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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 between $400k - $600k 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 1605 Hummingbird Road, Winter Haven, FL 33884 (MLS # TB8332239)
    $470,490
    Photo of 1605 Hummingbird Road, Winter Haven, FL 33884 (MLS # TB8332239)
    Photo of 1605 Hummingbird Road, Winter Haven, FL 33884 (MLS # TB8332239)
    1605 Hummingbird Road, Winter Haven, FL
    1605 Hummingbird Road
    Winter Haven, FL
    • 5 Beds
    • 3 Baths
    • 2,457 Home (sqft)
    • 3 Baths
    • 13,940 Lot (sqft)
  2. Photo of 1102 Berkley Lane, Winter Haven, FL 33880 (MLS # L4949431)
    $414,990
    Photo of 1102 Berkley Lane, Winter Haven, FL 33880 (MLS # L4949431)
    Photo of 1102 Berkley Lane, Winter Haven, FL 33880 (MLS # L4949431)
    1102 Berkley Lane, Winter Haven, FL
    1102 Berkley Lane
    Winter Haven, FL
    • 3 Beds
    • 3 Baths
    • 2,170 Home (sqft)
    • 3 Baths
    • 25,701 Lot (sqft)
  3. Photo of 5340 Nicklaus Drive, Winter Haven, FL 33884 (MLS # P4932995)
    $429,900
    Photo of 5340 Nicklaus Drive, Winter Haven, FL 33884 (MLS # P4932995)
    Photo of 5340 Nicklaus Drive, Winter Haven, FL 33884 (MLS # P4932995)
    5340 Nicklaus Drive, Winter Haven, FL
    5340 Nicklaus Drive
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 2,010 Home (sqft)
    • 2 Baths
    • 6,970 Lot (sqft)
  4. Photo of 2977 Dayton Drive, Winter Haven, FL 33884 (MLS # L4949360)
    $424,900
    Photo of 2977 Dayton Drive, Winter Haven, FL 33884 (MLS # L4949360)
    Photo of 2977 Dayton Drive, Winter Haven, FL 33884 (MLS # L4949360)
    2977 Dayton Drive, Winter Haven, FL
    2977 Dayton Drive
    Winter Haven, FL
    • 4 Beds
    • 3 Baths
    • 2,302 Home (sqft)
    • 3 Baths
    • 7,406 Lot (sqft)
  5. Photo of 231 Terranova Boulevard, Winter Haven, FL 33884 (MLS # P4933043)
    $484,900
    Photo of 231 Terranova Boulevard, Winter Haven, FL 33884 (MLS # P4933043)
    Photo of 231 Terranova Boulevard, Winter Haven, FL 33884 (MLS # P4933043)
    231 Terranova Boulevard, Winter Haven, FL
    231 Terranova Boulevard
    Winter Haven, FL
    • 4 Beds
    • 3 Baths
    • 2,479 Home (sqft)
    • 3 Baths
    • 11,762 Lot (sqft)
  6. Photo of 1872 Eloise Cove Drive, Winter Haven, FL 33884 (MLS # TB8329106)
    $529,000
    Photo of 1872 Eloise Cove Drive, Winter Haven, FL 33884 (MLS # TB8329106)
    Photo of 1872 Eloise Cove Drive, Winter Haven, FL 33884 (MLS # TB8329106)
    1872 Eloise Cove Drive, Winter Haven, FL
    1872 Eloise Cove Drive
    Winter Haven, FL
    • 4 Beds
    • 4 Baths
    • 3,716 Home (sqft)
    • 4 Baths
    • 11,326 Lot (sqft)
  7. Photo of 4338 Thomas Wood Lne Ln, Winter Haven, FL 33880 (MLS # TB8327668)
    $500,000
    Photo of 4338 Thomas Wood Lne Ln, Winter Haven, FL 33880 (MLS # TB8327668)
    Photo of 4338 Thomas Wood Lne Ln, Winter Haven, FL 33880 (MLS # TB8327668)
    4338 Thomas Wood Lne Ln, Winter Haven, FL
    4338 Thomas Wood Lne Ln
    Winter Haven, FL
    • 4 Beds
    • 3 Baths
    • 2,733 Home (sqft)
    • 3 Baths
    • 16,118 Lot (sqft)
  8. Photo of 7335 Bent Grass Drive, Winter Haven, FL 33884 (MLS # P4933023)
    $419,900
    Photo of 7335 Bent Grass Drive, Winter Haven, FL 33884 (MLS # P4933023)
    Photo of 7335 Bent Grass Drive, Winter Haven, FL 33884 (MLS # P4933023)
    7335 Bent Grass Drive, Winter Haven, FL
    7335 Bent Grass Drive
    Winter Haven, FL
    • 4 Beds
    • 3 Baths
    • 2,525 Home (sqft)
    • 3 Baths
    • 12,197 Lot (sqft)
  9. Photo of 5790 Crystal Beach Road, Winter Haven, FL 33880 (MLS # O6262743)
    $439,000
    Photo of 5790 Crystal Beach Road, Winter Haven, FL 33880 (MLS # O6262743)
    Photo of 5790 Crystal Beach Road, Winter Haven, FL 33880 (MLS # O6262743)
    5790 Crystal Beach Road, Winter Haven, FL
    5790 Crystal Beach Road
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,534 Home (sqft)
    • 2 Baths
    • 26,572 Lot (sqft)
  10. Photo of 128 Lake Sears Dr, Winter Haven, FL 33880 (MLS # L4949269)
    $400,000
    Photo of 128 Lake Sears Dr, Winter Haven, FL 33880 (MLS # L4949269)
    Photo of 128 Lake Sears Dr, Winter Haven, FL 33880 (MLS # L4949269)
    38
     
    128 Lake Sears Dr, Winter Haven, FL
    128 Lake Sears Dr
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,629 Home (sqft)
    • 2 Baths
    • 26,136 Lot (sqft)
  11. Photo of 2069 Canton Park Drive, Winter Haven, FL 33881 (MLS # O6264043)
    $475,000
    Photo of 2069 Canton Park Drive, Winter Haven, FL 33881 (MLS # O6264043)
    Photo of 2069 Canton Park Drive, Winter Haven, FL 33881 (MLS # O6264043)
    2069 Canton Park Drive, Winter Haven, FL
    2069 Canton Park Drive
    Winter Haven, FL
    • 4 Beds
    • 2 Baths
    • 2,110 Home (sqft)
    • 2 Baths
    • 6,099 Lot (sqft)
  12. Photo of 5808 Driftwood Drive, Winter Haven, FL 33884 (MLS # P4932914)
    $425,000
    Photo of 5808 Driftwood Drive, Winter Haven, FL 33884 (MLS # P4932914)
    Photo of 5808 Driftwood Drive, Winter Haven, FL 33884 (MLS # P4932914)
    5808 Driftwood Drive, Winter Haven, FL
    5808 Driftwood Drive
    Winter Haven, FL
    • 4 Beds
    • 2 Baths
    • 2,046 Home (sqft)
    • 2 Baths
    • 9,584 Lot (sqft)
  13. Photo of 817 Carlton Court, Winter Haven, FL 33884 (MLS # P4932913)
    $449,900
    Photo of 817 Carlton Court, Winter Haven, FL 33884 (MLS # P4932913)
    Photo of 817 Carlton Court, Winter Haven, FL 33884 (MLS # P4932913)
    46
     
    817 Carlton Court, Winter Haven, FL
    817 Carlton Court
    Winter Haven, FL
    • 4 Beds
    • 3 Baths
    • 2,604 Home (sqft)
    • 3 Baths
    • 13,940 Lot (sqft)
  14. Photo of 206 Clovis Pass, Winter Haven, FL 33880 (MLS # L4947668)
    $579,500
    Photo of 206 Clovis Pass, Winter Haven, FL 33880 (MLS # L4947668)
    Photo of 206 Clovis Pass, Winter Haven, FL 33880 (MLS # L4947668)
    206 Clovis Pass, Winter Haven, FL
    206 Clovis Pass
    Winter Haven, FL
    • 4 Beds
    • 3 Baths
    • 2,728 Home (sqft)
    • 3 Baths
    • 10,890 Lot (sqft)
  15. Photo of 4027 Island Lakes Drive, Winter Haven, FL 33881 (MLS # P4932905)
    $499,900
    Photo of 4027 Island Lakes Drive, Winter Haven, FL 33881 (MLS # P4932905)
    Photo of 4027 Island Lakes Drive, Winter Haven, FL 33881 (MLS # P4932905)
    4027 Island Lakes Drive, Winter Haven, FL
    4027 Island Lakes Drive
    Winter Haven, FL
    • 4 Beds
    • 2 Baths
    • 1,855 Home (sqft)
    • 2 Baths
    • 17,424 Lot (sqft)
  16. Photo of 4570 Chambliss Road, Winter Haven, FL 33884 (MLS # P4932888)
    $498,500
    Photo of 4570 Chambliss Road, Winter Haven, FL 33884 (MLS # P4932888)
    Photo of 4570 Chambliss Road, Winter Haven, FL 33884 (MLS # P4932888)
    4570 Chambliss Road, Winter Haven, FL
    4570 Chambliss Road
    Winter Haven, FL
    • 3 Beds
    • 3 Baths
    • 1,685 Home (sqft)
    • 3 Baths
    • 1.26 Lot (ac)
  17. Photo of 357 Ruby Lake Loop, Winter Haven, FL 33884 (MLS # P4932850)
    $433,900
    Photo of 357 Ruby Lake Loop, Winter Haven, FL 33884 (MLS # P4932850)
    Photo of 357 Ruby Lake Loop, Winter Haven, FL 33884 (MLS # P4932850)
    357 Ruby Lake Loop, Winter Haven, FL
    357 Ruby Lake Loop
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 2,107 Home (sqft)
    • 2 Baths
    • 10,019 Lot (sqft)
  18. Photo of 364 Fish Hawk Drive, Winter Haven, FL 33884 (MLS # P4932705)
    $507,000
    Photo of 364 Fish Hawk Drive, Winter Haven, FL 33884 (MLS # P4932705)
    Photo of 364 Fish Hawk Drive, Winter Haven, FL 33884 (MLS # P4932705)
    53
     
    364 Fish Hawk Drive, Winter Haven, FL
    364 Fish Hawk Drive
    Winter Haven, FL
    • 6 Beds
    • 5 Baths
    • 3,920 Home (sqft)
    • 5 Baths
    • 8,712 Lot (sqft)
  19. Photo of 4281 Stafford Drive, Winter Haven, FL 33880 (MLS # S5115805)
    $465,000
    Photo of 4281 Stafford Drive, Winter Haven, FL 33880 (MLS # S5115805)
    Photo of 4281 Stafford Drive, Winter Haven, FL 33880 (MLS # S5115805)
    4281 Stafford Drive, Winter Haven, FL
    4281 Stafford Drive
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,816 Home (sqft)
    • 2 Baths
    • 16,989 Lot (sqft)
  20. Photo of 1280 Denali Drive, Winter Haven, FL 33881 (MLS # L4948912)
    $450,000
    Photo of 1280 Denali Drive, Winter Haven, FL 33881 (MLS # L4948912)
    Photo of 1280 Denali Drive, Winter Haven, FL 33881 (MLS # L4948912)
    1280 Denali Drive, Winter Haven, FL
    1280 Denali Drive
    Winter Haven, FL
    • 3 Beds
    • 3 Baths
    • 2,566 Home (sqft)
    • 3 Baths
    • 7,406 Lot (sqft)
  21. Photo of 10 Pilot Place, Winter Haven, FL 33881 (MLS # O6259578)
    $439,000
    Photo of 10 Pilot Place, Winter Haven, FL 33881 (MLS # O6259578)
    Photo of 10 Pilot Place, Winter Haven, FL 33881 (MLS # O6259578)
    10 Pilot Place, Winter Haven, FL
    10 Pilot Place
    Winter Haven, FL
    • 3 Beds
    • 4 Baths
    • 2,798 Home (sqft)
    • 4 Baths
    • 13,068 Lot (sqft)
  22. Photo of 2106 Jonathan Lane, Winter Haven, FL 33884 (MLS # TB8323759)
    $430,000
    Photo of 2106 Jonathan Lane, Winter Haven, FL 33884 (MLS # TB8323759)
    Photo of 2106 Jonathan Lane, Winter Haven, FL 33884 (MLS # TB8323759)
    2106 Jonathan Lane, Winter Haven, FL
    2106 Jonathan Lane
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,801 Home (sqft)
    • 2 Baths
    • 11,762 Lot (sqft)
  23. Photo of 292 Lake Lucerne Way, Winter Haven, FL 33881 (MLS # L4948929)
    $420,000
    Photo of 292 Lake Lucerne Way, Winter Haven, FL 33881 (MLS # L4948929)
    Photo of 292 Lake Lucerne Way, Winter Haven, FL 33881 (MLS # L4948929)
    292 Lake Lucerne Way, Winter Haven, FL
    292 Lake Lucerne Way
    Winter Haven, FL
    • 5 Beds
    • 3 Baths
    • 3,075 Home (sqft)
    • 3 Baths
    • 6,099 Lot (sqft)
  24. Photo of 1215 Cypress Point E, Winter Haven, FL 33884 (MLS # L4948609)
    $589,000
    Photo of 1215 Cypress Point E, Winter Haven, FL 33884 (MLS # L4948609)
    Photo of 1215 Cypress Point E, Winter Haven, FL 33884 (MLS # L4948609)
    1215 Cypress Point E, Winter Haven, FL
    1215 Cypress Point E
    Winter Haven, FL
    • 4 Beds
    • 4 Baths
    • 3,400 Home (sqft)
    • 4 Baths
    • 15,682 Lot (sqft)
  25. Photo of 344 Lake Smart Circle, Winter Haven, FL 33881 (MLS # L4948634)
    $425,000
    Photo of 344 Lake Smart Circle, Winter Haven, FL 33881 (MLS # L4948634)
    Photo of 344 Lake Smart Circle, Winter Haven, FL 33881 (MLS # L4948634)
    344 Lake Smart Circle, Winter Haven, FL
    344 Lake Smart Circle
    Winter Haven, FL
    • 5 Beds
    • 3 Baths
    • 2,944 Home (sqft)
    • 3 Baths
    • 6,534 Lot (sqft)
  26. Photo of 24 Lake Avenue, Winter Haven, FL 33880 (MLS # L4948735)
    $469,000
    Photo of 24 Lake Avenue, Winter Haven, FL 33880 (MLS # L4948735)
    Photo of 24 Lake Avenue, Winter Haven, FL 33880 (MLS # L4948735)
    24 Lake Avenue, Winter Haven, FL
    24 Lake Avenue
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 2,464 Home (sqft)
    • 2 Baths
    • 28,750 Lot (sqft)
  27. Photo of 5783 Marsh Landing Drive, Winter Haven, FL 33881 (MLS # S5115333)
    $405,000
    Photo of 5783 Marsh Landing Drive, Winter Haven, FL 33881 (MLS # S5115333)
    Photo of 5783 Marsh Landing Drive, Winter Haven, FL 33881 (MLS # S5115333)
    5783 Marsh Landing Drive, Winter Haven, FL
    5783 Marsh Landing Drive
    Winter Haven, FL
    • 3 Beds
    • 3 Baths
    • 2,526 Home (sqft)
    • 3 Baths
    • 7,841 Lot (sqft)
  28. Photo of 108 Lake Region Boulevard N, Winter Haven, FL 33881 (MLS # L4948706)
    $469,900
    Photo of 108 Lake Region Boulevard N, Winter Haven, FL 33881 (MLS # L4948706)
    Photo of 108 Lake Region Boulevard N, Winter Haven, FL 33881 (MLS # L4948706)
    108 Lake Region Boulevard N, Winter Haven, FL
    108 Lake Region Boulevard N
    Winter Haven, FL
    • 4 Beds
    • 3 Baths
    • 2,495 Home (sqft)
    • 3 Baths
    • 11,762 Lot (sqft)
  29. Photo of 3002 Plantation Road, Winter Haven, FL 33884 (MLS # P4932668)
    $479,900
    Photo of 3002 Plantation Road, Winter Haven, FL 33884 (MLS # P4932668)
    Photo of 3002 Plantation Road, Winter Haven, FL 33884 (MLS # P4932668)
    3002 Plantation Road, Winter Haven, FL
    3002 Plantation Road
    Winter Haven, FL
    • 4 Beds
    • 3 Baths
    • 2,740 Home (sqft)
    • 3 Baths
    • 15,246 Lot (sqft)
  30. Photo of 1937 Rifle Range Road, Winter Haven, FL 33880 (MLS # P4932621)
    $499,500
    Photo of 1937 Rifle Range Road, Winter Haven, FL 33880 (MLS # P4932621)
    Photo of 1937 Rifle Range Road, Winter Haven, FL 33880 (MLS # P4932621)
    1937 Rifle Range Road, Winter Haven, FL
    1937 Rifle Range Road
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,624 Home (sqft)
    • 2 Baths
    • 1.52 Lot (ac)
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