Windermere Homes with Sailboat Water Water Frontage

Welcome to Windermere, Florida – a picturesque town nestled in the heart of Orange County, where charm meets luxury and nature thrives. Known for its serene lakes and lush landscapes, Windermere offers a unique blend of small-town warmth and upscale living. With its stunning waterfront views and vibrant community, this idyllic locale is not just a place to live, but a lifestyle to embrace.

One of the most sought-after features in Windermere is its homes with sailboat water frontage. Imagine waking up to the gentle lapping of waves and the soft glow of sunrise reflecting off the water. These exquisite properties provide direct access to the pristine lakes, allowing you to indulge in sailing, fishing, or simply enjoying a leisurely afternoon on the water. With ample dock space and breathtaking views, these homes are perfect for water enthusiasts and those who appreciate the beauty of nature.

Windermere boasts a range of architectural styles, from modern masterpieces to charming traditional homes, all designed to complement the stunning surroundings. The local community is vibrant, with top-rated schools, boutique shops, and gourmet dining options just a stone's throw away. Plus, the close-knit atmosphere fosters a sense of belonging that makes Windermere truly special.

Whether you’re looking for a serene retreat or an active lifestyle, Windermere’s sailboat waterfront homes offer the perfect blend of luxury and leisure. Experience the magic of lakeside living in this enchanting town, where every day feels like a vacation. Come explore Windermere – your dream home 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