Winter Park Luxury Homes for Sale

Gorgeous custom five-bedroom, five-and-one-half-bath residence built by Maroon Fine Homes in 2023 and ideally positioned on arguably one of the most sought after location...

Rarely does a property of this caliber grace the Winter Park market. Nestled along the coveted Venetian Canal with 95 feet of pristine waterfrontage, this magnificent mas...

Brand new 2026 custom residence in the heart of downtown Winter Park, just completed and showcasing elevated finishes thoughtfully curated by FG Schaub Construction & SOC...

Pre-Construction. To be built. (NOTE: Photos show features and finishes representative of the construction budget and selection allowances. All tile, colors, stone, cabin...

Experience timeless elegance and deliberate craftsmanship in the heart of prestigious Winter Park. This one-of- a-kind exceptional estate offers more than 7,300 square f...

Some homes are built, and some are composed. At 1200 Via Salerno, every finish, fixture, & detail was chosen with one goal in mind: a residence that is a pleasure to live...

Virtually Staged. This elegant transitional French Provincial residence was the feature home in the Orlando Museum of Art's 2022 "mystery home tour" and is located on a l...

Pre-Construction. To be built. PRE-CONSTRUCTION: Introducing an exceptional new construction residence by Nautilus Homes, ideally positioned in the heart of Winter Park n...

Virtually Staged. AN ARCHITECTURAL STATEMENT IN ONE OF WINTER PARK'S MOST COVETED LOCATIONS. Set on a prominent corner lot within exclusive Via Tuscany, this extraordina...

Pre-Construction. To be built. A rare convergence of timeless French Country architecture, brand-new custom construction, and coveted access to the Winter Park Chain of L...

Residing among the treelined streets of Winter Park, this stunning, contemporary pool home, designed and built by renowned Phil Kean, truly captures the essence of luxury...

Designed by renowned architect James Gamble Rogers II, 617 N Interlachen Ave presents a rare opportunity to own and thoughtfully reimagine a distinctive Spanish Revival e...

Brand new construction (2023) on a beautifully sized .29± acre lot in the heart of Winter Park. This 5BR/5.5BA estate offers an open-concept layout with high ceilings, ab...

Under Construction. Designed to capture the timeless character of Olde Winter Park while delivering an extraordinary level of modern luxury, this is a truly one-of-a-kind...

Completed in 2025 by Floridian Custom Homes, this distinguished English cottage-inspired residence brings refined character, thoughtful design, and exceptional craftsmans...

Rare Winter Park redevelopment opportunity on a NEARLY HALF-ACRE CORNER PARCEL JUST MINUTES FROM PARK AVENUE. Newly priced at $3,950,000, this R-3 ZONED (Medium-Density R...

Under Construction. Beautifully composed from every angle, this extraordinary residence captures something increasingly rare in new construction: a genuine sense of chara...

Welcome to an extraordinary private lakefront retreat in Winter Park, where expansive grounds, exceptional amenities, and breathtaking Lake Howell views come together in ...

From the moment you enter this custom residence you feel welcomed home by the understated elegance and gracious living spaces. SE corner location affording abundant natur...

Tucked away in the heart of Winter Park, this custom-built residence seamlessly blends modern luxury with the comfort of everyday living. Thoughtfully designed with excep...

Beautifully built in 2022 by Lonnie Richardson, this custom one-story home sits on a quiet cul-de-sac in the heart of Winter Park. Designed with a modern, timeless style,...

The Art of Living Well: A New Chapter at "Moon Haus" Winterpark From the moment the custom 10-foot glass pivot door swings open, you realize this is not just a house—it ...

Virtually Staged. Positioned on a quiet canal, this exceptional property features a covered boat dock with lift, offering effortless access to the renowned Winter Park Ch...

Long before this home stood gracefully on its prominent corner, it existed as a vision in the mind of master builder Keith D. Field. Conceived as the opposite of a produc...

Timeless elegance meets effortless modern living in this exceptional five-bedroom, 5.5-bath residence in Park Grove, one of Winter Park's most coveted neighborhoods. Desi...

Set along a picturesque brick street in Winter Park’s coveted Lake Sue District, this extraordinary residence delivers the scale, craftsmanship, and thoughtful design rar...

One of the most coveted neighborhoods in all of Winter Park, this exceptional custom-built residence offers a rare combination of timeless design, modern sophistication, ...

JUST COMPLETED NEW CONTRUCTION in the heart of Winter Park. Tucked away on a quiet cut-de-sac in an established neighborhood surrounded by beautiful newer residences, thi...

1825 Whitehall Drive announces itself in stone. Twin gables of whitewashed natural stone, a stately brick entry, and striking black-framed windows define its European-ins...

Pre-Construction. To be built. A striking new custom residence by FG Schaub Custom Homes, located at 2119 Howard Drive in Winter Park. This exceptional 5-bedroom, 5.5-bat...

Experience resort-style living at 1836 Whitehall Drive! Inspired by the warm breeze and seaside elegance of a tranquil island paradise, this new custom home by Urban Perc...

Virtually Staged. Welcome to South Interlachen Place, an exceptional luxury townhome ideally positioned in the heart of downtown Winter Park. Just steps from Park Avenue,...

Under Construction. Commanding attention with its striking architecture and exceptional presence, this brand-new Winter Park residence unfolds across an expansive 11,000-...

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 t...

Under Construction. Set within Winter Park’s highly sought-after Tree Streets, this exceptional new home delivers a sophisticated blend of architectural presence, refined...

Under Construction. Located in the Kenilworth Shores neighborhood, this stunning new residence brings an elevated level of new construction to an increasingly desirable p...

Hidden Gem! Designed and built by the acclaimed Phil Kean Design Group, this exceptional luxury townhome offers modern living in one of Downtown Winter Park’s most desira...

Under Construction. A striking interpretation of Modern Tudor design brings a fresh architectural presence to one of Winter Park’s charming brick streets. Newly built, th...

LUXURIOUS LIVING WITH FANTASTIC LOCATION This Winter Park three story townhouse is within walking distance to all the fun amenities of the city- the many restaurants, bo...

Under Construction. Nestled along a quiet street in Winter Park’s coveted Tree Streets, this stunning coastal farmhouse new build delivers the perfect combination of time...

Experience the pinnacle of modern luxury in this architectural masterpiece, perfectly situated in the highly coveted City of Winter Park. Boasting five bedrooms and four-...

Sophisticated Lakeside Living in the Heart of Winter Park! Experience the pinnacle of Florida luxury in this meticulously renovated estate, perfectly situated within wal...

Quintessential Winter Park Lakefront Living with your own covered boatslip! You must see this Stunning Lakefront Penthouse Residence overlooking Lake Osceola and just two...

Welcome to The Versailles of Winter Park, an extraordinary opportunity to own one of only seven exclusive private residences in one of Winter Park's most coveted luxury c...

Pre-Construction. To be built. Buyer incentive - limited time- $50,000 cash credit at closing or $70,000 credit towards upgrades. Thoughtfully designed with a refined co...

Under Construction. Experience modern luxury in this exceptional new construction residence by LUIH Luxury Homes, scheduled for completion in December 2026.Offering 5 bed...

Pre-Construction. To be built. Buyer incentive - limited time - $50,000 cash credit at closing or $70,000 credit towards upgrades. Lot 19 at 930 Enclave Place presents a...

A rare opportunity awaits to own a slice of paradise on Lake Spier in beautiful Winter Park! Set on over two acres and surrounded by mature landscaping, this stunning pro...

Pre-Construction. To be built. Buyer incentive - limited time - $50,000 cash credit at closing or $70,000 credit towards upgrades. The Hawthorn, an exceptional new custo...

Set on a generous corner lot, this stunning single-story pool home in Winter Park has been beautifully remodeled and offers the kind of effortless, one-level living that'...

Welcome to the Timberlane Shores area, one of Winter Park's most desirable and established neighborhoods. This beautifully updated home sits on over a third of an acre wi...

Resort-style living just minutes from Park Avenue and the Audubon Park Garden District. Built in 2014 by Clarkson Concepts, this Louisiana-inspired 4-bedroom, 4-bath home...

Pre-Construction. To be built. Buyer incentive - $50,000 cash credit at closing or $70,000 credit towards upgrades. Inspired by the timeless architecture of Alys Beach, ...