Town Of Windermere Homes with Private Entrance Exterior Features

Town Of Windermere Homes with Private Entrance Exterior Features

Welcome to the enchanting Town of Windermere, nestled in the heart of Orange County, Florida. This picturesque community is renowned for its stunning lakes, lush landscapes, and charming small-town ambiance, making it one of the most desirable places to call home in Central Florida. With its proximity to the vibrant city of Orlando, residents enjoy the perfect blend of serene suburban living and easy access to urban conveniences.

Windermere boasts a variety of beautifully designed homes, many of which feature private entrance exterior designs that enhance both privacy and curb appeal. These elegant residences often showcase lush gardens and meticulously landscaped yards, providing an inviting atmosphere for family gatherings and outdoor entertaining. Imagine stepping through your own private entrance, leading you into a sanctuary of comfort and style.

The community is characterized by its friendly neighborhoods, where residents take pride in their homes and enjoy a strong sense of community. With top-rated schools, picturesque parks, and a variety of recreational activities, Windermere is perfect for families, retirees, and everyone in between. The nearby Butler Chain of Lakes offers endless opportunities for boating, fishing, and enjoying the great outdoors.

Whether you're seeking a tranquil retreat or a vibrant community, the Town of Windermere has something for everyone. Discover your dream home in this idyllic setting, where the charm of small-town living meets the luxury of modern amenities. Come experience the magic of Windermere—where every day feels like a vacation!

Newest Town Of Windermere Homes with Private Entrance Exterior Features

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

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