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 town offers a perfect blend of natural beauty and suburban comfort. Windermere is not just a place to live; it’s a lifestyle that emphasizes community, recreation, and relaxation.

One of the standout features of this idyllic town is its exclusive homes with tennis courts. Imagine stepping out of your beautifully designed home and onto your private court, ready to enjoy a match with friends or family. These residences are crafted for both luxury and leisure, making them perfect for avid tennis players and those who appreciate an active lifestyle.

The community features in Windermere are truly remarkable. Residents enjoy access to lush parks, scenic walking trails, and vibrant community events that foster a strong sense of belonging. The nearby lakes provide opportunities for kayaking, fishing, and enjoying the outdoors, while the charming downtown area offers delightful shops and eateries to explore.

Windermere is also conveniently located near top-rated schools and major highways, making commuting to nearby cities a breeze. Whether you’re seeking a tranquil retreat or an active community, the Town of Windermere with its stunning homes and tennis court amenities is the perfect place to call home. Experience the magic of Windermere, where luxury meets lifestyle in a picturesque setting.

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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