Town Of Windermere Real Estate

Town Of Windermere Real Estate

Welcome to the enchanting Town of Windermere, a hidden gem nestled in the heart of Orange County, Florida. Known for its picturesque landscapes and serene lakes, Windermere offers a unique blend of small-town charm and modern conveniences. With its stunning waterfront properties and lush greenery, this vibrant community is the perfect place for those seeking a tranquil lifestyle without sacrificing accessibility to the excitement of the greater Orlando area.

Windermere is renowned for its beautiful homes, many of which boast breathtaking views of the pristine Butler Chain of Lakes. Whether you're looking for a luxurious estate or a cozy family home, the diverse real estate options here cater to a variety of tastes and budgets. The subdivision features well-maintained neighborhoods adorned with tree-lined streets, creating a warm and inviting atmosphere that residents cherish.

In addition to its scenic beauty, Windermere is home to top-rated schools, making it an ideal location for families. The town's commitment to maintaining a strong sense of community is evident through its numerous parks, recreational facilities, and local events that bring neighbors together throughout the year.

Outdoor enthusiasts will delight in the abundance of activities available, from boating and fishing on the lakes to hiking and biking on the surrounding trails. With its close proximity to Orlando's world-famous attractions, shopping, and dining, Windermere truly offers the best of both worlds.

Discover the allure of the Town of Windermere, where a peaceful lifestyle awaits you amidst the beauty of Central Florida. Come experience the magic of this charming community and find your dream home today!

Newest Listings in Town Of Windermere

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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