Winter Park, FL Homes for Sale

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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
• Explore Winter Park

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  /33

  $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. This luxurious Modern Style home epitomizes maintenance-free living, featuring a premium solar system you own outright, paying for your electricity. (Ask to see the bill.) Imagine relaxing on your private, expanded lanai, soaking in the breathtaking sunsets. Your spacious 4-bedroom, 3.5-bathroom home offers premium views of nature, and is just steps

  

  Rod Chevalier

  BHHS FLORIDA REALTY

  (321) 468-9784

  1090 Wildmeadow Run, Winter Park, FL 32792
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  /58

  $479,900 Open Sun 11AM - 2PM

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

  3463 Arnel Dr, Winter Park, FL 32792

  Your pool home in Winter Park. This home offers three bedrooms plus a versatile bonus room, approximately 1,770 sq ft of living space, built in 1967, along with a two-car garage and extended driveway for additional parking. Located in the established Eastbrook community with no HOA. Key updates include a roof replaced in 2018, solar panels installed in 2020 (fully paid off), water heater replaced

  

  Alexa Monasterio Flores

  KELLER WILLIAMS ADVANTAGE 2 REALTY

  (689) 356-6537

  3463 Arnel Dr, Winter Park, FL 32792
• 

  

  

  /19

  $179,700

  • 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
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  /41

  $245,000

  • 2 Beds
  • 2 Baths
  • 956 Sq Ft

  2500 Lee Rd Unit 229, Winter Park, FL 32789

  DRAMATIC PRICE ADJUSTMENT! Million Dollar Lakefront View of Lake Killarney from Private Balcony and multiple Rooms in the Unit and View of Courtyard with it's Gracious Old Tree and Meandering Walkways from second Private Balcony. Once in a lifetime opportunity to own this meticulously maintained and updated Mid-Century Modern Character that says "Home" when you walk through the Door! Kitchen has

  Janice Erickson

  REALCOM REAL ESTATE SERVICES INC

  (321) 252-5096

  2500 Lee Rd Unit 229, Winter Park, FL 32789
• 

  

  /65

  $1,150,000

  • 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. 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 ceilings

  

  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) 895-9463

  1695 Lee Rd Unit E103, Winter Park, FL 32789
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  /29

  $290,000

  • 2 Beds
  • 2 Baths
  • 1,008 Sq Ft

  5180 Lazy Oaks Dr, Winter Park, FL 32792

  Welcome to your Florida retreat.Whether you’re searching for the perfect first home or looking to downsize into a low-maintenance lifestyle, this single-story end-unit villa offers the ideal blend of comfort, convenience, and charm. With only one shared wall, it lives and feels like a single-family home.The HOA handles all exterior maintenance—including the roof, which was replaced just a

  

  Farzana Zalil

  CHARLES RUTENBERG REALTY ORLANDO

  (321) 221-5173

  5180 Lazy Oaks Dr, Winter Park, FL 32792
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  /36

  $269,900

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

  2501 Tahoe Cir Unit 32501, Winter Park, FL 32792

  Welcome home to this spacious two-story Winter Park condo located in the sought-after Cedarwood Village community. Tucked away among mature landscaping yet close to everything, this residence offers a comfortable blend of privacy, architectural character, and convenience in a prime Central Florida location.The main living area features soaring 16.5-foot vaulted ceilings, a wood-burning

  

  Sarah Doyer

  COLDWELL BANKER REALTY

  (321) 510-4129

  2501 Tahoe Cir Unit 32501, Winter Park, FL 32792
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  /41

  $525,000

  • 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
• 

  

  /21

  $264,000

  • 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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  /31

  $740,000

  • 2 Beds
  • 1 Bath
  • 1,396 Sq Ft

  841 W Swoope Ave, Winter Park, FL 32789

  Build your custom Winter Park home on one of the last available lots in this coveted 32789 corridor. Located at 841 W Swoope Ave, this 9,752 SF R-2 zoned parcel sits on W Swoope Avenue between Park Avenue and Orlando Avenue — walking distance to Winter Park Village, top-rated Winter Park schools, and the newly revitalized Park Avenue district. The existing shell structure is demo-ready, clearing

  

  Evelyn Alicea

  EXP REALTY LLC

  (321) 468-9259

  841 W Swoope Ave, Winter Park, FL 32789
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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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  /55

  $669,900 Open Sat 11AM - 2PM

  • 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
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  /43

  $550,000 Open Sun 1PM - 4PM

  • 3 Beds
  • 2 Baths
  • 1,356 Sq Ft

  720 W Webster Ave, Winter Park, FL 32789

  One or more photo(s) has been virtually staged. This home can be purchased with NO INCOME VERIFICATION needed! Welcome to 720 W Webster Avenue, a beautifully renovated home in the heart of historic Carver Town in Winter Park—one of the most sought-after locations in Central Florida. Just a short walk to downtown Winter Park, this charming residence blends modern updates with timeless character

  

  Vincent Cordaro

  SERHANT

  (321) 341-3712

  720 W Webster Ave, Winter Park, FL 32789
• 

  

  /21

  $255,000

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

  1500 Gay Rd Unit 18A, Winter Park, FL 32789

  REDUCED! Lakefront Community on beautiful Lake Killarney. 2 Bedroom/2 Bath First Floor Unit with Courtyard and Lake Views. Lovingly updated and meticulously maintained. Kitchen has raised ceilings, Maple Cabinets and Granite Counters. Dining Room has Cabinets matching those in Kitchen and Counters with pull-out Drawers for additional Storage. Tile Floors in Living Areas. New Carpets in both

  Janice Erickson

  REALCOM REAL ESTATE SERVICES INC

  (321) 449-7958

  1500 Gay Rd Unit 18A, Winter Park, FL 32789
• 

  

  /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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  /44

  $830,000 Open Sat 11AM - 2PM

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

  1183 Wildmeadow Run, Winter Park, FL 32792

  Welcome to this original-owner residence in The Meadows at Hawk’s Crest, where thoughtful design and exceptional privacy come together—featuring two true primary suites, one on the first floor and one on the second. Set on an oversized fenced homesite along a quiet non-thru street with no neighbor to the east, this beautifully maintained 4-bedroom, 3.5-bath home offers over 3,020 sq.ft. of living

  

  Kara Lushear

  COLDWELL BANKER REALTY

  (321) 621-0024

  1183 Wildmeadow Run, Winter Park, FL 32792
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  /40

  $2,650,000

  • 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
• 

  

  /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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  /60

  $574,000

  • 3 Beds
  • 2.5 Baths
  • 1,640 Sq Ft

  5441 Baldwin Park St, Orlando, FL 32814

  Welcome to Baldwin Park - a desirable, centrally-located Community loaded with Amenities! Picture yourself on these tree-line streets enjoying one of three Pools, Clubhouses, Exercise Facility, Parks, Playgrounds, Bike Trails, the Gazebo and Fountain on Lake Baldwin, access to Cady Way Trail and The Town Center with it's shopping and Restaurants. Top-Rated Schools within the Community!Now,

  Janice Erickson

  REALCOM REAL ESTATE SERVICES INC

  (407) 904-4080

  5441 Baldwin Park St, Orlando, FL 32814
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  /5

  $1,825,000 New Construction

  • 5 Beds
  • 5.5 Baths
  • 3,655 Sq Ft

  2305 Coldstream Dr, Winter Park, FL 32792

  Under Construction. A rare opportunity to own brand-new construction in desirable Brookshire Heights, this thoughtfully designed residence blends timeless finishes with modern functionality. Featuring 5 bedrooms, a dedicated office, and a spacious bonus room, the floor plan is both highly livable and exceptionally functional—ideal for everyday living and entertaining alike. All bedrooms are

  

  Jennifer King

  CORCORAN PREMIER REALTY

  (321) 490-4786

  2305 Coldstream Dr, Winter Park, FL 32792
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  /78

  $1,399,000 New Construction

  • 4 Beds
  • 3.5 Baths
  • 2,459 Sq Ft

  102 Bell Place, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. Dreams Do Come True! This spectacular brand-new 2025 block construction home, crafted with steel framing instead of wood, combines modern luxury with timeless design in one of Winter Park’s up incoming desirable areas—just moments from Interlachen Country Club and the Lakemont Heights neighborhood an NO HOA!Step through the double-door entry

  

  Freddie Crespo

  INVESTOR'S REAL ESTATE LLC

  (321) 490-4832

  102 Bell Place, Winter Park, FL 32792
• 

  

  /22

  $464,900

  • 3 Beds
  • 2 Baths
  • 1,715 Sq Ft

  2020 Cocos Ct, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. Beautifully renovated pool home in the highly desirable Eastbrook community of Winter Park, featuring major recent upgrades including a new AC system, windows, doors, and flooring throughout the home. This move-in ready 3-bedroom, 2-bath residence sits on an oversized 0.30-acre corner lot in a quiet cul-de-sac with no HOA. The home offers a bright

  Julimar Barreiro Pastrana SERHANT

  2020 Cocos Ct, Winter Park, FL 32792
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  /17

  $499,990

  • 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

  $2,395,000

  • 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

  $285,000

  • 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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  /54

  $424,900

  • 3 Beds
  • 2 Baths
  • 2,083 Sq Ft

  1367 Tierra Cir, Winter Park, FL 32792

  Located in the highly desirable Casa Aloma neighborhood of Winter Park, this updated 3-bedroom, 2-bath, 2,083 sq ft home offers Spanish architectural combined with thoughtful modern improvements. Built in 1969, the home features concrete block construction on a concrete foundation, providing durability and peace of mind. Situated on a corner lot with updated landscaping, the property offers

  Brian Bauer SOUTHERN LAND & HOMES

  1367 Tierra 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
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  /94

  $4,195,000 New Construction

  • 4 Beds
  • 4.5 Baths
  • 4,665 Sq Ft

  2020 Via Tuscany, Winter Park, FL 32789

  PRESTIGIOUS VIA TUSCANY NEW CONSTRUCTION. If location was a lottery ticket, you just hit the jackpot!!! Welcome to a masterpiece of modern elegance in the heart of the Winter Park Vias. Crafted by the renowned Element Home Builders, this stunning 4,665 sq. ft. estate offers an unparalleled blend of sophistication and comfort. The expansive open-concept floor plan features 5 generous bedrooms, 4.5

  Mauro Costa CORCORAN PREMIER REALTY

  2020 Via Tuscany, Winter Park, FL 32789
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  /34

  $574,999

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

  330 Elkhorn Ct, Winter Park, FL 32792

  330 Elkhorn Ct is a beautifully renovated, move-in-ready home located in the highly desired Winter Park Pines community. Inside, you’ll find a bright, open layout with wide-plank flooring, recessed lighting, and a modern neutral color palette that feels clean and inviting. The kitchen has been thoughtfully updated with shaker-style cabinetry, sleek countertops, stainless steel appliances, and

  Neil Chetram LA ROSA REALTY CW PROPERTIES L

  330 Elkhorn Ct, Winter Park, FL 32792
• 

  

  /20

  $350,000

  • 3 Beds
  • 2 Baths
  • 1,146 Sq Ft

  1033 Hamlet Dr, Maitland, FL 32751

  This charming 3-bedroom, 2-bathroom single-family home with the best of Florida living. Located in the north of Orlando (Maitland - Winter Park area). 1.3 miles to the Center of Winter Park Shopping Plaza (Office Depot, UPS, Ross, Marshalls, Home Goods, Five Below, LA Fitness, Petco and Michaels, Whole Foods Markets, and Banking). Access to major highways, minutes to downtown, and Orlando's

  Bennie Olivo BOX REAL ESTATE LLC

  1033 Hamlet Dr, Maitland, FL 32751
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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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  /66

  $1,350,000

  • 6 Beds
  • 4 Baths
  • 4,214 Sq Ft

  3711 Vinsetta Ct, Winter Park, FL 32792

  Elevate your lifestyle in the prestigious Lakeside Estates, a private gated Winter Park community anchored by Garden Lake. In a quiet cul-de-sac, on a wrapping corner lot on over 1/3 of an acre and only a short distance to the playground making it easy. A six-bedroom, four-bath home sprawls over 4,200 square feet with back of the house opening to a covered porch with a generously sized saltwater

  Alison Mosley PREMIER SOTHEBY'S INTL. REALTY

  3711 Vinsetta Ct, 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
• 

  

  /54

  $1,978,000

  • 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
• 

  

  /31

  $267,000

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

  1500 Gay Rd Unit 8D, Winter Park, FL 32789

  Welcome to the most beautifully updated 2 Bedroom 2 bath End Unit in a Lakefront Community on Lake Killarney. This home features Quartz counter tops with a Granite Island and stainless steel appliances, along with a beverage refrigerator, and luxury vinyl flooring through out the whole unit. A huge living room offers loads of gathering and entertaining space in this cheerful home. Enjoy Florida

  Trevor Laug. Realtor SOLID OAK REAL ESTATE LLC

  1500 Gay Rd Unit 8D, Winter Park, FL 32789
• 

  

  /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. 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

  Laura Earl CORCORAN PREMIER REALTY

  906 Enclave Place, Winter Park, FL 32792
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  /47

  $1,100,000

  • 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
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  /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

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 $957,674.

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?

1,015 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 $529,900. If you put a 20% down payment of $106,000 and had a 30-year fixed mortgage with an interest rate of 6.38%, your estimated principal and interest payment would be $2,650 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $114K 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 66 days on the market compared to the national average of 55 days. The median sale price for homes in Winter Park, FL over the last 12 months is $480,000, up 1% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price

$480,000

Median Single Family Sale Price

$600,000

Median Townhouse Sale Price

$455,000

Median 2 Bedroom Sale Price

$202,500

Median 1 Bedroom Sale Price

$154,000

Average Price Per Sq Ft

$369

Number of Homes for Sale

307

Last 12 months Home Sales

1,015

Months of Supply

3.60

Median List Price

$529,900

Median Change From 1st List Price

5%

Median Home Sale Price YoY Change

1%