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, a picturesque gem nestled in the heart of Orange County, Florida. Known for its stunning lakes, lush landscapes, and a welcoming community vibe, Windermere offers a serene escape from the hustle and bustle of city life while still being conveniently close to Orlando’s vibrant attractions.

As you explore this charming town, you’ll discover a variety of beautiful homes that capture the essence of Florida living. One standout feature of many residences in Windermere is their private entrance exterior. These homes are designed to provide a sense of exclusivity and privacy, perfect for families or individuals seeking a tranquil retreat. Imagine coming home to your own personal oasis, where you can unwind in peace after a long day.

The architecture in Windermere is as diverse as its residents, with stunning designs ranging from Mediterranean-style villas to modern craftsman homes. Many properties boast expansive outdoor spaces, ideal for hosting gatherings or enjoying the beautiful Florida weather. Whether you’re sipping coffee on your patio or taking a leisurely stroll along the tree-lined streets, the charm of Windermere is undeniable.

In addition to its beautiful homes, Windermere is rich in recreational opportunities. Residents can enjoy access to pristine lakes for boating, fishing, and water sports, as well as numerous parks and trails for outdoor enthusiasts. With a strong sense of community and a wealth of amenities, the Town of Windermere is not just a place to live; it’s a place to thrive. Come discover your dream home in this idyllic Florida enclave!

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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