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

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

Welcome to the enchanting Town of Windermere, nestled in the heart of Orange County, Florida. Known for its picturesque landscapes and serene lakes, this charming community offers a unique blend of luxury and tranquility, making it an ideal place to call home. With its lush greenery and stunning waterfront views, Windermere is a haven for those seeking a peaceful yet vibrant lifestyle.

One of the standout features of this delightful town is its exclusive homes with tennis courts. Imagine waking up to the sun-drenched Florida mornings and stepping outside to your own private court, perfect for honing your skills or enjoying a friendly match with neighbors. These residences are designed not just for comfort but for an active lifestyle, offering ample space for entertaining and relaxation.

The community features in Windermere are second to none. Residents enjoy access to beautifully maintained parks, scenic walking trails, and sparkling lakes, all of which foster a sense of community and promote outdoor living. The nearby Windermere Recreation Center provides a hub for social activities, fitness classes, and community events, ensuring there's always something happening.

Families will appreciate the highly-rated schools in the area, making Windermere an excellent choice for those with children. Plus, with its proximity to Orlando, residents can easily access world-class dining, shopping, and entertainment options.

In Windermere, you’re not just purchasing a home; you’re investing in a lifestyle filled with charm, community, and active living. Come discover the magic of Windermere, where your dream home awaits!

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

$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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