Town Of Windermere Homes with Lake Front Water Frontage

Town Of Windermere Homes with Lake Front Water Frontage

Welcome to the enchanting Town of Windermere, a picturesque gem nestled in Orange County, Florida. Known for its stunning natural beauty and vibrant community, Windermere offers a serene escape from the hustle and bustle of city life, while still being conveniently located near Orlando's attractions.

One of the most captivating features of this charming town is its array of beautiful homes with lakefront waterfrontage. Imagine waking up to the gentle lapping of water against your private dock, with breathtaking views of the shimmering lakes that Windermere is famous for. These homes provide not just a residence, but a lifestyle that embraces outdoor living, where fishing, boating, and sunset strolls along the water become part of your daily routine.

Windermere boasts a rich history and a close-knit community feel, with tree-lined streets and a welcoming atmosphere. The town is dotted with local boutiques, cozy cafes, and parks that encourage an active lifestyle. Families will appreciate the highly-rated schools and safe neighborhoods, making it an ideal place to raise children.

Whether you’re seeking a modern masterpiece with all the latest amenities or a charming lakeside cottage with character, Windermere has something to offer everyone. With its stunning waterfront properties, you can enjoy the tranquility of nature while being just a stone's throw away from the excitement of Orlando. Discover your dream home in Windermere, where every day feels like a vacation!

Newest Town Of Windermere Homes with Lake Front Water Frontage

$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