Town Of Windermere Real Estate

Town Of Windermere Real Estate

Welcome to the charming Town of Windermere, nestled in the heart of Orange County, Florida. This picturesque community is known for its stunning lakes, lush landscapes, and a serene atmosphere that feels like a retreat from the hustle and bustle of everyday life. With its rich history and commitment to preserving its natural beauty, Windermere offers a unique blend of small-town charm and modern conveniences.

As you explore the subdivision, you'll find an array of beautiful homes, each reflecting the distinct character of the area. From elegant waterfront properties to cozy family residences, Windermere caters to a variety of lifestyles and preferences. The tree-lined streets and meticulously maintained parks create an inviting environment, perfect for evening strolls or weekend picnics with family and friends.

Windermere is not just about beautiful homes; it’s also a community that values connection and engagement. Residents enjoy access to top-rated schools, local shops, and gourmet dining options, all within a short drive. The town hosts various community events throughout the year, fostering a sense of camaraderie among neighbors and making it easy to forge lasting friendships.

For outdoor enthusiasts, Windermere boasts an abundance of recreational opportunities. With numerous lakes for boating, fishing, and kayaking, along with scenic walking trails, it’s a paradise for those who love to embrace the great outdoors.

Discover the allure of Windermere, where a vibrant community, stunning natural beauty, and a peaceful lifestyle await you. Come and experience the magic of this enchanting town!

Newest Listings in Town Of 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