27+ Historic Homes for Sale in Winter Park

Steeped in history and masterfully reimagined, this 1926 Winter Park estate blends architectural pro...

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

Under contract-accepting backup offers. Discover an extraordinary opportunity to own a one-story lak...

Welcome to this beautifully renovated century home on one of the most picturesque brick streets in O...

Under contract-accepting backup offers. Nestled in the highly sought-after Orwin Manor neighborhood ...

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

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

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

Renovated and Charming One-Story Home in the Heart of Winter Park Nestled in the heart of Winter P...

Discover the ideal space to grow and elevate your business with this prime C1-zoned property, perfec...

Walk to beautiful downtown Winter Park for fabulous shopping, restaurants, SunRail/Amtrak station an...

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