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Winter Park Luxury Homes for Sale
When price is no object. When luxury, convenience, amenities, location, technology and privacy are what matter, Winter Park offers many options in the $2 million dollar plus home market. Several areas in Winter Park feature homes for the luxury market including those with one of a kind views of water, golf and exotic Florida preserves. Below is a list of all currently active luxury homes in Winter Park.
Winter Park Luxury Homes for Sale
Under Construction. Opportunities like this rarely present themself, just a eight-minute walk from the iconic shops, restaurants, and cafés of Park Avenue, 40 Palmer repr...
- 5 Beds
- 6 Baths
- Robert Dhu Macdonald Park SubDv.
- 32789 Zip Code
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...
- 6 Beds
- 7 Baths
- J Kronenberger Sub SubDv.
- 32789 Zip Code
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...
- 5 Beds
- 8 Baths
- Comstock Park SubDv.
- 32789 Zip Code
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...
- 4 Beds
- 5 Baths
- Maitland Shores First Add SubDv.
- 32789 Zip Code
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 large, elevated cor...
- 5 Beds
- 6 Baths
- Maitland Shores First Add SubDv.
- 32789 Zip Code
Pre-Construction. To be built. This extraordinary lakefront residence on beautiful Lake Sylvan, set on a .37-acre (16,603± square foot) homesite, presents a rare opportun...
- 4 Beds
- 5 Baths
- Sylvan Park SubDv.
- 32789 Zip Code
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...
- 4 Beds
- 7 Baths
- Forest Hills SubDv.
- 32789 Zip Code
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...
- 5 Beds
- 6 Baths
- Park Grove SubDv.
- 32789 Zip Code
There are luxury homes, and then there are homes that redefine luxury altogether. Crafted by renowned luxury builder Vimaro Homes, this extraordinary residence is the pro...
- 5 Beds
- 6 Baths
- Park Grove SubDv.
- 32789 Zip Code
Envisioned by acclaimed architect Phil Kean and originally commissioned as the International Showcase Home for the National Association of Home Builders, this award-winni...
- 4 Beds
- 6 Baths
- Alexander Place SubDv.
- 32789 Zip Code
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,...
- 4 Beds
- 6 Baths
- Winflor Court Pt Rep SubDv.
- 32789 Zip Code
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...
- 3 Beds
- 5 Baths
- South Interlachen Place SubDv.
- 32789 Zip Code
Under Construction. Beautifully composed from every angle, this extraordinary residence captures something increasingly rare in new construction: a genuine sense of chara...
- 6 Beds
- 5 Baths
- Timberlane Shores SubDv.
- 32789 Zip Code
Welcome to an extraordinary private lakefront retreat in Winter Park, where expansive grounds, exceptional amenities, and breathtaking Lake Howell views come together in ...
- 4 Beds
- 3 Baths
- Acreage & Unrec SubDv.
- 32792 Zip Code
Under Construction. Step into a world where the timeless charm of Old Winter Park meets the pinnacle of modern luxury designed by Winter Park Design and masterfully craft...
- 5 Beds
- 5 Baths
- Charmont SubDv.
- 32789 Zip Code
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...
- 4 Beds
- 5 Baths
- Detmar Terrace Winter Park SubDv.
- 32789 Zip Code
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...
- 4 Beds
- 4 Baths
- Maitland Shores 1st Add SubDv.
- 32789 Zip Code
Perfectly positioned in the heart of Old Winter Park, the quaint Forrest Hills neighborhood is lined with charming cobblestone streets that wind around Lake Sue. This cus...
- 5 Beds
- 6 Baths
- Forest Hills SubDv.
- 32789 Zip Code
One or more photo(s) has been virtually staged. Under Construction. Under construction. Experience approachable luxury combined with wellness-focused living in this newly...
- 5 Beds
- 6 Baths
- Sylvan Lake Shores SubDv.
- 32789 Zip Code
Virtually Staged. This exceptional Winter Park residence offers a floor plan rarely found in the area, with nearly all living spaces thoughtfully positioned on a single l...
- 4 Beds
- 6 Baths
- Ellno Willo SubDv.
- 32789 Zip Code
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, ...
- 5 Beds
- 6 Baths
- Green Oaks Rep 02 SubDv.
- 32789 Zip Code
Under Construction. Perfectly positioned along one of Winter Park's most picturesque tree-lined cobblestone streets, this exceptional new construction residence offers a ...
- 4 Beds
- 5 Baths
- Charmont SubDv.
- 32789 Zip Code
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,...
- 3 Beds
- 5 Baths
- South Interlachen Place SubDv.
- 32789 Zip Code
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...
- 5 Beds
- 6 Baths
- Forest Hills SubDv.
- 32789 Zip Code
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...
- 5 Beds
- 7 Baths
- Kenilworth Shores Sec 06 SubDv.
- 32789 Zip Code
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...
- 3 Beds
- 4 Baths
- Morse & Pennsylvania Twnhms SubDv.
- 32789 Zip Code
Under Construction. Located in the Kenilworth Shores neighborhood, this stunning new residence brings an elevated level of new construction to an increasingly desirable p...
- 5 Beds
- 5 Baths
- Kenilworth Shores Sec 06 SubDv.
- 32789 Zip Code
Timeless elegance meets boutique craftsmanship at 541 W Canton Ave., an exceptional new construction home by Urban Perch, proudly featured in the 2025 Parade of Homes Orl...
- 4 Beds
- 4 Baths
- Winter Park SubDv.
- 32789 Zip Code
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...
- 3 Beds
- 4 Baths
- Town Of Winter Park SubDv.
- 32789 Zip Code
Under Construction. Experience the very best of Winter Park living with this stunning new construction home, where sophisticated design, luxury finishes, and an incredibl...
- 5 Beds
- 5 Baths
- Orange Grove Sub SubDv.
- 32789 Zip Code
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...
- 5 Beds
- 5 Baths
- Lake Knowles Terrace Add 02 SubDv.
- 32789 Zip Code
Sophisticated Lakeside Living in the Heart of Winter Park! Experience the pinnacle of Florida luxury in this meticulously renovated estate, perfectly situated within wal...
- 5 Beds
- 6 Baths
- Osceola Shores Sec 03 SubDv.
- 32789 Zip Code
Pre-Construction. To be built. The Enclave is a premier, boutique community in the heart of Winter Park, featuring just 23 thoughtfully designed residences nestled beneat...
- 5 Beds
- 5 Baths
- The Enclave Winter Park SubDv.
- 32792 Zip Code
Pre-Construction. To be built. The Enclave is a premier, boutique community in the heart of Winter Park, featuring just 23 thoughtfully designed residences nestled beneat...
- 5 Beds
- 5 Baths
- The Enclave Winter Park SubDv.
- 32792 Zip Code
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...
- 3 Beds
- 4 Baths
- Versailles Winter Park Condo SubDv.
- 32789 Zip Code
Pre-Construction. To be built. Welcome to The Enclave, an exclusive boutique community in the heart of Winter Park featuring just 23 thoughtfully crafted residences by FG...
- 5 Beds
- 5 Baths
- The Enclave Winter Park SubDv.
- 32792 Zip Code
Under Construction. Experience modern luxury in this exceptional new construction residence by LUIH Luxury Homes, scheduled for completion in December 2026.Offering 5 bed...
- 5 Beds
- 5 Baths
- Charmont SubDv.
- 32789 Zip Code
Pre-Construction. To be built. The Enclave is a premier, boutique community in the heart of Winter Park, featuring just 23 thoughtfully designed residences nestled beneat...
- 5 Beds
- 5 Baths
- The Enclave Winter Park SubDv.
- 32792 Zip Code
Located in highly desirable Lugano Terrace just steps from the shores of Lake Knowles, this stunning all new interiors, 5-bedroom, 3.5-bath brick home effortlessly blends...
- 5 Beds
- 4 Baths
- Lugano Terrace SubDv.
- 32789 Zip Code
A rare opportunity to own nearly 7 acres on the pristine shores of Private Lake Howell! This exceptional lakefront property offers the perfect setting to build your custo...
- 3 Beds
- 2 Baths
- 32792 Zip Code
Pre-Construction. To be built. 914 Enclave Place is a beautiful Alys Beach inspired design. The Enclave is a premier, boutique community in the heart of Winter Park, feat...
- 5 Beds
- 5 Baths
- The Enclave Winter Park SubDv.
- 32792 Zip Code
A striking expression of modern luxury, this brand-new residence offers nearly 3,000 square feet of thoughtfully designed living space in one of Winter Park's most desira...
- 5 Beds
- 5 Baths
- Sylvan Heights SubDv.
- 32789 Zip Code
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