Windermere Homes with Sailboat Water Water Frontage

Welcome to Windermere, Florida, a hidden gem nestled in Orange County that offers a unique blend of luxury living and serene natural beauty. Known for its picturesque landscapes and tranquil ambiance, Windermere is the perfect escape from the hustle and bustle of city life, while still being conveniently located near Orlando's vibrant attractions.

One of the standout features of Windermere is its stunning homes with sailboat water frontage. Imagine waking up each morning to breathtaking views of the water, where you can indulge in your passion for sailing or simply enjoy the calming presence of the lake. These waterfront properties not only provide direct access to some of Florida’s most beautiful waterways but also offer a lifestyle that embraces outdoor activities, from fishing and kayaking to leisurely sunset cruises.

The community is renowned for its top-notch schools, lush parks, and charming local shops, making it an ideal place for families and individuals alike. Windermere’s commitment to preserving its natural surroundings is evident in the pristine lakes and scenic trails that invite residents to explore the great outdoors.

Whether you're searching for a luxurious estate or a cozy family home, Windermere’s real estate market has something for everyone. With its stunning sailboat water frontage properties, you can experience the ultimate Florida lifestyle, where every day feels like a vacation. Discover the magic of Windermere—where your dream home awaits amidst the beauty of nature and the allure of waterfront living.

Newest Windermere Homes with Sailboat Water Water Frontage

$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

$3,900,000

5 Beds ⋅ 5 Baths ⋅ Windermere Town SubDv. ⋅ 34786 Zip Code

Pre-Construction. To be built. Positioned along the coveted Butler Chain of Lakes, this waterfront residence offers an exceptional opportunity to live in the Town of Windermere. Boasting approximately 85 feet of private frontage, The property captures sweeping views across Wauseon Bay. Permits have been approved including a 900 sf covered boat dock with lift. There are 2 primary suites, one on the 1st floor and one on the 2nd that open to a private balcony and patio respectively overlooking the water creating a serene retreat. All secondary bedrooms have lake views and balconies. Open floor plan with 2 story great room and massive windows throughout. 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. ** Also listed as vacant land MLS S5147532 for $1,650,000

212 W 1st Avenue, Windermere

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