beautiful mature trees throughout. Amenities include an Olympic-size community pool, walking trails, playground, tennis court, volleyball court, and a clubhouse. Ideally situated just off State Road 434 Florida and Tuskawilla Road, this home offers quick access to Winter Springs Town Center for shopping and dining, and is just a short stroll from Torcaso Park—a lively neighborhood park featuring basketball courts, soccer and football fields, playgrounds for all ages, a splash pad, sand play areas, and picnic pavilions, perfect for both active days and relaxed family outings.

335 Kirkcaldy Drive, Winter Springs

4 Beds ⋅ 3 Baths ⋅ Deer Run Unit 20 SubDv. ⋅ 32708 Zip Code

PAID-OFF SOLAR + 2018 ROOF + WHOLE-HOME 10Gb ETHERNET all on a corner lot in the heart of Winter Springs! Welcome to 440 Buckskin Court, a 4-bedroom, 2.5-bath home in the established Deer Run community with the kind of character and charm you do not find in your average Florida home. Set on a spacious corner lot with fresh landscaping and a brand-new fence, this home blends classic curb appeal, thoughtful updates, and a location that makes everyday life easy. Inside, you’ll find an open floor plan with engineered hardwood flooring, a wood-burning fireplace, and a warm, inviting feel that makes the home instantly memorable. Whether you are hosting friends, working from home, cozying up by the fireplace, or settling into your daily routine, this home offers the space and flexibility to fit the way you actually live. One of the biggest perks? The paid-off 15kW solar system, giving you energy efficiency without the extra payment, so you can run your AC all summer long and enjoy Florida living a little more comfortably. The home also features a 2018 roof, whole-home fiber terminal, and 10Gb wired Ethernet in every room, making it a great fit for remote work, streaming, gaming, and connected living. The owner’s suite has been thoughtfully updated with a new shower and a custom closet with abundant storage. Additional upgrades like the smart thermostat with remote sensors, updated irrigation system, hardwired smoke detectors, GFIs in wet areas, and shower vent fans add convenience and peace of mind without taking away from the home’s personality. Located minutes from the 417, Red Bug Lake Road, Tuskawilla Road, parks, shopping, dining, and highly regarded Seminole County schools, this home puts you right in the middle of what makes Winter Springs so loved. Updated, charming, energy-efficient, and full of personality — 440 Buckskin Court is ready to welcome you home.

440 Buckskin Court, Winter Springs

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