28,400

Winter Park, FL Homes

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  • /32

    $579,000

    • 4 Beds
    • 2 Baths
    • 1,660 Sq Ft

    333 Cornwall Rd, Winter Park, FL 32792

    Located in the heart of Winter Park, Winter Park Pines is a well-established neighborhood known for its convenience, school zoning, and access to outdoor living. A place to slow down, where evening walks feel like something out of a storybook, and the Cady Way Trail is just steps from your back door for morning runs, bike rides, and everything in between. One of the standout features is having

    Melissa Johnson EXP REALTY LLC

    333 Cornwall Rd, Winter Park, FL 32792
  • /23

    $1,500 Per Month

    • 2 Beds
    • 1 Bath
    • 881 Sq Ft
    • Condo for Rent

    1695 Lee Rd Unit B114, Winter Park, FL 32789

    The unit has two spacious bedrooms, galley kitchen, walk in closet, living/dining room combo, washer and dryer combo brand new refrigerator , and lovely patio that leads to the community pool and playground. .This well-maintained unit features a spacious living area filled with natural light Cove is located centrally to major highways, schools, tons of shopping & restaurants so it is a great

    Yigit Orer EMPIRE NETWORK REALTY

    1695 Lee Rd Unit B114, Winter Park, FL 32789
  • /2

    $145,000

    Sold Apr 23, 2026

    2500 Lee Rd Unit 243, Winter Park, FL 32789

    • 1 Bed
    • 1 Bath
    • 645 Sq Ft
    • Built 1969

    Last Sold Summary

    • 28% Below List Price
    • $225/SF
    • 286 Days On Market

    Current Estimated Value $156,952

    Last Listing Agent Sue Gilman KELLER WILLIAMS WINTER PARK

    2500 Lee Rd Unit 243, Winter Park, FL 32789
    • /2

      Not Listed For Sale

      681 Grenadine Ct Unit S, Winter Park, FL 32792

      • 2 Beds
      • 2 Baths
      • 1,037 Sq Ft
      • Built 1981
      681 Grenadine Ct Unit S, Winter Park, FL 32792

      Last Sold Summary

      • 147 Days On Market

  • /25

    $284,900

    • 3 Beds
    • 2 Baths
    • 1,284 Sq Ft

    2335 Inagua Way, Winter Park, FL 32792

    Rare opportunity in beautiful Winter Park - Move in ready 3 bed 2 bath townhome for under $300,000. Super low HOA at only $92/month. Spacious split plan with new roof, newer AC, new carpet in bedrooms, freshly painted, tile, inside laundry, atrium off living room and open floor plan. Patio with storage room and shed. Front entrance & parking area with beautiful pavers. Townhome is on

    Marion McGrath ABSOLUTE REALTY GROUP, LLC

    2335 Inagua Way, Winter Park, FL 32792
  • /13

    $1,745 Per Month

    • 3 Beds
    • 2 Baths
    • 1,300 Sq Ft
    • Condo for Rent

    7526 University Garden Dr, Winter Park, FL 32792

    Fantastic 3 Bedrooms & 2 Bathrooms Home in Orlando ***Available 08/05/26***Located at 7526 University Garden Dr Winter Park, FL 32792Limited-time offer! Enjoy $150 off the base rent of $1,895 during months 2, 3, and 4 — advertised rent reflects this temporary discount.Tile Throughout Main Parts of Property and Master Bedroom.Carpet in Bedrooms.Private Covered Patio and One Car

    7526 University Garden Dr, Winter Park, FL 32792
  • /2

    $850,000

    Sold Mar 31, 2026

    1929 S Lakemont Ave, Winter Park, FL 32792

    • 3 Beds
    • 3.5 Baths
    • 2,160 Sq Ft
    • Built 2023

    Last Sold Summary

    • 10% Below List Price
    • $394/SF
    • 91 Days On Market

    Current Estimated Value $861,186

    Last Listing Agent Brandon Geers COMPASS FLORIDA LLC

    1929 S Lakemont Ave, Winter Park, FL 32792
    • /33

      Est $474,451

      Not Listed For Sale

      2260 Shadowland Loop, Winter Park, FL 32792

      • 3 Beds
      • 2.5 Baths
      • 2,308 Sq Ft
      • Built 2021
      2260 Shadowland Loop, Winter Park, FL 32792

      Last Sold Summary

      • 2 Days On Market

  • /36

    $3,095,000

    Pending
    • 3 Beds
    • 5 Baths
    • 4,425 Sq Ft

    1724 Pine Ave, Winter Park, FL 32789

    Under contract-accepting backup offers. Beautifully renovated and thoughtfully designed, this exceptional residence is nestled in the heart of Winter Park’s sought-after Tree Streets neighborhood. Privately behind entry gates, the home welcomes you with a picturesque front courtyard highlighted by a tranquil water feature, setting the tone for the sophisticated living experience that awaits.

    Mick Night PREMIER SOTHEBY'S INTL. REALTY

    1724 Pine Ave, Winter Park, FL 32789
  • /13

    $1,575 Per Month

    • 2 Beds
    • 2 Baths
    • 1,018 Sq Ft
    • Condo for Rent

    2918 Antique Oaks Cir Unit 26, Winter Park, FL 32792

    This 2/2, 1,018 sq. ft. second story condo in Parkview Village features a living room & dining room combo! Screened in balcony, inside utility closet. This unit is close to community pool! Water/Sewer Included!Sorry, No Pets!!Application Fee: $50 / adult (18+)Full Credit/Skip/Eviction/Background check is done on all applicants.**Please have the following documents ready to attach

    Kenneth Warren PREMIER MANAGEMENT GROUP INC

    2918 Antique Oaks Cir Unit 26, Winter Park, FL 32792
  • /2

    $912,500

    Sold Jan 14, 2026

    210 Laurel Park Ct, Winter Park, FL 32792

    • 4 Beds
    • 3 Baths
    • 2,838 Sq Ft
    • Built 2006

    Last Sold Summary

    • 4% Below List Price
    • $322/SF
    • 25 Days On Market

    Current Estimated Value $916,359

    Last Listing Agent Alireza Partovi EXP REALTY LLC

    210 Laurel Park Ct, Winter Park, FL 32792
    • /2

      Not Listed For Sale

      0 Grand Rd Unit MFRO6213919, Winter Park, FL 32792

      0 Grand Rd Unit MFRO6213919, Winter Park, FL 32792

      Last Sold Summary

      • 55 Days On Market

  • /36

    $154,900

    $4K PRICE DROP
    • 1 Bed
    • 1 Bath
    • 678 Sq Ft

    262 Lewfield Cir Unit 262, Winter Park, FL 32792

    Walk into this freshly painted, pool view unit. Updates include new vinyl plank flooring throughout, new lighting, window coverings and a new tub/shower fixtures in the bathroom! Residents enjoy access to two pools, lighted tennis courts, fitness center, car care facilities and a clubhouse. The clubhouse can be rented for hosted gatherings. There is a free on-site laundry facility. Location is

    Drew Bishop KELLER WILLIAMS REALTY FT MYER

    262 Lewfield Cir Unit 262, Winter Park, FL 32792
  • /3

    $2,000 Per Month

    • 3 Beds
    • 2 Baths
    • House for Rent

    5139 Oak Hill Dr, Winter Park, FL 32792

    3/2 home with updated kitchen, large yard & screen patio. 3/2 home with updated kitchen, large yard & screen patio. Lawn service included

    5139 Oak Hill Dr, Winter Park, FL 32792
  • /2

    $485,000

    Sold Aug 18, 2025

    1921 Japonica Rd, Winter Park, FL 32792

    • 4 Beds
    • 2 Baths
    • 2,171 Sq Ft
    • Built 1971

    Last Sold Summary

    • $223/SF
    • 11 Days On Market

    Current Estimated Value $494,279

    Last Listing Agent Jose Gabriel Rodriguez COLDWELL BANKER REALTY

    1921 Japonica Rd, Winter Park, FL 32792
    • /2

      Est $692,539

      Not Listed For Sale

      1360 Blue Stem Ln, Winter Park, FL 32792

      • 4 Beds
      • 2.5 Baths
      • 2,416 Sq Ft
      • Built 2021
      1360 Blue Stem Ln, Winter Park, FL 32792

      Last Sold Summary

      • 8 Days On Market

  • /35

    $649,000

    Open Sat 11AM - 1PM
    • 3 Beds
    • 1 Bath
    • 1,101 Sq Ft

    1037 N Virginia Ave, Winter Park, FL 32789

    THE best kept secret in WP! Newly renovated charming bungalow located directly on famed 4th Fairway on WP9 – Winter Park Golf Course! Quiet, private & secluded setting with gorgeous views on dead end street. Walk or bike to Park Avenue, dining and shopping, Rollins College and Winter Park Village. New roof and water heater 2023, refinished hardwood floors, new kitchen with stainless appliances,

    Lisa Gould KELLER WILLIAMS WINTER PARK

    1037 N Virginia Ave, Winter Park, FL 32789
  • /17

    $1,650 Per Month

    • 2 Beds
    • 2 Baths
    • 1,062 Sq Ft
    • Condo for Rent

    3045 Aaron Burr Ave Unit 12, Winter Park, FL 32792

    Condominium located in The Colonies in Winter Park. Conveniently situated near UCF (University of Central Florida) and Full Sail University, with easy access to shopping centers, major highways, restaurants, and Orlando's world-famous theme parks. Just 11 minutes from Orlando International Airport (Orlando International Airport).This cozy 2-bedroom apartment is perfectly located for quick access

    Angel Ramirez LPT REALTY, LLC

    3045 Aaron Burr Ave Unit 12, Winter Park, FL 32792
  • /2

    $335,000

    Sold Oct 31, 2025

    3525 Baxter Dr, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,560 Sq Ft
    • Built 1970

    Last Sold Summary

    • 14% Above List Price
    • $215/SF
    • 5 Days On Market

    Current Estimated Value $336,288

    Last Listing Agent Ashley Fisak COLDWELL BANKER REALTY

    3525 Baxter Dr, Winter Park, FL 32792
    • /2

      Est $145,315

      Not Listed For Sale

      160 Lewfield Cir Unit 160, Winter Park, FL 32792

      • 1 Bed
      • 1 Bath
      • 678 Sq Ft
      • Built 1973
      160 Lewfield Cir Unit 160, Winter Park, FL 32792

      Last Sold Summary

      • 18 Days On Market

  • /26

    $240,000

    $10K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 1,578 Sq Ft

    7484 Canford Ct Unit 8, Winter Park, FL 32792

    This three-bedroom, three-bath updated Winter Park townhome-style condo is located in a quiet complex, a perfect place to call home. It's just minutes away from the University of Central Florida, Full Sail University, & Valencia College. This location makes an excellent investment for a college (or parents of) student. The upgraded kitchen has granite countertops with a custom sink, newer

    Greg Harrison CHARLES RUTENBERG REALTY ORLANDO

    7484 Canford Ct Unit 8, Winter Park, FL 32792
  • /46

    $2,875 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,755 Sq Ft
    • Hawk's Crest Modern Townhome in Winter Park

    1351 Merrydale Way, Winter Park, FL 32792

    Fantastic, Modern townhome WITH 3 beds & 2.5 baths. Hawk's Crest is a gated community in Winter Park. This home is has a very spacious open floor plan with a water view! The kitchen has granite countertops and is fully equipped with stainless steel Whirlpool appliances; oven, stove, microwave, refrigerator, dishwasher, and garbage disposal. The kitchen area also has a large pantry! This energy

    1351 Merrydale Way, Winter Park, FL 32792
  • /2

    $715,000

    Sold Jun 12, 2026

    688 Brechin Dr, Winter Park, FL 32792

    • 4 Beds
    • 2 Baths
    • 1,599 Sq Ft
    • Built 1961

    Last Sold Summary

    • 1% Below List Price
    • $447/SF
    • 3 Days On Market

    Current Estimated Value $690,389

    Last Listing Agent Alison Mosley PREMIER SOTHEBY'S INTL. REALTY

    688 Brechin Dr, Winter Park, FL 32792
    • /2

      Est $831,334

      Not Listed For Sale

      1905 S Lakemont Ave, Winter Park, FL 32792

      • 3 Beds
      • 3.5 Baths
      • 2,066 Sq Ft
      • Built 2024
      1905 S Lakemont Ave, Winter Park, FL 32792

      Last Sold Summary

      • 251 Days On Market

  • /24

    $259,999

    Open Sun 1PM - 3PM
    • 2 Beds
    • 2 Baths
    • 956 Sq Ft

    2500 Lee Rd Unit 104, Winter Park, FL 32789

    Beautifully renovated and move-in ready 2-bedroom, 2-bath condominium offers thoughtful upgrades and a seamless open layout in one of Winter Park's most desirable lakefront communities. The heart of the home is the fully renovated kitchen (2025), featuring custom, soft close cabinetry with a built-in refrigerator surround, matching energy-efficient appliances, quartzite countertops, a white

    Stephen Hachey REALTY OF RIVERVIEW LLC

    2500 Lee Rd Unit 104, Winter Park, FL 32789
  • /24

    $3,200 Per Month

    • 2 Beds
    • 1 Bath
    • 1,250 Sq Ft
    • House for Rent

    438 Lakeview Ave, Winter Park, FL 32789

    Bring your boat and discover this charming Winter Park gem, perfectly nestled on a quiet, desirable brick-lined street. This inviting 2-bedroom, 1-bath home features beautiful hardwood floors and a warm, welcoming feel throughout. Enjoy a lakefront yard feet from the house that offers peaceful water views and the perfect setting for outdoor living. Step outside to an amazing backyard complete

    Alex Scures COLONIALTOWN REALTY

    438 Lakeview Ave, Winter Park, FL 32789
  • /2

    $699,000

    Sold Jun 30, 2025

    1632 Haven Dr, Orlando, FL 32803

    • 3 Beds
    • 2.5 Baths
    • 1,772 Sq Ft
    • Built 2025

    Last Sold Summary

    • 3% Below List Price
    • $394/SF
    • 110 Days On Market

    Current Estimated Value $496,000

    Last Listing Agent Robert St. Pierre WEEKLEY HOMES REALTY COMPANY

    1632 Haven Dr, Orlando, FL 32803
    • /2

      Est $446,289

      Not Listed For Sale

      2953 Clever Ln, Winter Park, FL 32792

      • 3 Beds
      • 2.5 Baths
      • 1,907 Sq Ft
      • Built 2024
      2953 Clever Ln, Winter Park, FL 32792

      Last Sold Summary

      • 7 Days On Market

  • /39

    $1,395,000

    Coming Soon
    • 3 Beds
    • 2.5 Baths
    • 2,821 Sq Ft

    321 Sylvan Blvd, Winter Park, FL 32789

    Set on a rare double lot in one of Winter Park's most coveted locations, this charming 1940 Craftsman-style residence presents an extraordinary opportunity to enjoy one of Central Florida's most celebrated lifestyles while envisioning the future. Just moments from the Winter Park Chain of Lakes, the boutiques and acclaimed dining of Park Avenue, and the timeless beauty of Rollins College, the

    Mel Bernstein PREMIER SOTHEBYS INT'L REALTY

    321 Sylvan Blvd, Winter Park, FL 32789
  • /26

    $2,350 Per Month

    • 3 Beds
    • 2 Baths
    • 1,200 Sq Ft
    • House for Rent

    1340 Paradise Ln, Winter Park, FL 32792

    Welcome to this charming and well-maintained home located in the heart of Winter Park at 1340 Paradise Lane. This beautiful property offers 3 spacious bedrooms and 2 full bathrooms with a comfortable and functional layout perfect for families or anyone looking for a cozy place to call home.The home features elegant tile flooring throughout the main living areas and stylish vinyl flooring

    1340 Paradise Ln, Winter Park, FL 32792
  • /2

    $179,900

    Sold Jun 02, 2026

    3651 N Goldenrod Rd Unit 101, Winter Park, FL 32792

    • 2 Beds
    • 2 Baths
    • 840 Sq Ft
    • Built 1990

    Last Sold Summary

    • 3% Below List Price
    • $214/SF
    • 44 Days On Market

    Current Estimated Value $175,255

    Last Listing Agent REZA Shirzad ANNE ROGERS REALTY GROUP INC

    3651 N Goldenrod Rd Unit 101, Winter Park, FL 32792
    • /18

      Est $193,026

      Not Listed For Sale

      3351 River View Way Unit 41, Winter Park, FL 32792

      • 2 Beds
      • 1.5 Baths
      • 990 Sq Ft
      • Built 1983
      3351 River View Way Unit 41, Winter Park, FL 32792

      Last Sold Summary

      • 53 Days On Market

  • /82

    $135,000

    $25K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,149 Sq Ft

    1695 Lee Rd Unit E215, Winter Park, FL 32789

    Located in the heart of Winter Park, this charming condo stands ready to welcome you home. This three-bedroom, two-bathroom sanctuary offers a blend of comfort and modern elegance, perfect for those who cherish both relaxation and entertaining. As you step inside, the spacious living and dining areas greet you with an abundance of natural light, creating a warm and inviting atmosphere. Imagine

    Jenaia Fowlkes FOWLKES REALTY CO

    1695 Lee Rd Unit E215, Winter Park, FL 32789
  • /30

    $2,750 Per Month

    • 2 Beds
    • 1 Bath
    • 768 Sq Ft
    • Condo for Rent

    151 N Orlando Ave Unit 238, Winter Park, FL 32789

    Experience lakefront living at its finest in this exceptional Winter Park condo overlooking beautiful Lake Killarney. Enjoy breathtaking sunset views from your private waterfront retreat, complete with access to a community dock, private boat ramp, and a fenced lakeside pool perfect for relaxing and entertaining. Ideally located just minutes from the heart of Winter Park, this home offers

    Alex Scures COLONIALTOWN REALTY

    151 N Orlando Ave Unit 238, Winter Park, FL 32789
  • /2

    $689,500

    Sold Jul 19, 2025

    1129 Golfside Dr, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,750 Sq Ft
    • Built 1978

    Last Sold Summary

    • 5% Below List Price
    • $394/SF
    • 21 Days On Market

    Current Estimated Value $687,363

    Last Listing Agent Tess Muccigrosso RE/MAX 200 REALTY

    1129 Golfside Dr, Winter Park, FL 32792
    • /42

      Est $493,289

      Not Listed For Sale

      2444 Firstlight Way, Winter Park, FL 32792

      • 3 Beds
      • 2.5 Baths
      • 2,376 Sq Ft
      • Built 2020
      2444 Firstlight Way, Winter Park, FL 32792

      Last Sold Summary

      • 11 Days On Market

  • /43

    $475,000

    $5K PRICE DROP Pending
    • 3 Beds
    • 2 Baths
    • 1,676 Sq Ft

    1468 Auburn Green Loop, Winter Park, FL 32792

    Under contract-accepting backup offers. Welcome to this fantastic home on beautiful Lake Florence in a great Winter Park location off of Howell Branch Road in Seminole County! This spacious 3-Bedroom, 2-Bathroom house features vaulted ceilings, wood burning fireplace, ceiling fans, and wonderful outdoor areas. The Living Room, Dining Room and Great Room make this home feel large. The main living

    Jodie Ma COLDWELL BANKER VANGUARD EDGE

    1468 Auburn Green Loop, Winter Park, FL 32792
  • /25

    $2,250 Per Month

    • 2 Beds
    • 1 Bath
    • 1,131 Sq Ft
    • House for Rent

    1671 Dale Ave, Winter Park, FL 32789

    SMALL PETS ACCEPTEDNestled in a quiet, established neighborhood, this beautifully maintained 2-bedroom, 1-bath home offers 1,131 square feet of comfortable living space with timeless charm and modern conveniences. The refinished original hardwood floors add warmth and character throughout, while abundant natural light enhances every room.A spacious bonus room provides the perfect

    1671 Dale Ave, Winter Park, FL 32789
  • /2

    $893,000

    Sold Oct 09, 2025

    2890 Wild Ginger Ct, Winter Park, FL 32792

    • 4 Beds
    • 4.5 Baths
    • 3,408 Sq Ft
    • Built 1993

    Last Sold Summary

    • 27% Below List Price
    • $262/SF
    • 78 Days On Market

    Current Estimated Value $899,928

    Last Listing Agent Alison Mosley PREMIER SOTHEBY'S INTL. REALTY

    2890 Wild Ginger Ct, Winter Park, FL 32792
    • /2

      Not Listed For Sale

      3069 Aaron Burr Ave Unit D, Winter Park, FL 32792

      • 1 Bed
      • 1 Bath
      • 600 Sq Ft
      • Built 1974
      3069 Aaron Burr Ave Unit D, Winter Park, FL 32792

      Last Sold Summary

      • 53 Days On Market

Showing Results 361 - 400, Page 10 of 18

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