Windermere Homes with Sailboat Water Water Frontage

Windermere Homes with Sailboat Water Water Frontage

Welcome to Windermere, Florida – a picturesque gem nestled in Orange County that perfectly blends the charm of small-town living with the allure of upscale amenities. Known for its stunning lakes, lush landscapes, and vibrant community, Windermere is an idyllic destination for those seeking a serene lifestyle just a stone's throw from the excitement of Orlando.

One of the most captivating features of Windermere is its sailboat water frontage. Imagine waking up to the gentle lapping of water against your dock, with the sun casting shimmering reflections across the lake. Homes in this enchanting area offer direct access to the pristine waters of the Butler Chain of Lakes, making it a paradise for boating enthusiasts and water lovers alike. Whether you're sailing into the sunset or enjoying a peaceful afternoon fishing from your backyard, the waterfront lifestyle here is truly unparalleled.

Windermere's real estate market is characterized by luxurious homes that boast modern designs, expansive outdoor spaces, and breathtaking views. Many properties feature private docks, allowing for easy access to the serene waters. The community is also known for its top-rated schools, picturesque parks, and a welcoming atmosphere that fosters a sense of belonging among residents.

With its combination of natural beauty, recreational opportunities, and vibrant community spirit, Windermere is more than just a place to live; it’s a lifestyle. Come explore the enchanting waterfront homes that await you in this charming Florida town and discover the perfect backdrop for your next chapter!

Newest Windermere Homes with Sailboat Water Water Frontage

$775,000
3 Beds ⋅ 2 Baths ⋅ Marsh Sub SubDv. ⋅ 34786 Zip Code
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
$3,300,000
4 Beds ⋅ 6 Baths ⋅ Windermere Town SubDv. ⋅ 34786 Zip Code
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
$1,150,000
4 Beds ⋅ 3 Baths ⋅ Windermere Downs SubDv. ⋅ 34786 Zip Code
Nestled within the highly sought-after Windermere Downs community this Lake-Access Residence, sitting on .74 acres, offers the ultimate Florida lifestyle surrounded by canopy-shaded, oak tree-lined streets. A walkway lined with custom pavers leads to the front door, where you're welcomed by the formal living and dining rooms on the right. Large bay windows let in plenty of natural light, creating a bright and inviting space. A barn door opens to the kitchen, which features travertine flooring, a gas stove, and stainless steel appliances—great for home cooking or entertaining. The living room is a cozy gathering space, with three skylights bringing in extra light and an Authentic Old Chicago Brick fireplace that adds warmth and character. The primary bedroom is spacious, with French doors that open to the screened-in pool lanai, offering easy access to outdoor living. The primary bathroom includes a Kohler clawfoot tub and Kohler fixtures, adding a touch of quality and comfort. Out back, the screened-in pool with travertine deck and patio provides a great spot to relax, while the larger open travertine patio off of the kitchen is perfect for hosting family and friends. The backyard is full of greenery, offering both beauty and privacy and an irrigation well. Home includes a 1,000 Underground Large Gas Tank and Full House Propane Generator and a hybrid water heater. A two-car attached garage is complemented by a large detached deep second two-car garage, perfect for extra parking, storage, or keeping your favorite lake-living toys. Living in Windermere Downs means access to a private community boat ramp, where you can launch your boat and explore Lake Down and the Butler Chain of Lakes. The community amenities include a dock with a roped-off swim area, tennis courts, pickleball courts, community park, playground—plenty of options for outdoor fun. Recent updates include whole house re-pipe (2026), freshly painted exterior and new soffit (2026).

2009 Woody Drive, Windermere
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