Windermere Town Homes for Sale

Windermere Town Homes for Sale

Welcome to Windermere Town, a picturesque subdivision nestled in the heart of Orange County, Florida. Known for its charming small-town atmosphere and stunning natural beauty, Windermere offers a unique blend of tranquility and modern conveniences. This idyllic community is surrounded by pristine lakes and lush landscapes, making it a haven for nature lovers and outdoor enthusiasts alike.

Windermere Town boasts a variety of homes for sale, catering to diverse preferences and lifestyles. From elegant single-family residences to contemporary townhomes, each property reflects the area’s commitment to quality and design. Many homes feature spacious layouts, gourmet kitchens, and serene outdoor spaces perfect for entertaining or unwinding after a long day. With a strong emphasis on community, Windermere Town fosters a friendly environment where neighbors become friends.

Residents of Windermere Town enjoy access to top-rated schools, vibrant local shops, and delightful dining options, all just a stone's throw away. The community is also conveniently located near major highways, providing easy access to the bustling attractions of Orlando, including theme parks, shopping centers, and cultural experiences.

Whether you're looking for a family home or a serene retreat, Windermere Town offers an exceptional living experience that combines luxury with a laid-back lifestyle. Explore the homes for sale in this charming subdivision and discover your dream home in one of Florida's most sought-after communities. Come and experience the magic of Windermere Town, where every day feels like a vacation!

Newest Windermere Town Homes for Sale

$3,300,000
4 Beds ⋅ 6 Baths ⋅ O6439554 MLS
Experience the extraordinary lifestyle of waterfront living in the heart of historic Windermere. Set on approximately 2/3rd of an acre with an impressive 100 feet of frontage on the renowned Butler Chain of Lakes, This home offers a rare combination of luxury, privacy, space, and direct access to one of Central Florida's most coveted boating destinations. This beautifully appointed custom residence offers nearly 4,000 square feet of living space with four bedrooms, soaring ceilings, elegant formal living and dining areas, a spacious kitchen and family room, game room, wet bar, and a thoughtfully designed split-bedroom floor plan. Rich wood and travertine marble flooring, refined architectural details, generous windows bath the main living areas with natural light, and multiple gathering spaces create an atmosphere that is both sophisticated and inviting. A whole house natural gas generator and city water provide peace of mind knowing your family is porotected during the worst Florida storms The primary suite is a private retreat, featuring a luxurious bath with spa-style amenities, a generous walk-in closet, and a serene connection to the surrounding grounds. The home's open living spaces are designed for effortless entertaining, while the separate formal areas provide an elegant setting for more intimate occasions. Outside, the property becomes a private resort. Enjoy the pool and spa surrounded by mature landscaping and expansive outdoor living areas. The private boathouse has a covered boat lift with a "Touchless" Canvas Boat cover that protects your boat from animals and the elements , 2 Jet Ski lifts, Sitting area with fan and mood lighting, Garden hose with city water for cleaning, seawall that has a small beach carved in to allow for playing in the sand of the crystal clear lake, and direct lake access make this an exceptional opportunity for boating, water sports, fishing, and sunset cruises throughout the Butler Chain. Life here extends beyond the property itself. Located on one of Windermere's most desirable paved streets, the home is just moments from the charm of historic downtown Windermere, with its tree-lined streets, local shops, restaurants, parks, community amenities, and small-town atmosphere. Residents enjoy the unique privilege of living among the lakes while remaining conveniently connected to Central Florida's premier dining, shopping, entertainment, and attractions. The Town of Windermere describes its lakes as a beloved community privilege, with the Butler Chain comprising a remarkable network of interconnected waterways. Whether you're enjoying coffee overlooking the water, entertaining beside the pool, stepping aboard your boat for an afternoon on the chain, or returning home to the peaceful canopy of mature trees, this home embodies the very best of Windermere lakefront living. Original house was built in 1961 but completely expanded and remodeled in 2000 - present owner made upgrades in 2023 - call for details

515 W 2nd Avenue, Windermere
$850,000
3 Beds ⋅ 3 Baths ⋅ O6439213 MLS
Welcome to your immaculate and charming home in the heart of Downtown Windermere, where timeless traditional style meets modern convenience. Nestled beneath beautiful mature oak trees, this inviting property offers a spacious yard and a welcoming front porch perfect for relaxing in a pair of rocking chairs and enjoying the peaceful surroundings. Step through the front door into a light-filled interior featuring freshly painted walls and warm wood-look tile throughout the first floor. Your remodeled kitchen is both stylish and functional, featuring stainless steel appliances, a gas range, and granite countertops, perfect for everyday living and entertaining. Upstairs, the home showcases its original hardwood floors throughout, adding warmth and character. The spacious primary suite features a beautifully updated bathroom with custom cabinetry, walk in closets, granite countertops, and quality finishes. Two additional bedrooms and a full bathroom complete the second floor, providing plenty of space for family, guests, or a home office. The expansive, fully fenced backyard offers endless possibilities. There is ample room for a pool, playset, fire pit, outdoor games, and entertaining creating a wonderful private space to enjoy Florida’s beautiful weather. Ideally located within walking distance of the Windermere Farmers Market, local shops, restaurants, and more, with beautiful Lake Butler just blocks away, this home offers the best of the Old Windermere lifestyle. Additional highlights include a new roof installed in 2025, water softner, and newer AC unit. Don’t miss the opportunity to make this special home your own. Schedule your private showing today!

706 Oakdale Street, Windermere
$1,895,000
4 Beds ⋅ 5 Baths ⋅ O6437093 MLS
Set along the shores of Lake Bessie in the heart of Downtown Windermere, this contemporary lakefront residence pairs clean architectural design with effortless single-story living. Completed in 2024, the home offers 2,868 square feet with four bedrooms, each featuring a private en-suite bath, along with a dedicated home office and an open-concept layout designed around the water views. Inside, wide-plank white oak hardwood floors, soaring ceilings and expansive black-framed glass doors create a bright, modern aesthetic while drawing the lake into the main living areas. The European-inspired kitchen anchors the home with an oversized island, quartz countertops, sleek cabinetry and smart appliances, flowing seamlessly into the dining and living spaces for easy everyday living and entertaining. The primary suite continues the home's refined design with a spa-like bath featuring a freestanding soaking tub, floating wood vanity, dual sinks and an oversized walk-in shower. Contemporary finishes and a light, neutral palette carry throughout the residence. Outdoors, a private heated pool and spa create a resort-like retreat, while the lakefront setting offers approximately 100 feet of frontage on Lake Bessie with the option to add a private dock. There is also a two car covered parking area. From morning sunrises and lake breezes to afternoons spent boating or fishing, the setting captures the relaxed lifestyle that makes Windermere so desirable. Just a short walk or golf cart ride from Downtown Windermere, the home places the weekly farmers market, parks, tennis courts, boat ramp to Lake Butler and Bessie, dining, local shops and a brewery within easy reach. Modern architecture, direct lake frontage and an exceptional in-town location come together for a rare opportunity to experience contemporary waterfront living in Windermere

930 East Boulevard, Windermere
$1,600,000
4 Beds ⋅ 2 Baths ⋅ S5155372 MLS
Virtually Staged. Positioned along the coveted Butler Chain of Lakes, this waterfront residence offers an exceptional opportunity in the Town of Windermere. Boasting approximately 65 feet of private frontage and a dedicated boat dock, the property captures sweeping views across Wauseon Bay. The current home is in good condition and ready to move in. The interior showcases a refined yet comfortable cabin style with some modern flair and a open-concept layout, four bedrooms and thoughtfully updated living spaces. A beautifully appointed kitchen features custom cabinetry, quartz surfaces, and premium appliances, while restored hardwood flooring adds timeless character throughout. The primary suite opens to a private balcony overlooking the water, creating a serene retreat. Outdoors, the property offers a fenced yard and a rare combination of circular driveway and rear-access garage. Just moments from Windermere’s parks, tennis courts, farmers market, and private boat ramp, this home embodies the charm and lifestyle of lakefront living in one of Central Florida’s most desirable communities. There is an option to build a new home and boat dock, Permits have been approved to build a new modern home 3,500sf and 900sf covered boat dock with lift. This option would be $3.9MM

212 W 1st Avenue, Windermere
$1,099,000
4 Beds ⋅ 3 Baths ⋅ S5147648 MLS
A beautiful home in the heart of downtown Windermere, this property offers four bedrooms and three bathrooms with a perfect blend of comfort, style, and convenience. The main residence features hardwood floors throughout, spacious living areas, and large sliding doors that open to a serene, beautiful backyard — ideal for both entertaining and unwinding. An added highlight is the fully equipped separate dwelling on the property offering a private one-bedroom, one-bathroom space perfect for entertaining, or a home office/gym. Situated just minutes from local shops, parks, boat ramps, and the renowned Windermere Chain of Lakes, this home places the best of the area right at your doorstep.

715 Magnolia Street, Windermere
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