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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 pool 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 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)
  2. 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)
  3. 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)
  4. 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)
  5. 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)
  6. 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)
  7. 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)
  8. 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)
  9. 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)
  10. 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)
  11. Photo of 4034 Doral, Winter Haven, FL 33884 (MLS # TB8317068)
    $425,000
    Photo of 4034 Doral, Winter Haven, FL 33884 (MLS # TB8317068)
    Photo of 4034 Doral, Winter Haven, FL 33884 (MLS # TB8317068)
    4034 Doral, Winter Haven, FL
    4034 Doral
    Winter Haven, FL
    • 4 Beds
    • 3 Baths
    • 2,674 Home (sqft)
    • 3 Baths
    • 11,326 Lot (sqft)
  12. Photo of 110 Covington Cove SE, Winter Haven, FL 33880 (MLS # P4932551)
    $589,000
    Photo of 110 Covington Cove SE, Winter Haven, FL 33880 (MLS # P4932551)
    Photo of 110 Covington Cove SE, Winter Haven, FL 33880 (MLS # P4932551)
    110 Covington Cove SE, Winter Haven, FL
    110 Covington Cove SE
    Winter Haven, FL
    • 4 Beds
    • 5 Baths
    • 2,857 Home (sqft)
    • 5 Baths
    • 22,652 Lot (sqft)
  13. Photo of 104 Sanderling Drive, Winter Haven, FL 33881 (MLS # L4948273)
    $449,000
    Photo of 104 Sanderling Drive, Winter Haven, FL 33881 (MLS # L4948273)
    Photo of 104 Sanderling Drive, Winter Haven, FL 33881 (MLS # L4948273)
    104 Sanderling Drive, Winter Haven, FL
    104 Sanderling Drive
    Winter Haven, FL
    • 4 Beds
    • 2 Baths
    • 2,277 Home (sqft)
    • 2 Baths
    • 13,068 Lot (sqft)
  14. Photo of 1303 Mirror Terrace NW, Winter Haven, FL 33881 (MLS # P4932310)
    $549,900
    Photo of 1303 Mirror Terrace NW, Winter Haven, FL 33881 (MLS # P4932310)
    Photo of 1303 Mirror Terrace NW, Winter Haven, FL 33881 (MLS # P4932310)
    1303 Mirror Terrace NW, Winter Haven, FL
    1303 Mirror Terrace NW
    Winter Haven, FL
    • 3 Beds
    • 4 Baths
    • 3,281 Home (sqft)
    • 4 Baths
    • 17,424 Lot (sqft)
  15. Photo of 937 Avenue L SE, Winter Haven, FL 33880 (MLS # P4932283)
    $409,900
    Photo of 937 Avenue L SE, Winter Haven, FL 33880 (MLS # P4932283)
    Photo of 937 Avenue L SE, Winter Haven, FL 33880 (MLS # P4932283)
    937 Avenue L SE, Winter Haven, FL
    937 Avenue L SE
    Winter Haven, FL
    • 4 Beds
    • 5 Baths
    • 2,368 Home (sqft)
    • 5 Baths
    • 13,940 Lot (sqft)
  16. Photo of 1865 15th Court NW, Winter Haven, FL 33881 (MLS # L4947858)
    $420,000
    Photo of 1865 15th Court NW, Winter Haven, FL 33881 (MLS # L4947858)
    Photo of 1865 15th Court NW, Winter Haven, FL 33881 (MLS # L4947858)
    1865 15th Court NW, Winter Haven, FL
    1865 15th Court NW
    Winter Haven, FL
    • 4 Beds
    • 2 Baths
    • 1,999 Home (sqft)
    • 2 Baths
    • 11,326 Lot (sqft)
  17. Photo of 3808 Gaines Drive, Winter Haven, FL 33884 (MLS # P4932117)
    $539,900
    Photo of 3808 Gaines Drive, Winter Haven, FL 33884 (MLS # P4932117)
    Photo of 3808 Gaines Drive, Winter Haven, FL 33884 (MLS # P4932117)
    3808 Gaines Drive, Winter Haven, FL
    3808 Gaines Drive
    Winter Haven, FL
    • 3 Beds
    • 3 Baths
    • 2,098 Home (sqft)
    • 3 Baths
    • 37,462 Lot (sqft)
  18. Photo of 191 Lake Thomas Drive, Winter Haven, FL 33880 (MLS # P4932073)
    $427,500
    Photo of 191 Lake Thomas Drive, Winter Haven, FL 33880 (MLS # P4932073)
    Photo of 191 Lake Thomas Drive, Winter Haven, FL 33880 (MLS # P4932073)
    191 Lake Thomas Drive, Winter Haven, FL
    191 Lake Thomas Drive
    Winter Haven, FL
    • 4 Beds
    • 2 Baths
    • 2,201 Home (sqft)
    • 2 Baths
    • 20,474 Lot (sqft)
  19. Photo of 318 Hamilton Shores Drive NE, Winter Haven, FL 33881 (MLS # L4944880)
    $549,000
    Photo of 318 Hamilton Shores Drive NE, Winter Haven, FL 33881 (MLS # L4944880)
    Photo of 318 Hamilton Shores Drive NE, Winter Haven, FL 33881 (MLS # L4944880)
    318 Hamilton Shores Drive NE, Winter Haven, FL
    318 Hamilton Shores Drive NE
    Winter Haven, FL
    • 4 Beds
    • 2 Baths
    • 2,806 Home (sqft)
    • 2 Baths
    • 16,553 Lot (sqft)
  20. Photo of 5866 Breakwater Drive, Winter Haven, FL 33884 (MLS # T3527987)
    $429,900
    Photo of 5866 Breakwater Drive, Winter Haven, FL 33884 (MLS # T3527987)
    Photo of 5866 Breakwater Drive, Winter Haven, FL 33884 (MLS # T3527987)
    5866 Breakwater Drive, Winter Haven, FL
    5866 Breakwater Drive
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,842 Home (sqft)
    • 2 Baths
    • 1.41 Lot (ac)
  21. Photo of 1396 Lucerne Loop Road NE, Winter Haven, FL 33881 (MLS # P4930362)
    $565,000
    Photo of 1396 Lucerne Loop Road NE, Winter Haven, FL 33881 (MLS # P4930362)
    Photo of 1396 Lucerne Loop Road NE, Winter Haven, FL 33881 (MLS # P4930362)
    1396 Lucerne Loop Road NE, Winter Haven, FL
    1396 Lucerne Loop Road NE
    Winter Haven, FL
    • 4 Beds
    • 3 Baths
    • 2,371 Home (sqft)
    • 3 Baths
    • 35,720 Lot (sqft)
  22. Photo of 856 Sun Burst Road, Winter Haven, FL 33880 (MLS # P4930041)
    $465,000
    Photo of 856 Sun Burst Road, Winter Haven, FL 33880 (MLS # P4930041)
    Photo of 856 Sun Burst Road, Winter Haven, FL 33880 (MLS # P4930041)
    856 Sun Burst Road, Winter Haven, FL
    856 Sun Burst Road
    Winter Haven, FL
    • 5 Beds
    • 3 Baths
    • 2,601 Home (sqft)
    • 3 Baths
    • 6,099 Lot (sqft)
  23. Photo of 132 Lake Region Circle, Winter Haven, FL 33881 (MLS # P4929523)
    $469,000
    Photo of 132 Lake Region Circle, Winter Haven, FL 33881 (MLS # P4929523)
    Photo of 132 Lake Region Circle, Winter Haven, FL 33881 (MLS # P4929523)
    132 Lake Region Circle, Winter Haven, FL
    132 Lake Region Circle
    Winter Haven, FL
    • 3 Beds
    • 3 Baths
    • 2,486 Home (sqft)
    • 3 Baths
    • 12,197 Lot (sqft)
  24. Photo of 292 Hernando Road, Winter Haven, FL 33884 (MLS # P4926639)
    $549,900
    Photo of 292 Hernando Road, Winter Haven, FL 33884 (MLS # P4926639)
    Photo of 292 Hernando Road, Winter Haven, FL 33884 (MLS # P4926639)
    292 Hernando Road, Winter Haven, FL
    292 Hernando Road
    Winter Haven, FL
    • 4 Beds
    • 3 Baths
    • 2,544 Home (sqft)
    • 3 Baths
    • 13,504 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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