47+ 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 ...

Under contract-accepting backup offers. Set on a sprawling half-acre, surrounded by meticulously man...

This newly adjusted price represents extraordinary value for one of Winter Park’s most coveted addre...

Experience the pinnacle of luxury living in the heart of downtown Winter Park with this stunning pen...

Under contract-accepting backup offers. BACK ON THE MARKET DUE TO BUYER FINANCING. BELOW Appraised V...

A Jewel Box: Curated for a Life Well Lived. Penthouse 404 at The Alabama is a rare architectural gem...

Commanding an elevated position with tranquil views of Lake Mizell, this quintessential 1926 estate ...

One or more photo(s) has been virtually staged. NEW IMPROVED PRICING! Newly Renovated Partially Furn...

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

Get Busy Living the Winter Park lifestyle in this custom 4-bedroom, 4.5-bathroom pool home tucked aw...