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 lakes and lush landscapes, Windermere offers a serene lifestyle that is both luxurious and inviting. This charming town is not just a place to live; it’s a community where neighbors become friends and outdoor adventures await at every turn.

Among the many desirable features of Windermere, the Homes with Tennis Court(s) community stands out as a perfect blend of elegance and active living. Imagine waking up in your stunning home, surrounded by beautiful architecture and manicured lawns, with the convenience of your very own tennis court just steps away. Whether you are a seasoned player or a casual enthusiast, having access to a tennis court within your community fosters a vibrant social atmosphere and encourages a healthy lifestyle.

Windermere is renowned for its top-rated schools, unique boutiques, and delightful dining options, making it a hub for families and professionals alike. The community is also conveniently located near major highways, providing easy access to the bustling city of Orlando, theme parks, and world-class shopping.

As you explore the Homes with Tennis Court(s) community, you’ll find a variety of exquisite properties that cater to diverse tastes and preferences. Each home is designed with comfort and luxury in mind, ensuring you have the perfect sanctuary to unwind after an active day.

Come and experience the charm of Windermere, where the beauty of nature meets the thrill of an active lifestyle. Your dream home awaits in this idyllic community!

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

101 Lee Street, Windermere
$1,300,000
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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