1120 PRESERVE POINT DRIVE
WINTER PARK FL 32789
Residential / Single Family Residence
7 Bed · 9 Bath · 2 Half Baths · 11,255 SqFt · $795/SqFt
Days on Market: 46
County: Orange
Complex/CommunityName: WINDSONG
Legal Subdivision Name: WINDSONG-PRESERVE POINT
Year built: 2009
Garage: Yes 4 vehicles
Private Pool: Yes
Waterfront: Yes
Lot Size (in acres): 1.63
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 beautifully landscaped lakefront lot, this residence offers an exceptional blend of elegance, charm and privacy rarely found in Winter Park. The home features seven spacious bedrooms and nine full and two half baths. Entertain in the all-glass conservatory, dedicated theater room with motorized seating and a fully equipped game room. Modern conveniences throughout including gas-powered generators, an elevator and dumbwaiter. Two above-garage apartments provide ideal accommodations for guests and family. Outdoors, ... Read more....»
1112 PRESERVE POINT DRIVE
WINTER PARK FL 32789
Residential / Single Family Residence
5 Bed · 6 Bath · 6,502 SqFt · $1,307/SqFt
Days on Market: 98
County: Orange
Legal Subdivision Name: WINDSONG PRESERVE POINT 43/76
Year built: 2013
Garage: Yes 3 vehicles
Private Pool: Yes
Community Pool: Yes
Waterfront: Yes
Lot Size (in acres): 1.94
Presenting 1112 Preserve Point Drive, Winter Park, FL! Offered at $8,500,000 this very rare and private, nearly 2-acre lakefront estate, is absolutely gorgeous and is available for the first time! Custom built by Phil Kean Design Group and located within Windsong's Preserve Point, this extraordinary Lake Berry home has it all including 1.97 acres of land adjacent to the historic Genius Preserve and 407' of pristine waterfront. The main house offers over 6,500 sf of luxurious living space and a modern and open floorplan with a great room for entertaining, a gourmet kitchen with double islands and high-end Miele and ... Read more....»
550 PALMER AVENUE
WINTER PARK FL 32789
Residential / Single Family Residence
5 Bed · 6 Bath · 1 Half Bath · 5,939 SqFt · $1,212/SqFt
Days on Market: 47
County: Orange
Legal Subdivision Name: OSCEOLA PLACE
Year built: 2025
Garage: Yes 3 vehicles
Private Pool: Yes
Exquisite new construction in the Heart of Winter Park perfectly positioned on an oversized lot just steps from Park Avenue’s renowned shops, fine dining, and the iconic Winter Park 9-hole golf course, this extraordinary custom residence is a showcase of timeless design and modern luxury. Conceived by acclaimed architect Dan Delong of Origins Residential Design and brought to life by Sean Wulff of Native Homes, every detail has been thoughtfully curated to impress even the most discerning buyer. The expansive floor plan encompasses 5 bedrooms, 6 full baths, and 1 half bath, blending sophistication and comfort across multiple living spaces. ... Read more....»
2661 VIA TUSCANY
WINTER PARK FL 32789
Residential / Single Family Residence
4 Bed · 4 Bath · 1 Half Bath · 4,636 SqFt · $1,424/SqFt
Days on Market: 294
County: Orange
Legal Subdivision Name: WINTER PARK
Year built: 2024
Garage: Yes 2 vehicles
Private Pool: Yes
CALLING HIGHEST AND BEST BY 09/26/2025!! SELLER FINANCING AVAILABLE WITH VERY ATTRACTIVE TERMS Introducing a Unique, Stunning Modern Home A groundbreaking architectural masterpiece, this one-of-a-kind residence is built with reinforced concrete, steel, and iron framing, featuring floor-to-ceiling glass walls with no traditional windows. Designed to exceed Florida’s strictest building codes, this home follows commercial-grade construction standards, making it a bunker-style fortress unlike any other. Luxury Meets Modern Innovation Nestled in the heart of Historic Winter Park, Florida, this exceptional residence blends contemporary design with timeless elegance, offering unparalleled craftsmanship, high-end finishes, and an open-concept layout for those who appreciate architectural brilliance and luxury living. Key ... Read more....»
887 GEORGIA AVENUE
WINTER PARK FL 32789
Residential / Single Family Residence
6 Bed · 5 Bath · 1 Half Bath · 5,759 SqFt · $1,024/SqFt
Days on Market: 95
County: Orange
Legal Subdivision Name: DYER SUSAN RESUB
Year built: 1924
Garage: Yes 2 vehicles
Private Pool: Yes
Lot Size (in acres): 1.07
Offered for the first time in over 50 years, this distinguished Winter Park estate is a true traditional gem, nestled on a picturesque brick street and situated on a full 1-acre lot. Exuding timeless charm with a subtle New England ambiance, this residence represents the best of historic Winter Park living—all within walking distance to Park Avenue. This stately 6-bedroom, 5.5-bathroom home offers 5,759 square feet of thoughtfully designed living space, plus an additional 1,859-square-foot unfinished basement that spans the entire length of the home, offering endless possibilities for expansion or customization. Upon entry, you'll be welcomed by coffered ceilings in the ... Read more....»
1400 ALABAMA DRIVE
WINTER PARK FL 32789
Residential / Single Family Residence
5 Bed · 5 Bath · 4 Half Baths · 7,916 SqFt · $745/SqFt
Days on Market: 173
Cumulative Days on Market: 438
County: Orange
Legal Subdivision Name: J KRONENBERGER SUB
Year built: 1996
Garage: Yes 4 vehicles
Private Pool: Yes
Waterfront: Yes
Extraordinary Waterfront Neoclassical Italian Estate situated on a prime .71-acre corner lot in one of Winter Park's most sought-after locations. This 7,916 SF property includes a main residence of over 7,100 SF, a detached guest house, and a poolside catering suite. The private covered boat dock is located just steps away, across the street, in the historic Kraft Azalea Garden, providing direct lake access with boat and personal watercraft storage on Lake Maitland, without the upkeep of a waterfront backyard. Inside, fresh neutral interiors and beautiful landscaping frame elegant arrival and living spaces. The thoughtful layout offers 5 bedrooms and ... Read more....»
2211 AZALEA PLACE
WINTER PARK FL 32789
Residential / Single Family Residence
5 Bed · 6 Bath · 1 Half Bath · 7,278 SqFt · $755/SqFt
Days on Market: 167
County: Orange
Legal Subdivision Name: MAITLAND SHORES
Year built: 2008
Garage: Yes 5 vehicles
Private Pool: Yes
Waterfront: Yes
Exquisite Waterfront Estate in the Heart of Winter Park - Welcome to 2211 Azalea Place, a rare and remarkable waterfront estate nestled on a quiet street in one of Winter Park’s most prestigious neighborhoods—just moments from the exclusive Winter Park Racquet Club. This extraordinary residence offers the perfect blend of timeless architecture, refined finishes, and state-of-the-art updates, all set on almost 3/4 acre of beautifully landscaped canal-front lot with direct access to the coveted Lake Maitland and Winter Park Chain of Lakes. Spanning an impressive 7,278 square feet, this two-story masterpiece rises 40 feet and is designed for both grand-scale entertaining ... Read more....»
1221 RICHMOND ROAD
WINTER PARK FL 32789
Residential / Single Family Residence
5 Bed · 5 Bath · 1 Half Bath · 5,164 SqFt · $1,055/SqFt
Days on Market: 153
County: Orange
Legal Subdivision Name: VIRGINIA HEIGHTS REP
Year built: 2024
Garage: Yes 2 vehicles
Private Pool: Yes
An award-winning architectural masterpiece built by Chris Salhab of Valdara Custom Homes. 5,164 square feet, 5 bedrooms and 6 baths. Welcome to 1221 Richmond Road, an extraordinary custom residence located in the coveted Virginia Heights neighborhood of Winter Park—offering deeded lake access to the Winter Park Chain of Lakes. This architectural showpiece was honored as the 2024 Parade of Homes Showcase Home – Grand Award Winner and recipient of the Aurora Award – Grand Award for Best Custom Home. Completed in 2024, this 5,164-square-foot estate redefines luxury living with bold design and state-of-the-art technology. A dramatic 10-foot steel pivot entry ... Read more....»
1302 RAINTREE PLACE
WINTER PARK FL 32789
Residential / Single Family Residence
5 Bed · 5 Bath · 1 Half Bath · 4,738 SqFt · $1,119/SqFt
Days on Market: 21
County: Orange
Legal Subdivision Name: CAMWOOD SUB
Year built: 2025
Garage: Yes 2 vehicles
Private Pool: Yes
An expression of modern luxury by SMRS Design and Cole Homes, The Maybourne masterfully blends Neoclassical elegance with Art Deco sophistication—all just steps from Winter Park’s iconic Park Avenue. A curved, manicured driveway leads to a grand entrance featuring bespoke double doors with electromagnetic privacy glass, setting the tone for the artistry within. Inside, a European hotel–inspired foyer greets guests with precast stone-clad walls, inlaid marble flooring, and a Murano-style polyhedral chandelier. Two first-floor guest suites, each with its own bath, are adorned with rift-cut white oak millwork, curved ceilings, and crystal chandeliers. At the heart of the home lies the main ... Read more....»
1660 PALMER AVENUE
WINTER PARK FL 32789
Residential / Single Family Residence
5 Bed · 6 Bath · 1 Half Bath · 6,406 SqFt · $773/SqFt
Days on Market: 195
County: Orange
Legal Subdivision Name: COMSTOCK PARK
Year built: 2024
Garage: Yes 3 vehicles
Private Pool: Yes
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 enjoying this exceptional estate. As you enter home, an impressive 2-story foyer with a glass-paneled staircase wraps around a temperature-controlled wine room and a transparent glass elevator, effortlessly connecting all levels including an expansive third-floor multi-purpose space. Designed for contemporary living, the thoughtfully curated floor plan features a spacious open concept kitchen/gathering room along with the dining area enjoy a wall of glass doors and picture window overlooking an expansive lanai, and ... Read more....»
1150 VIA SALERNO
WINTER PARK FL 32789
Residential / Single Family Residence
4 Bed · 5 Bath · 1 Half Bath · 3,850 SqFt · $1,234/SqFt
Days on Market: 165
County: Orange
Legal Subdivision Name: CLOISTER GROVE SUB
Year built: 2025
Garage: Yes 2 vehicles
Private Pool: Yes
In the heart of Winter Park’s coveted Vias neighborhood, 1150 Via Salerno is a newly completed Mediterranean-minimalist residence that blends architectural refinement w/ organic warmth. Designed and developed by Steve and Jodie Warrick Konold of Scout & Co., the 3,850 sf layout offers 4 bedrooms & 5.5 baths, wrapped in the intentional privacy of a luxury retreat. Beyond its terraced walkway and garden courtyard—envisioned in collaboration w/ architect Cynde Norris—French antique gates open to a native-planted entry garden, creating a soft transition to the interior. A glass foyer introduces a tongue-and-groove ceiling & woven rattan chandelier, sourced & designed in ... Read more....»
1525 GRANVILLE DRIVE
WINTER PARK FL 32789
Residential / Single Family Residence
5 Bed · 5 Bath · 1 Half Bath · 5,211 SqFt · $912/SqFt
Days on Market: 93
County: Orange
Legal Subdivision Name: PARK GROVE
Year built: 2026
Garage: Yes 2 vehicles
Private Pool: Yes
Under Construction. Just steps from the boutiques and fine dining of Park Avenue, this brand-new bespoke estate by acclaimed builder Vimaro Homes delivers a rare combination of architectural sophistication and thoughtful design. Perfectly positioned on an oversized 0.34-acre lot, the residence encompasses over 5,200 square feet of refined living space, crafted with the finest materials and an unrelenting attention to detail. From the moment you enter, the home radiates a sense of modern elegance. Wide-plank herringbone wood floors flow through expansive interiors, complemented by soaring ceilings, oversized windows, and meticulous millwork. At the heart of the residence, the chef’s kitchen ... Read more....»
1161 VALENCIA AVENUE
WINTER PARK FL 32789
Residential / Single Family Residence
4 Bed · 4 Bath · 1 Half Bath · 4,181 SqFt · $1,087/SqFt
Days on Market: 64
County: Orange
Legal Subdivision Name: VALENCIA TERRACE
Year built: 2021
Garage: Yes 2 vehicles
Private Pool: Yes
Conveniently situated near the Winter Park Country Club, this contemporary masterpiece, built by premier builder Z Properties, offers the ideal mix of style, comfort, and modern living. Completed in 2021, the residence has 4,181 square feet of thoughtfully designed living space, including four bedrooms each with a private ensuite bath and an additional powder room. A 412-square-foot casita with a wet bar and private entrance completes its functionality by providing extra flexibility, perfect for guests, extended family, workspace or workout area. The interiors showcase timeless design with high ceilings, glass walls, and carefully curated finishes. The chef’s kitchen and butler’s pantry ... Read more....»
702 VIA BELLA
WINTER PARK FL 32789
Residential / Single Family Residence
4 Bed · 5 Bath · 1 Half Bath · 3,720 SqFt · $1,142/SqFt
Days on Market: 75
County: Orange
Legal Subdivision Name: PALMER AVE LAKESIDE PROP
Year built: 2025
Garage: Yes 2 vehicles
Private Pool: Yes
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 craftsmanship. In one of Winter Park’s desirable residential corridors, warmth and beauty abound in this four-bedroom, six-bath residence spanning 3,720 square feet or air conditioned and 4,535 square feet total under roof, offering layered living, artisanal materials, and a modern infrastructure. Upon entry through a solid mahogany front door, warmth and beauty abounds with Botticino limestone flooring enhanced by a textured finish, extensive custom millwork, and an abundance of open concept living areas. Coffered ... Read more....»
1751 GLENCOE ROAD
WINTER PARK FL 32789
Residential / Single Family Residence
5 Bed · 5 Bath · 2 Half Baths · 4,520 SqFt · $862/SqFt
Days on Market: 36
County: Orange
Legal Subdivision Name: FOREST HILLS
Year built: 2025
Garage: Yes 2 vehicles
Private Pool: Yes
Nestled just moments from the boutiques and cafés on Park Avenue, this newly completed Davila Homes masterpiece redefines Winter Park luxury living. Perfectly positioned on an expansive 0.30-acre lot, this residence captures attention from the moment you arrive, with its striking architectural details, a sweeping driveway, and detached garage that together set a tone of timeless sophistication. Inside, soaring 20-foot ceilings welcome you into a grand foyer framed by curved archways and exceptional millwork. The living room is a true showpiece, centered around a statement fireplace with built-in shelving and subtle LED underlighting that accentuates every detail. The chef’s kitchen ... Read more....»
1820 GLENCOE ROAD
WINTER PARK FL 32789
Residential / Single Family Residence
5 Bed · 5 Bath · 2 Half Baths · 4,055 SqFt · $943/SqFt
Days on Market: 165
County: Orange
Legal Subdivision Name: FOREST HILLS
Year built: 2025
Garage: Yes 2 vehicles
Private Pool: Yes
Discover premier Winter Park luxury real estate at 1820 Glencoe Road—a stunning Dutch West Indies–inspired custom home built by FG Schaub Custom Homes. Ideally located minutes from Park Avenue, Rollins College, and downtown Winter Park, this residence offers the perfect blend of coastal architecture and modern Florida luxury living. With 4,055 sqft. of thoughtfully designed space, this Winter Park pool home features 5 bedrooms, 5 full bathrooms, 2 half baths, and a private home office. A grand entryway opens to a bright, open-concept interior with expansive Andersen windows that enhance indoor-outdoor flow—an essential feature for Florida homes. The chef’s kitchen is a ... Read more....»
207 E KINGS WAY
WINTER PARK FL 32789
Residential / Single Family Residence
5 Bed · 4 Bath · 1 Half Bath · 3,719 SqFt · $981/SqFt
Days on Market: 13
County: Orange
Legal Subdivision Name: CHARMONT
Year built: 2026
Garage: Yes 2 vehicles
Private Pool: Yes
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 crafted by renowned builder Vimaro Homes. Nestled on one of Winter Park’s most coveted tree-lined streets, this stately home immediately commands attention with its double-entry driveway, framed by manicured landscaping and a sense of grandeur like no other. Inside, the home unfolds across more than 3,600 square feet of impeccably designed living space, with every room telling a story of quality, craftsmanship, and comfort. Rich herringbone hardwood floors stretch throughout the residence, complemented ... Read more....»
1742 TEMPLE DRIVE
WINTER PARK FL 32789
Residential / Single Family Residence
4 Bed · 5 Bath · 3,658 SqFt · $984/SqFt
Days on Market: 155
County: Orange
Legal Subdivision Name: LAKE KNOWLES TERRACE ADD 02
Year built: 2003
Garage: Yes 2 vehicles
Private Pool: Yes
In one of Winter Park’s desirable neighborhoods, this stunning four-bedroom, five-bath modern masterpiece with Control4 automation offers a blend of luxury and function. Designed with sleek lines and open-concept living, the home showcases Italian engineered wood flooring throughout, creating an elegant yet inviting atmosphere. Expansive windows flood the interiors with natural light, seamlessly connecting to the private outdoor oasis. At the heart of the home lies the chef’s kitchen, thoughtfully appointed with hidden storage, light-toned wood-look melamine cabinetry, sintered stone countertops, and premium Sub-Zero and Wolf appliances. Each bedroom is an en suite featuring spacious walk-in closets with custom stone ... Read more....»
516 HENKEL CIRCLE
WINTER PARK FL 32789
Residential / Single Family Residence
5 Bed · 6 Bath · 4,143 SqFt · $869/SqFt
Days on Market: 42
County: Orange
Legal Subdivision Name: THOMAS M HENKELS ADD
Year built: 1940
Garage: No
Waterfront: Yes
Lot Size (in acres): 1.32
This beautiful Mediterranean style home offers a rare opportunity for prime waterfront living on Lake Mizell, part of the highly sought out after Winter Park Chain of Lakes. Situated on a 1.32 acre lot, the property is just a short walk or drive to Park Avenue’s restaurants, boutiques, and local attractions. The main home features three bedrooms and five bathrooms, each bedroom offering its own en suite bathroom. A separate guest house (ADU) provides an additional 932 square feet with two bedrooms, one bathroom, newly refinished original hardwood floors, fresh paint and a wood burning fireplace perfect for guests or ... Read more....»
1910 GLENCOE ROAD
WINTER PARK FL 32789
Residential / Single Family Residence
4 Bed · 4 Bath · 2 Half Baths · 4,205 SqFt · $830/SqFt
Days on Market: 240
County: Orange
Legal Subdivision Name: FOREST HILLS
Year built: 2025
Garage: Yes 2 vehicles
Private Pool: Yes
Under Construction. Stunning architectural masterpiece built by LUIH homes nestled in the heart of prestigious Winter Park. This brand-new construction embodies the perfect fusion of contemporary design, timeless elegance, and exceptional quality offering 4 bedrooms, 4 full bathrooms, 2 half bathrooms, and over 4,200 square feet of thoughtfully designed luxury living space. As you step through the grand custom glass door, you're greeted by soaring ceilings, sleek wood flooring, and an abundance of natural light streaming through oversized windows and glass doors. Every detail has been curated to perfection from the artisan millwork and designer lighting to the open floor ... Read more....»
1761 LEGION DRIVE
WINTER PARK FL 32789
Residential / Single Family Residence
5 Bed · 5 Bath · 1 Half Bath · 4,955 SqFt · $686/SqFt
Days on Market: 152
County: Orange
Legal Subdivision Name: GREEN OAKS REP 02
Year built: 2017
Garage: Yes 3 vehicles
Private Pool: Yes
One of the most coveted neighborhoods in all of Winter Park! This custom-built 5-bedroom, 5.5-bath residence was completed in 2017 and first sold in 2018. Lovingly maintained by the original owner and elevated with high-end designer finishes, the home showcases the impeccable vision of renowned designer Ted Maines, who reimagined much of the interior with timeless sophistication. Perfectly positioned on a prime over-sized corner lot, the home blends transitional architecture with modern elegance. Sunlight fills the open layout through expansive sliding doors, creating effortless indoor-outdoor flow. The main living area seamlessly connects a formal living room and spacious dining area ... Read more....»
1821 ENGLEWOOD ROAD
WINTER PARK FL 32789
Residential / Single Family Residence
5 Bed · 5 Bath · 1 Half Bath · 3,863 SqFt · $853/SqFt
Days on Market: 49
County: Orange
Legal Subdivision Name: FOREST HILLS
Year built: 2025
Garage: Yes 2 vehicles
Private Pool: Yes
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 standard for luxury living. Perfectly situated on a premium, quiet, charming brick street, the home blends clean architectural lines with timeless finishes and thoughtful design details. An elegant foyer immediately introduces the home’s refined aesthetic, offering a direct line of sight to the gorgeous herringbone white oak floors in the great room and the sparkling pool just beyond the full glass doors. Anchored by a sleek linear gas fireplace with custom built-ins and floating ... Read more....»
473 FLETCHER PLACE
WINTER PARK FL 32789
Residential / Single Family Residence
5 Bed · 5 Bath · 1 Half Bath · 4,296 SqFt · $757/SqFt
Days on Market: 1
County: Orange
Legal Subdivision Name: SORENSEN HEIGHTS
Year built: 2017
Garage: Yes 2 vehicles
Private Pool: Yes
Welcome to the best of Winter Park living, where luxury meets lifestyle and every day feels like a getaway. This stunning custom home, built by Lundev, sits on a quiet, tree-lined street just a mile from Park Avenue and only steps from beautiful Lake Osceola. Imagine walking to brunch on Park Ave, then coming home to launch your paddleboard from the end of your street. From the moment you pull up, the home makes an impression from its striking architecture to the curved driveway that feels both elegant and inviting. Inside, it’s designed for the way people actually live and entertain ... Read more....»
457 E NEW ENGLAND AVENUE
WINTER PARK FL 32789
Residential / Single Family Residence
5 Bed · 4 Bath · 1 Half Bath · 3,847 SqFt · $806/SqFt
Days on Market: 27
County: Orange
Legal Subdivision Name: WINTER PARK
Year built: 1920
Garage: No
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 modern amenities. From the moment you arrive, the wraparound porch and circular drive create a welcoming first impression, setting the tone for the timeless character found throughout. Step inside to a gracious foyer accented by a cozy fireplace, leading into the spacious formal living room with its own gas fireplace and the elegant formal dining room. Gorgeous heart-of-pine floors run throughout the first floor, adding warmth and authenticity. The kitchen has been thoughtfully updated ... Read more....»
1494 WESTCHESTER AVENUE
WINTER PARK FL 32789
Residential / Single Family Residence
5 Bed · 4 Bath · 1 Half Bath · 3,711 SqFt · $806/SqFt
Days on Market: 1
County: Orange
Subdiv/Community Name: Not Applicable
Legal Subdivision Name: ORWIN MANOR WESTMINSTER SEC
Year built: 1956
Garage: Yes 2 vehicles
Private Pool: Yes
Under Construction. Welcome to Westchester Avenue—an exceptional new construction residence just moments from the iconic Park Avenue in Winter Park, celebrated for its upscale dining, refined cafés, and luxury boutique shopping. This custom-built home exemplifies true craftsmanship, showcasing elegant architecture and exquisite finishes throughout. No expense was spared in its creation. From the moment you step inside, the grand foyer sets the tone with its striking checkerboard Calacatta and Armani porcelain tile—an elegant introduction to the refined design that unfolds. The open-concept living, dining, and kitchen areas provide a seamless layout, ideal for both intimate gatherings and large-scale entertaining. The ... Read more....»
541 W CANTON AVENUE
WINTER PARK FL 32789
Residential / Single Family Residence
4 Bed · 3 Bath · 1 Half Bath · 3,553 SqFt · $826/SqFt
Days on Market: 159
County: Orange
Legal Subdivision Name: WINTER PARK
Year built: 2024
Garage: Yes 2 vehicles
Private Pool: Yes
Timeless elegance meets boutique craftsmanship at 541 W Canton Avenue—an exceptional new construction home by Urban Perch, proudly featured in the 2025 Parade of Homes Orlando. Located just steps from Winter Park’s iconic Park Avenue, this French Quarter-inspired residence blends historic charm and rich character with elevated modern living and a refined sense of calm. From its dormer windows and custom-carved wood entry door, to its charming striped awnings and the flicker of gas lanterns, every detail of the exterior is carefully curated. Classic marble-paved patios frame the home, and a courtyard-style pool with fountain and sandblasted marble decking invite quiet ... Read more....»
1401 GREEN COVE ROAD
WINTER PARK FL 32789
Residential / Single Family Residence
3 Bed · 4 Bath · 3 Half Baths · 5,483 SqFt · $529/SqFt
Days on Market: 35
Cumulative Days on Market: 151
County: Orange
Legal Subdivision Name: CAMWOOD SUB
Year built: 2009
Garage: Yes 2 vehicles
Private Pool: Yes
Set across Lake Maitland on a street where every home is an architectural gem, this Award-winning Villa Toscana blends Old-World craftsmanship with timeless architectural elegance in one of Winter Park’s most coveted enclaves. Built in 2009 and named “Best of Show” in the Parade of Homes, this 5,483 sq ft estate offers 3 bedrooms, 7 bathrooms, and 7 versatile bonus rooms, including a private guest casita and a fully finished basement. Total area including outdoor spaces: 6,821 sq ft. The exterior showcases a stone façade, barrel-tile roof, wrought-iron detailing, and lush courtyards. A gated entry with outdoor fireplace leads to the ... Read more....»
2503 VERSAILLES AVENUE
WINTER PARK FL 32789
Residential / Single Family Residence
5 Bed · 5 Bath · 4,026 SqFt · $689/SqFt
Days on Market: 1
County: Orange
Legal Subdivision Name: FONTAINEBLEAU
Year built: 2015
Garage: Yes 3 vehicles
Private Pool: Yes
Beautifully updated and offered for the first time, this 2015 David Weekley home sits on a rare cul-de-sac in the heart of Winter Park, zoned for Dommerich Elementary and Winter Park schools. This 5-bedroom, 5-bath home features an office, large bonus room, covered lanai with full summer kitchen, and a backyard putting green. Additional highlights include a 3-car garage, a gated parking pad ideal for extra vehicles, a boat, or jet skis, a tankless gas water heater, and a new roof installed in 2021. Thoughtful improvements include custom built-ins in the living room, office, flex space, and dining room; upgraded ... Read more....»
426 WORTHINGTON DRIVE
WINTER PARK FL 32789
Residential / Single Family Residence
5 Bed · 4 Bath · 1 Half Bath · 3,520 SqFt · $761/SqFt
Days on Market: 4
County: Orange
Legal Subdivision Name: KENILWORTH SHORES SEC 01
Year built: 2026
Garage: Yes 2 vehicles
Private Pool: Yes
Under Construction. Designed with intention and built with precision, this brand-new LUIH Luxury home exemplifies the elegance and livability Winter Park is known for. Every inch of this residence has been curated for those who demand extraordinary design, flawless craftsmanship, and a lifestyle that feels both elevated and effortless. Step through the front door and into a grand two-story foyer where natural light cascades from above, illuminating the level of detail that unfolds in every direction. The main living space is an elegant composition of scale, comfort, and style. A dramatic fireplace anchors the room, while expansive glass sliders dissolve ... Read more....»
2550 VENETIAN WAY
WINTER PARK FL 32789
Residential / Single Family Residence
4 Bed · 3 Bath · 2 Half Baths · 4,875 SqFt · $513/SqFt
Days on Market: 384
Cumulative Days on Market: 385
County: Orange
Legal Subdivision Name: MAITLAND SHORES FIRST ADD
Year built: 2008
Garage: Yes 2 vehicles
Waterfront: Yes
"The richness of an artist is the fusion of influences that have shaped his life and work", ~ Fernando Botero. WELCOME HOME to 2550 Venetian Way, located in the historic and renowned city of Winter Park, accessing the Maitland/Winter Park CHAIN OF LAKES! This custom modern/contemporary 2008 build, derives it's over 4800 sq/ft of essence and uniqueness by fusing vibrant colors and eloquence with high-end home features and artistic details. Upon entry, visitors are greeted by a gorgeous rotunda accented with stained glass panels and vaulted, recessed ceilings. With 4 bedrooms, 3 full baths, and 2 half baths, this split ... Read more....»
The information relating to real estate for sale on this website comes in part from the My Florida Regional MLS DBA Stellar MLS. This information is provided exclusively for consumers' personal, non-commercial use. It may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed accurate by the MLS.
