248+ Contemporary Homes for Sale in Winter Park

Nestled within the exclusive community of Windsong on Lake Berry, this magnificent 1.6-acre gated Me...

CALLING HIGHEST AND BEST BY 4/30/2025!! Introducing a Unique, Stunning Modern Home A groundbreaki...

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

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 ...

This elegant Winter Park lakefront residence offers luxury lakeside living, situated on the pictures...

Oak trees line the brick street as you arrive at this exquisite Hollywood Regency style home. Situa...

On one of Winter Park’s most scenic brick-lined streets, this exceptional two-story residence comman...

Welcome to a stunning new home positioned near Windsong and the AdventHealth Hospital. This extraord...

One of the most coveted neighborhoods in all of Winter Park! This custom-built 5-bedroom, 5.5-bath r...

Under Construction. Stunning architectural masterpiece built by LUIH homes nestled in the heart of p...

Award-winning Phil Kean design on a prominent corner lot in the heart of Winter Park, just minutes f...