21+ Historic Homes for Sale in Winter Park

Discover a rare opportunity in the heart of Winter Park, where classic charm meets modern potential....

Welcome to this charming 1935 Winter Park bungalow that blends timeless character with smart, modern...

Prime Winter Park Redevelopment Opportunity – R-2 Zoned Rare opportunity to acquire an R-2 zoned pa...

This charming, income-producing property is a standout investment opportunity offering the rare abil...

Welcome to this beautifully renovated historic home in the heart of Orwin Manor, one of Winter Park’...

Set on over half an acre in Winter Park’s coveted Orwin Manor, this 1935 French Provincial estate of...

Perched on the top floor in the heart of Winter Park, this luxury, open-concept residence offers a r...

Set in one of Winter Park’s most sought-after locations, this 1940 home delivers something that’s ha...

Under contract-accepting backup offers. Investor Special – Fixer Upper Opportunity in Winter Park / ...

Income-producing home with a detached in-law apartment in a prime central Orlando location — ideal f...

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

Under contract-accepting backup offers. Don't miss this rare opportunity to own a slice of historic ...