Town Of Windermere Real Estate

Town Of Windermere Real Estate

Welcome to the charming Town of Windermere, a picturesque community nestled in the heart of Orange County, Florida. Known for its stunning lakes, lush landscapes, and friendly atmosphere, Windermere offers a unique blend of suburban tranquility and vibrant lifestyle opportunities. With its rich history dating back to the late 1800s, this enchanting town has evolved into a sought-after destination for families, professionals, and retirees alike.

Windermere is renowned for its beautiful waterfront properties, many of which boast breathtaking views of the Butler Chain of Lakes. Residents enjoy a wealth of recreational activities, from boating and fishing to hiking and biking along scenic trails. The town’s commitment to preserving its natural beauty is evident in the meticulously maintained parks and green spaces, perfect for family picnics or leisurely strolls with your furry friends.

The community is also home to a variety of top-rated schools, making it an ideal location for families seeking quality education. With a charming downtown area filled with boutique shops, delightful cafes, and local eateries, Windermere fosters a strong sense of community and connection among its residents.

Conveniently located just a short drive from Orlando, Windermere offers easy access to world-class attractions, shopping, and dining, while still providing a serene retreat away from the hustle and bustle of city life. Whether you’re looking for a peaceful place to call home or an active lifestyle surrounded by nature, the Town of Windermere has something for everyone. Discover the magic of this enchanting community and make it your next home!

Newest Listings in Town Of Windermere

$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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