Town Of Windermere Homes for Sale

Town Of Windermere Homes for Sale

Welcome to the Town of Windermere, a picturesque enclave nestled in the heart of Orange County, Florida. Renowned for its serene lakes and lush landscapes, Windermere is a charming town that perfectly blends small-town warmth with modern conveniences. This vibrant community is not just a place to live; it’s a lifestyle choice that offers residents a unique blend of tranquility and activity.

Windermere boasts a variety of homes for sale, catering to diverse tastes and lifestyles. From elegant waterfront estates with stunning views of the Butler Chain of Lakes to cozy family homes in friendly neighborhoods, there’s something for everyone. Each property reflects the town's commitment to quality living, with many featuring spacious layouts, contemporary designs, and beautifully manicured gardens. Whether you’re looking for a luxurious retreat or a charming starter home, Windermere has you covered.

The town’s prime location also means you’re just a stone’s throw away from Orlando’s bustling attractions, yet far enough to enjoy a peaceful retreat at the end of the day. Residents can indulge in outdoor activities like boating, fishing, and hiking, or savor the local dining scene that showcases the best of Florida’s culinary offerings.

With its strong sense of community, excellent schools, and an array of recreational opportunities, the Town of Windermere is not just a place to call home—it’s a place to thrive. Explore the available homes for sale and discover the perfect backdrop for your next chapter in this idyllic Florida town. Your dream home awaits!

Newest Town Of Windermere Homes for Sale

$1,395,000
5 Beds 4 Baths Town Of Windermere SubDv. 34786 Zip Code
Virtually Staged. Nestled in the heart of Windermere, and featuring more than $300,000 in recent improvements including a brand new roof September 2026, this character-rich home offers nearly 4,200 square feet of versatile living space just steps from Windermere's charming downtown. Situated on nearly half an acre, this five-bedroom, four-bath residence pairs distinctive architectural character with thoughtful updates, abundant natural light and exceptional flexibility. The main living level brings together the kitchen, dining area and expansive great room, where high ceilings and a striking gas fireplace create a warm and inviting gathering space. Four sets of beautiful, new sliding glass doors open to an expansive balcony overlooking the screened pool, extending the living and entertaining space outdoors. A private-entry in-law suite adds another compelling feature to this unique home, offering exceptional possibilities for multigenerational living, extended-stay guests or a private work-from-home space. This lower level includes two bedrooms, two full baths, spacious living area, and a wet bar with mini-refrigerator. The fifth bedroom, currently enjoyed as a home gym, is also perfect for an office, playroom or hobby room. Privately positioned on its own level, the generous primary suite provides a peaceful retreat with a spacious sitting area and private balcony. Recent, significant investments throughout the property include new windows and doors, three newer HVAC units, new roof September 2026, interior and exterior paint, updated astroturf in the side yard, as well as numerous other improvements, all while preserving the character and scale of this established Windermere home. The pool and patio, featuring a screen enclosure just added in 2020, and newer cabanas, perfect for entertaining, relaxing and enjoying Florida living year-round. The location offers a lifestyle all its own, with downtown Windermere’s weekly farmers market, community events, parks and small-town charm just a short walk or golf cart ride away. Town of Windermere residents also enjoy private access to a boat ramp on the renowned Butler Chain of Lakes, as well as to the town tennis and pickleball courts! Zoned for top rated Windermere Elementary and Olympia High, and situated just minutes from the shopping and dining of The Grove at Isleworth and Restaurant Row, this distinctive home delivers a rare combination of space, flexibility, and character all in a desirable, downtown Windermere location.

101 Lee Street, Windermere

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