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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 above $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 428 Ituna Circle, Winter Haven, FL 33881 (MLS # L4949122)
    $298,790
    Photo of 428 Ituna Circle, Winter Haven, FL 33881 (MLS # L4949122)
    Photo of 428 Ituna Circle, Winter Haven, FL 33881 (MLS # L4949122)
    428 Ituna Circle, Winter Haven, FL
    428 Ituna Circle
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,358 Home (sqft)
    • 2 Baths
    • 5,228 Lot (sqft)
  2. Photo of 444 Ituna Circle, Winter Haven, FL 33881 (MLS # L4949123)
    $394,785
    Photo of 444 Ituna Circle, Winter Haven, FL 33881 (MLS # L4949123)
    Photo of 444 Ituna Circle, Winter Haven, FL 33881 (MLS # L4949123)
    444 Ituna Circle, Winter Haven, FL
    444 Ituna Circle
    Winter Haven, FL
    • 4 Beds
    • 3 Baths
    • 2,029 Home (sqft)
    • 3 Baths
    • 6,099 Lot (sqft)
  3. Photo of 3136 Country Club Circle, Winter Haven, FL 33881 (MLS # L4949082)
    $314,900
    Photo of 3136 Country Club Circle, Winter Haven, FL 33881 (MLS # L4949082)
    Photo of 3136 Country Club Circle, Winter Haven, FL 33881 (MLS # L4949082)
    3136 Country Club Circle, Winter Haven, FL
    3136 Country Club Circle
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,690 Home (sqft)
    • 2 Baths
    • 6,534 Lot (sqft)
  4. 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)
  5. Photo of 1324 Mirror Terrace NW, Winter Haven, FL 33881 (MLS # P4932730)
    $1,174,000
    Photo of 1324 Mirror Terrace NW, Winter Haven, FL 33881 (MLS # P4932730)
    Photo of 1324 Mirror Terrace NW, Winter Haven, FL 33881 (MLS # P4932730)
    1324 Mirror Terrace NW, Winter Haven, FL
    1324 Mirror Terrace NW
    Winter Haven, FL
    • 4 Beds
    • 3 Baths
    • 3,897 Home (sqft)
    • 3 Baths
    • 17,424 Lot (sqft)
  6. Photo of 2010 Overlook Drive, Winter Haven, FL 33884 (MLS # O6260592)
    $320,000
    Photo of 2010 Overlook Drive, Winter Haven, FL 33884 (MLS # O6260592)
    Photo of 2010 Overlook Drive, Winter Haven, FL 33884 (MLS # O6260592)
    2010 Overlook Drive, Winter Haven, FL
    2010 Overlook Drive
    Winter Haven, FL
    • 3 Beds
    • 3 Baths
    • 1,922 Home (sqft)
    • 3 Baths
    • 21,780 Lot (sqft)
  7. Photo of 1392 Innsbruck Ct, Winter Haven, FL 33884 (MLS # P4932837)
    $224,000
    Photo of 1392 Innsbruck Ct, Winter Haven, FL 33884 (MLS # P4932837)
    Photo of 1392 Innsbruck Ct, Winter Haven, FL 33884 (MLS # P4932837)
    1392 Innsbruck Ct, Winter Haven, FL
    1392 Innsbruck Ct
    Winter Haven, FL
    • 2 Beds
    • 2 Baths
    • 1,369 Home (sqft)
    • 2 Baths
    • 3,921 Lot (sqft)
  8. Photo of 4570 Chambliss Road, Winter Haven, FL 33884 (MLS # P4932888)
    $490,000
    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)
  9. Photo of 422 21st Street SW, Winter Haven, FL 33880 (MLS # P4932975)
    $260,000
    Photo of 422 21st Street SW, Winter Haven, FL 33880 (MLS # P4932975)
    Photo of 422 21st Street SW, Winter Haven, FL 33880 (MLS # P4932975)
    422 21st Street SW, Winter Haven, FL
    422 21st Street SW
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,132 Home (sqft)
    • 2 Baths
    • 14,811 Lot (sqft)
  10. Photo of 3309 Raleigh Dr, Winter Haven, FL 33884 (MLS # P4932877)
    $225,000
    Photo of 3309 Raleigh Dr, Winter Haven, FL 33884 (MLS # P4932877)
    Photo of 3309 Raleigh Dr, Winter Haven, FL 33884 (MLS # P4932877)
    3309 Raleigh Dr, Winter Haven, FL
    3309 Raleigh Dr
    Winter Haven, FL
    • 2 Beds
    • 2 Baths
    • 1,118 Home (sqft)
    • 2 Baths
    • 4,792 Lot (sqft)
  11. 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)
  12. Photo of 819 Sunset Cove Drive, Winter Haven, FL 33880 (MLS # P4932874)
    $339,000
    Photo of 819 Sunset Cove Drive, Winter Haven, FL 33880 (MLS # P4932874)
    Photo of 819 Sunset Cove Drive, Winter Haven, FL 33880 (MLS # P4932874)
    819 Sunset Cove Drive, Winter Haven, FL
    819 Sunset Cove Drive
    Winter Haven, FL
    • 4 Beds
    • 3 Baths
    • 2,208 Home (sqft)
    • 3 Baths
    • 16,553 Lot (sqft)
  13. Photo of 4953 Kaia Avenue, Winter Haven, FL 33884 (MLS # O6255000)
    $322,090
    Photo of 4953 Kaia Avenue, Winter Haven, FL 33884 (MLS # O6255000)
    Photo of 4953 Kaia Avenue, Winter Haven, FL 33884 (MLS # O6255000)
    4953 Kaia Avenue, Winter Haven, FL
    4953 Kaia Avenue
    Winter Haven, FL
    • 4 Beds
    • 2 Baths
    • 1,840 Home (sqft)
    • 2 Baths
    • 5,663 Lot (sqft)
  14. Photo of 3745 Giorgio Drive, Winter Haven, FL 33884 (MLS # O6255001)
    $292,105
    Photo of 3745 Giorgio Drive, Winter Haven, FL 33884 (MLS # O6255001)
    Photo of 3745 Giorgio Drive, Winter Haven, FL 33884 (MLS # O6255001)
    3745 Giorgio Drive, Winter Haven, FL
    3745 Giorgio Drive
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,695 Home (sqft)
    • 2 Baths
    • 5,663 Lot (sqft)
  15. Photo of 267 Kings Pond Avenue, Winter Haven, FL 33880 (MLS # L4948966)
    $275,000
    Photo of 267 Kings Pond Avenue, Winter Haven, FL 33880 (MLS # L4948966)
    Photo of 267 Kings Pond Avenue, Winter Haven, FL 33880 (MLS # L4948966)
    267 Kings Pond Avenue, Winter Haven, FL
    267 Kings Pond Avenue
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,233 Home (sqft)
    • 2 Baths
    • 7,406 Lot (sqft)
  16. Photo of 364 Fish Hawk Drive, Winter Haven, FL 33884 (MLS # P4932705)
    $499,900
    Photo of 364 Fish Hawk Drive, Winter Haven, FL 33884 (MLS # P4932705)
    Photo of 364 Fish Hawk Drive, Winter Haven, FL 33884 (MLS # P4932705)
    86
     
    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)
  17. Photo of 439 San Jose Drive, Winter Haven, FL 33884 (MLS # TB8325270)
    $250,000
    Photo of 439 San Jose Drive, Winter Haven, FL 33884 (MLS # TB8325270)
    Photo of 439 San Jose Drive, Winter Haven, FL 33884 (MLS # TB8325270)
    439 San Jose Drive, Winter Haven, FL
    439 San Jose Drive
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,747 Home (sqft)
    • 2 Baths
    • 6,099 Lot (sqft)
  18. Photo of 105 Elliott Lane, Winter Haven, FL 33884 (MLS # P4932887)
    $255,000
    Photo of 105 Elliott Lane, Winter Haven, FL 33884 (MLS # P4932887)
    Photo of 105 Elliott Lane, Winter Haven, FL 33884 (MLS # P4932887)
    105 Elliott Lane, Winter Haven, FL
    105 Elliott Lane
    Winter Haven, FL
    • 2 Beds
    • 1 Bath
    • 800 Home (sqft)
    • 1 Bath
    • 9,148 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 4121 Fishermans Landing, Winter Haven, FL 33884 (MLS # P4932841)
    $255,000
    Photo of 4121 Fishermans Landing, Winter Haven, FL 33884 (MLS # P4932841)
    Photo of 4121 Fishermans Landing, Winter Haven, FL 33884 (MLS # P4932841)
    4121 Fishermans Landing, Winter Haven, FL
    4121 Fishermans Landing
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,581 Home (sqft)
    • 2 Baths
    • 5,228 Lot (sqft)
  21. Photo of 2825 Attwater Loop, Winter Haven, FL 33884 (MLS # O6260348)
    $235,000
    Photo of 2825 Attwater Loop, Winter Haven, FL 33884 (MLS # O6260348)
    Photo of 2825 Attwater Loop, Winter Haven, FL 33884 (MLS # O6260348)
    2825 Attwater Loop, Winter Haven, FL
    2825 Attwater Loop
    Winter Haven, FL
    • 2 Beds
    • 2 Baths
    • 1,385 Home (sqft)
    • 2 Baths
    • 3,050 Lot (sqft)
  22. Photo of 2108 Bretton Ridge Boulevard, Winter Haven, FL 33884 (MLS # L4949027)
    $290,000
    Photo of 2108 Bretton Ridge Boulevard, Winter Haven, FL 33884 (MLS # L4949027)
    Photo of 2108 Bretton Ridge Boulevard, Winter Haven, FL 33884 (MLS # L4949027)
    2108 Bretton Ridge Boulevard, Winter Haven, FL
    2108 Bretton Ridge Boulevard
    Winter Haven, FL
    • 4 Beds
    • 2 Baths
    • 1,568 Home (sqft)
    • 2 Baths
    • 6,534 Lot (sqft)
  23. Photo of 1280 Denali Drive, Winter Haven, FL 33881 (MLS # L4948912)
    $440,000
    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)
  24. Photo of 1956 28th Street NW, Winter Haven, FL 33881 (MLS # TB8323728)
    $277,000
    Photo of 1956 28th Street NW, Winter Haven, FL 33881 (MLS # TB8323728)
    Photo of 1956 28th Street NW, Winter Haven, FL 33881 (MLS # TB8323728)
    1956 28th Street NW, Winter Haven, FL
    1956 28th Street NW
    Winter Haven, FL
    • 2 Beds
    • 1 Bath
    • 1,974 Home (sqft)
    • 1 Bath
    • 7,841 Lot (sqft)
  25. Photo of 10 Pilot Place, Winter Haven, FL 33881 (MLS # O6259578)
    $429,000
    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
    • 4 Beds
    • 3 Baths
    • 2,798 Home (sqft)
    • 3 Baths
    • 13,068 Lot (sqft)
  26. Photo of 1383 Buckeye Trace Boulevard, Winter Haven, FL 33881 (MLS # S5115943)
    $299,000
    Photo of 1383 Buckeye Trace Boulevard, Winter Haven, FL 33881 (MLS # S5115943)
    Photo of 1383 Buckeye Trace Boulevard, Winter Haven, FL 33881 (MLS # S5115943)
    1383 Buckeye Trace Boulevard, Winter Haven, FL
    1383 Buckeye Trace Boulevard
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,507 Home (sqft)
    • 2 Baths
    • 6,970 Lot (sqft)
  27. Photo of 1644 Linz Ct, Winter Haven, FL 33884 (MLS # P4932813)
    $254,000
    Photo of 1644 Linz Ct, Winter Haven, FL 33884 (MLS # P4932813)
    Photo of 1644 Linz Ct, Winter Haven, FL 33884 (MLS # P4932813)
    1644 Linz Ct, Winter Haven, FL
    1644 Linz Ct
    Winter Haven, FL
    • 2 Beds
    • 2 Baths
    • 1,329 Home (sqft)
    • 2 Baths
    • 4,356 Lot (sqft)
  28. Photo of 309 SE Avenue G SE, Winter Haven, FL 33880 (MLS # K4902704)
    $249,900
    Photo of 309 SE Avenue G SE, Winter Haven, FL 33880 (MLS # K4902704)
    Photo of 309 SE Avenue G SE, Winter Haven, FL 33880 (MLS # K4902704)
    309 SE Avenue G SE, Winter Haven, FL
    309 SE Avenue G SE
    Winter Haven, FL
    • 3 Beds
    • 3 Baths
    • 1,564 Home (sqft)
    • 3 Baths
    • 10,455 Lot (sqft)
  29. Photo of 346 Sterling Drive, Winter Haven, FL 33884 (MLS # L4948871)
    $355,000
    Photo of 346 Sterling Drive, Winter Haven, FL 33884 (MLS # L4948871)
    Photo of 346 Sterling Drive, Winter Haven, FL 33884 (MLS # L4948871)
    346 Sterling Drive, Winter Haven, FL
    346 Sterling Drive
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,929 Home (sqft)
    • 2 Baths
    • 8,277 Lot (sqft)
  30. 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)
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