Windermere Downs Homes 

Windermere Downs, nestled in the charming town of Windermere, FL, is a coveted real estate gem offering an exceptional living experience. This upscale community boasts an array of elegant homes that exude timeless charm and modern comfort. The highlight of Windermere Downs is its stunning lakefront properties, providing residents with breathtaking views and direct access to the serene Butler Chain of Lakes.

Apart from its picturesque lakefront setting, Windermere Downs offers a plethora of amenities that cater to residents' every need. From well-manicured parks and tennis courts to jogging trails and playgrounds, the neighborhood is designed for an active and social lifestyle. Residents can indulge in waterfront activities, such as boating and fishing, while also enjoying the lush green spaces for relaxation and gatherings.

The community's allure is further enhanced by its proximity to numerous attractions and amenities. Within a short drive, residents can explore the magic of Walt Disney World, the upscale shopping at The Mall at Millenia, and the vibrant dining scene of Orlando. Additionally, excellent schools, healthcare facilities, and convenient shopping centers are within easy reach, making Windermere Downs an idyllic blend of luxury, natural beauty, and convenience.

Available Windermere Downs Homes For Sale

$1,200,000
4 Beds ⋅ 3 Baths ⋅ O6422132 MLS
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

Courtesy of REVEL REALTY LLC

$679,000
3 Beds ⋅ 3 Baths ⋅ O6421738 MLS
Under contract-accepting backup offers. Welcome to 2053 Woody Drive, where timeless Windermere charm meets modern updates. From the moment you arrive, you’ll appreciate the mature trees, spacious homesite, and the peaceful lifestyle this sought-after community offers. Through Windermere Downs HOA you will have access to a private beach -Chain of Lakes- Step inside and you’ll find a beautifully updated kitchen that’s truly the heart of the home—perfect for everyday living and entertaining family and friends. The generous living spaces, oversized lot and mature landscaping, with a prime location make this home an incredible opportunity for anyone looking to enjoy everything- Windermere. ROOF: 2020 NEW ELECTRIC PANEL (2026)-AC 2019

2053 Woody Drive, Windermere

Courtesy of LPT REALTY, LLC

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