Town Of Windermere Homes with Tennis Court(s) Community Features

Town Of Windermere Homes with Tennis Court(s) Community Features

Welcome to the picturesque Town of Windermere, nestled in the heart of Orange County, Florida. Known for its charming lakes, lush landscapes, and vibrant community spirit, Windermere is a hidden gem that perfectly combines the tranquility of suburban living with the excitement of nearby urban amenities.

One of the standout features of this enchanting town is its exclusive homes with tennis courts, offering residents a unique blend of luxury and leisure. Imagine waking up each morning in your beautifully designed home, where your private tennis court awaits just steps from your back door. Whether you're a seasoned player or a casual enthusiast, having your own court provides the perfect opportunity to enjoy a friendly match with family and friends, or simply practice your serve in the comfort of your own space.

The community features in Windermere enhance the overall living experience, fostering a sense of belonging and camaraderie among residents. With well-maintained parks, scenic walking trails, and access to stunning lakes, outdoor activities abound. The town's commitment to preserving its natural beauty is evident in its lush green spaces and vibrant landscaping, making it an ideal place for families and individuals alike.

In addition to its recreational offerings, Windermere is conveniently located near top-rated schools, upscale shopping, and fine dining options. With its charming small-town atmosphere and luxurious amenities, the Town of Windermere is not just a place to live; it's a lifestyle waiting to be embraced. Come discover the perfect home with a tennis court in this idyllic community, where every day feels like a vacation!

Newest Town Of Windermere Homes with Tennis Court(s) Community Features

101 Lee Street, 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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