Windermere Homes for Sale

Windermere Homes for Sale

Welcome to Windermere, a charming city located in Orange County, Florida. Known for its picturesque landscapes and luxurious homes, Windermere offers a truly exceptional living experience.

Nestled in the heart of the Sunshine State, Windermere boasts a prime location with easy access to major cities and attractions. Residents enjoy a peaceful and serene environment, surrounded by pristine lakes and lush greenery. With its small-town charm and close-knit community, Windermere is the perfect place to call home.

If you're in the market for a new home, Windermere has a wide range of options to suit every lifestyle and budget. From stunning waterfront properties to spacious family homes, there is something for everyone in this thriving real estate market. Whether you're looking for a modern contemporary design or a classic Mediterranean-style villa, Windermere has it all.

In addition to its beautiful homes, Windermere offers a host of amenities and attractions. The city is home to top-rated schools, making it an ideal choice for families. Outdoor enthusiasts will appreciate the abundance of parks, golf courses, and recreational activities available. And with its close proximity to Orlando, residents can easily access world-class entertainment, shopping, and dining options.

Don't miss out on the opportunity to experience the best of Windermere's real estate market. Explore the homes for sale in this vibrant city and find your dream home today.

Newest Windermere Homes for Sale

$559,000
3 Beds ⋅ 3 Baths ⋅ C7529514 MLS ⋅ 2014 BLDG.
This beautifully renovated 3-bedroom, 2.5-bath luxury home in a prime Windermere location offers the perfect blend of modern elegance, comfort, and peaceful Florida living. The bright open-concept layout creates a seamless flow between the living, dining, and kitchen areas, ideal for both everyday living and entertaining. Recent renovations include new stairs with sleek glass railings, beautifully updated bathrooms, a smart bidet toilet, and new appliances, giving the home a fresh feel, while the downstairs showcases beautiful high-gloss tile flooring that adds to the bright, upscale atmosphere. Upstairs, an additional flex/living area offers the perfect space for a home office, yoga studio, reading retreat, or lounge. One of the home’s standout features is the expansive upstairs balcony, accessible from two bedrooms and overlooking the lake, where you can enjoy your morning coffee or unwind surrounded by mature trees, birds, and nature in a wonderfully quiet setting. The home also features a two-car garage and is conveniently located near the best schools, shopping, dining, entertainment, major roadways, and everyday amenities. With its lake views, open-concept design, extensive updates, flexible living spaces, peaceful natural surroundings, and sought-after Windermere location, this move-in-ready home offers an exceptional combination of luxury, tranquility, and convenience.

8630 Powder Ridge Trail, Windermere
$1,249,000
5 Beds ⋅ 5 Baths ⋅ O6429898 MLS
Stunning William P Campbell custom home on a private, oversized lot of more than half an acre in one of the most desirable communities in the Town of Windermere-Willows at Lake Rhea! From the moment you arrive, the soaring 14-foot ceilings, abundant windows, and elegant glass French doors create a light-filled, inviting atmosphere with beautiful views of the pool and spa from nearly every room. Mature landscaping surrounds the property, creating a peaceful and private setting that is increasingly rare. Designed for both sophisticated entertaining and comfortable everyday living, the open-concept layout seamlessly connects the living room, dining room, gourmet kitchen, and family room, creating an exceptional space for gatherings. The chef’s kitchen is truly the heart of the home, featuring an induction cooktop, Wolf double ovens, Sub-Zero refrigerator, Bosch dishwasher, brand-new disposal, upgraded granite countertops, farmhouse sink, prep sink and an abundance of custom cabinetry for exceptional storage. The expansive private primary suite overlooks the sparkling pool and spa and offers two oversized walk-in closets. The luxurious primary bath features a massive walk-in-shower with dual shower heads, jetted tub, and an impressive dual vanity. Two additional generously sized bedrooms share a Jack-and-Jill bath, while the fourth bedroom offers privacy and direct access to the pool bath-perfect for guests. Upstairs an oversized bonus room/fifth bedroom provides incredible flexibility and includes a full bath and wet bar, making it an ideal guest suite, media room, office, or entertaining space. Step outside to your private pool and spa and enjoy the Florida lifestyle in complete comfort, with a fabulous outdoor kitchen, creating the perfect setting for al fresco dining and entertaining. This exceptional home is truly move-in ready with a new roof in 2016, newer AC systems in 2021 and 2026, and a repipe completed in 2024. A three-car side-entry garage, expansive brick-paver driveway, and circular drive provide impressive curb appeal and abundant parking. Enjoy all the benefits of living in the Town of Windermere, including access to the Butler Chain of Lakes boat ramp, weekly Farmers Market, Public Library, and year-round community events. Willows At Lake Rhea offers an exceptional setting within one of Windermere’s most desirable communities, combining an outstanding custom home, a rare oversized private lot, and the lifestyle, charm and amenities that make Windermere so sought after.

2031 Willow Lauren Lane Unit L, Windermere
$510,000
4 Beds ⋅ 3 Baths ⋅ O6429767 MLS
Your dream home in Windermere is waiting for you! This beautiful home features 4 bedrooms, 2.5 bathrooms, and a 2-car garage, offering the perfect combination of comfort and style. The spacious kitchen is equipped with granite countertops, complemented by matching granite in all bathrooms. The first floor features durable tile flooring throughout, creating a bright, open, and easy-to-maintain living space. Located in the desirable Vineyard Square community, residents enjoy fantastic amenities, including a community swimming pool, cabana, tot lot, and passive park. The neighborhood is ideally situated near Central Florida's world-famous attractions, shopping, dining, major highways, and charming Downtown Windermere. Just minutes away, you'll find Winter Garden Village, known for its exceptional shopping, restaurants, outdoor events, and seasonal festivals. Outdoor enthusiasts will also appreciate the nearby Tibet-Butler Preserve, offering scenic walking and biking trails. Don't miss this incredible opportunity to own a home in one of Central Florida's most sought-after locations. Schedule your private showing today!

13831 Farella Alley, Windermere
$975,000
3 Beds ⋅ 3 Baths ⋅ O6433478 MLS
Welcome to this beautifully updated home situated on a full 1-acre homesite in a highly desirable, established community surrounded by mature trees. Enjoy access to the Butler Chain of Lakes for just $100 annually, offering an incredible opportunity for boating, fishing, and the Florida lake lifestyle. Inside, the home features a spacious open layout with an updated kitchen, white cabinetry, stone countertops, stainless-steel appliances, and a large island overlooking the living area. A rare double primary suite configuration provides exceptional flexibility for guests, multigenerational living, or a private retreat. The home also offers three full bathrooms, including beautifully updated baths with spacious walk-in showers. Two separate A/C systems help keep the home comfortable year-round. Generous living spaces and large bedrooms provide plenty of room to spread out. Outside, the acre-sized property and mature trees offer privacy and space that are increasingly hard to find. Add in an outstanding location with convenient access to shopping, dining, entertainment, and area attractions, and this home truly delivers. One-acre living, Butler Chain access, and a fantastic location—this is Florida living at its best.

9600 Ambleside Drive, Windermere
$682,000
4 Beds ⋅ 3 Baths ⋅ O6430765 MLS
Beautiful 4 bedrooms, 2.5 bathrooms single-family home in the desirable Windermere area. This spacious home features a thoughtfully designed floor plan with the primary bedroom and en-suite bathroom conveniently located on the first floor, along with a dedicated office and laundry room. The main level also offers a formal dining room, a welcoming family room, and a well-appointed kitchen, creating an ideal space for everyday living and entertaining. Upstairs, you’ll find additional bedrooms offering privacy and flexibility for family or guests. Enjoy a comfortable outdoor space with a conservation area in the backyard and a convenient location close to shopping, dining, major highways, and nearby amenities. This home offers the perfect combination of comfort, functionality, and location. Schedule your showing today!

5421 Gemgold Court, Windermere
$1,500,000
5 Beds ⋅ 4 Baths ⋅ O6433513 MLS
An exceptional residence where refined design and effortless living converge. Meticulously remodeled throughout, the home welcomes you with bespoke modern woodwork gracing the foyer, living room, bedrooms, and loft — a testament to artisan-level craftsmanship rarely found at any price point. The loft has been reimagined as a private cinema, complete with a high-resolution projector, integrated ceiling speaker system, and commanding 120-inch screen, delivering a true theater experience within the comfort of home. Beyond the interiors, the residence reveals its most captivating feature: an infinity-edge pool that appears to dissolve into the tranquil lake beyond, framed each evening by the Disney Magic Kingdom fireworks illuminating the horizon — a nightly spectacle reserved for a fortunate few. Offered FULLY FURNISHED with curated modern pieces, the home transitions seamlessly to its next owner. A three-car garage, perimeter security camera system, and smart lock entry complete the offering, balancing sophistication with modern convenience. A rare opportunity to acquire a turnkey residence of this caliber — private showings available by appointment.

17526 Black Rail Street, Windermere
$1,870,000
6 Beds ⋅ 7 Baths ⋅ O6432932 MLS
Welcome to lakefront living in Windermere! Set along the shores of Lake Burden, this impressive 6-bedroom, 6.5-bath home offers more than 5,100 square feet of living space, a 3-car garage, and a flexible layout designed for both everyday living and entertaining. Featuring the builder’s major upgrades and owned by just one owner since purchased directly from the builder, this home has been exceptionally well maintained. Inside, soaring ceilings and generous living spaces create an immediate sense of openness, while expansive sliding doors bring the beautiful lake views right into the heart of the home. The spacious kitchen is ready for everything from quiet family dinners to a full house of guests. With two primary suites — one downstairs and one upstairs — plus an additional first-floor bedroom, the floor plan offers great flexibility for guests, multigenerational living, or a home office setup. Upstairs, oversized bedrooms, a large bonus room, and private balconies provide even more room to spread out and enjoy the views. The outdoor space is just as special, featuring an extended covered lanai, outdoor kitchen, mature landscaping, and a peaceful lakefront backdrop. Morning coffee by the water, weekend barbecues, sunset dinners — this home was made for Florida living. Located in Lake Burden South, in the heart of Windermere, this home offers a peaceful residential setting with convenient access to shopping, dining, entertainment, and everything the area has to offer. Big home, beautiful setting, fantastic layout — and a lake view that never gets old. Come see this one in person!

7467 Lake Albert Drive, Windermere
$749,000
4 Beds ⋅ 3 Baths ⋅ O6433234 MLS
A distinctive one-story Windermere retreat in Roberts Landing, set on an oversized 1.01-acre corner parcel with peek-a-boo lake views. The split-bedroom floor plan offers formal living and dining areas, an open kitchen/family-room configuration, high ceilings, crown molding and a wood-burning fireplace. French and sliding doors open to an expansive screened outdoor living area featuring a private pool, outdoor kitchen, grill, propane fire pit and dedicated dog run. The property also offers mature landscaping, oak and fruit trees, a workshop area, EV charging and substantial usable land. Be in one of the best school districts in Central Florida and in the highly desirable area of Windermere. Be close to everything but feel like you are miles away from the crowds. House was photographed with furniture but house is currently empty.

9237 Mcdavid Court, Windermere
$4,500,000
4 Beds ⋅ 5 Baths ⋅ O6425262 MLS
Experience luxury living in this custom-built Tuscan-style estate located in the exclusive gated community of Chain Du Lac in Windermere. Situated on a 1.06-acre lot, this exceptional home offers over 6,000 square feet of living space with four bedrooms and five full baths. From the grand arched wood entry doors and soaring 15-foot ceilings to the floor-to-ceiling windows overlooking the pool, every detail reflects quality craftsmanship and timeless elegance. The open-concept floor plan features a gourmet kitchen with Wolf and Thermador appliances, dual islands, a walk-in pantry, a private guest suite with separate entrance, a dedicated movie room and spacious living areas designed for entertaining. The screened outdoor living space includes automatic screens, a fully equipped summer kitchen, a brand-new pool and a large fenced backyard. The luxurious primary suite offers a double-sided fireplace, spa-inspired bath, oversized walk-in closet and an adjacent flex space perfect for an office or gym. Additional highlights include a three-car garage with EV charger, a separate one-car garage, custom millwork throughout and smart home technology controlling approximately 85% of the home.

12237 Park Avenue, Windermere
$1,995,000
6 Beds ⋅ 6 Baths ⋅ O6432910 MLS
Welcome to 4282 McKinnon Rd, a beautifully updated Windermere estate offering exceptional space, privacy, and flexibility on approximately 1.15 acres—with NO HOA. Featuring 6 bedrooms, 6 baths, nearly 5,900 square feet of living space, a private pool, and 3-car garage, this custom home combines an impressive floor plan with extensive recent improvements. Move-in ready and refreshed inside and out, the home features new windows and doors, new interior and exterior paint, new flooring, new AC systems, a new water heater, and a beautifully renovated pool. The thoughtfully designed floor plan is a standout, beginning with a spacious first-floor primary suite offering privacy and convenience. Also on the main level is a separate guest suite, ideal for visitors or multigenerational living, along with a private dedicated office for working from home. Generous living and entertaining spaces are filled with natural light, while the spacious kitchen offers abundant cabinetry, a center island, walk-in pantry, breakfast bar, and casual dining area. Upstairs, a junior primary suite with a private balcony creates another inviting retreat. Additional bedrooms provide plenty of room for family and guests, while the large bonus room over the garage offers endless possibilities as a home theater, game room, fitness studio, playroom, or additional living space. Step outside to enjoy the Florida lifestyle from the covered lanai and renovated private pool, surrounded by an expansive homesite and mature landscaping. With over an acre to enjoy and NO HOA, there is a rare sense of freedom, privacy, and breathing room. Offering extensive updates, multiple bedroom suites, a private office, oversized bonus room, pool, 3-car garage, over an acre of land, and NO HOA, 4282 McKinnon Rd delivers an exceptional combination of space and versatility in sought-after Windermere.

4282 Mckinnon Road, Windermere
$5,500,000
6 Beds ⋅ 8 Baths ⋅ S5155388 MLS
Virtually Staged. Pre-Construction. To be built. This is where high-end living meets possibility. A lakefront estate currently under construction in Windermere, set on the shores of Lake Olivia with wide, unobstructed water views and rare privacy. This future residence will have 6 bedrooms, 6 full baths, and 2 half baths across 6,400+ sq ft, with 12’ ceilings on the main level, 10’ ceilings above, and expansive windows designed to frame the lake. Planned features include a gourmet kitchen with premium cabinetry and quartz surfaces, dual primary suites, private elevator, theater room, wet bar, and 4-car garage. Outdoor living will include a resort-style lanai, summer kitchen, custom pool and spa, and a private dock with direct lake access. Set on approximately 1.6+ acres in one of Windermere’s most desirable locations, this is a rare opportunity to secure a brand-new lakefront residence before completion.

1330 Lake Olivia, Windermere
$3,990,000
6 Beds ⋅ 7 Baths ⋅ O6430081 MLS
Welcome to this beautifully furnished luxury residence in the guard-gated community of Casabella in Windermere. Situated on a private half-acre homesite, this impressive Toll Brothers Villa Divina model offers approximately 6,881 square feet of thoughtfully designed living space featuring 6 bedrooms, and 7 full bathrooms. The home showcases elegant architectural details, soaring ceilings, abundant natural light, and expansive living areas designed for both everyday comfort and entertaining. The gourmet kitchen features premium appliances, custom cabinetry, an oversized island, generous workspace, and a seamless connection to the family room and dining areas. The first-floor primary suite provides a private retreat with a spa-inspired bathroom featuring dual vanities, a walk-in shower, and spacious closet areas. Additional bedrooms, a second-floor media room, loft, office, and flexible living spaces provide exceptional versatility. The outdoor living area features a private in-ground pool, covered lanai, and beautifully landscaped surroundings. Additional highlights include a three-car garage, tile roof, refined finishes, abundant storage, and carefully selected furnishings throughout. Offered fully furnished, this residence provides a seamless opportunity to enjoy Windermere living in one of Central Florida’s desirable gated communities. Conveniently located near premier shopping, dining, golf, entertainment, major roadways, and area attractions, this Casabella estate combines elegance, comfort, and convenience.

4201 Isabella Circle, Windermere
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