Town Of Windermere Homes with Lake Front Water Frontage

Town Of Windermere Homes with Lake Front Water Frontage

Welcome to the picturesque Town of Windermere, a hidden gem nestled in the heart of Orange County, Florida. Known for its stunning lakes and serene landscapes, this charming town offers a unique blend of small-town warmth and modern sophistication. With its lush greenery and tranquil ambiance, Windermere is the perfect retreat for those seeking a peaceful lifestyle while remaining close to the vibrant city of Orlando.

One of the most enchanting features of Windermere is its breathtaking lakefront properties. Imagine waking up each morning to the soothing sounds of water lapping at the shore and enjoying panoramic views of shimmering lakes from your own backyard. Homes with lakefront waterfrontage here are not just residences; they are a lifestyle choice. These exquisite properties often boast private docks, allowing residents to indulge in boating, fishing, or simply soaking in the beauty of Florida’s natural surroundings.

The community of Windermere is also known for its exceptional schools, family-friendly parks, and a variety of recreational activities. Whether you’re strolling along the scenic paths, participating in local events, or enjoying the vibrant culture that surrounds you, there’s always something to love about this charming town.

With its inviting atmosphere and stunning waterfront homes, Windermere is not just a place to live; it’s a place to thrive. Discover the magic of lakefront living in Windermere, where every day feels like a vacation, and the beauty of nature is always at your doorstep. Come and experience the allure of this idyllic community; your dream home awaits!

Newest Town Of Windermere Homes with Lake Front Water Frontage

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

Start Your Search