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 hidden gem nestled in the heart of Orange County, Florida. Known for its picturesque landscapes and charming small-town feel, Windermere offers a tranquil escape while being conveniently located just a stone’s throw away from the bustling city of Orlando. This vibrant community is renowned for its stunning lakes, lush greenery, and an array of outdoor recreational opportunities, making it a perfect haven for families and nature enthusiasts alike.

Windermere is characterized by its exquisite homes, many of which feature private entrance exterior designs that exude elegance and sophistication. Imagine stepping into your own sanctuary, where the beauty of the outdoors seamlessly blends with the comfort of your home. These residences often boast spacious layouts, modern amenities, and beautifully manicured gardens, all designed to enhance your living experience.

The allure of Windermere extends beyond its stunning homes; the community is also home to top-rated schools, delightful local eateries, and a variety of shopping options. Residents can enjoy leisurely strolls along scenic tree-lined streets or partake in community events that foster a strong sense of belonging.

Whether you’re looking for a serene place to raise a family or a vibrant community to enjoy life’s moments, Windermere offers it all. With its charming homes featuring private entrances and a welcoming atmosphere, this town is not just a place to live; it’s a place to thrive. Discover your dream home in Windermere today, 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

Start Your Search

How much is your home worth?

Get instant property value now!