Windermere Homes with Sailboat Water Water Frontage

Welcome to Windermere, Florida—a picturesque gem nestled in Orange County, where idyllic landscapes and serene waters create an enchanting living experience. Known for its charming small-town atmosphere, Windermere boasts tree-lined streets, stunning lakes, and a close-knit community that welcomes newcomers with open arms. With its rich history and vibrant culture, this charming town is the perfect backdrop for your dream home.

One of the standout features of Windermere is its breathtaking sailboat water frontage. Imagine waking up every morning to the gentle lapping of water against your dock, with the promise of endless adventures just a sail away. Homes with sailboat access offer not only a luxurious lifestyle but also an unparalleled connection to nature. Whether you’re an avid sailor or simply enjoy the tranquility of waterfront living, these properties provide a unique opportunity to embrace the beauty of Florida’s lakes.

Windermere is more than just a beautiful place to live; it’s a hub for outdoor enthusiasts and families alike. With an abundance of parks, recreational facilities, and top-rated schools, residents enjoy a wealth of activities right at their doorstep. Plus, the vibrant downtown area offers delightful boutiques, gourmet restaurants, and community events that foster a sense of belonging.

If you’re seeking a home that combines stunning natural beauty with a vibrant community spirit, Windermere is the perfect choice. Explore our selection of homes with sailboat water frontage and discover the lifestyle you’ve always dreamed of—where every day feels like a vacation. Welcome to Windermere, where your waterfront paradise awaits!

$1,200,000

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

Windermere Homes with Sailboat Water Water Frontage

Newest Windermere Homes with Sailboat Water Water Frontage