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Winter Park is home to a plethora of world-class museums, high-end boutiques, some of the area's finest restaurants, and is centrally located being only minutes from downtown Orlando. Use our custom search tool to view all homes for sale under $400k in Winter Park or click here to return to the list of surrounding towns and cities in the Orlando area. Have questions? Contact us here.


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  1. Photo of 1970 Laurel Road, Winter Park, FL 32789 (MLS # O6265919)
    $1,999,999
    Photo of 1970 Laurel Road, Winter Park, FL 32789 (MLS # O6265919)
    Photo of 1970 Laurel Road, Winter Park, FL 32789 (MLS # O6265919)
    1970 Laurel Road, Winter Park, FL
    1970 Laurel Road
    Winter Park, FL
    • 4 Beds
    • 4 Baths
    • 3,440 Home (sqft)
    • 4 Baths
    • 9,148 Lot (sqft)
  2. Photo of 5357 Orange Avenue, Winter Park, FL 32792 (MLS # O6266043)
    $300,000
    Photo of 5357 Orange Avenue, Winter Park, FL 32792 (MLS # O6266043)
    Photo of 5357 Orange Avenue, Winter Park, FL 32792 (MLS # O6266043)
    5357 Orange Avenue, Winter Park, FL
    5357 Orange Avenue
    Winter Park, FL
    • 2 Beds
    • 1 Bath
    • 912 Home (sqft)
    • 1 Bath
    • 10,455 Lot (sqft)
  3. Photo of 311 E Morse Boulevard #7-15, Winter Park, FL 32789 (MLS # O6265966)
    $329,900
    Photo of 311 E Morse Boulevard #7-15, Winter Park, FL 32789 (MLS # O6265966)
    Photo of 311 E Morse Boulevard #7-15, Winter Park, FL 32789 (MLS # O6265966)
    311 E Morse Boulevard #7-15, Winter Park, FL
    311 E Morse Boulevard #7-15
    Winter Park, FL
    • 1 Bed
    • 1 Bath
    • 482 Home (sqft)
    • 1 Bath
    • 2.77 Lot (ac)
  4. Photo of 1263 Verdant Glade Place, Winter Park, FL 32792 (MLS # TB8331485)
    $895,000
    Photo of 1263 Verdant Glade Place, Winter Park, FL 32792 (MLS # TB8331485)
    Photo of 1263 Verdant Glade Place, Winter Park, FL 32792 (MLS # TB8331485)
    1263 Verdant Glade Place, Winter Park, FL
    1263 Verdant Glade Place
    Winter Park, FL
    • 4 Beds
    • 4 Baths
    • 2,589 Home (sqft)
    • 4 Baths
    • 5,228 Lot (sqft)
  5. Photo of 2690 Granada Run, Winter Park, FL 32792 (MLS # O6265961)
    $299,900
    Photo of 2690 Granada Run, Winter Park, FL 32792 (MLS # O6265961)
    Photo of 2690 Granada Run, Winter Park, FL 32792 (MLS # O6265961)
    2690 Granada Run, Winter Park, FL
    2690 Granada Run
    Winter Park, FL
    • 3 Beds
    • 2 Baths
    • 1,467 Home (sqft)
    • 2 Baths
    • 4,356 Lot (sqft)
  6. Photo of 260 Scottsdale Square #260, Winter Park, FL 32792 (MLS # O6265656)
    $125,000
    Photo of 260 Scottsdale Square #260, Winter Park, FL 32792 (MLS # O6265656)
    Photo of 260 Scottsdale Square #260, Winter Park, FL 32792 (MLS # O6265656)
    260 Scottsdale Square #260, Winter Park, FL
    260 Scottsdale Square #260
    Winter Park, FL
    • 2 Beds
    • 2 Baths
    • 1,085 Home (sqft)
    • 2 Baths
    • 8,712 Lot (sqft)
  7. Photo of 232 Lewfield Circle #232, Winter Park, FL 32792 (MLS # S5117382)
    $197,995
    Photo of 232 Lewfield Circle #232, Winter Park, FL 32792 (MLS # S5117382)
    Photo of 232 Lewfield Circle #232, Winter Park, FL 32792 (MLS # S5117382)
    232 Lewfield Circle #232, Winter Park, FL
    232 Lewfield Circle #232
    Winter Park, FL
    • 2 Beds
    • 2 Baths
    • 953 Home (sqft)
    • 2 Baths
    • 872 Lot (sqft)
  8. Photo of 108 Scottsdale Square #108, Winter Park, FL 32792 (MLS # O6265811)
    $169,999
    Photo of 108 Scottsdale Square #108, Winter Park, FL 32792 (MLS # O6265811)
    Photo of 108 Scottsdale Square #108, Winter Park, FL 32792 (MLS # O6265811)
    108 Scottsdale Square #108, Winter Park, FL
    108 Scottsdale Square #108
    Winter Park, FL
    • 3 Beds
    • 2 Baths
    • 1,300 Home (sqft)
    • 2 Baths
    • 8,712 Lot (sqft)
  9. Photo of 2774 Bright Bird Lane, Winter Park, FL 32792 (MLS # O6266098)
    $580,000
    Photo of 2774 Bright Bird Lane, Winter Park, FL 32792 (MLS # O6266098)
    Photo of 2774 Bright Bird Lane, Winter Park, FL 32792 (MLS # O6266098)
    2774 Bright Bird Lane, Winter Park, FL
    2774 Bright Bird Lane
    Winter Park, FL
    • 3 Beds
    • 3 Baths
    • 1,907 Home (sqft)
    • 3 Baths
    • 1,743 Lot (sqft)
  10. Photo of 585 Via Lugano, Winter Park, FL 32789 (MLS # O6265815)
    $2,999,999
    Photo of 585 Via Lugano, Winter Park, FL 32789 (MLS # O6265815)
    Photo of 585 Via Lugano, Winter Park, FL 32789 (MLS # O6265815)
    585 Via Lugano, Winter Park, FL
    585 Via Lugano
    Winter Park, FL
    • 5 Beds
    • 4 Baths
    • 4,390 Home (sqft)
    • 4 Baths
    • 27,443 Lot (sqft)
  11. Photo of 3251 Crown Jewel Court, Winter Park, FL 32792 (MLS # O6265459)
    $355,000
    Photo of 3251 Crown Jewel Court, Winter Park, FL 32792 (MLS # O6265459)
    Photo of 3251 Crown Jewel Court, Winter Park, FL 32792 (MLS # O6265459)
    3251 Crown Jewel Court, Winter Park, FL
    3251 Crown Jewel Court
    Winter Park, FL
    • 3 Beds
    • 3 Baths
    • 1,408 Home (sqft)
    • 3 Baths
    • 1,743 Lot (sqft)
  12. Photo of 2310 Cady Way, Winter Park, FL 32792 (MLS # O6265551)
    $629,000
    Photo of 2310 Cady Way, Winter Park, FL 32792 (MLS # O6265551)
    Photo of 2310 Cady Way, Winter Park, FL 32792 (MLS # O6265551)
    2310 Cady Way, Winter Park, FL
    2310 Cady Way
    Winter Park, FL
    • 3 Beds
    • 2 Baths
    • 1,856 Home (sqft)
    • 2 Baths
    • 9,584 Lot (sqft)
  13. Photo of 2112 Staunton Avenue, Winter Park, FL 32789 (MLS # O6265145)
    $449,000
    Photo of 2112 Staunton Avenue, Winter Park, FL 32789 (MLS # O6265145)
    Photo of 2112 Staunton Avenue, Winter Park, FL 32789 (MLS # O6265145)
    2112 Staunton Avenue, Winter Park, FL
    2112 Staunton Avenue
    Winter Park, FL
    • 3 Beds
    • 1 Bath
    • 1,438 Home (sqft)
    • 1 Bath
    • 9,584 Lot (sqft)
  14. Photo of 3505 Balsam Drive, Winter Park, FL 32792 (MLS # V4939945)
    $349,900
    Photo of 3505 Balsam Drive, Winter Park, FL 32792 (MLS # V4939945)
    Photo of 3505 Balsam Drive, Winter Park, FL 32792 (MLS # V4939945)
    3505 Balsam Drive, Winter Park, FL
    3505 Balsam Drive
    Winter Park, FL
    • 4 Beds
    • 2 Baths
    • 1,709 Home (sqft)
    • 2 Baths
    • 10,019 Lot (sqft)
  15. Photo of 328 Scottsdale Square #328, Winter Park, FL 32792 (MLS # O6265403)
    $105,000
    Photo of 328 Scottsdale Square #328, Winter Park, FL 32792 (MLS # O6265403)
    Photo of 328 Scottsdale Square #328, Winter Park, FL 32792 (MLS # O6265403)
    328 Scottsdale Square #328, Winter Park, FL
    328 Scottsdale Square #328
    Winter Park, FL
    • 1 Bed
    • 1 Bath
    • 756 Home (sqft)
    • 1 Bath
    • 2,614 Lot (sqft)
  16. Photo of 143 Lewfield Circle #143, Winter Park, FL 32792 (MLS # O6265001)
    $145,000
    Photo of 143 Lewfield Circle #143, Winter Park, FL 32792 (MLS # O6265001)
    Photo of 143 Lewfield Circle #143, Winter Park, FL 32792 (MLS # O6265001)
    143 Lewfield Circle #143, Winter Park, FL
    143 Lewfield Circle #143
    Winter Park, FL
    • 1 Bed
    • 1 Bath
    • 678 Home (sqft)
    • 1 Bath
    • 0 Lot (sqft)
  17. Photo of 315 E New England Avenue #9, Winter Park, FL 32789 (MLS # O6264767)
    $1,599,000
    Photo of 315 E New England Avenue #9, Winter Park, FL 32789 (MLS # O6264767)
    Photo of 315 E New England Avenue #9, Winter Park, FL 32789 (MLS # O6264767)
    315 E New England Avenue #9, Winter Park, FL
    315 E New England Avenue #9
    Winter Park, FL
    • 2 Beds
    • 2 Baths
    • 1,637 Home (sqft)
    • 2 Baths
    • 27,443 Lot (sqft)
  18. Photo of 2260 Mulbry Drive, Winter Park, FL 32789 (MLS # O6264761)
    $2,000,000
    Photo of 2260 Mulbry Drive, Winter Park, FL 32789 (MLS # O6264761)
    Photo of 2260 Mulbry Drive, Winter Park, FL 32789 (MLS # O6264761)
    2260 Mulbry Drive, Winter Park, FL
    2260 Mulbry Drive
    Winter Park, FL
    • 5 Beds
    • 4 Baths
    • 3,246 Home (sqft)
    • 4 Baths
    • 9,584 Lot (sqft)
  19. Photo of 1550 Indiana Avenue, Winter Park, FL 32789 (MLS # O6264959)
    $459,990
    Photo of 1550 Indiana Avenue, Winter Park, FL 32789 (MLS # O6264959)
    Photo of 1550 Indiana Avenue, Winter Park, FL 32789 (MLS # O6264959)
    1550 Indiana Avenue, Winter Park, FL
    1550 Indiana Avenue
    Winter Park, FL
    • 2 Beds
    • 2 Baths
    • 1,032 Home (sqft)
    • 2 Baths
    • 6,970 Lot (sqft)
  20. Photo of 1608 Bomi Circle, Winter Park, FL 32792 (MLS # O6265870)
    $525,000
    Photo of 1608 Bomi Circle, Winter Park, FL 32792 (MLS # O6265870)
    Photo of 1608 Bomi Circle, Winter Park, FL 32792 (MLS # O6265870)
    1608 Bomi Circle, Winter Park, FL
    1608 Bomi Circle
    Winter Park, FL
    • 3 Beds
    • 2 Baths
    • 1,807 Home (sqft)
    • 2 Baths
    • 19,602 Lot (sqft)
  21. Photo of 7484 Canford Court #8, Winter Park, FL 32792 (MLS # O6264178)
    $294,900
    Photo of 7484 Canford Court #8, Winter Park, FL 32792 (MLS # O6264178)
    Photo of 7484 Canford Court #8, Winter Park, FL 32792 (MLS # O6264178)
    39
     
    7484 Canford Court #8, Winter Park, FL
    7484 Canford Court #8
    Winter Park, FL
    • 3 Beds
    • 3 Baths
    • 1,698 Home (sqft)
    • 3 Baths
    • 6.71 Lot (ac)
  22. Photo of 3324 Alena Court, Winter Park, FL 32792 (MLS # O6263431)
    $435,000
    Photo of 3324 Alena Court, Winter Park, FL 32792 (MLS # O6263431)
    Photo of 3324 Alena Court, Winter Park, FL 32792 (MLS # O6263431)
    3324 Alena Court, Winter Park, FL
    3324 Alena Court
    Winter Park, FL
    • 3 Beds
    • 2 Baths
    • 1,873 Home (sqft)
    • 2 Baths
    • 8,712 Lot (sqft)
  23. Photo of 411 Sylvan Drive, Winter Park, FL 32789 (MLS # O6263469)
    $925,000
    Photo of 411 Sylvan Drive, Winter Park, FL 32789 (MLS # O6263469)
    Photo of 411 Sylvan Drive, Winter Park, FL 32789 (MLS # O6263469)
    411 Sylvan Drive, Winter Park, FL
    411 Sylvan Drive
    Winter Park, FL
    • 3 Beds
    • 2 Baths
    • 2,270 Home (sqft)
    • 2 Baths
    • 16,553 Lot (sqft)
  24. Photo of 2923 Antique Oaks Circle #37, Winter Park, FL 32792 (MLS # A4632112)
    $227,462
    Photo of 2923 Antique Oaks Circle #37, Winter Park, FL 32792 (MLS # A4632112)
    Photo of 2923 Antique Oaks Circle #37, Winter Park, FL 32792 (MLS # A4632112)
    2923 Antique Oaks Circle #37, Winter Park, FL
    2923 Antique Oaks Circle #37
    Winter Park, FL
    • 2 Beds
    • 2 Baths
    • 1,105 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  25. Photo of 225 Scottsdale Square #225, Winter Park, FL 32792 (MLS # O6263923)
    $145,000
    Photo of 225 Scottsdale Square #225, Winter Park, FL 32792 (MLS # O6263923)
    Photo of 225 Scottsdale Square #225, Winter Park, FL 32792 (MLS # O6263923)
    225 Scottsdale Square #225, Winter Park, FL
    225 Scottsdale Square #225
    Winter Park, FL
    • 2 Beds
    • 2 Baths
    • 1,020 Home (sqft)
    • 2 Baths
    • 8,712 Lot (sqft)
  26. Photo of 1005 Carvell Drive, Winter Park, FL 32792 (MLS # O6263657)
    $469,995
    Photo of 1005 Carvell Drive, Winter Park, FL 32792 (MLS # O6263657)
    Photo of 1005 Carvell Drive, Winter Park, FL 32792 (MLS # O6263657)
    1005 Carvell Drive, Winter Park, FL
    1005 Carvell Drive
    Winter Park, FL
    • 3 Beds
    • 2 Baths
    • 1,932 Home (sqft)
    • 2 Baths
    • 9,148 Lot (sqft)
  27. Photo of 184 Sandlewood Trail #2, Winter Park, FL 32789 (MLS # A4631908)
    $365,000
    Photo of 184 Sandlewood Trail #2, Winter Park, FL 32789 (MLS # A4631908)
    Photo of 184 Sandlewood Trail #2, Winter Park, FL 32789 (MLS # A4631908)
    184 Sandlewood Trail #2, Winter Park, FL
    184 Sandlewood Trail #2
    Winter Park, FL
    • 2 Beds
    • 3 Baths
    • 1,133 Home (sqft)
    • 3 Baths
    • 8,277 Lot (sqft)
  28. Photo of 830 Overspin Drive, Winter Park, FL 32789 (MLS # O6263021)
    $390,000
    Photo of 830 Overspin Drive, Winter Park, FL 32789 (MLS # O6263021)
    Photo of 830 Overspin Drive, Winter Park, FL 32789 (MLS # O6263021)
    830 Overspin Drive, Winter Park, FL
    830 Overspin Drive
    Winter Park, FL
    • 2 Beds
    • 1 Bath
    • 1,150 Home (sqft)
    • 1 Bath
    • 6,970 Lot (sqft)
  29. Photo of 425 Alberta Drive, Winter Park, FL 32789 (MLS # O6263168)
    $3,000,000
    Photo of 425 Alberta Drive, Winter Park, FL 32789 (MLS # O6263168)
    Photo of 425 Alberta Drive, Winter Park, FL 32789 (MLS # O6263168)
    425 Alberta Drive, Winter Park, FL
    425 Alberta Drive
    Winter Park, FL
    • 3 Beds
    • 2 Baths
    • 2,310 Home (sqft)
    • 2 Baths
    • 14,375 Lot (sqft)
  30. Photo of 2161 Sharon Road, Winter Park, FL 32789 (MLS # O6263091)
    $4,985,000
    Photo of 2161 Sharon Road, Winter Park, FL 32789 (MLS # O6263091)
    Photo of 2161 Sharon Road, Winter Park, FL 32789 (MLS # O6263091)
    90
     
    2161 Sharon Road, Winter Park, FL
    2161 Sharon Road
    Winter Park, FL
    • 5 Beds
    • 7 Baths
    • 6,338 Home (sqft)
    • 7 Baths
    • 25,265 Lot (sqft)
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The information contained herein has been provided by My Florida Regional MLS DBA Stellar MLS. IDX information is provided exclusively for consumers' personal, non-commercial use, that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, and that the data is deemed reliable but is not guaranteed accurate by the MLS. Listings last updated 12/22/24 12:20 PM PST.

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