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

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

Now offered with a significant price improvement, this award-winning custom residence presents a rare opportunity in Winter Park's sought-after Virginia Heights neighborhood,...

Presented by Audra Wilks | Premier Sotheby's International Realty

Steeped in history and masterfully reimagined, this 1926 Winter Park estate blends architectural provenance with modern refinement. Thoughtfully restored by E2 Homes, the...

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 702 Via Bella, an impressive 2025 English cottage estate by Floridian Custom Homes that captures the essence of timeless architecture exemplifying elegance and artisan...

Presented by Mick Night | Premier Sotheby's International Realty

Totally traditional. This luxury single-story home is in the desirable Sevilla neighborhood in Winter Park. Sitting high and dry on approximately a half-acre, beautifully...

Presented by Jan Walker | Premier Sotheby's International Realty

Nestled in the heart of downtown Winter Park, this beautifully maintained 1920s traditional residence captures the essence of Old Florida charm while offering the comfort of...

Presented by Mick Night | Premier Sotheby's International Realty

Elevate your lifestyle in the prestigious Lakeside Estates, a private gated Winter Park community anchored by Garden Lake. In a quiet cul-de-sac, on a wrapping corner lot on over...

Presented by Alison Mosley | Premier Sotheby's International Realty

Experience lakefront living in the heart of Winter Park. One of only two residences in The Cloisters with soaring 9-foot ceilings, this first-floor, three-bedroom, two-bath home...

Presented by Drew Henner | Premier Sotheby's International Realty

Residence 415 at The Cloisters offers a rare opportunity to own a comprehensively rebuilt home in one of Winter Park's enduring lakefront communities. Set on the fourth...

Presented by Drew Henner | Premier Sotheby's International Realty

Welcome to this inviting single-family home at 7641 Village Green Dr in desirable Winter Park, fl. This well-maintained residence features 3 bedrooms and 3 full bathrooms across...

Presented by Globalty Investment

Welcome to 870 Carver Street, a versatile three-bedroom, three-bath residence offering privacy, thoughtful design, and two distinct living experiences in the heart of Winter Park....

Presented by Drew Henner | Premier Sotheby's International Realty

Welcome to 1451 Cavendish Road, a beautifully renovated home in the heart of Orwin Manor, one of Winter Park's most desirable and family-friendly neighborhoods. Set on a large and...

Presented by Globalty Investment

Welcome to The Cloisters, one of Winter Park's established lakefront communities, ideally between Park Avenue and Lake Osceola. This top-floor residence, rarely available in...

Presented by Drew Henner | Premier Sotheby's International Realty