Winter Park, FL Homes for Sale

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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
• Explore Winter Park

• 

  

  

  /21

  $261,500

  • 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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  /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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  /42

  $435,000

  • 3 Beds
  • 3 Baths
  • 2,346 Sq Ft

  2224 Shadowland Loop, 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.** Nestled in the heart of Winter Park, 2224 Shadowland Loop offers a beautiful blend of comfort, style, and low-maintenance living in this spacious 3-bedroom, 3-bathroom townhouse. The interior features an inviting open layout

  

  Thomas Nickley

  KELLER WILLIAMS REALTY AT THE PARKS

  (321) 450-7733

  2224 Shadowland Loop, Winter Park, FL 32792
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  /35

  $845,000

  • 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. One or more photos have 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....Just ask to see the bill. The premium solar system is PAID OFF with a TRANSFERABLE WARRANTY by manufacturer. This

  

  Rod Chevalier

  BHHS FLORIDA REALTY

  (321) 468-9784

  1090 Wildmeadow Run, Winter Park, FL 32792
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  /58

  $449,900

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

  3463 Arnel Dr, Winter Park, FL 32792

  Your pool home in Winter Park just became one of the best opportunities under $450K. Now priced at $449,900, this home offers 3 bedrooms plus a versatile bonus room, approximately 1,770 sq ft, a 2-car garage, and extended driveway — all in the established Eastbrook community with NO HOA. Major systems are already taken care of: roof 2018, solar panels 2020 (fully paid off), water heater 2019, and

  

  Alexa Monasterio Flores

  KELLER WILLIAMS ADVANTAGE 2 REALTY

  (689) 356-6537

  3463 Arnel Dr, Winter Park, FL 32792
• 

  

  /19

  $174,700

  • 2 Beds
  • 2 Baths
  • 1,003 Sq Ft

  1000 S Semoran Blvd Unit 805, Winter Park, FL 32792

  Beautifully updated condo in a prime Winter Park location! This move-in ready unit features a beautifully renovated kitchen, updated bathrooms, and tile flooring throughout, offering a modern and low-maintenance living space. Ideally situated on South Semoran Blvd, you’ll love the convenience of being just minutes to Baldwin Park, Full Sail University, UCF, and Downtown Winter Park, with easy

  

  Carrie Shawfield

  SHAWFIELD REALTY GROUP

  (321) 334-3379

  1000 S Semoran Blvd Unit 805, Winter Park, FL 32792
• 

  

  /17

  $280,000

  • 3 Beds
  • 2 Baths
  • 1,050 Sq Ft

  5450 Peaco Place, Winter Park, FL 32792

  Welcome Home! Winter Park property for under $300k! As you step up to this property you notice the fresh paint and the fresh mulch. Step into the home and you see consistent floor tile throughout the home as well as freshly painted walls. Take a step to the left and you see the large kitchen space to be able to freely move around as you cook. The primary bedroom is located in the rear and has

  

  Dean Gonzalez

  KELLER WILLIAMS ADVANTAGE 2 REALTY

  (321) 475-2203

  5450 Peaco Place, Winter Park, FL 32792
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  /65

  $1,100,000

  • 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. NEW PRICE! Experience refined living in this exquisitely renovated custom home, positioned on an oversized 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. Inside, soaring 10-foot

  

  Kathy Summers

  FLORIDA REALTY INVESTMENTS

  (321) 306-4359

  1800 Magnolia Ave, Winter Park, FL 32789
• 

  

  /23

  $139,990

  • 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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  /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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  /77

  $424,900 Open Fri 4PM - 7PM

  • 4 Beds
  • 2.5 Baths
  • 1,616 Sq Ft

  1871 Casselwood St, Winter Park, FL 32792

  Beautifully updated, move-in ready home in Winter Park. A brand new A/C system is scheduled to be installed. This 4-bedroom, 2.5-bath home with a 2-car garage features waterproof luxury vinyl flooring, fresh interior finishes, new recessed lighting, and updated ceiling fans, all combined with a bright and functional layout. As you enter, you are welcomed by a custom wood decorative accent wall

  

  Alexa Monasterio Flores

  KELLER WILLIAMS ADVANTAGE 2 REALTY

  (321) 252-6747

  1871 Casselwood St, Winter Park, FL 32792
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  /41

  $510,000

  • 2 Beds
  • 1 Bath
  • 1,073 Sq Ft

  1036 Aragon Ave, Winter Park, FL 32789

  One or more photo(s) has been virtually staged. Welcome to 1036 Aragon Avenue, a charming Winter Park bungalow perfectly positioned in one of Central Florida’s most sought-after locations. Nestled along picturesque cobblestone roads and surrounded by mature, tree-lined streets, this move-in ready home captures the character and warmth that make Winter Park real estate so desirable. Located just

  

  Tim Veigle

  WATSON REALTY CORP

  (321) 516-0689

  1036 Aragon Ave, Winter Park, FL 32789
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  /42

  $370,000 Open Sat 11AM - 1PM

  • 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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  /50

  $850,000

  • 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
• 

  

  /55

  $649,900

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

  1174 Wildmeadow Run, Winter Park, FL 32792

  Welcome to 1174 Wildmeadow Run in Winter Park’s gated Hawk’s Crest community. Located on a quiet, non-thru street, this SINGLE-STORY residence offers modern construction, refined finishes, and a comfortable, well-designed layout in the heart of Winter Park. Built in 2021, the home was thoughtfully planned for everyday living and easy entertaining. The open-concept design feels light and

  

  Kara Lushear

  COLDWELL BANKER REALTY

  (321) 280-1735

  1174 Wildmeadow Run, Winter Park, FL 32792
• 

  

  /19

  $225,000

  • 3 Beds
  • 2 Baths
  • 1,230 Sq Ft

  7706 Country Place Unit A8, Winter Park, FL 32792

  Great investment opportunity. Ideal for a growing family or investor. Well established neighborhood of Goldenrod Villas, 3 bedroom, 2 full bathrooms, 1,230 square feet of living area. Exterior of the home is concrete block and stucco. The eat-in-kitchen sits in the heart of the home which creates a warm and social atmosphere. Nice covered patio with back yard great for relaxing and entertaining

  

  Carmen Vazquez

  REALTY TECH INC

  (321) 339-0107

  7706 Country Place Unit A8, Winter Park, FL 32792
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  /41

  $2,495,000

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

  1130 Park North Place, Winter Park, FL 32789

  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

  

  Jennifer King

  CORCORAN PREMIER REALTY

  (321) 257-9480

  1130 Park North Place, Winter Park, FL 32789
• 

  

  /41

  $554,900

  • 3 Beds
  • 2 Baths
  • 1,570 Sq Ft

  330 Elkhorn Ct, Winter Park, FL 32792

  330 Elkhorn Ct is a beautifully renovated home located in the highly desired Winter Park Pines community. Freshly updated with a 2025 electric panel, 2025 A/C system, and a 2024 roof, offering modern efficiency, peace of mind, and big-ticket upgrades already taken care of! Inside, you’ll find a bright, open layout with wide-plank flooring, recessed lighting, and a modern neutral color palette

  Neil Chetram LA ROSA REALTY CW PROPERTIES L

  330 Elkhorn Ct, Winter Park, FL 32792
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  /49

  $1,349,000

  • 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
• 

  

  /17

  $489,990

  • 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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  /66

  $2,295,000

  • 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

  $265,000

  • 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

  $699,900

  • 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
• 

  

  /42

  $624,000

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

  1822 Yorkshire Dr, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. 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 for modern living. Enjoy the

  MaryAnne Branner PREMIER SOTHEBY'S INTL. REALTY

  1822 Yorkshire Dr, Winter Park, FL 32792
• 

  

  /23

  $250,000

  • 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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  /54

  $1,950,000

  • 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
• 

  

  /17

  $241,900

  • 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 more contemporary open floor plans and high ceilings. Enjoy the One story living. No apartment living with noisy neighbors. Another BONUS is *** NO condo neighbors across the street from you - private!!** This unit is second to

  Tom Bercini CHARLES RUTENBERG REALTY ORLANDO

  7794 Country Place Unit 2, 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

  Pre-Construction. To be built. This 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 designed with

  Laura Earl CORCORAN PREMIER REALTY

  906 Enclave Place, Winter Park, FL 32792
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  /29

  $1,925,000

  • 4 Beds
  • 4 Baths
  • 2,653 Sq Ft

  721 Pansy Ave, Winter Park, FL 32789

  Ideally on a quiet residential street just near Park Avenue, this custom-built transitional residence offers the best of Winter Park living, accessible, refined and thoughtfully designed from the ground up. Built in 2018 by Carlos Posada, the home delivers 2,653 square feet of living space across two floors, with an additional 365 square feet walk-up attic, four bedrooms and four full baths. From

  Drew Henner PREMIER SOTHEBY'S INTL. REALTY

  721 Pansy Ave, Winter Park, FL 32789
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  /47

  $1,090,000

  • 3 Beds
  • 2.5 Baths
  • 2,578 Sq Ft

  1541 Westchester Ave, Winter Park, FL 32789

  Set on over half an acre in Winter Park’s coveted Orwin Manor, this 1935 French Provincial estate offers a rare blend of architectural character, modern system updates, and extraordinary future potential. The property offers the unique opportunity to own an estate in a beautifully historic Winter Park neighborhood. Whether thoughtfully renovated, expanded, or reimagined, this property stands as a

  Lisa Gould KELLER WILLIAMS WINTER PARK

  1541 Westchester Ave, Winter Park, FL 32789
• 

  

  /20

  $205,000

  • 2 Beds
  • 2 Baths
  • 1,018 Sq Ft

  3038 Antique Oaks Cir Unit 166, Winter Park, FL 32792

  This unit was restored, with new kitchen cabinets, new ceramic tile in kitchen, living room, dining room and 2ndbathroom. It has been impeccably maintained. Walking distance from Full Sail and only 6.9 miles to UCF.Spacious bedrooms and baths and very comfortable layout. Lovely screened patio off living room. Complexoffers pool, and club house. A/C unit is brand new, installed on

  Manny Celi YOUNG REAL ESTATE

  3038 Antique Oaks Cir Unit 166, Winter Park, FL 32792
• 

  

  /25

  $209,900

  • 2 Beds
  • 2 Baths
  • 1,058 Sq Ft

  4858 Tangerine Ave Unit 4858, Winter Park, FL 32792

  Charming Updated Home in Prime Winter Park Location Welcome to this beautifully updated home located in the highly desirable area of Winter Park. Combining comfort, style, and convenience, this property offers a thoughtfully designed open floor plan that creates a seamless flow between the main living spaces, making it ideal for both everyday living and entertaining. The home features two

  Angelica Diaz Bajo WRA BUSINESS & REAL ESTATE

  4858 Tangerine Ave Unit 4858, Winter Park, FL 32792
• 

  

  /45

  $205,000 Open Sat 12PM - 2PM

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

  3371 River View Way Unit 46, Winter Park, FL 32792

  Welcome to Unit 46 at Hidden Oaks, a townhome-style condo nestled in one of Winter Park's most convenient and well-established communities. Ideal for first-time buyers, down-sizers, or investors looking for location and lifestyle in one. The floor plan offers three bedrooms upstairs with two full bathrooms, plus a half bath on the main level — perfect for guests and everyday living. Two reserved

  Safiya Bourne REALTY ONE GROUP EVOLVE

  3371 River View Way Unit 46, Winter Park, FL 32792
• 

  

  /25

  $1,350,000

  • 3 Beds
  • 2 Baths
  • 1,750 Sq Ft

  1881 Lake Spier Dr, Winter Park, FL 32789

  Lakefront home on over 1 acre in Winter Park with direct frontage on Lake Spier.Positioned on a private, spring-fed lake, this property presents a rare opportunity to build a brand-new luxury residence or thoughtfully renovate the existing home into a refined lakefront retreat. The expansive lot, tranquil water views, and ownership extending into the lake create a setting defined by privacy,

  Rafael Zenke Pinhao NOVA REAL ESTATE SERVICES INC

  1881 Lake Spier Dr, Winter Park, FL 32789
• 

  

  /64

  $444,900

  • 3 Beds
  • 2.5 Baths
  • 1,782 Sq Ft

  1951 Canny Cove, Winter Park, FL 32792

  Welcome to easy, light-filled living in this beautifully maintained 3-bedroom, 2.5-bath corner townhome in the gated Grayson Square community. Freshly painted and designed for comfort, the open living and dining spaces feel bright and inviting, flowing effortlessly to a covered lanai—perfect for relaxing evenings or casual gatherings. The kitchen offers a clean, modern look with stainless steel

  Denise Del Castillo LPT REALTY, LLC

  1951 Canny Cove, Winter Park, FL 32792
• 

  

  /11

  $198,000

  • 2 Beds
  • 2 Baths
  • 1,062 Sq Ft

  3060 George Mason Ave Unit 12, Winter Park, FL 32792

  Welcome to your new home in Winter Park!Completely remodeled unit with luxury finishes, ceramic floors, modern bathrooms, brand new kitchen with steel appliances and a nice quartz counter. Community amenities include pool, tennis and playground. Great Schools - zoned for Winter Park HS. Just minutes to Full Sail, UCF & Valencia. Don’t miss out on this gem!

  Adriana Sanchez WF REALTY CORP.

  3060 George Mason Ave Unit 12, Winter Park, FL 32792
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  /49

  $189,999

  • 2 Beds
  • 1.5 Baths
  • 1,365 Sq Ft

  7468 Canford Ct Unit 24, Winter Park, FL 32792

  This charming 2-bedroom, 1.5-bath condo offers a desirable townhome-style layout with spacious living areas and thoughtful storage throughout. The community features deluxe vinyl fencing installed by the HOA, along with a clubhouse and a community pool, providing great amenities for residents to enjoy. Inside, you’ll find the convenience of an in-unit washer and dryer combo, ample storage under

  Javier Albelo Rivera EMPIRE NETWORK REALTY

  7468 Canford Ct Unit 24, 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 $937,862.

Are home prices dropping in Winter Park?

Yes, home prices in Winter Park are down 3% in the last 12 months.

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

986 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 $530,000. If you put a 20% down payment of $106,000 and had a 30-year fixed mortgage with an interest rate of 6.3%, your estimated principal and interest payment would be $2,620 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $112K 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 Trends in Winter Park, FL

On average, homes in Winter Park, FL sell after 68 days on the market compared to the national average of 57 days. The median sale price for homes in Winter Park, FL over the last 12 months is $479,000, consistent with the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price

$479,000

Median Single Family Sale Price

$621,250

Median Townhouse Sale Price

$447,450

Median 2 Bedroom Sale Price

$198,500

Median 1 Bedroom Sale Price

$147,500

Average Price Per Sq Ft

$367

Number of Homes for Sale

299

Last 12 months Home Sales

986

Months of Supply

3.60

Median List Price

$530,000

Median Change From 1st List Price

5%

Median Home Sale Price YoY Change

0%