Town Of Windermere Homes with Three+ Story Property Description

Town Of Windermere Homes with Three+ Story Property Description

Welcome to the picturesque Town of Windermere, nestled in the heart of Orange County, Florida. Known for its charming small-town atmosphere and stunning natural beauty, Windermere offers an idyllic lifestyle for families, retirees, and anyone seeking a serene escape from the hustle and bustle of city life.

This enchanting community is surrounded by pristine lakes and lush landscapes, providing residents with ample opportunities for outdoor activities such as boating, fishing, and hiking. Windermere is not just a place to live; it’s a lifestyle defined by tranquility and community spirit. With its tree-lined streets and friendly neighborhoods, you’ll feel right at home from the moment you arrive.

One of the standout features of Windermere is its selection of exquisite homes, particularly those with three or more stories. These spacious properties are designed to maximize both comfort and luxury, often featuring open floor plans, high ceilings, and breathtaking views of the surrounding landscape. Imagine hosting gatherings in your expansive living area or enjoying quiet mornings on a private balcony overlooking the serene waters of Lake Butler.

Many of these stunning homes also come equipped with modern amenities, including gourmet kitchens, spa-like bathrooms, and energy-efficient systems, ensuring that you have everything you need for a contemporary lifestyle. Whether you’re looking for a family home or a retreat to unwind, the three-plus story homes in Windermere cater to diverse tastes and needs.

Discover the charm of Windermere—where your dream home awaits amidst a vibrant community and natural beauty. Come explore the possibilities today!

Newest Town Of Windermere Homes with Three+ Story Property Description

$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