Winter Park, FL Homes for Sale

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  /36

  $259,900

  • 2 Beds
  • 2 Baths
  • 1,026 Sq Ft

  1500 Gay Rd Unit 17D, Winter Park, FL 32789

  Fantastic Winter Park Location on Lake Killarney. This 2 Bedroom 2 Bath Upstairs Unit has Lake and Pool Views. Spacious Living Spaces and Generously-sized Bedrooms. Unique Updated Kitchen has Sub Zero Refrigerator, Bosch Dishwasher, Solid Surface Counters, unbelievable amount of Storage with Corner Cabinets, Drawers, pull-out Shelving and 3 Tiers of Lighting! Updates include: Water Heater in

  Janice Erickson

  REALCOM REAL ESTATE SERVICES INC

  (321) 475-5617

  1500 Gay Rd Unit 17D, Winter Park, FL 32789
• Explore Winter Park

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  /29

  $229,000

  • 3 Beds
  • 2.5 Baths
  • 1,151 Sq Ft

  7454 Wynnewood Square Unit 188, Winter Park, FL 32792

  Updated Winter Park Townhome!! If you are looking for LOCATION this is the property for you. This well maintained unit is move in ready: two-story 3 Bedrooms 2.5 Bath townhome style condo with two designated parking spaces. Upon entering you are greeted with a large living and dining room space. Tiled floors, tons of light, neutral colors, wet bar area are a few of the amazing qualities of this

  

  Manoj Patel

  APPLE REALTY

  (321) 497-0912

  7454 Wynnewood Square Unit 188, Winter Park, FL 32792
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  /22

  $262,000

  • 2 Beds
  • 2 Baths
  • 1,026 Sq Ft

  1500 Gay Rd Unit 20D, Winter Park, FL 32789

  LAKEFRONT COMMUNITY WITH SPECTACULAR SUNSETS OVER BEAUTIFUL LAKE KILLARNEY. LOCATED IN THE CHARMING AND ELLEGANT NEIGHBORHOOD OF WINTER PARK, IN A FULLY REVITALIZED AREA.CONVENIENT TO I-4, PARK AVENUE, FARMER'S MARKETS, TRADER JOE'S, AS WELL AS A MOVIE THEATER, BOUTIQUE SHOPS, RENOWNED RESTAURANTS AND A NATIONALLY RATED ART FESTIVAL - ALL WITHIN A SHORT WALKING DISTANCE.BRIGHT SUN-FILLED

  Janice Erickson

  REALCOM REAL ESTATE SERVICES INC

  (689) 399-5336

  1500 Gay Rd Unit 20D, Winter Park, FL 32789
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  /23

  $259,500

  $16K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,026 Sq Ft

  1500 Gay Rd Unit 24B, Winter Park, FL 32789

  ANOTHER PRICE REDUCTION! OWNER WILL CONSIDER ALL REASONABLE OFFERS!Highly Desirable Winter Park Lakefront Community on Skiable Lake Killarney. Enjoy Peaceful Water Views and Million-Dollar Sunsets on Lakefront Deck! Private Community Ramp, Heated Pool, Men's and Women's Saunas!Don't miss this! Beautifully Renovated 2 Bedroom 2 Bath End Unit. New Kitchen Cabinets and Quartz Counters,

  Janice Erickson

  REALCOM REAL ESTATE SERVICES INC

  (321) 450-8960

  1500 Gay Rd Unit 24B, Winter Park, FL 32789
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  /42

  $370,000

  • 3 Beds
  • 2.5 Baths
  • 1,397 Sq Ft

  3374 Hamlet Loop, Winter Park, FL 32792

  Tucked inside a quiet Winter Park neighborhood, this three-bedroom, two-bath home offers a comfortable layout and a sense of privacy that’s hard to find. No rear neighbors and a tree-lined backyard create a peaceful setting you’ll appreciate every day. The main living area is open and versatile, allowing you to arrange the space in a way that truly fits your lifestyle. The living room and dining

  

  Barrett Spray

  KELLER WILLIAMS ADVANTAGE REALTY

  (689) 334-1742

  3374 Hamlet Loop, Winter Park, FL 32792
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  /52

  $1,150,000

  • 4 Beds
  • 2 Baths
  • 2,750 Sq Ft

  1981 Blue Ridge Rd, Winter Park, FL 32789

  Welcome to 1981 Blue Ridge Rd in Winter Park, a spacious 4-bedroom, 2-bath home featuring an open floorplan, a generous family room, and a layout designed for both comfortable everyday living and easy entertaining. The home offers a well-connected flow between the main living spaces, creating an inviting setting with room to gather, relax, and spread out. Inside, the living room, dining room, and

  

  Thomas Nickley

  KELLER WILLIAMS REALTY AT THE PARKS

  (689) 232-3531

  1981 Blue Ridge Rd, Winter Park, FL 32789
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  /37

  $835,000

  $10K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 2,589 Sq Ft

  1090 Wildmeadow Run, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. This luxurious Modern Style home epitomizes maintenance-free living, featuring a premium, state of the art solar system YOU OWN OUTRIGHT, nearly eliminating your cost of electricity. Ask to see the bill. The premium solar system is PAID OFF with a TRANSFERABLE WARRANTY by manufacturer. This off-grid solar system comes with a WHOLE HOUSE BATTERY

  

  Rod Chevalier

  BHHS FLORIDA REALTY

  (321) 468-9784

  1090 Wildmeadow Run, Winter Park, FL 32792
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  /52

  $639,900

  $40K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,287 Sq Ft

  1830 Edwin Blvd, Winter Park, FL 32789

  Beautifully RENOVATED and MOVE-IN READY/TURN-KEY home in the heart of Winter Park. From the moment you enter, you’re welcomed by an open, airy layout with VAULTED CEILINGS that make the home feel spacious and inviting. Beautiful TILE flooring throughout creates a seamless flow from room to room, while abundant natural light pours in through DOUBLE-PANED WINDOWS (2018) and German Velux SKYLIGHTS

  

  Nydia Marrero

  ZEN LIVING HOMES LLC

  (689) 210-5554

  1830 Edwin Blvd, Winter Park, FL 32789
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  /36

  $429,900

  $50K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,770 Sq Ft

  3463 Arnel Dr, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. NEW PRICE! Pool Home + Paid-Off Solar Panels + No HOA in Winter Park! Welcome to this move-in-ready 3-bedroom, 2-bathroom home with approximately 1,770 square feet of living space, a 2-car garage, and a private pool, all located in the established Eastbrook community. Major updates have already been completed, including a roof replaced in 2018,

  

  Alexa Monasterio Flores

  KELLER WILLIAMS ADVANTAGE 2 REALTY

  (689) 356-6537

  3463 Arnel Dr, Winter Park, FL 32792
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  /65

  $1,000,000

  $150K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,431 Sq Ft

  1800 Magnolia Ave, Winter Park, FL 32789

  One or more photo(s) has been virtually staged. PRICE IMPROVEMENT! NO HOA! Experience refined living in this renovated custom designed home on a corner lot in one of the area’s most peaceful and private neighborhoods. Tucked away at the end of a quiet dead-end street, this residence offers an exceptional blend of craftsmanship, sophistication, and modern comfort. With soaring 10-foot ceilings

  

  Kathy Summers

  FLORIDA REALTY INVESTMENTS

  (321) 306-4359

  1800 Magnolia Ave, Winter Park, FL 32789
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  /23

  $134,900

  $5K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 881 Sq Ft

  1695 Lee Rd Unit E103, Winter Park, FL 32789

  One or more photo(s) has been virtually staged. One or more photo(s) has been virtually staged. Waterfall Cove, where urban convenience meets tranquil living. This charming 2-bedroom, 1-bathroom condo offers a cozy retreat with all the perks of modern living. Located in the heart of Orlando, this condo is perfect for those looking for a blend of city life and natural beauty. As you step into the

  

  Jason Price

  RE/MAX SELECT GROUP

  (321) 324-0916

  1695 Lee Rd Unit E103, Winter Park, FL 32789
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  /41

  $2,495,000

  $155K PRICE DROP

  • 5 Beds
  • 3.5 Baths
  • 4,011 Sq Ft

  1130 Park North Place, Winter Park, FL 32789

  Half-acre lot just steps from Park Avenue shopping and dining, tucked on a quiet cul-de-sac in the heart of Winter Park.This traditional two-story home offers a well-designed floorplan for both everyday living and entertaining. From the moment you enter, the home feels warm and inviting. The main level features a spacious primary suite along with connected living spaces that flow easily from

  

  Jennifer King

  CORCORAN PREMIER REALTY

  (321) 257-9480

  1130 Park North Place, Winter Park, FL 32789
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  /50

  $847,000

  $3K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 3,020 Sq Ft

  1287 Verdant Glade Place, Winter Park, FL 32792

  **This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.** Welcome to 1287 Verdant Glade Place in Winter Park, a spacious two-story home offering 4 bedrooms, 3 full baths, 1 half bath, and a dedicated office, all thoughtfully arranged within an open floorplan designed for both

  

  Thomas Nickley

  KELLER WILLIAMS REALTY AT THE PARKS

  (321) 384-3331

  1287 Verdant Glade Place, Winter Park, FL 32792
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  /33

  $220,000

  • 2 Beds
  • 2 Baths
  • 953 Sq Ft

  225 Lewfield Cir, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. **This property qualifies for a closing cost credit up to $3,300 through the Seller’s preferred lender.** Welcome to this updated 2-bedroom, 2-bath first-floor condo in the heart of Winter Park. Tucked away at the back right corner of the building, this bright unit features hardwood floors throughout and an open living room with sliding glass doors

  

  Thomas Nickley

  KELLER WILLIAMS REALTY AT THE PARKS

  (321) 237-3113

  225 Lewfield Cir, Winter Park, FL 32792
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  /66

  $2,295,000

  $100K PRICE DROP

  • 4 Beds
  • 5.5 Baths
  • 4,392 Sq Ft

  1760 Legion Dr, Winter Park, FL 32789

  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

  Steven Looper CHARLES RUTENBERG REALTY ORLANDO

  1760 Legion Dr, Winter Park, FL 32789
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  /26

  $449,990

  • 3 Beds
  • 2 Baths
  • 1,534 Sq Ft

  5117 Cypress Ct, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. Welcome to this beautifully renovated home tucked away on a quiet cul-de-sac in Winter Park.Thoughtfully redesigned with a modern open-concept layout, this home offers an expansive single-story layout with over 1,500 square feet of inviting living space designed for both everyday living and effortless entertaining. From the moment you enter,

  Kristin McIntosh EXP REALTY LLC

  5117 Cypress Ct, Winter Park, FL 32792
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  /26

  $265,000

  $20K PRICE DROP

  • 2 Beds
  • 2.5 Baths
  • 1,495 Sq Ft

  2401 Sun Valley Cir, Winter Park, FL 32792

  Welcome to this charming 2-bedroom, 2-bath condo with a versatile loft, perfectly situated just minutes from shopping and the vibrant downtown Winter Park area! This light-filled end unit offers an open floor plan with vaulted ceilings and skylights, creating a bright and airy feel throughout. You’ll appreciate the newer flooring, crown molding, and the comfortable, functional layout. Relax and

  Jamie Vanosdol EXP REALTY LLC

  2401 Sun Valley Cir, Winter Park, FL 32792
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  /71

  $685,000

  $15K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,702 Sq Ft

  3114 Heartleaf Place, Winter Park, FL 32792

  Tucked away on a rare and breathtaking .96-acre homesite, this one-of-a-kind property in Lost Creek offers a setting that feels more like a private nature retreat than a suburban neighborhood. Surrounded by protected wooded conservation land and stretching back to the serene Howell Creek, this home delivers unmatched privacy, beauty, and a daily connection to nature. From the moment you arrive,

  Nadia Kurakin CHAMPION HOMES

  3114 Heartleaf Place, Winter Park, FL 32792
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  /22

  $190,000

  • 2 Beds
  • 2 Baths
  • 1,105 Sq Ft

  2923 Antique Oaks Cir Unit 34, Winter Park, FL 32792

  TOP FLOOR CORNER UNIT in the heart of Winter Park! This well-maintained 2-bedroom, 2-bath condo offers spacious living, abundant natural light, and a functional open layout perfect for everyday living or investment potential. Step inside to find a bright and airy living and dining area with sliding glass doors leading to a private screened-in balcony — the perfect spot to relax and enjoy the

  Steven Pugh EXP REALTY LLC

  2923 Antique Oaks Cir Unit 34, Winter Park, FL 32792
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  /42

  $598,000

  Open Sun 12PM - 2PM $26K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 1,620 Sq Ft

  1822 Yorkshire Dr, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. PRICE REDUCTION...priced to move! Charming three-bedroom, three-bath one-story home features a split floor plan with two primary suites, ideal for multigenerational living or guest flexibility, in a prime Winter Park location. In the desirable Park Manor subdivision, this beautifully designed split floor plan home offers comfort and privacy, perfect

  MaryAnne Branner PREMIER SOTHEBY'S INTL. REALTY

  1822 Yorkshire Dr, Winter Park, FL 32792
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  /48

  $1,175,000

  Open Sat 1PM - 3PM $274K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,426 Sq Ft

  1651 Westchester Ave, Winter Park, FL 32789

  One or more photo(s) has been virtually staged. Set on a prized corner lot in Winter Parks sought after Orwin Manor Neighborhood, 1651 Westchester Ave is a timeless classic with Cape Cod inspired architecture that has been meticulously reimagined with today’s luxury finishes while preserving its original charm. Refinished Original Pine hardwood flooring and a beautifully updated fireplace welcome

  Shawn Layton SERHANT

  1651 Westchester Ave, Winter Park, FL 32789
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  /20

  $479,900

  $20K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,376 Sq Ft

  501 Heritage Blvd, Winter Park, FL 32792

  Welcome to this fully remodeled, move-in ready home in the highly sought-after Winter Park area! This beautifully updated single-story residence features 4 bedrooms and 2 bathrooms, offering comfortable living with a bright and inviting layout.Step inside to discover a bright, open floor plan with modern finishes and thoughtfully updated living spaces, designed for both comfort and

  Bernardo Carrasquel B EXP REALTY LLC

  501 Heritage Blvd, Winter Park, FL 32792
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  /51

  $1,199,000

  • 5 Beds
  • 4.5 Baths
  • 3,652 Sq Ft

  1448 Lake Florence Way, Winter Park, FL 32792

  Located within an intimate gated community of just 28 homes and only a short drive to Downtown Winter Park, this exceptional former model home by K. Hovnanian Homes showcases over $200,000 in builder and custom upgrades with luxury finishes and thoughtful design throughout. Residents enjoy access to a private community dock, perfect for launching a canoe or paddleboard or simply relaxing while

  Abby Nelson RE/MAX 200 REALTY

  1448 Lake Florence Way, Winter Park, FL 32792
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  /20

  $375,000

  $25K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 913 Sq Ft

  2482 Roxbury Rd, Winter Park, FL 32789

  Winter Park Charm Today — Endless Possibilities Tomorrow. Welcome to a rare find in one of Winter Park’s most sought-after neighborhoods. This cozy 2BR/1BA bungalow is full of charm and sits on a spacious quarter-acre lot, giving you room to dream big. The home itself is in great condition—bright, clean, and move-in ready.But what truly sets this property apart is the location and land. With

  Gary Cohl COLDWELL BANKER REALTY

  2482 Roxbury Rd, Winter Park, FL 32789
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  /59

  $695,000

  $55K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,968 Sq Ft

  744 Cornwall Rd, Winter Park, FL 32792

  Welcome to your dream home! This exceptional 4-bedroom residence features a desirable split floor plan, offering both privacy and functionality. Nestled on a quiet corner lot in the serene Winter Park Pines community, this property is just a few steps away from the scenic Cady Way Trail, perfect for outdoor enthusiasts.This home is surrounded by recreational opportunities, including a refreshing

  Tammy Cuddy VERSALIS REALTY POWERED BY SELLSTATE

  744 Cornwall Rd, Winter Park, FL 32792
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  /51

  $2,800,000

  New Construction

  • 4 Beds
  • 3.5 Baths
  • 3,553 Sq Ft

  541 W Canton Ave, Winter Park, FL 32789

  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

  Bianca Rey PREMIER SOTHEBY'S INTL. REALTY

  541 W Canton Ave, Winter Park, FL 32789
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  /30

  $495,000

  • 4 Beds
  • 2 Baths
  • 1,596 Sq Ft

  2803 Banchory Rd, Winter Park, FL 32792

  Located in Winter Park Pines, this 4-bedroom, 2-bath home offers a warm, flexible layout with comfortable living spaces and everyday functionality throughout. With 1,596 square feet, the home provides room to gather, relax, entertain, and adapt to changing needs over time. Inside, the floor plan includes both a living room and a separate family room, creating useful separation for daily life. One

  Melissa Johnson EXP REALTY LLC

  2803 Banchory Rd, Winter Park, FL 32792
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  /77

  $1,995,000

  Open Sat 1PM - 3PM

  • 4 Beds
  • 3 Baths
  • 3,696 Sq Ft

  2261 Mulbry Dr, Winter Park, FL 32789

  Welcome to this extraordinary, better-than-new residence in the heart of Winter Park, a thoughtfully designed and impeccably upgraded custom, one-owner home built in 2020 that effortlessly blends timeless elegance with today’s most sought-after luxury features. Situated on a wonderfully deep, private lot with no HOA, this remarkable two-story home was crafted for elevated everyday living,

  Jo-Ann Lamar PREMIER SOTHEBY'S INTL. REALTY

  2261 Mulbry Dr, Winter Park, FL 32789
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  /50

  $2,000,000

  • 4 Beds
  • 4 Baths
  • 3,065 Sq Ft

  723 Symonds Ave, Winter Park, FL 32789

  Built by Clarkson Concepts and ideally located in the heart of Winter Park just moments from Park Avenue, this sophisticated modern residence blends luxury design, smart-home innovation, and effortless indoor-outdoor living across three thoughtfully designed levels. From the moment you arrive, the striking foyer makes a memorable first impression with its bold geometric detailing, designer

  Nickolas McKee KELLER WILLIAMS WINTER PARK

  723 Symonds Ave, Winter Park, FL 32789
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  /23

  $250,000

  $15K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,068 Sq Ft

  7707 Country Place Unit 4, Winter Park, FL 32792

  Beautifully updated 2BD/2BA single-story condo in peaceful Goldenrod Villas, Winter Park. Enjoy an insulated, screen-enclosed lanai with its own AC unit, plus a brand-new backyard deck and private patio. Both bedrooms offer ensuite baths with updated vanities and large walk-in closets. NEW luxury vinyl plank flooring throughout. Extended kitchen with added cabinets and bar seating. Laundry room

  Stephanie Sanchez WEICHERT REALTORS HALLMARK PRO

  7707 Country Place Unit 4, Winter Park, FL 32792
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  /28

  $375,000

  • 3 Beds
  • 2.5 Baths
  • 1,872 Sq Ft

  7522 Aloma Pines Ct, Winter Park, FL 32792

  Beautifully maintained 3-bedroom, 2.5-bath two-story townhome featuring a bright and functional open-concept floor plan. The first floor offers tile flooring throughout the spacious living and dining areas, kitchen, and half bath. The modern kitchen is designed for both style and convenience, featuring granite countertops, abundant cabinetry, a large center island, and a walk-in pantry, along

  Vildan Nigro RIVA REALTY GROUP LLC

  7522 Aloma Pines Ct, Winter Park, FL 32792
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  /37

  $370,000

  • 3 Beds
  • 2.5 Baths
  • 1,978 Sq Ft

  1920 Heathwood Dr, Winter Park, FL 32792

  Winter Park value-add opportunity with renovated homes ranging between $465K- $470K+. ideal for investors, end-users, or buyers looking to build equity. Solid layout with strong upside! Great two-story layout with living/dining and family room. All bedrooms upstairs. Spacious primary with separate sitting area, walk-in closet and ensuite bath. Inside laundry room. Oversized 2-car Garage. Fully

  Allison Day RE/MAX TOWN & COUNTRY REALTY

  1920 Heathwood Dr, Winter Park, FL 32792
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  /54

  $1,924,450

  $371K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 3,307 Sq Ft

  2614 Parkland Dr, Winter Park, FL 32789

  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

  Ryan Gaston JW GASTON LLC

  2614 Parkland Dr, Winter Park, FL 32789
• 

  

  /10

  $1,250,000

  New Construction

  • 4 Beds
  • 3.5 Baths
  • 2,525 Sq Ft

  1870 Staunton Ave, Winter Park, FL 32789

  Pre-Construction. To be built. Discover a rare opportunity to build a fully custom residence in the highly sought-after Killarney Shores neighborhood of Winter Park—one of the last areas where new construction at this level remains attainable below $1.3M. Exclusively curated by The Hope Group, this offering pairs premier design with a seamless build experience alongside Deep Roots Construction,

  Vinny Lay COMPASS FLORIDA LLC

  1870 Staunton Ave, Winter Park, FL 32789
• 

  

  /48

  $719,000

  • 4 Beds
  • 2 Baths
  • 1,877 Sq Ft

  2333 Westminster Ct, Winter Park, FL 32789

  Settled on a rare double lot in the heart of Winter Park, this 4-bedroom, 2-bath home delivers the Florida lifestyle you've been waiting for–without a single item on your to-do list. Resort style pool with Travertine pavers, renovated in 2025– brand new and ready for summer.Inside, a complete renovation in 2020 touched every corner of the home. Every major system has been replaced within the

  Ernest Middleton CHARLES RUTENBERG REALTY ORLANDO

  2333 Westminster Ct, Winter Park, FL 32789
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  /39

  $589,900

  $10K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,269 Sq Ft

  1354 Indiana Ave, Winter Park, FL 32789

  One or more photo(s) has been virtually staged. Fabulous location in Winter Park! Completely remodeled from top to bottom this stunning home blends modern design with everyday comfort in a highly desirable Winter Park location. Thoughtfully updated with stylish and contemporary finishes throughout this home offers a bright and open feel that’s perfect for today’s lifestyle.The beautifully

  Ellen Bessette CHARLES RUTENBERG REALTY ORLANDO

  1354 Indiana Ave, Winter Park, FL 32789
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  /76

  $6,495,000

  New Construction $705K PRICE DROP

  • 5 Beds
  • 6.5 Baths
  • 5,939 Sq Ft

  550 Palmer Ave, Winter Park, FL 32789

  Exquisite new construction with 5 Bedrooms 6.5 Baths and a 3 car garage, 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

  John McDade FANNIE HILLMAN & ASSOCIATES

  550 Palmer Ave, Winter Park, FL 32789
• 

  

  /17

  $232,000

  $8K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,068 Sq Ft

  7794 Country Place Unit 2, Winter Park, FL 32792

  Winter Park Clean, UPDATED and in Move In Condition - The newest condo's year built are located on the last street in the complex where this unit is located which features a more contemporary open floor plan. Enjoy the One story living with no steps. No apartment living with noisy neighbors. Another BONUS is *** NO condo neighbors across the street from you - PRIVATE!** Located second to the end

  Tom Bercini CHARLES RUTENBERG REALTY ORLANDO

  7794 Country Place Unit 2, Winter Park, FL 32792
• 

  

  /18

  $379,900

  $10K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,529 Sq Ft

  3245 Coleus Ct, Winter Park, FL 32792

  This home sits at the end of a cul-de-sac with an attractive courtyard entry to the 2 car garage. The Kitchen has been updated with new cabinets and tile flooring and the baths all have tile flooring. The Primary Bedroom has Luxury Vinyl Flooring. The screened porch overlooks a spacious fenced backyard that includes a block building (summer cottage) with electric and plumbing that is currently

  Diane Gerry PA RE/MAX 200 REALTY

  3245 Coleus Ct, Winter Park, FL 32792
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  /5

  $1,925,000

  New Construction

  • 5 Beds
  • 4.5 Baths
  • 3,618 Sq Ft

  906 Enclave Place, Winter Park, FL 32792

  Under Construction. This modern farmhouse designed home is under construction proposed completion March 2027. 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

  Laura Earl CORCORAN PREMIER REALTY

  906 Enclave Place, Winter Park, FL 32792

Showing Results 1 - 40, Page 1 of 9

Why Live in Winter Park

Winter Park, located near Orlando, Florida, began in the 1880s as a planned community appealing to northern ex-pats with its warm winters, good schools, and lively arts scene. Today, it maintains its "City of Arts and Culture" nickname with museums and a vibrant cultural atmosphere. The main commercial district, Park Avenue, features high-end boutiques and bistros, including The Ravenous Pig, a renowned gastropub. Rollins College and The Rollins Museum of Art are local highlights, along with The Alfond Inn, which serves as a social hub. The city’s nearly 30,000 residents enjoy highly rated schools such as Winter Park High and Trinity Preparatory School of Florida. Housing options range from petite bungalows to lakeside mansions, with styles including New Traditional, midcentury-era ranch homes, Colonial Revival, and Contemporary homes. The Winter Park Chain of Lakes offers boating, kayaking, and paddleboarding opportunities, while Central Park provides 11 acres of green space with walking paths and a rose garden. Annual events like the Winter Park Sidewalk Arts Festival and Christmas on Park attract visitors and foster community spirit. Residents have access to Interstate 4, SunRail, and Lynx buses for transportation, with Orlando International Airport about 20 miles away. Winter Park’s crime rates are lower than the national average, making it a safer area compared to nearby Orlando.

Learn more about living in Winter Park

Frequently Asked Questions

What is the average home price in Winter Park, FL?

Homes for sale in Winter Park, FL have an average home price of $954,251.

Are home prices dropping in Winter Park?

Yes, home prices in Winter Park are down 1% in the last 12 months.

How many homes have sold over the last 12 months in Winter Park, FL?

987 homes have sold in Winter Park, FL over the last 12 months.

What are the most popular zip codes in Winter Park, FL?

The most popular zip codes in Winter Park, FL include 32789, 32792, 32751, 32803 and 32814.

How much do you need to make to afford a house in Winter Park?

The median home price in Winter Park is $549,000. If you put a 20% down payment of $109,800 and had a 30-year fixed mortgage with an interest rate of 6.31%, your estimated principal and interest payment would be $2,720 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $117K a year to afford the median home price in Winter Park. Learn how much home you can afford with our Home Affordability Calculator.

How are the schools in Winter Park, FL?

Winter Park, FL has highly rated public and private schools. Some of the best schools in Winter Park based on Niche Grades are Lake Highland Preparatory School, Park Maitland School and Trinity Preparatory School. Browse all the schools in Winter Park, FL to learn more.

Home Prices in Winter Park, FL

The median home sale price in Winter Park, FL is $480,000, consistent with the median home sale price year-over-year. Homes in Winter Park sell in 67 days on average, compared to the national average of 58 days.

Home Price Trends

Median Sale Price $480,000	Median Single Family Sale Price $628,000
Median Townhouse Sale Price $459,000	Median 2 Bedroom Sale Price $200,000
Median 1 Bedroom Sale Price $154,900	Average Price Per Sq Ft $372
Number of Homes for Sale 325	Last 12 months Home Sales 987
Months of Supply 4.00	Median List Price $549,000
Median Change From 1st List Price 5%	Median Home Sale Price YoY Change 0%