Town Of Windermere Real Estate

Town Of Windermere Real Estate

Welcome to the enchanting Town of Windermere, a picturesque gem nestled in Orange County, Florida. Known for its stunning lakes, lush landscapes, and serene atmosphere, Windermere offers an idyllic setting for families, retirees, and anyone seeking a peaceful retreat from the hustle and bustle of city life.

This charming town is famous for its stunning waterfront properties and luxurious homes, many of which boast breathtaking views of the shimmering Butler Chain of Lakes. With a rich history dating back to the early 1900s, Windermere has maintained its small-town charm while embracing modern amenities, making it a perfect blend of tradition and contemporary living.

Windermere's community spirit is palpable, with a variety of local events and festivals that bring residents together throughout the year. The town is home to beautiful parks, scenic walking trails, and top-rated schools, ensuring that families have everything they need to thrive. For those who love the outdoors, the nearby lakes offer opportunities for boating, fishing, and kayaking, while the lush golf courses provide a perfect escape for golf enthusiasts.

Conveniently located just a short drive from the vibrant city of Orlando, residents of Windermere enjoy access to world-class dining, shopping, and entertainment, while still being able to retreat to their tranquil oasis at the end of the day. Whether you're looking to buy your dream home or simply explore the area, Windermere promises a lifestyle of comfort, community, and natural beauty. Come discover why this charming town is one of Florida's best-kept secrets!

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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