Town Of Windermere Homes with Private Mailbox Exterior Features

Town Of Windermere Homes with Private Mailbox Exterior Features

Welcome to the enchanting Town of Windermere, nestled in the heart of Orange County, Florida. This picturesque community is renowned for its serene lakes, lush landscapes, and charming small-town atmosphere. With its prime location just minutes from the vibrant city of Orlando, Windermere offers the perfect blend of tranquility and accessibility, making it an ideal choice for families and professionals alike.

As you explore this delightful subdivision, you’ll discover a stunning array of homes that boast unique architectural styles and exquisite designs. One of the standout features of many properties in Windermere is the presence of private mailboxes, adding a touch of elegance and personalization to your home’s exterior. These charming mailboxes not only enhance the curb appeal but also contribute to the community's warm and inviting aesthetic.

Windermere is home to a variety of recreational opportunities, from scenic parks to waterfront activities, ensuring that residents can enjoy the great outdoors year-round. The local community is vibrant and welcoming, with frequent events that bring neighbors together, fostering a strong sense of belonging.

Whether you’re looking for a cozy family home or a luxurious retreat, the Town of Windermere has something for everyone. Experience the charm and beauty of this exceptional community, where you can enjoy the comforts of home while being surrounded by nature’s splendor. Come and discover why Windermere is not just a place to live, but a place to thrive!

Newest Town Of Windermere Homes with Private Mailbox Exterior Features

$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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