Windermere Town Rep Real Estate

Welcome to Windermere Town Rep, a picturesque subdivision nestled in the heart of Windermere, Florida, within the vibrant Orange County. This charming community is renowned for its idyllic surroundings, where serene lakes meet lush landscapes, creating a perfect backdrop for your dream home.

Windermere Town Rep offers a unique blend of small-town charm and modern conveniences. As you stroll through the tree-lined streets, you'll be captivated by the stunning architecture and meticulously maintained properties that define this neighborhood. The community fosters a friendly atmosphere, where neighbors become friends, and everyone enjoys the tranquil lifestyle that Windermere is known for.

One of the highlights of living in Windermere Town Rep is the abundance of outdoor activities available at your fingertips. The area is surrounded by beautiful parks, scenic walking trails, and pristine lakes, perfect for kayaking or paddleboarding. With the famous Butler Chain of Lakes nearby, residents have endless opportunities for water recreation and relaxation.

Families will appreciate the top-rated schools in the area, providing quality education and enriching experiences for children of all ages. Additionally, Windermere Town Rep is conveniently located just a short drive from Orlando, granting easy access to world-class dining, shopping, and entertainment options, including the magical attractions of Walt Disney World.

Experience the charm and warmth of Windermere Town Rep, where community spirit thrives, and every day feels like a vacation. Discover your perfect home in this enchanting subdivision and embrace the lifestyle you’ve always dreamed of!

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. Multiple offers on lots 29 & 30. Highest and best by Friday, 9/18 at 5:00 pm.

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

Start Your Search