Town Of Windermere Homes with Private Pool type

Town Of Windermere Homes with Private Pool type

Welcome to the enchanting Town of Windermere, a hidden gem nestled in the heart of Orange County, Florida. Known for its picturesque lakes and serene landscapes, Windermere offers a tranquil lifestyle that perfectly balances suburban charm with modern conveniences. Just a stone's throw away from Orlando, this vibrant community is ideal for families and individuals seeking both relaxation and adventure.

Windermere is renowned for its stunning homes, many of which feature private pools, creating an oasis of comfort right in your backyard. Imagine soaking up the Florida sun, hosting barbecues, or enjoying a refreshing dip in your own pool after a long day. These homes are designed for both leisure and luxury, boasting spacious layouts, modern amenities, and beautifully landscaped yards that enhance the outdoor living experience.

The community itself is rich with recreational opportunities, from scenic walking trails and parks to access to pristine lakes perfect for kayaking or fishing. Windermere’s charming downtown area is filled with boutique shops, delightful cafes, and fine dining options, making it a wonderful place to unwind and socialize with neighbors.

Families will appreciate the highly-rated schools in the area, ensuring that children receive an excellent education while enjoying the benefits of a close-knit community. Whether you’re looking to buy your dream home or invest in a property with rental potential, Windermere’s real estate market is thriving, particularly for homes with private pools that cater to the Florida lifestyle.

Explore the beauty and tranquility of Windermere, where your dream home awaits amidst the lush landscapes and friendly community. Experience the perfect blend of luxury and leisure in this idyllic Florida town!

Newest Town Of Windermere Homes with Private Pool type

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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