116+ Pool Homes for Sale in Winter Park

In the exclusive community of Windsong on Lake Berry, this magnificent 1.6-acre gated Mediterranean ...

Presenting 1112 Preserve Point Drive, Winter Park, FL! Offered at $8,500,000 this very rare and priv...

Exquisite new construction in the Heart of Winter Park perfectly positioned on an oversized lot just...

CALLING HIGHEST AND BEST BY 09/26/2025!! SELLER FINANCING AVAILABLE WITH VERY ATTRACTIVE TERMS Int...

Offered for the first time in over 50 years, this distinguished Winter Park estate is a true traditi...

Extraordinary Waterfront Neoclassical Italian Estate situated on a prime .71-acre corner lot in one ...

Exquisite Waterfront Estate in the Heart of Winter Park - Welcome to 2211 Azalea Place, a rare and r...

An award-winning architectural masterpiece built by Chris Salhab of Valdara Custom Homes. 5,164 squa...

An expression of modern luxury by SMRS Design and Cole Homes, The Maybourne masterfully blends Neocl...

New Hamptons-style residence offering a seamless blend of elegance and modern sophistication. A gate...

In the heart of Winter Park’s coveted Vias neighborhood, 1150 Via Salerno is a newly completed Medit...

Under Construction. Just steps from the boutiques and fine dining of Park Avenue, this brand-new bes...