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

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

Welcome to the Town of Windermere, a picturesque community nestled in the heart of Orange County, Florida. Known for its stunning lakes, lush landscapes, and charming small-town atmosphere, Windermere offers residents a unique blend of tranquility and modern living. As you explore this vibrant town, you’ll find a variety of homes that cater to diverse lifestyles, including those seeking the perfect blend of luxury and leisure.

One of the standout features of Windermere is its exclusive Homes with Tennis Courts community. Imagine stepping out of your beautifully designed home and onto your private tennis court, ready to enjoy a friendly match or hone your skills in the sun-drenched Florida weather. This community is perfect for tennis enthusiasts and families alike, fostering a healthy, active lifestyle right at your doorstep.

Beyond the courts, Windermere boasts an array of community amenities that enhance the living experience. Residents can enjoy scenic walking trails, lush parks, and access to the sparkling lakes that define the area. The town also hosts a variety of events throughout the year, bringing neighbors together and creating a strong sense of community.

With its prime location just a short drive from Orlando, Windermere is also conveniently close to world-class shopping, dining, and entertainment options. Whether you’re looking for a serene retreat or an active lifestyle, the Town of Windermere offers an exceptional living experience that truly feels like home. Come discover why so many choose to call this charming community their own!

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

Start Your Search