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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 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)
  2. Photo of 4002 Bedford Avenue, Winter Haven, FL 33884 (MLS # O6258540)
    $460,000
    Photo of 4002 Bedford Avenue, Winter Haven, FL 33884 (MLS # O6258540)
    Photo of 4002 Bedford Avenue, Winter Haven, FL 33884 (MLS # O6258540)
    36
     
    4002 Bedford Avenue, Winter Haven, FL
    4002 Bedford Avenue
    Winter Haven, FL
    • 4 Beds
    • 3 Baths
    • 2,615 Home (sqft)
    • 3 Baths
    • 7,841 Lot (sqft)
  3. Photo of 603 14th Street NE, Winter Haven, FL 33881 (MLS # L4948902)
    $449,900
    Photo of 603 14th Street NE, Winter Haven, FL 33881 (MLS # L4948902)
    Photo of 603 14th Street NE, Winter Haven, FL 33881 (MLS # L4948902)
    603 14th Street NE, Winter Haven, FL
    603 14th Street NE
    Winter Haven, FL
    • 4 Beds
    • 2 Baths
    • 2,648 Home (sqft)
    • 2 Baths
    • 11,326 Lot (sqft)
  4. Photo of 344 Lake Smart Circle, Winter Haven, FL 33881 (MLS # L4948634)
    $435,000
    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)
  5. Photo of 220 Escambia Drive, Winter Haven, FL 33884 (MLS # TB8319450)
    $405,000
    Photo of 220 Escambia Drive, Winter Haven, FL 33884 (MLS # TB8319450)
    Photo of 220 Escambia Drive, Winter Haven, FL 33884 (MLS # TB8319450)
    220 Escambia Drive, Winter Haven, FL
    220 Escambia Drive
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,701 Home (sqft)
    • 2 Baths
    • 12,197 Lot (sqft)
  6. 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)
  7. 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)
  8. 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)
  9. Photo of 3659 Plymouth Drive, Winter Haven, FL 33884 (MLS # P4932623)
    $414,000
    Photo of 3659 Plymouth Drive, Winter Haven, FL 33884 (MLS # P4932623)
    Photo of 3659 Plymouth Drive, Winter Haven, FL 33884 (MLS # P4932623)
    3659 Plymouth Drive, Winter Haven, FL
    3659 Plymouth Drive
    Winter Haven, FL
    • 4 Beds
    • 3 Baths
    • 2,294 Home (sqft)
    • 3 Baths
    • 6,099 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 3823 Eloise Estates Court, Winter Haven, FL 33881 (MLS # P4932553)
    $449,000
    Photo of 3823 Eloise Estates Court, Winter Haven, FL 33881 (MLS # P4932553)
    Photo of 3823 Eloise Estates Court, Winter Haven, FL 33881 (MLS # P4932553)
    3823 Eloise Estates Court, Winter Haven, FL
    3823 Eloise Estates Court
    Winter Haven, FL
    • 5 Beds
    • 4 Baths
    • 3,592 Home (sqft)
    • 4 Baths
    • 6,534 Lot (sqft)
  12. Photo of 3180 Lake Drive NW, Winter Haven, FL 33881 (MLS # P4932656)
    $425,000
    Photo of 3180 Lake Drive NW, Winter Haven, FL 33881 (MLS # P4932656)
    Photo of 3180 Lake Drive NW, Winter Haven, FL 33881 (MLS # P4932656)
    3180 Lake Drive NW, Winter Haven, FL
    3180 Lake Drive NW
    Winter Haven, FL
    • 3 Beds
    • 3 Baths
    • 1,821 Home (sqft)
    • 3 Baths
    • 10,455 Lot (sqft)
  13. 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)
  14. Photo of 2626 Sage Valley Way, Winter Haven, FL 33884 (MLS # O6255106)
    $419,990
    Photo of 2626 Sage Valley Way, Winter Haven, FL 33884 (MLS # O6255106)
    Photo of 2626 Sage Valley Way, Winter Haven, FL 33884 (MLS # O6255106)
    2626 Sage Valley Way, Winter Haven, FL
    2626 Sage Valley Way
    Winter Haven, FL
    • 5 Beds
    • 3 Baths
    • 2,601 Home (sqft)
    • 3 Baths
    • 6,099 Lot (sqft)
  15. Photo of 4314 Thomas Wood Lane E, Winter Haven, FL 33880 (MLS # L4948605)
    $400,000
    Photo of 4314 Thomas Wood Lane E, Winter Haven, FL 33880 (MLS # L4948605)
    Photo of 4314 Thomas Wood Lane E, Winter Haven, FL 33880 (MLS # L4948605)
    4314 Thomas Wood Lane E, Winter Haven, FL
    4314 Thomas Wood Lane E
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,981 Home (sqft)
    • 2 Baths
    • 13,068 Lot (sqft)
  16. 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)
  17. Photo of 110 Covington Cove SE, Winter Haven, FL 33880 (MLS # P4932551)
    $599,900
    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)
  18. Photo of 1178 Michelangelo Lane, Winter Haven, FL 33884 (MLS # O6253058)
    $430,000
    Photo of 1178 Michelangelo Lane, Winter Haven, FL 33884 (MLS # O6253058)
    Photo of 1178 Michelangelo Lane, Winter Haven, FL 33884 (MLS # O6253058)
    1178 Michelangelo Lane, Winter Haven, FL
    1178 Michelangelo Lane
    Winter Haven, FL
    • 4 Beds
    • 3 Baths
    • 2,503 Home (sqft)
    • 3 Baths
    • 8,277 Lot (sqft)
  19. Photo of 714 Terranova Avenue, Winter Haven, FL 33884 (MLS # O6253083)
    $450,000
    Photo of 714 Terranova Avenue, Winter Haven, FL 33884 (MLS # O6253083)
    Photo of 714 Terranova Avenue, Winter Haven, FL 33884 (MLS # O6253083)
    714 Terranova Avenue, Winter Haven, FL
    714 Terranova Avenue
    Winter Haven, FL
    • 4 Beds
    • 3 Baths
    • 2,372 Home (sqft)
    • 3 Baths
    • 14,811 Lot (sqft)
  20. Photo of 296 Grady Polk Road, Winter Haven, FL 33880 (MLS # TB8315672)
    $444,000
    Photo of 296 Grady Polk Road, Winter Haven, FL 33880 (MLS # TB8315672)
    Photo of 296 Grady Polk Road, Winter Haven, FL 33880 (MLS # TB8315672)
    296 Grady Polk Road, Winter Haven, FL
    296 Grady Polk Road
    Winter Haven, FL
    • 3 Beds
    • 3 Baths
    • 2,669 Home (sqft)
    • 3 Baths
    • 1.10 Lot (ac)
  21. Photo of 209 Santa Rosa Drive, Winter Haven, FL 33884 (MLS # P4932531)
    $440,000
    Photo of 209 Santa Rosa Drive, Winter Haven, FL 33884 (MLS # P4932531)
    Photo of 209 Santa Rosa Drive, Winter Haven, FL 33884 (MLS # P4932531)
    209 Santa Rosa Drive, Winter Haven, FL
    209 Santa Rosa Drive
    Winter Haven, FL
    • 3 Beds
    • 3 Baths
    • 2,338 Home (sqft)
    • 3 Baths
    • 11,762 Lot (sqft)
  22. Photo of 2642 Sage Valley Way, Winter Haven, FL 33884 (MLS # O6252887)
    $464,490
    Photo of 2642 Sage Valley Way, Winter Haven, FL 33884 (MLS # O6252887)
    Photo of 2642 Sage Valley Way, Winter Haven, FL 33884 (MLS # O6252887)
    2642 Sage Valley Way, Winter Haven, FL
    2642 Sage Valley Way
    Winter Haven, FL
    • 4 Beds
    • 3 Baths
    • 2,336 Home (sqft)
    • 3 Baths
    • 10,455 Lot (sqft)
  23. Photo of 1806 17th Street NW, Winter Haven, FL 33881 (MLS # L4948291)
    $410,000
    Photo of 1806 17th Street NW, Winter Haven, FL 33881 (MLS # L4948291)
    Photo of 1806 17th Street NW, Winter Haven, FL 33881 (MLS # L4948291)
    1806 17th Street NW, Winter Haven, FL
    1806 17th Street NW
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,750 Home (sqft)
    • 2 Baths
    • 13,068 Lot (sqft)
  24. Photo of 4726 Monterey Drive, Winter Haven, FL 33880 (MLS # P4932311)
    $425,000
    Photo of 4726 Monterey Drive, Winter Haven, FL 33880 (MLS # P4932311)
    Photo of 4726 Monterey Drive, Winter Haven, FL 33880 (MLS # P4932311)
    4726 Monterey Drive, Winter Haven, FL
    4726 Monterey Drive
    Winter Haven, FL
    • 4 Beds
    • 3 Baths
    • 2,370 Home (sqft)
    • 3 Baths
    • 19,167 Lot (sqft)
  25. Photo of 2502 Sage Valley Way, Winter Haven, FL 33884 (MLS # O6250897)
    $429,490
    Photo of 2502 Sage Valley Way, Winter Haven, FL 33884 (MLS # O6250897)
    Photo of 2502 Sage Valley Way, Winter Haven, FL 33884 (MLS # O6250897)
    2502 Sage Valley Way, Winter Haven, FL
    2502 Sage Valley Way
    Winter Haven, FL
    • 4 Beds
    • 3 Baths
    • 2,773 Home (sqft)
    • 3 Baths
    • 10,455 Lot (sqft)
  26. Photo of 2602 Sage Valley Way, Winter Haven, FL 33884 (MLS # O6250873)
    $429,990
    Photo of 2602 Sage Valley Way, Winter Haven, FL 33884 (MLS # O6250873)
    Photo of 2602 Sage Valley Way, Winter Haven, FL 33884 (MLS # O6250873)
    2602 Sage Valley Way, Winter Haven, FL
    2602 Sage Valley Way
    Winter Haven, FL
    • 4 Beds
    • 3 Baths
    • 2,773 Home (sqft)
    • 3 Baths
    • 7,406 Lot (sqft)
  27. Photo of 109 Odin Drive, Winter Haven, FL 33884 (MLS # P4932441)
    $449,000
    Photo of 109 Odin Drive, Winter Haven, FL 33884 (MLS # P4932441)
    Photo of 109 Odin Drive, Winter Haven, FL 33884 (MLS # P4932441)
    109 Odin Drive, Winter Haven, FL
    109 Odin Drive
    Winter Haven, FL
    • 4 Beds
    • 3 Baths
    • 2,884 Home (sqft)
    • 3 Baths
    • 5,228 Lot (sqft)
  28. Photo of 1965 Quail Fields Circle, Winter Haven, FL 33884 (MLS # W7869204)
    $433,095
    Photo of 1965 Quail Fields Circle, Winter Haven, FL 33884 (MLS # W7869204)
    Photo of 1965 Quail Fields Circle, Winter Haven, FL 33884 (MLS # W7869204)
    1965 Quail Fields Circle, Winter Haven, FL
    1965 Quail Fields Circle
    Winter Haven, FL
    • 4 Beds
    • 3 Baths
    • 2,748 Home (sqft)
    • 3 Baths
    • 6,970 Lot (sqft)
  29. 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)
  30. Photo of 2526 Sage Valley Way, Winter Haven, FL 33884 (MLS # O6250475)
    $403,990
    Photo of 2526 Sage Valley Way, Winter Haven, FL 33884 (MLS # O6250475)
    Photo of 2526 Sage Valley Way, Winter Haven, FL 33884 (MLS # O6250475)
    2526 Sage Valley Way, Winter Haven, FL
    2526 Sage Valley Way
    Winter Haven, FL
    • 4 Beds
    • 3 Baths
    • 2,372 Home (sqft)
    • 3 Baths
    • 6,099 Lot (sqft)
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