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Winter Haven is located in Central Florida and known for its canal-linked Chain of Lakes. Several lakes have waterside parks and eateries, as well as boat ramps and water-sports rentals. On Lake Eloise, Legoland Florida Resort includes Cypress Gardens, a 1930s botanical garden, and Lego-brick attractions, rides and a water park. West of the city, Circle B Bar Reserve has forest trails and alligator-inhabited wetlands. Use our custom search tool to view all homes for sale under $400k in Winter Haven or click here to return to the list of surrounding towns and cities in the Kissimmee area. Have questions? Contact us here or schedule your FREE consultation here.


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  1. Photo of 307 La Serena, Winter Haven, FL 33884 (MLS # L4948538)
    $250,000
    Photo of 307 La Serena, Winter Haven, FL 33884 (MLS # L4948538)
    Photo of 307 La Serena, Winter Haven, FL 33884 (MLS # L4948538)
    307 La Serena, Winter Haven, FL
    307 La Serena
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,389 Home (sqft)
    • 2 Baths
    • 6,534 Lot (sqft)
  2. Photo of 2910 Plantation Road, Winter Haven, FL 33884 (MLS # P4932602)
    $369,900
    Photo of 2910 Plantation Road, Winter Haven, FL 33884 (MLS # P4932602)
    Photo of 2910 Plantation Road, Winter Haven, FL 33884 (MLS # P4932602)
    2910 Plantation Road, Winter Haven, FL
    2910 Plantation Road
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 2,064 Home (sqft)
    • 2 Baths
    • 14,375 Lot (sqft)
  3. Photo of 1908 Emily Boulevard, Winter Haven, FL 33884 (MLS # P4932600)
    $280,000
    Photo of 1908 Emily Boulevard, Winter Haven, FL 33884 (MLS # P4932600)
    Photo of 1908 Emily Boulevard, Winter Haven, FL 33884 (MLS # P4932600)
    1908 Emily Boulevard, Winter Haven, FL
    1908 Emily Boulevard
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,636 Home (sqft)
    • 2 Baths
    • 6,534 Lot (sqft)
  4. Photo of 1274 Zambrana Court, Winter Haven, FL 33884 (MLS # P4932560)
    $320,000
    Photo of 1274 Zambrana Court, Winter Haven, FL 33884 (MLS # P4932560)
    Photo of 1274 Zambrana Court, Winter Haven, FL 33884 (MLS # P4932560)
    1274 Zambrana Court, Winter Haven, FL
    1274 Zambrana Court
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,961 Home (sqft)
    • 2 Baths
    • 5,663 Lot (sqft)
  5. Photo of 3124 Sunset Hills Rd, Winter Haven, FL 33881 (MLS # S5114738)
    $319,990
    Photo of 3124 Sunset Hills Rd, Winter Haven, FL 33881 (MLS # S5114738)
    Photo of 3124 Sunset Hills Rd, Winter Haven, FL 33881 (MLS # S5114738)
    3124 Sunset Hills Rd, Winter Haven, FL
    3124 Sunset Hills Rd
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,426 Home (sqft)
    • 2 Baths
    • 7,841 Lot (sqft)
  6. Photo of 3128 Sunset Hills Rd, Winter Haven, FL 33881 (MLS # S5114728)
    $337,990
    Photo of 3128 Sunset Hills Rd, Winter Haven, FL 33881 (MLS # S5114728)
    Photo of 3128 Sunset Hills Rd, Winter Haven, FL 33881 (MLS # S5114728)
    3128 Sunset Hills Rd, Winter Haven, FL
    3128 Sunset Hills Rd
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,761 Home (sqft)
    • 2 Baths
    • 6,099 Lot (sqft)
  7. Photo of 618 Ridge Terrace, Winter Haven, FL 33881 (MLS # L4948543)
    $156,000
    Photo of 618 Ridge Terrace, Winter Haven, FL 33881 (MLS # L4948543)
    Photo of 618 Ridge Terrace, Winter Haven, FL 33881 (MLS # L4948543)
    29
     
    618 Ridge Terrace, Winter Haven, FL
    618 Ridge Terrace
    Winter Haven, FL
    • 2 Beds
    • 2 Baths
    • 1,073 Home (sqft)
    • 2 Baths
    • 1,307 Lot (sqft)
  8. Photo of 3316 Fox Ridge Drive, Winter Haven, FL 33884 (MLS # O6252221)
    $224,900
    Photo of 3316 Fox Ridge Drive, Winter Haven, FL 33884 (MLS # O6252221)
    Photo of 3316 Fox Ridge Drive, Winter Haven, FL 33884 (MLS # O6252221)
    15
     
    3316 Fox Ridge Drive, Winter Haven, FL
    3316 Fox Ridge Drive
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,418 Home (sqft)
    • 2 Baths
    • 6,099 Lot (sqft)
  9. Photo of 976 Cambridge Drive, Winter Haven, FL 33881 (MLS # O6253986)
    $335,000
    Photo of 976 Cambridge Drive, Winter Haven, FL 33881 (MLS # O6253986)
    Photo of 976 Cambridge Drive, Winter Haven, FL 33881 (MLS # O6253986)
    976 Cambridge Drive, Winter Haven, FL
    976 Cambridge Drive
    Winter Haven, FL
    • 4 Beds
    • 2 Baths
    • 1,840 Home (sqft)
    • 2 Baths
    • 6,534 Lot (sqft)
  10. Photo of 4320 Thomas Wood Lane E, Winter Haven, FL 33880 (MLS # TB8316666)
    $385,000
    Photo of 4320 Thomas Wood Lane E, Winter Haven, FL 33880 (MLS # TB8316666)
    Photo of 4320 Thomas Wood Lane E, Winter Haven, FL 33880 (MLS # TB8316666)
    4320 Thomas Wood Lane E, Winter Haven, FL
    4320 Thomas Wood Lane E
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 2,035 Home (sqft)
    • 2 Baths
    • 13,068 Lot (sqft)
  11. Photo of 3612 Julius Estates Boulevard, Winter Haven, FL 33881 (MLS # O6253490)
    $365,000
    Photo of 3612 Julius Estates Boulevard, Winter Haven, FL 33881 (MLS # O6253490)
    Photo of 3612 Julius Estates Boulevard, Winter Haven, FL 33881 (MLS # O6253490)
    3612 Julius Estates Boulevard, Winter Haven, FL
    3612 Julius Estates Boulevard
    Winter Haven, FL
    • 4 Beds
    • 3 Baths
    • 2,759 Home (sqft)
    • 3 Baths
    • 4,792 Lot (sqft)
  12. Photo of 2006 Garden Lake Drive #2006, Winter Haven, FL 33884 (MLS # P4932549)
    $185,000
    Photo of 2006 Garden Lake Drive #2006, Winter Haven, FL 33884 (MLS # P4932549)
    Photo of 2006 Garden Lake Drive #2006, Winter Haven, FL 33884 (MLS # P4932549)
    2006 Garden Lake Drive #2006, Winter Haven, FL
    2006 Garden Lake Drive #2006
    Winter Haven, FL
    • 2 Beds
    • 2 Baths
    • 1,103 Home (sqft)
    • 2 Baths
    • 436 Lot (sqft)
  13. Photo of 4656 Ostero Street, Winter Haven, FL 33884 (MLS # O6253881)
    $330,990
    Photo of 4656 Ostero Street, Winter Haven, FL 33884 (MLS # O6253881)
    Photo of 4656 Ostero Street, Winter Haven, FL 33884 (MLS # O6253881)
    4656 Ostero Street, Winter Haven, FL
    4656 Ostero Street
    Winter Haven, FL
    • 5 Beds
    • 3 Baths
    • 2,447 Home (sqft)
    • 3 Baths
    • 4,356 Lot (sqft)
  14. Photo of 720 Avenue E SE, Winter Haven, FL 33880 (MLS # L4948536)
    $299,999
    Photo of 720 Avenue E SE, Winter Haven, FL 33880 (MLS # L4948536)
    Photo of 720 Avenue E SE, Winter Haven, FL 33880 (MLS # L4948536)
    720 Avenue E SE, Winter Haven, FL
    720 Avenue E SE
    Winter Haven, FL
    • 5 Beds
    • 2 Baths
    • 2,569 Home (sqft)
    • 2 Baths
    • 15,246 Lot (sqft)
  15. Photo of 4675 Ostero Street, Winter Haven, FL 33884 (MLS # O6253810)
    $332,990
    Photo of 4675 Ostero Street, Winter Haven, FL 33884 (MLS # O6253810)
    Photo of 4675 Ostero Street, Winter Haven, FL 33884 (MLS # O6253810)
    26
     
    4675 Ostero Street, Winter Haven, FL
    4675 Ostero Street
    Winter Haven, FL
    • 5 Beds
    • 3 Baths
    • 2,447 Home (sqft)
    • 3 Baths
    • 4,356 Lot (sqft)
  16. Photo of 123 Morning Glory Circle, Winter Haven, FL 33884 (MLS # P4932572)
    $329,900
    Photo of 123 Morning Glory Circle, Winter Haven, FL 33884 (MLS # P4932572)
    Photo of 123 Morning Glory Circle, Winter Haven, FL 33884 (MLS # P4932572)
    123 Morning Glory Circle, Winter Haven, FL
    123 Morning Glory Circle
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,851 Home (sqft)
    • 2 Baths
    • 7,406 Lot (sqft)
  17. Photo of 241 Hibiscus Street, Winter Haven, FL 33881 (MLS # S5115039)
    $320,000
    Photo of 241 Hibiscus Street, Winter Haven, FL 33881 (MLS # S5115039)
    Photo of 241 Hibiscus Street, Winter Haven, FL 33881 (MLS # S5115039)
    241 Hibiscus Street, Winter Haven, FL
    241 Hibiscus Street
    Winter Haven, FL
    • 4 Beds
    • 2 Baths
    • 1,743 Home (sqft)
    • 2 Baths
    • 5,663 Lot (sqft)
  18. Photo of 104 Brad Circle, Winter Haven, FL 33880 (MLS # TB8316132)
    $270,000
    Photo of 104 Brad Circle, Winter Haven, FL 33880 (MLS # TB8316132)
    Photo of 104 Brad Circle, Winter Haven, FL 33880 (MLS # TB8316132)
    104 Brad Circle, Winter Haven, FL
    104 Brad Circle
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,370 Home (sqft)
    • 2 Baths
    • 7,841 Lot (sqft)
  19. Photo of 81 Surf Drive, Winter Haven, FL 33880 (MLS # P4932535)
    $230,000
    Photo of 81 Surf Drive, Winter Haven, FL 33880 (MLS # P4932535)
    Photo of 81 Surf Drive, Winter Haven, FL 33880 (MLS # P4932535)
    21
     
    81 Surf Drive, Winter Haven, FL
    81 Surf Drive
    Winter Haven, FL
    • 4 Beds
    • 2 Baths
    • 1,373 Home (sqft)
    • 2 Baths
    • 6,534 Lot (sqft)
  20. Photo of 129 Homewood Drive, Winter Haven, FL 33880 (MLS # L4948509)
    $265,000
    Photo of 129 Homewood Drive, Winter Haven, FL 33880 (MLS # L4948509)
    Photo of 129 Homewood Drive, Winter Haven, FL 33880 (MLS # L4948509)
    129 Homewood Drive, Winter Haven, FL
    129 Homewood Drive
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,462 Home (sqft)
    • 2 Baths
    • 20,909 Lot (sqft)
  21. Photo of 222 Okaloosa Drive, Winter Haven, FL 33884 (MLS # P4932554)
    $289,900
    Photo of 222 Okaloosa Drive, Winter Haven, FL 33884 (MLS # P4932554)
    Photo of 222 Okaloosa Drive, Winter Haven, FL 33884 (MLS # P4932554)
    222 Okaloosa Drive, Winter Haven, FL
    222 Okaloosa Drive
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,835 Home (sqft)
    • 2 Baths
    • 9,148 Lot (sqft)
  22. Photo of 524 Coleman Drive W, Winter Haven, FL 33884 (MLS # P4932556)
    $389,900
    Photo of 524 Coleman Drive W, Winter Haven, FL 33884 (MLS # P4932556)
    Photo of 524 Coleman Drive W, Winter Haven, FL 33884 (MLS # P4932556)
    22
     
    524 Coleman Drive W, Winter Haven, FL
    524 Coleman Drive W
    Winter Haven, FL
    • 4 Beds
    • 3 Baths
    • 2,340 Home (sqft)
    • 3 Baths
    • 15,246 Lot (sqft)
  23. Photo of 2256 Firestone Place, Winter Haven, FL 33884 (MLS # L4948491)
    $245,000
    Photo of 2256 Firestone Place, Winter Haven, FL 33884 (MLS # L4948491)
    Photo of 2256 Firestone Place, Winter Haven, FL 33884 (MLS # L4948491)
    2256 Firestone Place, Winter Haven, FL
    2256 Firestone Place
    Winter Haven, FL
    • 2 Beds
    • 2 Baths
    • 1,422 Home (sqft)
    • 2 Baths
    • 2,178 Lot (sqft)
  24. Photo of 2304 Rose Boulevard, Winter Haven, FL 33881 (MLS # P4932557)
    $299,900
    Photo of 2304 Rose Boulevard, Winter Haven, FL 33881 (MLS # P4932557)
    Photo of 2304 Rose Boulevard, Winter Haven, FL 33881 (MLS # P4932557)
    2304 Rose Boulevard, Winter Haven, FL
    2304 Rose Boulevard
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,725 Home (sqft)
    • 2 Baths
    • 5,663 Lot (sqft)
  25. Photo of 4687 Ostero Street, Winter Haven, FL 33884 (MLS # O6253194)
    $354,990
    Photo of 4687 Ostero Street, Winter Haven, FL 33884 (MLS # O6253194)
    Photo of 4687 Ostero Street, Winter Haven, FL 33884 (MLS # O6253194)
    4687 Ostero Street, Winter Haven, FL
    4687 Ostero Street
    Winter Haven, FL
    • 4 Beds
    • 3 Baths
    • 2,371 Home (sqft)
    • 3 Baths
    • 6,970 Lot (sqft)
  26. Photo of 218 King Rd, Winter Haven, FL 33880 (MLS # L4948464)
    $294,000
    Photo of 218 King Rd, Winter Haven, FL 33880 (MLS # L4948464)
    Photo of 218 King Rd, Winter Haven, FL 33880 (MLS # L4948464)
    218 King Rd, Winter Haven, FL
    218 King Rd
    Winter Haven, FL
    • 3 Beds
    • 1 Bath
    • 1,236 Home (sqft)
    • 1 Bath
    • 30,057 Lot (sqft)
  27. Photo of 1706 Garden Lake Drive #1706, Winter Haven, FL 33884 (MLS # P4932477)
    $164,900
    Photo of 1706 Garden Lake Drive #1706, Winter Haven, FL 33884 (MLS # P4932477)
    Photo of 1706 Garden Lake Drive #1706, Winter Haven, FL 33884 (MLS # P4932477)
    1706 Garden Lake Drive #1706, Winter Haven, FL
    1706 Garden Lake Drive #1706
    Winter Haven, FL
    • 1 Bed
    • 1 Bath
    • 828 Home (sqft)
    • 1 Bath
    • 436 Lot (sqft)
  28. Photo of 718 Eagle Landing Boulevard, Winter Haven, FL 33880 (MLS # O6254493)
    $339,000
    Photo of 718 Eagle Landing Boulevard, Winter Haven, FL 33880 (MLS # O6254493)
    Photo of 718 Eagle Landing Boulevard, Winter Haven, FL 33880 (MLS # O6254493)
    718 Eagle Landing Boulevard, Winter Haven, FL
    718 Eagle Landing Boulevard
    Winter Haven, FL
    • 4 Beds
    • 3 Baths
    • 1,900 Home (sqft)
    • 3 Baths
    • 6,099 Lot (sqft)
  29. Photo of 3116 Sunset Hills Road, Winter Haven, FL 33881 (MLS # O6253860)
    $329,990
    Photo of 3116 Sunset Hills Road, Winter Haven, FL 33881 (MLS # O6253860)
    Photo of 3116 Sunset Hills Road, Winter Haven, FL 33881 (MLS # O6253860)
    21
     
    3116 Sunset Hills Road, Winter Haven, FL
    3116 Sunset Hills Road
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,536 Home (sqft)
    • 2 Baths
    • 5,663 Lot (sqft)
  30. Photo of 3119 Sunset Hiils Road, Winter Haven, FL 33881 (MLS # O6253850)
    $329,990
    Photo of 3119 Sunset Hiils Road, Winter Haven, FL 33881 (MLS # O6253850)
    Photo of 3119 Sunset Hiils Road, Winter Haven, FL 33881 (MLS # O6253850)
    21
     
    3119 Sunset Hiils Road, Winter Haven, FL
    3119 Sunset Hiils Road
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,589 Home (sqft)
    • 2 Baths
    • 6,099 Lot (sqft)
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