Windermere Homes with 2 Car Garage Garage Description

Windermere Homes with 2 Car Garage Garage Description

Welcome to Windermere, Florida—a picturesque gem nestled in the heart of Orange County. Known for its stunning lakes, lush landscapes, and charming small-town atmosphere, Windermere offers a unique blend of tranquility and convenience. With a rich history dating back to the late 19th century, this enchanting town boasts beautiful tree-lined streets and a close-knit community feel, making it a perfect place to call home.

Windermere is not just a haven for nature lovers; it also provides easy access to the vibrant culture and entertainment of the greater Orlando area. Residents enjoy a plethora of recreational activities, from boating on the pristine Butler Chain of Lakes to exploring the scenic parks and trails that wind through the area. The local dining and shopping scene is thriving, with quaint boutiques and delightful eateries that capture the essence of Florida living.

When it comes to homes in Windermere, many properties feature the much-coveted two-car garage, offering both convenience and ample storage space. These true two-car garages are perfect for families and individuals alike, providing secure parking for vehicles and additional room for outdoor gear, tools, or even a workshop. Whether you're looking for a modern single-family home or a charming cottage, Windermere’s real estate market has something to suit every taste and lifestyle.

Discover the charm of Windermere, where stunning homes with two-car garages await you, and experience a lifestyle that perfectly blends leisure and luxury in one of Florida's most desirable locations. Your dream home is just around the corner!

Newest Windermere Homes with 2 Car Garage Garage Description

$360,000
2 Beds 3 Baths Lakes/Windermere-Lk Reams Twhm SubDv. 34786 Zip Code
Welcome to the peaceful townhome community of The Lakes of Windermere, conveniently nestled just behind Walt Disney World’s Magic Kingdom! Enjoy beautiful green space out front and a tranquil conservation area in the back. The affordable HOA provides added peace of mind by covering exterior and roof maintenance, landscaping, and access to the sparkling community pool. This 2-bedroom, 2.5-bath townhome with a 2-car garage offers a flexible floor plan filled with inviting living spaces. A tiled entry foyer welcomes you into the first floor. Crown molding throughout adds an elegant finishing touch to the home’s inviting interior. The open kitchen features granite countertops, white subway tile backsplash, an undermount sink with a beautiful view, 42" wood-grain cabinetry, closet pantry and stainless steel appliances. The adjoining breakfast nook provides plenty of space for casual dining. Just off the kitchen is a separate dining room with beautiful wood flooring that could easily serve as a home office, den or flex space. The wood flooring continues into the bright and comfortable living room overlooking the private courtyard. Step outside to your fenced courtyard, complete with grass, pavers and a concrete patio area ready to accommodate your outdoor living needs. The courtyard also provides convenient access to the detached 2-car garage. Upstairs the beautiful wood flooring continues. The spacious primary suite is a true retreat. A modern barn door opens to the ensuite bath featuring dual undermount sinks, a walk-in closet, linen closet and an oversized soaking tub and shower combination. The second bedroom also offers a walk-in closet and its own private ensuite bathroom—ideal for guests, family or a roommate arrangement. An upstairs laundry area adds everyday convenience. Enjoy easy access out front to the bike/walking path that leads just over 1 mile to Lakeside Village Center, home to Publix, Starbucks, cafés, banks, recreation areas, and other everyday conveniences. The Lakes of Windermere is highly sought after for its desirable location, convenient access to high rated schools, shopping, dining, and all of the Walt Disney World parks. And with the Magic Kingdom nearby, you can even enjoy the magic of nightly fireworks right from your front door. With its flexible floor plan, private outdoor space, conservation setting, 2-car garage, and exceptional location, this townhome has so much to offer. Now is your opportunity to own a beautiful home in one of Windermere’s most convenient communities!

12417 Cruxbury Drive, Windermere

$375,000
4 Beds 3 Baths Southbridge Village SubDv. 34786 Zip Code
Virtually Staged. Welcome home to Lensdale Lane! This 4-bedroom updated townhome and move-in ready peace of mind: fresh interior paint and trim (2025), new windows and sliding glass door (2022), a newer roof (2021), new exterior paint and siding (2021), and an updated A/C (2019). Step inside to a light and bright open-concept layout where the living, dining, and kitchen flow together effortlessly. The kitchen features sleek quartz countertops, ample storage, and a breakfast bar, perfect for everyday meals or casual entertaining. The main-floor primary suite offers privacy and convenience, while three spacious secondary bedrooms and a second full bath complete the upstairs. Ceramic tile and wood laminate flooring flow throughout; no carpet anywhere! A half bath and laundry round out the main floor. Outside, enjoy your morning coffee on the privacy-fenced courtyard patio, while the covered front porch adds instant curb appeal. The 2-car rear-facing garage keeps the streetscape clean and charming. This home pairs low-maintenance living with an impressive amenity package. The HOA covers exterior maintenance and includes access to a community POOL, clubhouse, FITNESS center, sports courts and walking trails. Zoned for TOP-RATED schools: Windermere High ,Keene's Crossing Elementary, and Bridgewater Middle and just minutes from Winter Garden Vineland Rd, the 429, shopping, dining, and Central Florida's theme parks.Southbridge, part of the sought-after Summerport/Horizon West community, offers an unbeatable sense of community and lifestyle.

13730 Lensdale Lane, Windermere

$3,189,000
4 Beds 5 Baths Isleworth SubDv. 34786 Zip Code
Positioned along the 6th fairway of Isleworth Golf & Country Club, this thoughtfully updated single-story residence offers a rare combination of privacy, golf-course views and effortless everyday living. A welcoming circular drive and mature oaks set the stage, while inside, nearly 3,400 square feet unfolds in a light-filled collection of spaces designed to feel equally comfortable for quiet evenings at home or a house full of guests. Natural light pours through the glass entry into a dramatic foyer with a groin-vaulted ceiling, introducing the architectural character found throughout the home. Arched openings lead into the formal living room, where a striking stone fireplace creates a natural gathering place and walls of glass frame views of the garden and fairway beyond. The formal dining space provides an elegant backdrop for entertaining while remaining connected to the heart of the home. The renovated kitchen is both inviting and exceptionally functional, featuring a professional-style gas range, integrated appliances and a 40-bottle wine refrigerator. Custom cabinetry, marble countertops and a distinctive tile range hood complete the space, while additional cabinetry flows seamlessly into the family room to create a built-in entertainment center. Natural light reflects beautifully across the large-format tile floors, creating a bright, cohesive feel from room to room. The primary suite is privately positioned on the northeast wing, welcoming golden morning light into the space. The retreat features a distinctive dual-bath arrangement—one with a walk-in shower and the other with a freestanding soaking tub—along with a cedar-lined walk-in closet with custom built-ins. Three additional bedrooms provide comfortable accommodations for family and guests, including one with an ensuite bath, while the updated hall bath offers dual sinks and convenient pool access. A separate flex room easily adapts as an office, library, fitness room or additional retreat. Outside, a covered patio with fireplace extends the living space year-round, overlooking the open-air pool and spa with the manicured fairway beyond. A rear motor court, two-car garage and dedicated golf-cart parking complete the property. Recent improvements, including a 2020 slate roof, refreshed exterior paint, renovated kitchen and baths, complement the home’s established character. With its single-story footprint, private setting and half-acre golf-course homesite, the opportunity is as compelling as the lifestyle within the gates.

5050 Isleworth Country Club Drive, Windermere

$647,000
3 Beds 3 Baths Lakes Windermere Ph 01 49 108 SubDv. 34786 Zip Code
Modern elegance meets resort-style living in the Lakes of Windermere. Welcome to a beautifully renovated craftsman-style home. Thoughtfully updated for today's lifestyle, this move-in-ready residence blends timeless architectural character with modern comfort, quality finishes, and inviting indoor-outdoor living. From the moment you step inside, natural light fills open-concept living spaces, creating a bright and welcoming atmosphere throughout the home. The thoughtful layout and carefully selected finishes provide the perfect balance of style, functionality and everyday comfort. At the center of the home is a beautifully appointed kitchen designed for both everyday living and entertaining. It features an oversized 36-in professional Electrolux induction range with convection oven, a 36-inch range hood, built-in wine cooler, granite countertops, and a classic farmhouse sink. Whether preparing a casual meal or entertaining guests, the kitchen is designed to be both functional and impressive. The majestic dining room table, chairs, sideboard and barstools convey with the home as an attractive option. The primary suite includes an added layer of flexibility with a versatile suite located adjacent to the master. Use it as a nursery, private home office, fitness space, reading room, or whatever best fits your lifestyle. Step outside and discover one of the home's standout features: a private tropical-inspired outdoor retreat. The professionally landscaped backyard includes an outdoor kitchen, custom-paved seating area, and integrated LED lighting--creating an inviting setting for entertaining, outdoor dining, or simply enjoying your own private space. Recent upgrades & features include the following: Roof (2022); 2-stage AC system (2023); water-softening filtration system (2022); enclosed patio (2024); Ecobee thermostat (2022); B-Hyve automated irrigation system (2022); outdoor kitchen refrigerator (2026); luxury vinyl plank flooring (2022); and carpeting (2022). Beyond the property itself, residents enjoy access to desirable community amenities, including a community pool, tennis court, playgrounds, and a scenic fishing dock. This is a home designed for the way live today, with beautiful interior spaces, meaningful upgrades, flexible living areas, and an exceptional outdoor environment.

7033 Bramlea Lane, Windermere

$759,000
4 Beds 4 Baths Lake Sawyer South Ph 05 SubDv. 34786 Zip Code
Welcome to 8104 Jailene Drive, a beautifully updated 4-bedroom, 3.5-bath pool home offering nearly 2,900 square feet of thoughtfully designed living space in the desirable Lake Sawyer community in Windermere. Set against a peaceful conservation backdrop with no rear neighbors, this home pairs privacy and outdoor living with a long list of recent improvements—including a NEW ROOF completed in May 2026, fresh interior paint and landscape lighting that beautifully highlights the property after sunset. Inside, an open, light-filled floor plan creates an easy flow for both everyday living and entertaining. The centrally located kitchen features upgraded cabinetry, Topazio White granite countertops a butler pantry, stainless steel appliances with a Bosch dishwasher, and generous workspace and storage. Custom details continue throughout the home, including upgraded wood and laminate flooring, a built-in credenza in the family room and built-in shelving in the office. The spacious primary suite offers a private retreat of its own, complete with a separate sitting area, oversized walk-in closet with built-in cabinetry. Step outside to the screened pool and enjoy a private backyard setting surrounded by mature landscaping and peaceful conservation views—an ideal place to unwind, entertain, or spend a quiet Florida afternoon. Additional conveniences include a washer and dryer, Vivant security system, and an attached 2-car garage. Some furnishings may also be negotiable. Lake Sawyer residents enjoy a community pool, basketball and tennis courts, walking trails, dog-walking areas, and more, all in a sought-after Windermere location convenient to shopping, dining, top area attractions, and everything that makes this part of Central Florida such a desirable place to call home. With significant updates already completed and an inviting indoor-outdoor lifestyle, 8104 Jailene Drive is ready for its next chapter.

8104 Jailene Drive, Windermere

$399,000
3 Beds 3 Baths Summerport Edens Hammock SubDv. 34786 Zip Code
There is something truly special about coming home to Summerport, and this move-in-ready townhome captures that feeling perfectly. From the moment you arrive, the inviting front porch offers a peaceful spot to sit back and watch the sunset over Ancilla Pond. Inside, the functional main level features a highly desirable first-floor primary suite. The bright kitchen connects seamlessly to a private, fenced patio area. Upstairs, you will find an additional bedroom, a versatile loft area, and a secondary bedroom featuring a charming alcove that makes a wonderful home office or study nook. Out back, enjoy ultimate privacy with an attached garage accessed by a rear road and extended driveway. Because the property backs up to the tranquil marshland of Walsh Pond there are no rear neighbors and you are also just steps from the community playground! Summerport features resort-style amenities, including scenic walking paths, small lakes, a clubhouse pool, a fitness center, a fishing dock, volleyball, and a sand beach area right next to the tennis and basketball courts. Unbeatable Location & Convenience: * Top-Rated Schools: Just a short drive to Keene’s Crossing Elementary, Bridgewater Middle and Windermere High School. Elite private options like Windermere Preparatory School and Foundation Academy are also nearby. * Moments from Disney World and all major theme parks. * Easy Commute: Quick access to SR-429, SR-408, and the Florida Turnpike makes driving a breeze. * Shopping & Dining: Minutes from local restaurants, grocery stores, and the popular Winter Garden Village. Low-Maintenance Living, the HOA fully maintains the exterior including the lawn, exterior painting and roof replacements (new roof installed in 2022), allowing for a truly easy lifestyle. Schedule your showing today!

14077 Ancilla Boulevard, Windermere

$1,399,900
5 Beds 3 Baths Lake Down Cove SubDv. 34786 Zip Code
Virtually Staged. Set on just over an acre in Windermere, this updated 5-bedroom, 3-bath pool home offers 3,356 square feet of living space, plus a separate flex/bonus room that can be used as a media room, game room, office or additional living space. Located on a cul-de-sac in Lake Down Cove, the property offers something increasingly hard to find in Windermere: an updated home with a private pool, a flexible floor plan and more than an acre of land. Inside, high ceilings and large windows bring in plenty of natural light, while large-format marble-look porcelain tile runs throughout the main living areas. The spacious family room features a modern linear electric fireplace and opens to the kitchen and casual dining area, with views of the pool and backyard. A separate dining room is located just off the entry, and an interior Juliet balcony from the second floor overlooks the family room. The updated kitchen features dark shaker-style soft-close cabinetry, quartz countertops, a large island, farmhouse sink and glass tile backsplash. A six-burner ZLINE gas range with griddle, pot filler and stainless steel hood anchors the cooking area, along with double ovens, a microwave drawer and stainless steel appliances. Three of the five bedrooms are located downstairs, including the primary suite. The primary bedroom overlooks the pool and features crown molding, two walk-in closets and double doors leading outside. The primary bathroom includes dual vanities with quartz countertops, a freestanding soaking tub and a large frameless glass shower finished with marble-look porcelain tile. Two additional bedrooms and a second full bathroom are also downstairs, with one bedroom well suited for use as a home office. The second bathroom has direct access to the pool area. Upstairs are two additional bedrooms, a full bathroom and a separate flex room that could be used as a media room, game room, office or additional living area. The upstairs bathroom features a dual vanity with quartz countertops, a tub/shower combination and updated finishes. One of the upstairs bedrooms also features a private outdoor balcony and an interior Juliet balcony overlooking the family room below. Outside, the 1+ acre lot provides plenty of room to enjoy the property. The private pool is surrounded by a large patio with a partially covered area, while the fenced backyard offers mature trees and generous open space. The outdoor kitchen includes a built-in grill, refrigerator, sink, stone surround and counter space, and a wood-burning fire pit adds another gathering area in the backyard. Additional features include a downstairs laundry room with quartz countertops, sink and extensive cabinetry, plus an oversized two-car garage with workspace and additional storage. With five bedrooms plus a flex room, 3,356 square feet, an updated interior, private pool and more than an acre of land, this Windermere home offers an uncommon amount of space both inside and out. Conveniently located near shopping, dining, community events and major roadways, with easy access throughout Windermere and the greater Orlando area.

2540 Hempel Cove Ct, Windermere

$600,000
4 Beds 3 Baths Summerport Phase 1 SubDv. 34786 Zip Code
Fresh interior/exterior paint and HVAC serviced! Residing in Summerport, this delightful home features a practical design with spacious room sizes and a tranquil pond view, providing the ideal atmosphere for everyday living and entertaining guests. Four comfortable bedrooms in tandem with multiple living areas and two covered patios offer ample space for any occasion, while granite countertops, extensive cabinetry, and custom accents throughout add an elegant touch to the interior. Summerport offers residents a list of amenities, including a clubhouse, community pool, sports courts, and multiple trails, parks, playgrounds, and dog parks for endless fun without leaving the neighborhood. Beyond these exceptional amenities, the location provides easy access to daily necessities, medical services, recreation activities, and major highways. The Summerport Village, Winter Garden Village, Shoppes at Lake Butler, and Shoppes at Windward Cay are moments away, placing numerous dining and retail needs right at your fingertips. Nearby Braddock Park and Tibet-Butler Nature Preserve provide natural beauty and outdoor activities close by, while just moments from Disney and Universal, making it ideal for those seeking both tranquil residential living and entertainment accessibility. This combination of a practical design, peaceful pond view, quality amenities, and strategic positioning creates the ideal living experience. Don't let this exceptional opportunity slip away – schedule your private showing today!

13844 Amelia Pond Drive, Windermere

$2,500,000
5 Beds 5 Baths Lake Davis Reserve A & B SubDv. 34786 Zip Code
A rare opportunity to own one of just 18 custom estate homes in this exclusive Windermere enclave of Lake Davis Reserve. Set on more than half an acre, this impressive five-bedroom residence spans over 4,600 square feet, offering a remarkable sense of privacy and seclusion while remaining right in the heart of Windermere. From the moment you enter through the custom iron doors, the craftsmanship and attention to detail are unmistakable. Expansive living spaces, beautiful wood-look porcelain flooring, custom millwork and thoughtfully designed lighting create a home that feels luxurious yet exceptionally comfortable. Custom-designed fireplaces throughout the home provide striking focal points and give each living space its own sense of character and warmth. The chef's kitchen features abundant cabinetry, generous counter space, a large prep island, granite countertops, water softener and a vented cooktop, all opening seamlessly to the main living areas. The spacious primary suite is conveniently located on the first floor and offers a true private retreat, complete with its own custom fireplace, oversized walk-in shower and soaking tub. Additional generously sized bedrooms ensure everyone enjoys ample space, while upstairs, a large flex room with custom built-in cabinetry provides an ideal setting for entertaining, relaxing or movie nights. A dedicated gym adds even more versatility to the floor plan. Outside, the home's sense of privacy becomes even more apparent. A covered lanai, with wiring for remote-controlled screens, opens to a secluded backyard retreat framed by mature tropical landscaping. Completed in 2022, the heated saltwater pool features a PebbleTec finish, multicolor LED lighting, dual sun shelves and an illuminated pergola waterfall. An extended pool deck, outdoor audio, summer kitchen with natural gas, exterior bathroom and app-controlled pool and landscape lighting create an exceptional environment for entertaining or simply enjoying the Florida lifestyle in complete comfort. As evening approaches, the west-facing backyard provides beautiful sunset views in front of your patio gas fireplace. That feeling of seclusion is what makes Lake Davis Reserve so special. Despite its peaceful, private setting, the home sits in the heart of Windermere, with Windermere Preparatory School, Windermere High School and zoning for Windermere Elementary all close by. Disney, SR-429 and premier shopping and dining are just minutes away. Opportunities to purchase in Lake Davis Reserve are exceedingly rare, with only 18 custom estate homes behind its gates. Beautiful in photographs and even better in person, this is a home that simply needs to be experienced. The privacy, scale, custom finishes and atmosphere are difficult to fully capture in photographs. If your buyers are looking for luxury, security and seclusion without sacrificing the convenience of Windermere living, 5526 Marleon Drive deserves to be at the top of their viewing list.

5526 Marleon Drive, Windermere

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