31+ Gated Homes for Sale in Winter Park

Nestled within the exclusive community of Windsong on Lake Berry, this magnificent 1.6-acre gated Me...

Custom Waterfront Estate located in the heart of Winter Park with a covered Boat Dock on Lake Maitla...

Experience refined luxury in this newly constructed 2024 Hamptons-style residence, a seamless blend ...

INTRODUCING THE COVETED CORNER PENTHOUSE UNIT IN ONE OF WINTER PARK'S LUXURY CONDO BUILDING. THE LAN...

One or more photo(s) has been virtually staged. Luxury lock & leave living from 147 S Interlachen Av...

Under contract-accepting backup offers. Discover your own slice of paradise on this extraordinary pr...

One or more photo(s) has been virtually staged. Newly Renovated Partially Furnished Home in the Beau...

Under contract-accepting backup offers. Elegant French Country Estate in Prestigious Winter ParkNest...

Located just steps to the Golf Course and Park Avenue, in downtown Winter Park, 622 Penn Place is in...

One or more photo(s) has been virtually staged. This one-of-a-kind duplex in the heart of Winter Par...

Introducing 210 Laurel Park Ct—a captivating, eco-friendly residence in the heart of Winter Park, FL...

Your Dream Home Awaits! Imagine a home that blends luxury, comfort, & convenience that’s exactly wha...