Luxury Properties for sale in Winter Park, Florida

In the exclusive community of Windsong on Lake Berry, this magnificent 1.6-acre gated Mediterranean estate is a private oasis. With over 11,000 square feet of living area and a...

Presented by William George | Premier Sotheby's International Realty

Winter Park living at its best! This custom brownstone with an exclusive Park Avenue address offers an unparalleled Winter Park lifestyle. Ideally situated in the heart of Winter...

Presented by Sara Cambron | Premier Sotheby's International Realty

New Hamptons-style residence offering a seamless blend of elegance and modern sophistication. A gated entrance opening to a circular driveway and motor court, set the stage for...

Presented by Mick Night | Premier Sotheby's International Realty

Set in the perfect Winter Park location, within exclusive Via Tuscany, this unique, resilient construction residence built by Developer & Builder Group, offers a rare blend of...

Presented by Globalty Investment

Along one of the cobblestone brick streets in the prestigious Via's of Winter Park, this completely renovated residence pairs timeless European influence with clean architectural...

Presented by Mick Night | Premier Sotheby's International Realty

Set along a picturesque brick street, 2040 Randall Circle is a beautifully crafted residence that pairs timeless architecture with elevated, designer finishes and a functional...

Presented by Mick Night | Premier Sotheby's International Realty

This stunning new contemporary residence, a five-bedroom, five-and-a-half bath home by the renowned Rex-Tibbs Development, a custom builder for over 40 years, continues to set the...

Presented by Mick Night | Premier Sotheby's International Realty

Welcome to an exceptional opportunity in the highly desirable Park Grove community, an impeccably updated one-story residence ideally situated just moments from the vibrant shops...

Presented by Mick Night | Premier Sotheby's International Realty

Discover refined living in this stunning custom-built home located in the coveted community of Windsong. Thoughtfully designed and expertly constructed by Goehring & Morgan, this...

Presented by Mick Night | Premier Sotheby's International Realty

Ideally on a quiet residential street just near Park Avenue, this custom-built transitional residence offers the best of Winter Park living, accessible, refined and thoughtfully...

Presented by Drew Henner | Premier Sotheby's International Realty

Welcome to 1750 Carollee Lane, where timeless charm meets modern luxury. Set on a homesite with desirable southern exposure in the heart of Winter Park, this four-bedroom,...

Presented by Michelle Hochfelder | Premier Sotheby's International Realty

This custom 2014-built Winter Park residence is stretched over a double lot with a backyard resort style retreat yet close to all Winter Park offers. A home with function and...

Presented by Alison Mosley | Premier Sotheby's International Realty

A distinctive offering where design, location and performative upgrades come together seamlessly. One of the original modern homes in Winter Park, this iconic residence has been...

Presented by Audra Wilks | Premier Sotheby's International Realty

Welcome to this beautifully maintained home in the heart of Winter Park, where comfort, charm, and convenience come together effortlessly. Nestled in a central Florida community,...

Presented by Globalty Investment

On the first floor within The Cloisters, this three-bedroom, two-bath residence offers 1,734 square feet of renovated living space in one of Winter Park's accessible lakefront...

Presented by Drew Henner | Premier Sotheby's International Realty