27+ Historic Homes for Sale in Winter Park

Nestled on a sprawling 0.89-acre estate, this luxurious home offers the perfect balance of privacy a...

Under contract-accepting backup offers. One of Winter Park’s iconic and cherished homes, just a shor...

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

Under contract-accepting backup offers. Prime opportunity in the heart of Winter Park! This 3 bedroo...

PRICE IMPROVEMENT! Fabulous Top-to-Bottom Renovation on Coveted Brick Street in Prime Winter Park ...

Renovated to perfection in 2022, this home combines sleek, modern design with an inviting atmosphere...

Seller Financing Available!!! Discover the ideal space to grow and elevate your business with this p...

An extraordinary and rare opportunity awaits in the highly sought-after Virginia Heights neighborhoo...

Welcome to 2330 Westminster Court, a stunning 5-bedroom, 3-bathroom residence nestled in the heart o...

Beautiful Winter Park historic home that's been totally gutted and renovated. Comes complete with n...

Under contract-accepting backup offers. Elegant Spanish 4 bedroom, 2.5 bathroom home. Beautifully u...

One or more photo(s) has been virtually staged. Experience the Charm of Winter Park in This Renovate...