Windermere Town Rep Real Estate

Welcome to Windermere Town Rep, a picturesque subdivision nestled in the heart of Windermere, Florida. This charming community is perfectly situated in Orange County, offering residents a serene lifestyle while being just a stone's throw away from the vibrant attractions of Orlando.

Windermere Town Rep is known for its inviting atmosphere, characterized by tree-lined streets, beautifully manicured lawns, and a strong sense of community. The subdivision features a variety of stunning homes, each showcasing unique architectural styles that reflect the area's rich history and culture. Whether you’re seeking a cozy single-family home or a spacious property for your growing family, Windermere Town Rep has something for everyone.

One of the standout features of this community is its access to outdoor recreational activities. Residents can enjoy nearby parks, picturesque lakes, and scenic walking trails, making it an ideal location for nature enthusiasts and families alike. The renowned Windermere Recreation Center offers a plethora of activities, from sports leagues to seasonal events, fostering a close-knit community spirit.

In addition to its natural beauty, Windermere Town Rep is conveniently located near top-rated schools, shopping centers, and dining options. With easy access to major highways, residents can explore the attractions of Orlando, including world-famous theme parks and entertainment venues, all within a short drive.

Experience the charm and tranquility of Windermere Town Rep, where community, convenience, and natural beauty come together to create the perfect place to call home. Come discover why this enchanting subdivision is one of Windermere’s best-kept secrets!

Newest Listings in Windermere Town Rep

$650,000

Windermere Town Rep SubDv. ⋅ 34786 Zip Code

A rare opportunity to build your dream home in the heart of Old Windermere. This cleared, vacant parcel consists of 7 total lots being offered for the first time — a truly unique chance to secure land in the Town of Windermere before it's gone. Enjoy golf cart-friendly streets, access to the famed Butler Chain of Lakes, and the convenience of natural gas and county water already available. With no HOA, you have the freedom to design and build exactly the home you envision. Just a short walk to downtown shops, restaurants, and community events, this homesite combines small-town charm with unbeatable convenience. Opportunities like this don't last long — bring your builder and make it yours! Lots approx. 100' x 167'. Lots 19-22: $650,000 each | Lot 18: $700,000 | Lot 29: $750,000 | Lot 30: $800,000.

618 Ridgewood Drive, Windermere

$2,175,000

4 Beds ⋅ 5 Baths ⋅ Windermere Town Rep SubDv. ⋅ 34786 Zip Code

Seller is Motivated and open to negotiate! Luxury new construction lakefront home in Windermere, newly completed. Situated on Lake Bessie, this modern custom residence delivers architectural elegance, premium finishes, and a prime location just steps from the Town Center. The home offers 3,136 sq ft of air-conditioned space, featuring 4 en-suite bedrooms, a dedicated office at the entry, 5 full bathrooms, an outdoor shower, and an oversized 3-car garage. A dramatic two-story living area sets the tone with clean lines, expansive glass, and natural light throughout. The chef’s kitchen pairs performance and elegance, with a waterfall-edge quartz island, full-height book-matched backsplash, custom cabinetry, and high-end appliances including a Sub-Zero refrigerator, Wolf vent hood, and a full Thermador suite with double ovens and microwave drawer. A hidden walk-in pantry blends seamlessly into the design for added utility and clean aesthetics.Upstairs, the owner’s suite offers lake views, a spacious layout, and a sleek en-suite bath with a large walk-in shower and dual vanity. Secondary bedrooms include en-suite baths and reach-in closets. The home is finished with oversized rectangular porcelain tile throughout the entire main level including the expansive covered lanai and wide plank engineered wood flooring from the staircase through the second floor. Additional highlights include a glass-framed staircase and an abundance of natural light in every space. Located just blocks from Downtown Windermere, this home places you at the center of a highly coveted lakefront lifestyle. Enjoy tennis courts, playgrounds, boat ramps on both Lake Bessie and the Butler Chain, plus a vibrant local culture with weekly farmers markets, food truck nights, and seasonal events in Town Square. Cruise oak-lined sandy streets by golf cart, or explore nearby dining, shops, and fitness at The Grove and along Restaurant Row. World-class golf, theme parks, and the airport are all within easy reach and with the hard work already done, all that’s left is to move in and enjoy. Private showings by appointment only. Seller is Motivated and open to negotiate! We completed the closets upgrades in this beautiful home, thoughtfully designed for the family who will soon call this place home.

436 E 7th Avenue, Windermere

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