1821 ENGLEWOOD ROAD
WINTER PARK FL 32789
Residential / Single Family Residence
5 Bed · 5 Bath · 1 Half Bath · 3,863 SqFt · $812/SqFt
Days on Market: 197
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....»
670 WILLIAMS DRIVE
WINTER PARK FL 32789
Residential / Single Family Residence
5 Bed · 4 Bath · 1 Half Bath · 4,091 SqFt · $732/SqFt
Days on Market: 56
County: Orange
Legal Subdivision Name: PARK GROVE
Year built: 2016
Garage: Yes 2 vehicles
Private Pool: Yes
This stunning custom residence built by respected Winter Park Builder Charles Clayton blends classic elegance with refined modern comfort, offering seamless indoor–outdoor living and impeccable craftsmanship throughout. From the manicured lawn and stately traditional exterior to the welcoming front porch with old Detroit brick, the home’s curb appeal sets a tone of understated luxury, all wrapped in an elegant exterior. A foyer with extensive custom molding immediately captures attention, with sightlines extending to the private backyard and pool which creates a natural flow between interior living spaces and the outdoor retreat. Flanking the foyer, a richly detailed private study features ... Read more....»
151 OAKWOOD WAY
WINTER PARK FL 32789
Residential / Single Family Residence
4 Bed · 4 Bath · 1 Half Bath · 4,129 SqFt · $714/SqFt
Days on Market: 55
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....»
1529 HOLTS GROVE CIRCLE
WINTER PARK FL 32789
Residential / Single Family Residence
4 Bed · 4 Bath · 2 Half Baths · 4,356 SqFt · $654/SqFt
Days on Market: 3
County: Orange
Legal Subdivision Name: WINDSONG LAKESIDE SEC 02 43/71
Year built: 2005
Garage: Yes 3 vehicles
Private Pool: Yes
Tucked within the prestigious enclave of Windsong Lakeside in Winter Park, this extraordinary estate is a masterclass in refined living—where thoughtful design, cutting-edge technology, and timeless elegance converge. From the moment you arrive, the circular drive and stately presence set a tone of quiet grandeur. Step inside, and the home unfolds with an effortless sense of scale, defined by soaring vaulted ceilings and an abundance of natural light filtering through custom windows. Every detail has been meticulously curated—from the rich new flooring installed in 2025 to the soft glow of Currey & Co. lighting that adds warmth and sophistication to ... Read more....»
1300 MAYFIELD AVENUE
WINTER PARK FL 32789
Residential / Single Family Residence
5 Bed · 5 Bath · 1 Half Bath · 4,389 SqFt · $649/SqFt
Days on Market: 4
County: Orange
Legal Subdivision Name: TEMPLE HEIGHTS
Year built: 1958
Garage: Yes 4 vehicles
Private Pool: Yes
Tucked behind towering hedges on a coveted brick-lined street, this estate sits on an approximately ½-acre corner lot and has been enhanced with thoughtful improvements, delivering a rare combination of modern functionality, Old World charm, and a fabulous lifestyle. Notable updates include newer HVAC systems (2020 and 2025), a tankless gas water heater, a fully renovated laundry room with new LG stackable washer and dryer, newer kitchen appliances, new copper gutters and downspouts, fresh exterior paint (2025), a newly designed primary bathroom, and much more. The main residence spans over 3,600+ SF with an attached 2-car garage and is complemented ... Read more....»
609 S PHELPS AVENUE
WINTER PARK FL 32789
Residential / Single Family Residence
5 Bed · 4 Bath · 1 Half Bath · 4,018 SqFt · $704/SqFt
Days on Market: 11
County: Orange
Legal Subdivision Name: KENILWORTH SHORES SEC 06
Year built: 2026
Garage: Yes 2 vehicles
Private Pool: Yes
Under Construction. Introducing the newest showpiece from LUIH Luxury Homes, perfectly positioned in the heart of Winter Park. Set on an oversized homesite along a quiet, tree-lined street, this residence immediately captivates with its expansive front lawn and timeless architectural presence. Inside, the home unfolds with a thoughtfully designed and highly functional floor plan that balances refined living with effortless entertaining. The spacious family room serves as the heart of the home, anchored by a sleek electric fireplace and framed by open sightlines into the kitchen and main living spaces, creating a warm yet sophisticated gathering environment. At the center ... Read more....»
541 W CANTON AVENUE
WINTER PARK FL 32789
Residential / Single Family Residence
4 Bed · 3 Bath · 1 Half Bath · 3,553 SqFt · $788/SqFt
Days on Market: 2
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 Ave., an exceptional new construction home by Urban Perch, proudly featured in the 2025 Parade of Homes Orlando. Near 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 invites quiet relaxation ... Read more....»
432 WORTHINGTON DRIVE
WINTER PARK FL 32789
Residential / Single Family Residence
5 Bed · 4 Bath · 1 Half Bath · 3,845 SqFt · $707/SqFt
Days on Market: 1
County: Orange
Legal Subdivision Name: KENILWORTH SHORES SEC 01
Year built: 2026
Garage: Yes 2 vehicles
Private Pool: Yes
Under Construction. Spectacular new LUIH Luxury Home in the heart of Winter Park! Clean architectural lines, a bold façade, and curated exterior detailing set the tone for what unfolds inside. Beyond the entry, the home opens into a dramatic, light-filled living space featuring a sleek electric fireplace, framed by custom built-ins with ambient LED underlighting, while a glass-enclosed wine display serves as a stunning architectural detail. The kitchen is a true centerpiece, designed to impress at every level. Outfitted with a full suite of premium Thermador appliances, striking Calacatta quartz countertops, custom cabinetry, and a spacious walk-in pantry. Privately ... Read more....»
1130 PARK NORTH PLACE
WINTER PARK FL 32789
Residential / Single Family Residence
5 Bed · 3 Bath · 1 Half Bath · 4,011 SqFt · $661/SqFt
Days on Market: 11
County: Orange
Legal Subdivision Name: PARK NORTH
Year built: 1968
Garage: Yes 2 vehicles
Located on a quiet cul-de-sac in the heart of Winter Park, this traditional two-story home offers a functional, well-designed floorplan for both everyday living and entertaining. From the moment you step inside, the home has an inviting warmth that you can immediately feel. The main level features a spacious primary suite along with connected living spaces that flow easily from room to room. The primary suite and family room both feature tall ceilings and an abundance of natural light, creating a bright and inviting wing of the home. The kitchen opens to the casual dining area and family room, creating a ... Read more....»
2550 VENETIAN WAY
WINTER PARK FL 32789
Residential / Single Family Residence
4 Bed · 3 Bath · 2 Half Baths · 5,051 SqFt · $485/SqFt
Days on Market: 22
County: Orange
Legal Subdivision Name: MAITLAND SHORES FIRST ADD
Year built: 2008
Garage: Yes 2 vehicles
Waterfront: Yes
Chain of Lakes Water- Front Home with Private Boat Dock, Winter Park Luxury Living. Step into your future with this extraordinary custom built residence, inspired by the artistic richness of Fernando Botero. From your back lanai, step directly onto your private, custom boat dock featuring a covered, remote-operated boat lift, and cruise the Venetian Canal with direct access to WinterPark’s exclusive Chain of Lakes-Lake Virginia, Lake Mizell, Lake Osceola, Lake Maitland, Lake Nina, and Lake Minnehaha. Morning sunrises and golden afternoon sunsets create unforgettable moments to enjoy privately or share with family and friends. Built in 2008, this exceptional ... Read more....»
1760 LEGION DRIVE
WINTER PARK FL 32789
Residential / Single Family Residence
4 Bed · 5 Bath · 1 Half Bath · 4,392 SqFt · $545/SqFt
Days on Market: 13
County: Orange
Subdiv/Community Name: Not Applicable
Legal Subdivision Name: GREEN OAKS REP
Year built: 1964
Garage: Yes 2 vehicles
Private Pool: Yes
Winter Park 1964 Charmer! This wonderful ranch is located just minutes to Downtown Orlando as well as Park Ave. With over 4300 sq ft of living space, this, 4 bed/5.5 bath home is in the prime location. Upon entering you'll notice just how light and bright this home shows, to your right you will find a home office space. Rich dark wood, custom cabinetry and dramatic lighting provide the perfect space to start your morning or end your day. To the left of the entry, you will find the large formal living room with 1 of 2 gas fires places ... Read more....»
2412 CHANTILLY AVENUE
WINTER PARK FL 32789
Residential / Single Family Residence
5 Bed · 6 Bath · 1 Half Bath · 4,506 SqFt · $532/SqFt
Days on Market: 53
Cumulative Days on Market: 141
County: Orange
Legal Subdivision Name: WINTER PARK VILLAGE
Year built: 2026
Garage: Yes 3 vehicles
Private Pool: Yes
Exceptional design meets refined luxury in this brand-new architectural masterpiece by DaVinci. This 5 bedroom, 6.5 bath home offers over 4,500 square feet of bright, open living space designed for both comfort and functionality. Enter through your custom glass front door into the foyer leading to your main living area featuring a fireplace and sliding glass walls for indoor-outdoor living. This flows effortlessly into a gorgeous gourmet kitchen with high-end appliances featuring a Wolf range, Sub-Zero refrigerator, Euro-style cabinetry, oversized island, and walk-in pantry. The downstairs primary suite overlooks the pool and includes a spa-like bath with soaking tub and ... Read more....»
1760 ALABAMA DRIVE
WINTER PARK FL 32789
Residential / Single Family Residence
4 Bed · 2 Bath · 1 Half Bath · 2,841 SqFt · $809/SqFt
Days on Market: 21
County: Orange
Legal Subdivision Name: J KRONENBERGER SUB
Year built: 1971
Garage: Yes 2 vehicles
Welcome to 1760 Alabama Drive, a striking mid-century residence where architectural character, thoughtful modernization, and exceptional livability come together in one of Winter Park’s most desirable neighborhoods. Spanning 2,841 square feet, this distinctive home celebrates authentic mid-century design with clean lines, intentional geometry, and expansive walls of glass that bring the outdoors in. Natural light pours through oversized windows throughout the home, while dramatic 20 foot hedges on both sides create a rare sense of privacy. The result is a space that feels bright, open, and connected to nature while remaining remarkably secluded. At the heart of the home is ... Read more....»
2299 VIA TUSCANY
WINTER PARK FL 32789
Residential / Single Family Residence
4 Bed · 3 Bath · 1 Half Bath · 3,986 SqFt · $576/SqFt
Days on Market: 109
County: Orange
Legal Subdivision Name: MAITLAND SHORES
Year built: 1953
Garage: Yes 2 vehicles
Private Pool: Yes
Welcome to 2299 Via Tuscany, a remarkable 4-bedroom, 3.5 bathroom residence in the prestigious Winter Park Vias. This 3,986 square foot home, set on a .40-acre private lot, offers a blend of luxury and comfort. The property has seen recent updates in the kitchen and bathrooms and features a new architectural shingle roof (2023), Pebble-tech style pool finish and a manicured landscape. Inside, enjoy the elegance of solid hardwood and modern tile flooring, high ceilings, and two wood burning fireplaces. The chef's kitchen is equipped with premium appliances, including SubZero refrigeration and a Viking 6-burner gas cooktop. The main floor ... Read more....»
2015 N PARK AVENUE
WINTER PARK FL 32789
Residential / Single Family Residence
5 Bed · 4 Bath · 1 Half Bath · 3,963 SqFt · $579/SqFt
Days on Market: 50
County: Orange
Legal Subdivision Name: TWIN ACRES
Year built: 2023
Garage: Yes 2 vehicles
Private Pool: Yes
Boasting a prestigious Park Avenue address, this striking modern architectural residence perfectly balances bold design with spa-like serenity. Set on a beautifully landscaped corner lot, the home embodies the rare combination of privacy and proximity, just a leisurely 25-minute stroll from Park Avenue’s world-class boutiques and dining. Every element of the design has been meticulously curated to evoke a sense of refined tranquility, where clean lines, natural textures, and warm tones create a timeless yet inviting atmosphere. Inside, expansive open concept living spaces are bathed in natural light, showcasing designer lighting, custom millwork, and seamless indoor-outdoor integration. The chef’s kitchen ... Read more....»
240 N PHELPS AVENUE
WINTER PARK FL 32789
Residential / Single Family Residence
5 Bed · 4 Bath · 1 Half Bath · 2,889 SqFt · $789/SqFt
Days on Market: 12
County: Orange
Legal Subdivision Name: SYLVAN HEIGHTS
Year built: 2026
Garage: Yes 2 vehicles
Private Pool: Yes
Brand new construction luxury home in the heart of Winter Park! This stunning two-story custom residence offers nearly 3,000 sq ft of heated living space with 5 bedrooms and 4 1/2 bathrooms. A soaring two-story foyer creates a dramatic first impression and opens into an expansive great room featuring 12-foot ceilings, wide-plank flooring, and abundant natural light. The family room showcases a custom paneled feature wall with a sleek built-in electric fireplace, creating a striking focal point for the space. The gourmet kitchen is designed for both everyday living and entertaining, highlighted by a large center island with seating, European slab ... Read more....»
1624 BARCELONA WAY
WINTER PARK FL 32789
Residential / Single Family Residence
4 Bed · 3 Bath · 3,828 SqFt · $594/SqFt
Days on Market: 110
County: Orange
Legal Subdivision Name: SEVILLA
Year built: 1972
Garage: Yes 2 vehicles
Private Pool: Yes
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 landscaped lot. Original home was mostly gutted down to the studs in 2011-2012 and completely re-done. Interior layout boasts formal living with bay window and tall ceilings, dining room with antiqued mirror set into extensive moldings and trim, plus a library/den with a tongue and groove wood vaulted ceiling and a wall of bookshelves and built-ins. The spacious family room with a white-washed brick, wood-burning fireplace wall and vaulted ceiling is all open to the ... Read more....»
1885 TEMPLE DRIVE
WINTER PARK FL 32789
Residential / Single Family Residence
5 Bed · 3 Bath · 1 Half Bath · 3,691 SqFt · $614/SqFt
Days on Market: 123
Cumulative Days on Market: 164
County: Orange
Legal Subdivision Name: LUGANO TERRACE
Year built: 1963
Garage: Yes 2 vehicles
Private Pool: Yes
NEW 2026 Black Steel doors windows with low e-dual pane glass ($150k value!). 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 timeless charm with extensive modern updates. Set on a beautifully oversized landscaped lot with a roundabout driveway. Winter Park’s most sought-after neighborhoods near the Vias, Winter Park Racquet Club and Dommerich Elementary. Inside, wide-plank engineered white pine flooring flows throughout, complementing vaulted ceilings, wood-burning fireplace in the living room, and a spacious open layout ideal for entertaining. The informal dining room overlooks ... Read more....»
318 VITORIA AVENUE
WINTER PARK FL 32789
Residential / Single Family Residence
3 Bed · 2 Bath · 1 Half Bath · 2,433 SqFt · $904/SqFt
Days on Market: 10
County: Orange
Complex/CommunityName: COLLEGE QUARTER
Legal Subdivision Name: COLLEGE PLACE REP
Year built: 1922
Garage: No
Private Pool: Yes
Elegant 1922 Mission Revival home, located in popular College Quarter is a registered historic place in Winter Park, FL. Lifestyle is neighborly/relaxed/pet friendly/enhanced by proximity to Lake Virginia/lakeshore sidewalks/Rollins College campus/downtown Winter Park/Central Park/museums/shops/restaurants/cultural events, most walking distance. College Quarter residents enjoy exclusive use of Park/Dock on Lake Virginia to kayak/paddleboard/motor through Chain of Lakes or meet up for holiday fireworks/once-in-a-lifetime or yearly celestial events. College Quarter is one of the oldest/most architecturally diverse neighborhoods. This 1922 home represents the Florida Mission Revival vernacular through a timeless blend of stucco exterior walls/asymmetrical façade/prominent arches above doors/large windows/a flat roof/barrel red ... Read more....»
2423 VIA SIENNA
WINTER PARK FL 32789
Residential / Single Family Residence
4 Bed · 3 Bath · 1 Half Bath · 3,472 SqFt · $634/SqFt
Days on Market: 23
County: Orange
Legal Subdivision Name: CINNAMON SHORES
Year built: 1990
Garage: Yes 2 vehicles
Private Pool: Yes
Welcome to 2423 Via Sienna, gracefully positioned on a quiet cul-de-sac in the heart of Winter Park. This charming, established enclave is just moments from the Winter Park Racquet Club, Phelps Park, the YMCA, and the renowned boutiques and dining of Park Avenue. This exceptional four-bedroom, three-and-a-half-bath pool residence has been taken to the studs and masterfully reimagined with timeless finishes and thoughtful design throughout. Upon entry, soaring ceilings and expansive windows create a light-filled, open interior ideal for both everyday living and elegant entertaining. The living and dining spaces are accented by tongue-and-groove ceilings, a gas fireplace, and bespoke built-ins, ... Read more....»
1636 ELIZABETHS WALK
WINTER PARK FL 32789
Residential / Single Family Residence
4 Bed · 4 Bath · 1 Half Bath · 3,412 SqFt · $643/SqFt
Days on Market: 3
County: Orange
Legal Subdivision Name: WINDSONG ELIZABETHS WALK 43/81
Year built: 2016
Garage: Yes 2 vehicles
Private Pool: Yes
Discover refined living in this stunning custom-built home located in the coveted community of Windsong. Thoughtfully designed and expertly constructed by Goehring & Morgan, this four-bedroom, 4.5 bath residence offers a perfect balance of elegance, comfort and functionality. From the moment you enter, the home impresses with its airy, open-concept design, ideal for both relaxed living and effortless entertaining. The kitchen serves as a focal point, appointed with leathered granite countertops, a generous center island with seating and a seamless connection to the inviting family room, where a gas fireplace adds warmth and charm. Walls of sliding glass doors extend ... Read more....»
2503 VERSAILLES AVENUE
WINTER PARK FL 32789
Residential / Single Family Residence
5 Bed · 5 Bath · 4,026 SqFt · $542/SqFt
Days on Market: 104
County: Orange
Legal Subdivision Name: FONTAINEBLEAU
Year built: 2015
Garage: Yes 3 vehicles
Private Pool: Yes
Back on the market—an exceptional opportunity in Winter Park. Now offered below appraised value, this residence has been thoughtfully refreshed with new carpet, interior paint, and thoughtful enhancements. Presented for the first time, this beautifully appointed 2014 David Weekley home is tucked away on a large corner lot within a rare cul-de-sac in the heart of Winter Park, zoned for Dommerich Elementary and Winter Park schools. Featuring 5 bedrooms and 5 bathrooms, the home is designed for both refined living and effortless entertaining, this home includes a private office and expansive bonus spaces. A standout feature of this property is its exceptional ... Read more....»
1711 BARCELONA WAY
WINTER PARK FL 32789
Residential / Single Family Residence
5 Bed · 3 Bath · 3,669 SqFt · $572/SqFt
Days on Market: 71
County: Orange
Complex/CommunityName: SEVILLA
Legal Subdivision Name: SEVILLA
Year built: 1979
Garage: Yes 3 vehicles
Private Pool: Yes
Walk in and feel instantly at home in this stunning 5-bedroom, 3-bath POOL home with a 3-car garage, offering over 3,600 square feet of living space on more than ¾ of an acre in the highly desirable Sevilla neighborhood of Winter Park. Backing directly to Howell Creek and Mead Gardens, this property offers the rare luxury of no rear neighbors and exceptional privacy. Upon entry, you’re welcomed by beautiful wood floors and versatile spaces to the left that can serve as a formal living room, dining room, office, or playroom. Continue into the impressive family room, featuring vaulted ceilings, skylights, ... Read more....»
785 N PHELPS AVENUE
WINTER PARK FL 32789
Residential / Single Family Residence
5 Bed · 3 Bath · 1 Half Bath · 2,964 SqFt · $691/SqFt
Days on Market: 10
County: Orange
Legal Subdivision Name: COMSTOCK PARK
Year built: 2026
Garage: Yes 2 vehicles
Private Pool: Yes
Exquisite new construction in the heart of Winter Park, this LUIH Luxury Homes residence distinguishes itself through refined design, thoughtful efficiency, and an elevated level of craftsmanship. From the moment you enter, the home reveals itself with deliberate intention, clean architectural lines and a light-filled, open-concept layout create an effortless flow throughout. The main living space is both sophisticated and inviting, anchored by a sleek electric fireplace and expansive pocketing glass doors that gracefully blur the line between indoor and outdoor living. At the heart of the home, the chef’s kitchen is as striking as it is functional. Adorned with ... Read more....»
2036 VIA TUSCANY
WINTER PARK FL 32789
Residential / Single Family Residence
3 Bed · 2 Bath · 2,148 SqFt · $931/SqFt
Days on Market: 1
County: Orange
Legal Subdivision Name: TUSCANIA
Year built: 1957
Garage: Yes 2 vehicles
WINTER PARK VIA’S!!! Incredible Oversized Lot is located in the “Heart” of Winter Park. Very Unique opportunity in Winter Park for a high-quality custom build. The brick lined lighted street with sidewalks is located across from the Winter Park Racquet Club. This location is a wonderful opportunity to build your Estate Home. The lot size is 112’ X 140’. Value is in the land.
1750 CAROLLEE LANE
WINTER PARK FL 32789
Residential / Single Family Residence
4 Bed · 3 Bath · 1 Half Bath · 3,249 SqFt · $614/SqFt
Days on Market: 5
County: Orange
Legal Subdivision Name: GREEN TERRACE V/140 LOT 3 BLK B
Year built: 2012
Garage: Yes 2 vehicles
Private Pool: Yes
Welcome to 1750 Carollee Lane, where timeless charm meets modern luxury. In one of Winter Park’s established neighborhoods, residents enjoy access to top-rated schools, tree-lined streets, and proximity to Park Avenue’s renowned dining and shopping, as well as the area’s scenic Chain of Lakes. Originally built in 2012, this four-bedroom, 3.5-bath home offers over 3,200 square feet of thoughtfully designed living space, enhanced by a comprehensive series of recent upgrades. The fully renovated 2025 kitchen serves as centerpiece of the home, featuring quartzite countertops, a custom wood hood, Zellige-style backsplash, induction cooktop, oversized workstation sink, refinished cabinetry and designer hardware, ... Read more....»
2614 PARKLAND DRIVE
WINTER PARK FL 32789
Residential / Single Family Residence
4 Bed · 3 Bath · 1 Half Bath · 3,307 SqFt · $598/SqFt
Days on Market: 322
County: Orange
Legal Subdivision Name: PARKLANDO 03
Year built: 2007
Garage: Yes 2 vehicles
Private Pool: Yes
Fully remodeled! One of the most competitively priced homes featuring over 3,300 SF, in the 32789 zip code, and in the K-8 Audubon Park School District. The K-8 Audubon Park School District is a small pocket, and ranked one of the best district's in the state. Fully remodeled luxury pool homes in the highly sought-after Audubon K-8 and Winter Park school district with over 3,300 square feet of exceptional living space, capped with a brand-new, architecturally stunning tile barrel roof that blends timeless Mediterranean elegance with lasting durability. 2614 Parkland Drive, a fully reimagined luxury residence in the heart of ... Read more....»
640 ARJAY WAY
WINTER PARK FL 32789
Residential / Single Family Residence
5 Bed · 3 Bath · 2 Half Baths · 3,953 SqFt · $500/SqFt
Days on Market: 74
Cumulative Days on Market: 139
County: Orange
Legal Subdivision Name: TIMBERLANE SHORES
Year built: 1958
Garage: Yes 3 vehicles
Private Pool: Yes
Price Improvement on this amazing oversized lot! Located in one of Winter Park’s most desirable and picturesque neighborhoods, Timberlane Shores! This stunning five-bedroom residence has been recently renovated in an elegant, European style blending timeless character with modern luxury. Situated on over one-third of an acre, the property is accented by majestic oak trees and lush Florida-native landscaping that's creates a private and serene retreat where peacocks often roam freely through your yard. The heart of the home is the beautifully designed chef’s kitchen, featuring quartz countertops, a gas range with custom hood, double built-in convection ovens, stainless steel appliances, ... Read more....»
2501 LAFAYETTE AVENUE
WINTER PARK FL 32789
Residential / Single Family Residence
4 Bed · 4 Bath · 2,810 SqFt · $694/SqFt
Days on Market: 19
County: Orange
Legal Subdivision Name: WINTER PARK VILLAGE
Year built: 2026
Garage: Yes 2 vehicles
Private Pool: Yes
Under Construction. Exceptional design meets refined luxury in this brand-new architectural masterpiece by DaVinci. This 4 bedroom, 4 bath home offers over 2,800 square feet of bright, open living space designed for both comfort and functionality. Enter through your custom pivot front door into the foyer leading to your main living area featuring sliding glass walls for indoor-outdoor living. This flows effortlessly into a gorgeous chefs kitchen with high-end appliances featuring Thermador appliances throughout, Euro-style cabinetry, oversized island, and walk-in pantry. The downstairs primary suite overlooks the pool and includes a spa-like bath with soaking tub and rain shower. An ... Read more....»
906 ENCLAVE PLACE
WINTER PARK FL 32792
Residential / Single Family Residence
5 Bed · 4 Bath · 1 Half Bath · 3,618 SqFt · $532/SqFt
Days on Market: 9
County: Orange
Legal Subdivision Name: THE ENCLAVE WINTER PARK
Year built: 2026
Garage: Yes 2 vehicles
Private Pool: Yes
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 beneath mature oak canopies being built by FG Schaub Custom Homes. A short walk to Phelps Park, YMCA, dinner and shopping. Surrounded by natural beauty and designed with intention, The Enclave offers a rare opportunity to enjoy a private, residential setting while remaining connected to the area’s finest dining, shopping, and cultural amenities just minutes away in downtown Winter Park.. With a limited collection of custom homes, this community delivers an elevated lifestyle defined by architecture, ... 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.
