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: 241
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....»
40 PALMER AVENUE
WINTER PARK FL 32789
Residential / Single Family Residence
5 Bed · 5 Bath · 1 Half Bath · 5,905 SqFt · $1,177/SqFt
Days on Market: 11
County: Orange
Legal Subdivision Name: ROBERT DHU MACDONALD PARK
Year built: 2026
Garage: Yes 4 vehicles
Private Pool: Yes
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 represents a rare convergence of architectural significance, uncompromising craftsmanship, and premier Winter Park location. Built by Vimaro Homes, this extraordinary new construction estate is a statement piece that redefines what luxury living looks like in the heart of Winter Park. The exterior architecture is refined yet commanding, with classical influences interpreted through a modern lens, setting the tone for the exceptional level of design and finishes found inside. One of the most remarkable features, and ... Read more....»
550 PALMER AVENUE
WINTER PARK FL 32789
Residential / Single Family Residence
5 Bed · 6 Bath · 1 Half Bath · 5,939 SqFt · $1,161/SqFt
Days on Market: 101
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: 443
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....»
1200 VIA SALERNO
WINTER PARK FL 32789
Residential / Single Family Residence
5 Bed · 5 Bath · 1 Half Bath · 5,476 SqFt · $1,178/SqFt
Days on Market: 5
County: Orange
Legal Subdivision Name: CLOISTER GROVE SUB
Year built: 2001
Garage: Yes 3 vehicles
Private Pool: Yes
Along one of the cobblestone brick streets in the prestigious Via’s of Winter Park, this completely renovated residence pairs timeless European influence with clean architectural lines and bespoke finishes throughout. A circular driveway and manicured grounds designed by Signature Landscapes create a graceful approach. Inside, a dramatic curved staircase crowned by a breathtaking 1960s vintage Venini chandelier immediately sets the tone for the exceptional craftsmanship carried throughout the home. The main gathering room is striking and inviting, defined by vaulted ceilings, a Sequoia leathered stone fireplace hearth, and a wall of glass sliders that open seamlessly to the covered lanai ... Read more....»
887 GEORGIA AVENUE
WINTER PARK FL 32789
Residential / Single Family Residence
6 Bed · 5 Bath · 1 Half Bath · 5,759 SqFt · $990/SqFt
Days on Market: 179
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....»
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 · $1,017/SqFt
Days on Market: 21
Cumulative Days on Market: 206
County: Orange
Legal Subdivision Name: VIRGINIA HEIGHTS REP
Year built: 2024
Garage: Yes 2 vehicles
Private Pool: Yes
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, prized for its proximity to Park Avenue, placement within an A-rated school district, and deeded access to the Winter Park Chain of Lakes. Created by an award-winning builder as a personal family residence, this home reflects a level of craftsmanship and finish typically reserved for private custom builds. Soaring ceilings, walls of glass and an open-concept layout create seamless indoor-outdoor living ideal for everyday comfort and elevated entertaining. The chef’s kitchen is complemented by bespoke custom cabinetry throughout ... Read more....»
1302 RAINTREE PLACE
WINTER PARK FL 32789
Residential / Single Family Residence
5 Bed · 5 Bath · 1 Half Bath · 4,738 SqFt · $1,087/SqFt
Days on Market: 89
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: 362
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: 208
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....»
1336 COLLEGE POINT
WINTER PARK FL 32789
Residential / Single Family Residence
4 Bed · 3 Bath · 2 Half Baths · 3,181 SqFt · $1,445/SqFt
Days on Market: 4
County: Orange
Legal Subdivision Name: VIRGINIA HEIGHTS
Year built: 1926
Garage: No
Private Pool: Yes
Waterfront: Yes
Steeped in history and masterfully reimagined, this 1926 Winter Park estate blends architectural provenance with modern refinement. Thoughtfully restored by E2 Homes, the residence honors its past while offering contemporary sophistication. Unlike many historic properties, it is free from preservation restrictions, allowing for seamless enhancements. On the shores of Lake Virginia along the desirable Winter Park Chain of Lakes, this 3,181-square-foot estate features four bedrooms, three full baths and two half baths, with three bedrooms in the main house plus a detached one-bedroom guest cottage. The second-floor primary suite is a private retreat with a Juliet balcony, dual closets and ... Read more....»
1161 VALENCIA AVENUE
WINTER PARK FL 32789
Residential / Single Family Residence
4 Bed · 4 Bath · 1 Half Bath · 4,181 SqFt · $1,051/SqFt
Days on Market: 176
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....»
1417 WILLIAMS DRIVE
WINTER PARK FL 32789
Residential / Single Family Residence
5 Bed · 5 Bath · 1 Half Bath · 4,891 SqFt · $859/SqFt
Days on Market: 37
County: Orange
Legal Subdivision Name: PARK GROVE
Year built: 2026
Garage: Yes 3 vehicles
Private Pool: Yes
Under Construction. Tucked away on a quiet cul-de-sac in the coveted Park Grove community, this home sits on an expansive 0.37-acre lot, just moments from the boutiques, dining, and charm of Park Avenue. The exterior makes a striking first impression with a refined architectural façade that feels both timeless and distinctive. Inside, a dramatic 20-foot foyer welcomes you with abundant natural light and a sense of scale that is impressive yet inviting. The layout flows seamlessly into a warm, elevated great room featuring soaring ceilings, wide-plank hardwood floors, exposed wood beams, handcrafted millwork with integrated shelving, subtle LED accent lighting, ... Read more....»
1120 PALMER AVENUE
WINTER PARK FL 32789
Residential / Single Family Residence
3 Bed · 3 Bath · 1 Half Bath · 3,413 SqFt · $1,157/SqFt
New Listing!!! Days on Market: 1
County: Orange
Legal Subdivision Name: 3223171-3223171
Year built: 1951
Garage: Yes 2 vehicles
Private Pool: Yes
Miami Beach/Coral Gables meets Winter Park high-end luxury for today's upscale lifestyle. Phil Kean completely re-imagined this 3400 sq ft one story home from top to bottom leaving virtually nothing untouched! If you are looking for one level living, all of the most up-to-date Bells and Whistles, in a #10 location, this will blow your socks off! Available to tour by appointment only. This is a show home for the International Builders Show, and is fully furnished and curated with artwork (all available for purchase as well). Home will be available to convey in April. Home comes with a ... Read more....»
1681 BLUE RIDGE ROAD
WINTER PARK FL 32789
Residential / Single Family Residence
5 Bed · 4 Bath · 2 Half Baths · 4,247 SqFt · $894/SqFt
Days on Market: 12
County: Orange
Legal Subdivision Name: TIMBERLANE SHORES
Year built: 1960
Garage: Yes 3 vehicles
Private Pool: Yes
Pre-Construction. To be built. Build your dream home with premier custom home builder, FG Schaub Custom Homes on this highly desirable Winter Park homesite. Located at 1681 Blue Ridge Rd., this thoughtfully designed new construction Transitional-style residence will feature 5 bedrooms plus a dedicated office, 4 full bathrooms, 2 half bathrooms, 4,272 square feet of living space, and a 3-car garage, blending timeless architectural elements with modern sophistication. Designed for today’s lifestyle, the open and functional floor plan features elegant architectural details, expansive living areas filled with natural light, and seamless indoor-outdoor living. The outdoor retreat will include a resort-style pool ... Read more....»
1751 GLENCOE ROAD
WINTER PARK FL 32789
Residential / Single Family Residence
5 Bed · 5 Bath · 2 Half Baths · 4,520 SqFt · $829/SqFt
Days on Market: 108
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....»
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: 86
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....»
948 POINCIANA LANE
WINTER PARK FL 32789
Residential / Single Family Residence
4 Bed · 3 Bath · 1 Half Bath · 3,676 SqFt · $979/SqFt
Days on Market: 37
County: Orange
Legal Subdivision Name: MAITLAND SHORES FIRST ADD
Year built: 2001
Garage: Yes 2 vehicles
Private Pool: Yes
Timeless Elegance Meets Modern Luxury in Winter Park's Most Coveted Location Discover an extraordinary residence where exceptional craftsmanship and sophisticated design converge at 948 Poinciana Lane. This meticulously reimagined estate represents the pinnacle of refined living in one of Winter Park's most prestigious neighborhoods, offering an effortless blend of classic architecture and contemporary luxury. From the moment you step through the elegant foyer, you're greeted by sun-drenched interiors showcasing gleaming hardwood floors, soaring coffered ceilings, and designer details at every turn. The thoughtful floor plan reveals a private home office with custom built-ins and fireplace to the right, and a gracious formal ... Read more....»
1742 TEMPLE DRIVE
WINTER PARK FL 32789
Residential / Single Family Residence
4 Bed · 5 Bath · 3,658 SqFt · $970/SqFt
Days on Market: 1
Cumulative Days on Market: 188
County: Orange
Legal Subdivision Name: LAKE KNOWLES TERRACE ADD 02
Year built: 2003
Garage: Yes 2 vehicles
Private Pool: Yes
A New Standard of Modern Sophistication in Winter Park In a city known for its heritage, this ground-up architectural renovation emerges as a bold statement of modern luxury. Located within one of Winter Park’s most coveted enclaves, this four-bedroom, five-bathroom residence is not merely a place to live, but a meticulously crafted experience where high-design meets intuitive living. Step through the striking 10-foot glass pivot doors into a world defined by light and scale. The soaring foyer gives way to an expansive open-concept floor plan, where the boundary between indoors and out begins to blur. Sleek Italian wood flooring guides you through ... Read more....»
516 HENKEL CIRCLE
WINTER PARK FL 32789
Residential / Single Family Residence
5 Bed · 6 Bath · 4,143 SqFt · $809/SqFt
Days on Market: 108
County: Orange
Legal Subdivision Name: THOMAS M HENKELS ADD
Year built: 1940
Garage: No
Waterfront: Yes
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. 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 extended family. Inside the main residence, ... 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: 141
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....»
1761 LEGION DRIVE
WINTER PARK FL 32789
Residential / Single Family Residence
5 Bed · 5 Bath · 1 Half Bath · 4,955 SqFt · $665/SqFt
Days on Market: 253
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....»
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....»
151 OAKWOOD WAY
WINTER PARK FL 32789
Residential / Single Family Residence
4 Bed · 4 Bath · 1 Half Bath · 4,129 SqFt · $770/SqFt
Days on Market: 10
County: Orange
Legal Subdivision Name: CHARMONT
Year built: 2023
Garage: Yes 2 vehicles
Private Pool: Yes
Welcome to 151 Oakwood Way. This is a rare Winter Park showpiece by LunDev Custom Homes, tucked on a quiet, tree-lined street in the heart of Winter Park. This newer luxury pool home delivers the perfect blend of timeless architecture and modern comfort, pairing clean transitional design with warm, high-end selections and true Florida indoor/outdoor living. Inside, a bright open-concept floor plan is elevated by engineered hardwood flooring, quartz finishes, and a chef’s kitchen designed to perform. Featuring premium Thermador appliances and a layout built for entertaining and everyday life. The home lives beautifully with thoughtful flow, generous natural light, ... Read more....»
457 E NEW ENGLAND AVENUE
WINTER PARK FL 32789
Residential / Single Family Residence
5 Bed · 4 Bath · 1 Half Bath · 3,896 SqFt · $796/SqFt
Days on Market: 108
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: 86
County: Orange
Subdiv/Community Name: Not Applicable
Legal Subdivision Name: ORWIN MANOR WESTMINSTER SEC
Year built: 2026
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....»
2012 LOCH BERRY ROAD
WINTER PARK FL 32792
Residential / Single Family Residence
5 Bed · 4 Bath · 1 Half Bath · 3,800 SqFt · $710/SqFt
Days on Market: 2
County: Orange
Legal Subdivision Name: KENILWORTH SHORES SEC 03
Year built: 2026
Garage: Yes 2 vehicles
Private Pool: Yes
Under Construction. Under Construction. Welcome to a brand-new luxury residence coming to one of Winter Park’s most desirable locations. This thoughtfully designed home blends modern elegance with functional living, offering a refined layout, quality craftsmanship, and a lifestyle tailored for comfort and entertaining. Planned features include an open-concept floor plan with spacious living and dining areas, a designer kitchen with custom cabinetry, premium appliances, and stone countertops, along with carefully curated finishes throughout. The primary suite is designed as a private retreat with a well-appointed bathroom and generous closet space, while additional bedrooms provide flexibility for guests, office space, or multi-generational ... 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: 73
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....»
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.
