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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 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)
  2. Photo of 1202 12th Court NE, Winter Haven, FL 33881 (MLS # P4932544)
    $249,900
    Photo of 1202 12th Court NE, Winter Haven, FL 33881 (MLS # P4932544)
    Photo of 1202 12th Court NE, Winter Haven, FL 33881 (MLS # P4932544)
    1202 12th Court NE, Winter Haven, FL
    1202 12th Court NE
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,334 Home (sqft)
    • 2 Baths
    • 10,455 Lot (sqft)
  3. Photo of 2028 Kings Crossing SW, Winter Haven, FL 33880 (MLS # TB8315524)
    $229,000
    Photo of 2028 Kings Crossing SW, Winter Haven, FL 33880 (MLS # TB8315524)
    Photo of 2028 Kings Crossing SW, Winter Haven, FL 33880 (MLS # TB8315524)
    22
     
    2028 Kings Crossing SW, Winter Haven, FL
    2028 Kings Crossing SW
    Winter Haven, FL
    • 2 Beds
    • 2 Baths
    • 1,131 Home (sqft)
    • 2 Baths
    • 3,921 Lot (sqft)
  4. Photo of 2030 Leisure Drive, Winter Haven, FL 33881 (MLS # G5088674)
    $319,000
    Photo of 2030 Leisure Drive, Winter Haven, FL 33881 (MLS # G5088674)
    Photo of 2030 Leisure Drive, Winter Haven, FL 33881 (MLS # G5088674)
    2030 Leisure Drive, Winter Haven, FL
    2030 Leisure Drive
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 2,023 Home (sqft)
    • 2 Baths
    • 7,406 Lot (sqft)
  5. Photo of 2618 Sage Valley Way, Winter Haven, FL 33884 (MLS # O6252898)
    $379,990
    Photo of 2618 Sage Valley Way, Winter Haven, FL 33884 (MLS # O6252898)
    Photo of 2618 Sage Valley Way, Winter Haven, FL 33884 (MLS # O6252898)
    2618 Sage Valley Way, Winter Haven, FL
    2618 Sage Valley Way
    Winter Haven, FL
    • 5 Beds
    • 3 Baths
    • 2,077 Home (sqft)
    • 3 Baths
    • 6,099 Lot (sqft)
  6. Photo of 2630 Sage Valley Way, Winter Haven, FL 33884 (MLS # O6252863)
    $394,990
    Photo of 2630 Sage Valley Way, Winter Haven, FL 33884 (MLS # O6252863)
    Photo of 2630 Sage Valley Way, Winter Haven, FL 33884 (MLS # O6252863)
    2630 Sage Valley Way, Winter Haven, FL
    2630 Sage Valley Way
    Winter Haven, FL
    • 4 Beds
    • 3 Baths
    • 2,372 Home (sqft)
    • 3 Baths
    • 6,099 Lot (sqft)
  7. Photo of 2530 Sage Valley Way, Winter Haven, FL 33884 (MLS # O6252852)
    $388,990
    Photo of 2530 Sage Valley Way, Winter Haven, FL 33884 (MLS # O6252852)
    Photo of 2530 Sage Valley Way, Winter Haven, FL 33884 (MLS # O6252852)
    2530 Sage Valley Way, Winter Haven, FL
    2530 Sage Valley Way
    Winter Haven, FL
    • 5 Beds
    • 3 Baths
    • 2,077 Home (sqft)
    • 3 Baths
    • 6,099 Lot (sqft)
  8. Photo of 1039 Medinah Drive, Winter Haven, FL 33884 (MLS # P4932532)
    $234,900
    Photo of 1039 Medinah Drive, Winter Haven, FL 33884 (MLS # P4932532)
    Photo of 1039 Medinah Drive, Winter Haven, FL 33884 (MLS # P4932532)
    1039 Medinah Drive, Winter Haven, FL
    1039 Medinah Drive
    Winter Haven, FL
    • 2 Beds
    • 2 Baths
    • 1,278 Home (sqft)
    • 2 Baths
    • 2,178 Lot (sqft)
  9. Photo of 645 Augusta Road, Winter Haven, FL 33884 (MLS # P4932495)
    $349,000
    Photo of 645 Augusta Road, Winter Haven, FL 33884 (MLS # P4932495)
    Photo of 645 Augusta Road, Winter Haven, FL 33884 (MLS # P4932495)
    645 Augusta Road, Winter Haven, FL
    645 Augusta Road
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 2,140 Home (sqft)
    • 2 Baths
    • 6,099 Lot (sqft)
  10. Photo of 3027 Buckeye Pointe Drive, Winter Haven, FL 33881 (MLS # S5114569)
    $380,000
    Photo of 3027 Buckeye Pointe Drive, Winter Haven, FL 33881 (MLS # S5114569)
    Photo of 3027 Buckeye Pointe Drive, Winter Haven, FL 33881 (MLS # S5114569)
    3027 Buckeye Pointe Drive, Winter Haven, FL
    3027 Buckeye Pointe Drive
    Winter Haven, FL
    • 4 Beds
    • 3 Baths
    • 2,132 Home (sqft)
    • 3 Baths
    • 7,406 Lot (sqft)
  11. Photo of 2715 Rutledge Court, Winter Haven, FL 33884 (MLS # P4932453)
    $249,900
    Photo of 2715 Rutledge Court, Winter Haven, FL 33884 (MLS # P4932453)
    Photo of 2715 Rutledge Court, Winter Haven, FL 33884 (MLS # P4932453)
    2715 Rutledge Court, Winter Haven, FL
    2715 Rutledge Court
    Winter Haven, FL
    • 2 Beds
    • 2 Baths
    • 1,419 Home (sqft)
    • 2 Baths
    • 3,050 Lot (sqft)
  12. Photo of 728 Waterbridge Drive, Winter Haven, FL 33880 (MLS # P4932527)
    $280,000
    Photo of 728 Waterbridge Drive, Winter Haven, FL 33880 (MLS # P4932527)
    Photo of 728 Waterbridge Drive, Winter Haven, FL 33880 (MLS # P4932527)
    728 Waterbridge Drive, Winter Haven, FL
    728 Waterbridge Drive
    Winter Haven, FL
    • 3 Beds
    • 3 Baths
    • 1,320 Home (sqft)
    • 3 Baths
    • 5,228 Lot (sqft)
  13. Photo of 2511 Avenue E SW, Winter Haven, FL 33880 (MLS # TB8314758)
    $319,500
    Photo of 2511 Avenue E SW, Winter Haven, FL 33880 (MLS # TB8314758)
    Photo of 2511 Avenue E SW, Winter Haven, FL 33880 (MLS # TB8314758)
    2511 Avenue E SW, Winter Haven, FL
    2511 Avenue E SW
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 2,063 Home (sqft)
    • 2 Baths
    • 6,970 Lot (sqft)
  14. Photo of 525 Terranova Circle, Winter Haven, FL 33884 (MLS # P4932586)
    $299,000
    Photo of 525 Terranova Circle, Winter Haven, FL 33884 (MLS # P4932586)
    Photo of 525 Terranova Circle, Winter Haven, FL 33884 (MLS # P4932586)
    525 Terranova Circle, Winter Haven, FL
    525 Terranova Circle
    Winter Haven, FL
    • 4 Beds
    • 2 Baths
    • 1,538 Home (sqft)
    • 2 Baths
    • 7,841 Lot (sqft)
  15. Photo of 1489 Austin Street, Winter Haven, FL 33884 (MLS # O6249428)
    $330,000
    Photo of 1489 Austin Street, Winter Haven, FL 33884 (MLS # O6249428)
    Photo of 1489 Austin Street, Winter Haven, FL 33884 (MLS # O6249428)
    1489 Austin Street, Winter Haven, FL
    1489 Austin Street
    Winter Haven, FL
    • 4 Beds
    • 2 Baths
    • 1,935 Home (sqft)
    • 2 Baths
    • 7,841 Lot (sqft)
  16. Photo of 1710 Garden Lake Drive #1710, Winter Haven, FL 33884 (MLS # L4948430)
    $215,000
    Photo of 1710 Garden Lake Drive #1710, Winter Haven, FL 33884 (MLS # L4948430)
    Photo of 1710 Garden Lake Drive #1710, Winter Haven, FL 33884 (MLS # L4948430)
    1710 Garden Lake Drive #1710, Winter Haven, FL
    1710 Garden Lake Drive #1710
    Winter Haven, FL
    • 2 Beds
    • 2 Baths
    • 1,103 Home (sqft)
    • 2 Baths
    • 436 Lot (sqft)
  17. Photo of 1236 6th Street NE, Winter Haven, FL 33881 (MLS # TB8314976)
    $229,777
    Photo of 1236 6th Street NE, Winter Haven, FL 33881 (MLS # TB8314976)
    Photo of 1236 6th Street NE, Winter Haven, FL 33881 (MLS # TB8314976)
    1236 6th Street NE, Winter Haven, FL
    1236 6th Street NE
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,035 Home (sqft)
    • 2 Baths
    • 6,970 Lot (sqft)
  18. Photo of 579 Saint Andrews Road, Winter Haven, FL 33884 (MLS # P4932519)
    $310,000
    Photo of 579 Saint Andrews Road, Winter Haven, FL 33884 (MLS # P4932519)
    Photo of 579 Saint Andrews Road, Winter Haven, FL 33884 (MLS # P4932519)
    579 Saint Andrews Road, Winter Haven, FL
    579 Saint Andrews Road
    Winter Haven, FL
    • 2 Beds
    • 2 Baths
    • 1,746 Home (sqft)
    • 2 Baths
    • 6,099 Lot (sqft)
  19. Photo of 3715 1/2 Avenue J NW, Winter Haven, FL 33881 (MLS # S5114379)
    $215,000
    Photo of 3715 1/2 Avenue J NW, Winter Haven, FL 33881 (MLS # S5114379)
    Photo of 3715 1/2 Avenue J NW, Winter Haven, FL 33881 (MLS # S5114379)
    3715 1/2 Avenue J NW, Winter Haven, FL
    3715 1/2 Avenue J NW
    Winter Haven, FL
    • 3 Beds
    • 1 Bath
    • 892 Home (sqft)
    • 1 Bath
    • 6,534 Lot (sqft)
  20. Photo of 899 5th Street, Winter Haven, FL 33881 (MLS # O6252198)
    $274,999
    Photo of 899 5th Street, Winter Haven, FL 33881 (MLS # O6252198)
    Photo of 899 5th Street, Winter Haven, FL 33881 (MLS # O6252198)
    899 5th Street, Winter Haven, FL
    899 5th Street
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,710 Home (sqft)
    • 2 Baths
    • 7,841 Lot (sqft)
  21. Photo of 174 Andreas Street, Winter Haven, FL 33881 (MLS # S5114494)
    $325,000
    Photo of 174 Andreas Street, Winter Haven, FL 33881 (MLS # S5114494)
    Photo of 174 Andreas Street, Winter Haven, FL 33881 (MLS # S5114494)
    174 Andreas Street, Winter Haven, FL
    174 Andreas Street
    Winter Haven, FL
    • 4 Beds
    • 3 Baths
    • 1,959 Home (sqft)
    • 3 Baths
    • 5,663 Lot (sqft)
  22. Photo of 466 Muirfield Court, Winter Haven, FL 33884 (MLS # P4932458)
    $258,500
    Photo of 466 Muirfield Court, Winter Haven, FL 33884 (MLS # P4932458)
    Photo of 466 Muirfield Court, Winter Haven, FL 33884 (MLS # P4932458)
    466 Muirfield Court, Winter Haven, FL
    466 Muirfield Court
    Winter Haven, FL
    • 2 Beds
    • 2 Baths
    • 1,232 Home (sqft)
    • 2 Baths
    • 6,534 Lot (sqft)
  23. Photo of 210 Lake Thomas Drive, Winter Haven, FL 33880 (MLS # P4932497)
    $368,900
    Photo of 210 Lake Thomas Drive, Winter Haven, FL 33880 (MLS # P4932497)
    Photo of 210 Lake Thomas Drive, Winter Haven, FL 33880 (MLS # P4932497)
    210 Lake Thomas Drive, Winter Haven, FL
    210 Lake Thomas Drive
    Winter Haven, FL
    • 4 Beds
    • 3 Baths
    • 1,456 Home (sqft)
    • 3 Baths
    • 12,197 Lot (sqft)
  24. Photo of 1674 Teagan Lane, Winter Haven, FL 33884 (MLS # TB8314574)
    $299,999
    Photo of 1674 Teagan Lane, Winter Haven, FL 33884 (MLS # TB8314574)
    Photo of 1674 Teagan Lane, Winter Haven, FL 33884 (MLS # TB8314574)
    1674 Teagan Lane, Winter Haven, FL
    1674 Teagan Lane
    Winter Haven, FL
    • 4 Beds
    • 3 Baths
    • 1,879 Home (sqft)
    • 3 Baths
    • 6,534 Lot (sqft)
  25. Photo of 111 Leslie Avenue, Winter Haven, FL 33880 (MLS # L4948371)
    $244,900
    Photo of 111 Leslie Avenue, Winter Haven, FL 33880 (MLS # L4948371)
    Photo of 111 Leslie Avenue, Winter Haven, FL 33880 (MLS # L4948371)
    111 Leslie Avenue, Winter Haven, FL
    111 Leslie Avenue
    Winter Haven, FL
    • 4 Beds
    • 2 Baths
    • 2,262 Home (sqft)
    • 2 Baths
    • 16,989 Lot (sqft)
  26. Photo of 3511 Avenue R NW, Winter Haven, FL 33881 (MLS # P4932504)
    $249,900
    Photo of 3511 Avenue R NW, Winter Haven, FL 33881 (MLS # P4932504)
    Photo of 3511 Avenue R NW, Winter Haven, FL 33881 (MLS # P4932504)
    3511 Avenue R NW, Winter Haven, FL
    3511 Avenue R NW
    Winter Haven, FL
    • 5 Beds
    • 2 Baths
    • 1,740 Home (sqft)
    • 2 Baths
    • 7,406 Lot (sqft)
  27. Photo of 1623 3rd Street NW, Winter Haven, FL 33881 (MLS # O6252155)
    $230,000
    Photo of 1623 3rd Street NW, Winter Haven, FL 33881 (MLS # O6252155)
    Photo of 1623 3rd Street NW, Winter Haven, FL 33881 (MLS # O6252155)
    1623 3rd Street NW, Winter Haven, FL
    1623 3rd Street NW
    Winter Haven, FL
    • 4 Beds
    • 2 Baths
    • 1,195 Home (sqft)
    • 2 Baths
    • 9,148 Lot (sqft)
  28. Photo of 200 El Camino Drive #202, Winter Haven, FL 33884 (MLS # O6251764)
    $129,000
    Photo of 200 El Camino Drive #202, Winter Haven, FL 33884 (MLS # O6251764)
    Photo of 200 El Camino Drive #202, Winter Haven, FL 33884 (MLS # O6251764)
    200 El Camino Drive #202, Winter Haven, FL
    200 El Camino Drive #202
    Winter Haven, FL
    • 2 Beds
    • 2 Baths
    • 1,378 Home (sqft)
    • 2 Baths
    • 436 Lot (sqft)
  29. Photo of 2013 San Marcos Drive SE #21, Winter Haven, FL 33880 (MLS # O6251293)
    $115,000
    Photo of 2013 San Marcos Drive SE #21, Winter Haven, FL 33880 (MLS # O6251293)
    Photo of 2013 San Marcos Drive SE #21, Winter Haven, FL 33880 (MLS # O6251293)
    2013 San Marcos Drive SE #21, Winter Haven, FL
    2013 San Marcos Drive SE #21
    Winter Haven, FL
    • 1 Bed
    • 1 Bath
    • 792 Home (sqft)
    • 1 Bath
    • 436 Lot (sqft)
  30. Photo of 555 Avenue O SE, Winter Haven, FL 33880 (MLS # P4932467)
    $274,900
    Photo of 555 Avenue O SE, Winter Haven, FL 33880 (MLS # P4932467)
    Photo of 555 Avenue O SE, Winter Haven, FL 33880 (MLS # P4932467)
    555 Avenue O SE, Winter Haven, FL
    555 Avenue O SE
    Winter Haven, FL
    • 4 Beds
    • 2 Baths
    • 1,554 Home (sqft)
    • 2 Baths
    • 10,455 Lot (sqft)
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