Windermere Homes for Sale

Windermere Homes for Sale

Welcome to Windermere, Florida, a picturesque town nestled in the heart of Orange County. Known for its stunning lakes and serene landscapes, Windermere offers a unique blend of small-town charm and modern conveniences. With its lush greenery and beautiful waterfront views, this community is perfect for those seeking a tranquil lifestyle while still being close to the vibrant attractions of Orlando.

Windermere is renowned for its family-friendly atmosphere, top-rated schools, and a variety of recreational activities. Residents enjoy access to numerous parks, trails, and lakes, making it an ideal spot for outdoor enthusiasts. The town hosts a number of community events throughout the year, fostering a strong sense of belonging among its residents. Whether you’re strolling through the quaint downtown area or enjoying a sunset by the lake, Windermere is a place where memories are made.

For those looking to call Windermere home, you’ll find a diverse selection of homes for sale that cater to various lifestyles and budgets. From luxurious waterfront estates to charming single-family homes, the real estate offerings in Windermere are as varied as its residents. Many properties boast stunning architectural designs, spacious backyards, and close proximity to top-notch amenities, including shopping, dining, and entertainment options.

If you’re considering a move to this enchanting town, now is the perfect time to explore the homes for sale in Windermere. Experience the beauty and warmth of this community, where every day feels like a vacation. Let Windermere be the backdrop for your next chapter!

Newest Windermere Homes for Sale

4 Beds ⋅ 3 Baths ⋅ O6438323 MLS

Home at the Ashton Park of Windermere community, 4 bedroom 3 full bath, spacious kitchen with all new stainless steel appliances. Island sink with a bar counter open to breakfast nook and family great room. Formal dining room. Inside Laundry, cabinet desk and laundry storage. Security system installed, cable/internet pre-wired with distribution box. Double garage with 2 separate electric doors. Community pool & Club.

7252 Backwoods Trail, Windermere

4 Beds ⋅ 4 Baths ⋅ O6442193 MLS

Welcome to your beautiful corner lot home in the sought after Berkshire Park community of Windermere! Don’t miss the opportunity to own this thoughtfully designed 4 bedroom, 3.5-bath home with a bonus room and 3-car garage, offering an ideal blend of space, comfort, and functionality. Major updates include a new roof installed in 2022 and a new AC system installed in 2025, providing added peace of mind for the next owner. A brick-paver driveway and charming walkway welcome you to the inviting front porch, perfectly positioned along a quiet, tree-lined street. Step inside to a spacious foyer featuring soaring ceilings and an open, airy feel that continues throughout the main living areas. The formal dining room flows seamlessly into the open concept kitchen and family room, creating an ideal space for both everyday living and entertaining. The kitchen features a large center island, granite counters, stainless steel appliances, ample cabinetry, and a dedicated eat-in area, while the family room opens to a screened in patio overlooking the generously sized backyard making a wonderful setting for morning coffee, outdoor dining, or relaxing with family and friends. The main level owner’s suite offers convenience and privacy with dual vanities, tub, shower, and walk in closet. Your well appointed laundry room provides direct access to the spacious three-car garage. Upstairs, a versatile bonus room serves as the perfect media room, playroom, home office, or additional gathering space. Three generously sized bedrooms and two full bathrooms complete the second floor, providing plenty of room for family and guests. Residents of Berkshire Park enjoy community amenities including a beautiful neighborhood pool and playground, all within the highly desirable Windermere area. The close proximity to Disney World, shopping, restaurants, and "A" rated schools make this an unbeatable location. With its spacious floor plan, prime Windermere location, 3-car garage, newer roof, newer AC, and inviting outdoor living space makes this a home you won’t want to miss. Be sure to click on the virtual tours.

13324 Jervey Street, Windermere

3 Beds ⋅ 2 Baths ⋅ O6435895 MLS

Virtually Staged. Welcome to this spacious 3-bedroom, 2-bathroom single-story home in the gated Belmere community of Windermere. The open floor plan provides a comfortable flow between the living spaces, with a formal living room and dining room offering flexibility for entertaining, gatherings, or everyday use. The family room features high ceilings and opens to the kitchen and breakfast area, creating a central space for relaxing and spending time together. The primary suite offers a private retreat with a walk-in closet and an ensuite bathroom featuring a garden tub, separate shower, and dual vanities. Two additional bedrooms provide comfortable space for family, guests, a home office, or other needs. A screened-in patio extends the living space outdoors and overlooks the landscaped backyard. The home also includes an attached 2-car garage and convenient interior laundry area. Belmere offers residents access to community amenities including a pool, clubhouse, fitness center, tennis courts, basketball court, and playground. Conveniently located near shopping, dining, major roadways, and Orlando-area attractions, this home offers a practical layout in a desirable Windermere community.

929 Lascala Drive, Windermere

5 Beds ⋅ 3 Baths ⋅ S5157579 MLS

The best family living location! Welcome home to this fabulous 5 bedrooms, 3 full baths, 2 car garage located in the peaceful community of Vineyards in Windermere Florida. Gorgeous subdivision convenient to major roadways, A+ Rated Schools, Shopping, entertainment and so much more. Just minutes away from Walt Disney World. Spacious Master ensuite with walk-in closet. Modern Kitchen with stainless steel appliances with a gas range, granite counter tops and dark wood cabinets! Screened patio with beautiful spacious view of the large yard and conservation. Community comes with a Park/playground and community pool. Do not miss this awesome opportunity!!!

6614 Bridgewater Village Rd, Windermere

6 Beds ⋅ 9 Baths ⋅ O6441249 MLS

Virtually Staged. Pre-Construction. To be built. Poised on a remarkable .69-acre homesite along the shores of Lake Bessie, this exceptional new residence offers a rare opportunity to create a substantial private estate in one of Isleworth’s most coveted lakefront settings. Designed and to be built by Supreme International Construction, the residence will encompass approximately 15,337 square feet of living space across three levels, with six bedrooms, including two private primary suites, an elevator and a four-car garage accommodating up to eight vehicles with lifts. Created for both grand entertaining and effortless everyday living, the main level will feature a dramatic great hall, formal dining room, family room, expansive kitchen, private study and serene primary retreat. Soaring architectural spaces and multiple covered balconies create a natural connection to the lakefront setting. The lower level is envisioned as a private destination for leisure, with a beautifully appointed theater delivering an immersive viewing experience, complemented by a separate popcorn and snack room for added convenience and fun. A generous entertainment area, bar, summer kitchen, gym, yoga/Pilates studio, sauna and spa complete the level. The upper floor offers a second primary suite, additional bedroom suites, viewing lounge and PJ lounge. The outdoor living space is designed to maximize the breathtaking lakefront setting. Landlocked and private, Lake Bessie offers an intimate waterfront experience for boating, water sports and fishing, with no public access to the lake. This rare pre-construction opportunity offers the privilege of securing an extraordinary lakefront residence while personalizing select finishes as the residence takes shape. Within Isleworth’s 600-acre residential community, Isleworth Golf & Country Club, consistently recognized among the world’s finest private clubs, offers an exceptional lifestyle, with Membership offered separately and subject to application and approval.

5036 Latrobe Drive, Windermere

1 Beds ⋅ 1 Baths ⋅ O6441329 MLS

Pro pics coming soon * Charming 1 Bedroom 1 Bath Craftsman Cottage on a spacious lot in Downtown Windermere * Mature Oak Trees * The covered porches on the front and rear offer additional spaces to entertain, watch nature or read your favorite book while you slow down and truly experience the "Old Windermere" lifestyle * Home has been lovingly maintained and will impress even the most finicky Buyer * Don't miss this rare opportunity * Must see inside to really appreciate the home

628 Forest Street, Windermere

3 Beds ⋅ 2 Baths ⋅ O6441248 MLS

Professional Pics Coming Soon - They say Good Things Come in Small Packages & This Proves It * Must see this Gem to really appreciate the craftsmanship and attention to detail throughout * Completely renovated in 2020 & 2023, this exceptional Windermere property seamlessly blends timeless character with modern luxury, offering thoughtfully designed spaces, quality finishes, and an impressive level of care in every detail. From the beautifully appointed kitchen featuring Kitchenaid Fridge, Miele Dishwasher, Kitchenaid Gas Range, to the versatile in-law apartment with Sub Zero Double Drawer Fridge, every aspect of this home has been designed for comfort, functionality, and effortless Florida living * Everything was improved, the Roof, AO Smith Water Heater, Septic, A/C, Hardwood Flooring, Tile * Fireplace * Natural Gas * 1 Block from the Boat Ramp to Lake Butler and the Chain of Lakes * Downtown Windermere offers many fun events and the New Frescos Italian Restaurant, Dixie Cafe' and the Windermere Brewery are just a few places you can walk to get a great meal * Mature Landscaping and Oak Trees * 2 Covered Carports for Boat or Auto * Storage Shed with Electric provides ample room for a workshop * Book your Private Tour Now

611 Butler Street, Windermere

4 Beds ⋅ 2 Baths ⋅ O6438808 MLS

Virtually Staged. Space, flexibility, and a fantastic Windermere location! Set on a prime CUL-DE-SAC LOT in the GATED Lakes of Windermere-Peachtree community, this spacious 3-bedroom + BONUS, 2-bath, 2-car garage home offers a versatile floor plan with the convenience of MAIN-LEVEL LIVING plus an oversized BONUS ROOM upstairs. A NEWER A/C (2022) adds to the appeal. Inside, you will find a welcoming foyer that opens to combined formal living and dining spaces before making your way into the kitchen that connects seamlessly with a casual dining area and spacious family room, creating an easy layout for everyday living and entertaining. Sliding glass doors extend the living space outdoors to a COVERED LANAI. Privately positioned at the back of the home, your PRIMARY SUITE features a WALK-IN CLOSET and private EN-SUITE BATH. Bedrooms two and three share a second full bath, keeping the primary living spaces, bedrooms and baths conveniently together on one level. Upstairs, the bonus room delivers valuable flexibility and can easily serve as a MEDIA ROOM, second living area, HOME OFFICE, guest space or 4TH BEDROOM. Lakes of Windermere-Peachtree offers a beautiful natural setting surrounded by trees and conservation, along with a COMMUNITY POOL and PLAYGROUND. The home is ZONED FOR “A” RATED SCHOOLS, including WINDERMERE HIGH SCHOOL, and is ideally located just off Reams Road with easy access to SR-429. Walt Disney World, Orange County National Golf Center, Four Seasons Golf & Sports Club, ESPN Wide World of Sports, shopping, dining and everyday conveniences are all just minutes away. LOCATION, LAYOUT & VERSATILITY – this Windermere home delivers all three. Call today to schedule a tour and let us say WELCOME HOME!

13424 Hopkinton Court, Windermere

6 Beds ⋅ 5 Baths ⋅ O6431854 MLS

Experience elevated Florida living in this extraordinary 4,585-square-foot estate, ideally positioned in the heart of Windermere and just 2 miles from Magic Kingdom. Built in 2025 and presented in pristine, like-new condition, this remarkable residence offers an exceptional combination of sophisticated design, expansive living spaces, and an enviable location. Every detail has been thoughtfully considered to create a home that is as impressive as it is functional. From the moment you enter, the scale and elegance of this residence are immediately apparent. The expansive floor plan features six generously sized bedrooms, a dedicated private office, and a substantial bonus room, providing an extraordinary level of flexibility for today's lifestyle. The separate office is ideal for working from home, while the spacious bonus room can easily be transformed into a home gym, media room, children's playroom, or additional entertainment space. Upstairs, an impressive nearly 600-square-foot loft creates an entirely separate living and entertainment experience. Complete with a built-in wet bar, this remarkable space is perfectly suited for movie nights, game days, entertaining guests, or simply relaxing with family. Designed with modern luxury and everyday convenience in mind, the home features a dedicated laundry room on each floor, an abundance of additional closets, a large walk-in pantry, and generous garage space. There is no shortage of room for storage, hobbies, vehicles, and everything that comes with an elevated lifestyle. Perhaps the most exceptional feature is the location. Situated just minutes from Walt Disney World, you can enjoy the convenience of being only 2 miles from Magic Kingdom while even taking in the spectacular nightly Disney fireworks from your own home. The community also offers a playground, providing a wonderful space for children to play and enjoy the outdoors. At the same time, you'll be close to the highly sought-after Windermere school district, shopping, dining, golf, and everything Central Florida has to offer. Impeccably maintained, exceptionally spacious, and truly move-in ready, this stunning Windermere residence delivers a rare combination of luxury, convenience, and location. With six bedrooms, a dedicated office, a massive bonus room, an expansive loft with wet bar, two laundry rooms, and extraordinary storage, this is a home designed to accommodate both grand entertaining and effortless everyday living.

14360 Crest Palm Avenue, Windermere

5 Beds ⋅ 7 Baths ⋅ O6440385 MLS

BELLARIA ESTATE. Toll Brothers-built Spanish/Mediterranean estate on a 0.76-acre homesite in Bellaria, Windermere's 64-home, 24-hour guard-gated enclave off Lake Butler Road. Built in 2014 and offering 5 bedrooms, 6 baths, 1 office, and 5,667 sq ft across two stories, with block-and-stucco construction, a tile roof, and mature, tree-lined landscaping framing a paver drive and 3-car garage. LIVING SPACES. The plan is designed around everyday living and entertaining alike, with generous formal and casual gathering areas, an open kitchen at the heart of the home, and a first-floor primary suite. Upstairs, the secondary bedrooms and bonus space give family and guests room of their own. OUTDOOR LIVING. Out back, the covered lanai opens to a heated pool and spa with a full summer kitchen, all set against the privacy of the oversized lot, a true year-round Florida outdoor room. LOCATION. Zoned for Windermere Elementary, Bridgewater Middle, and Windermere High, and minutes to Winter Garden Village, Downtown Windermere, Disney, and the 429 for a quick run to the airport or downtown Orlando. Quarterly HOA covers the manned gate, and community park. SHOWINGS. Private showings by appointment. Pre-approval or proof of funds requested prior to scheduling.

13322 Bellaria Circle, Windermere

2 Beds ⋅ 2 Baths ⋅ B26074013 MLS

GORGEOUS LIGHT AND BRIGHT CORNER TOWNHOUSE IN PERFECT PEACEFUL LOCATION FEATURES A STAINLESS GRANITE KITCHEN, OPEN SPLIT FLOORPLAN, SPACIOUS PRIMARY SUITE WITH TRAY CEILING AND WALK-IN CLOSET, LUXURY WALK-IN SHOWER, BEAUTIFUL PORCELAIN TILE AND NEW LIGHT FIXTURES THROUGHOUT ENTIRE HOME, TWO CAR GARAGE, FENCED YARD, AND THREE YEAR OLD ROOF. AS YOU SIT ON YOUR COZY FRONT PORCH, YOU CAN AN ENJOY A SERENE WATER VIEW OF A LARGE POND ADJOINING A CONSERVATION AREA. LOW HOA COMMUNITY OFFERS A RESORT STYLE POOL, TENNIS COURTS, BASKETBALL COURTS, VOLLEYBALL COURTS, FITNESS CENTER, CLUBHOUSE, PLAYGROUNDS, TREE LINED STREETS AND WALKING TRAILS AS WELL AS ALL A RATED SCHOOLS. IDEAL LOCATION OFFERS NEARBY SHOPPING, DINING, AND ENTERTAINMENT AT WINTERGARDEN VILLAGE AND THE GROVE. MAY BE RENTED RIGHT AWAY

5426 Kumquat Loop, Windermere

5 Beds ⋅ 7 Baths ⋅ O6439995 MLS

Welcome to an exceptional luxury residence in the prestigious gated community of Casabella in Windermere. Set on a private 0.71-acre homesite, this stunning Toll Brothers residence offers approximately 5,502 square feet of beautifully appointed living space, featuring 5 private ensuite bedrooms and 2 half bathrooms. From the moment you enter, the home impresses with sophisticated architectural details, soaring ceilings, abundant natural light, and expansive spaces thoughtfully designed for both refined everyday living and effortless entertaining. The gourmet kitchen is equipped with premium appliances, custom cabinetry, an oversized island, ample counter space, and an open-concept design that flows seamlessly into the family room and dining areas. The first-floor primary suite offers a tranquil private retreat, complete with a spa-inspired bathroom featuring dual vanities, a spacious walk-in shower, and generous his-and-her closet areas. Also located on the first floor is an additional private suite and a dedicated office, while the second floor offers the remaining bedrooms, a secondary primary suite, a spacious loft, and versatile living areas. Step outside to an impressive outdoor living space featuring a private heated in-ground pool, upgraded covered lanai with a summer kitchen, and beautifully landscaped surroundings, creating an ideal setting for entertaining or relaxing in complete privacy. Additional features include a three-car garage, tile roof, elegant finishes, abundant storage, and carefully curated furnishings throughout. Offered fully furnished, this exceptional residence presents a rare opportunity to enjoy a turnkey Windermere lifestyle within one of Central Florida’s sought-after gated communities. Ideally positioned near premier shopping, fine dining, golf, entertainment, major roadways, and world-renowned attractions, this Casabella estate brings together luxury, privacy, comfort, and convenience.

4243 Isabella Circle, Windermere

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