Winter Park, Villas and Luxury Homes for sale - Prestigious Properties in Winter Park

A timeless brownstone in the exclusive Park Hill provides a lifestyle that is unparalleled. Enjoy world-class restaurants, shopping, events and museums within a short walk, and...

Presented by Alison Mosley | Premier Sotheby's International Realty

This elegant Winter Park lakefront residence offers luxury lakeside living, situated on the picturesque shores of Lake Osceola. This exquisite home invites you in with a grand...

Presented by Mick Night | Premier Sotheby's International Realty

Backup offers requested. Beautifully appointed on one of the most coveted streets in Winter Park, this exquisite transitional masterpiece combines grandeur and elegance for your...

Presented by Harif Hazera | Premier Sotheby's International Realty

Custom built in 2019 by Clarkson Concepts. This five-bedroom, 5.5-bath Winter Park home offers the ideal blend of luxury and practicality. Eleven-foot ceilings, European white oak...

Presented by Michelle Hochfelder | Premier Sotheby's International Realty

Located in the heart of Winter Park, this exquisitely redesigned custom home blends transitional elegance with Mediterranean architectural nuances. Designed by the esteemed...

Presented by Alison Mosley | Premier Sotheby's International Realty

Stunning traditional family home is ideally on a tree-lined street in Old Winter Park. Overwhelming attention to detail with custom trim woodworking and architectural details such...

Presented by Pamela Ryan | Premier Sotheby's International Realty

Gorgeous Alys-Rosemary Beach-style coastal residence in the sought-after Vias neighborhood near the wprc and icc. Built in 2020, nothing was overlooked with many custom finishes...

Presented by Mick Night | Premier Sotheby's International Realty

This is your opportunity to live the ultimate lock-and-leave lifestyle and have the lakefront living that makes Winter Park so special. Perle Du Lac is a gorgeous condominium...

Presented by Mick Night | Premier Sotheby's International Realty

Located within the heart of the Vias, this premier property boasts an expansive, almost half-acre lot spanning 19,800 square feet, with dimensions of 120 by 165 feet, all set...

Presented by Mick Night | Premier Sotheby's International Realty

Nestled at the end of a picturesque street in the prestigious Dommerich Hills, this one-of-a-kind property in the coveted 32789 area code presents a unique opportunity to own over...

Presented by Drew Henner | Premier Sotheby's International Realty

Exquisite total remodel in downtown Winter Park. Walk to Park Avenue, restaurants, shops and parks. No detail was overlooked! From the flooring to the appliances, light fixtures,...

Presented by Pamela Ryan | Premier Sotheby's International Realty

Under Construction. Welcome to your custom-designed oasis of contemporary living in the esteemed Vias neighborhood of Winter Park, crafted by Z Properties. Scheduled for...

Presented by Megan Byers | Premier Sotheby's International Realty

Welcome to this stunning downtown Winter Park lakefront luxury condo with picturesque views overlooking Lake Osceola offering the very best of walk to Park Avenue lifestyle. This...

Presented by Mick Night | Premier Sotheby's International Realty

Nestled in the heart of Winter Park's finest gated community awaits your contemporary masterpiece. Spanning over 2,400 square feet of impeccably designed, energy efficient living...

Presented by Harif Hazera | Premier Sotheby's International Realty

Welcome to your exclusive opportunity to own a luxurious condo in the Douglas Grand, situated in the heart of downtown Winter Park. This impeccable property offers the epitome of...

Presented by Alison Mosley | Premier Sotheby's International Realty