Town Of Windermere Real Estate

Town Of Windermere Real Estate

Welcome to the Town of Windermere, a picturesque gem nestled in Orange County, Florida. Known for its stunning lakes, lush landscapes, and a strong sense of community, Windermere offers a unique blend of suburban tranquility and vibrant living. With its charming streets lined with oak trees and beautiful homes, this town is the perfect place for families, retirees, and anyone looking to enjoy the serene Florida lifestyle.

Windermere is renowned for its scenic beauty, boasting access to several pristine lakes, including the enchanting Lake Butler and Lake Bessie. These sparkling bodies of water not only provide opportunities for boating, fishing, and swimming but also create a stunning backdrop for leisurely strolls and picnics at the local parks. The town’s commitment to preserving its natural surroundings is evident in its beautifully maintained green spaces and walking trails, making it a haven for outdoor enthusiasts.

In addition to its natural allure, Windermere is home to a thriving community spirit. The town hosts numerous events throughout the year, fostering connections among residents and creating a welcoming atmosphere. Local shops, boutique cafes, and fine dining establishments offer a delightful array of options for dining and shopping, ensuring that you have everything you need within reach.

Families will appreciate the highly-rated schools in the area, which are known for their exceptional educational programs and dedicated staff. With a focus on community, quality of life, and a picturesque setting, the Town of Windermere is not just a place to live—it’s a place to thrive. Discover your dream home in this enchanting town and experience the best that Florida living has to offer!

Newest Listings in Town Of Windermere

101 Lee Street, Windermere
$1,395,000
5 Beds ⋅ 4 Baths ⋅ O6437573 MLS
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