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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 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 9 Skidmore Road, Winter Haven, FL 33884 (MLS # P4933073)
    $1,250,000
    Photo of 9 Skidmore Road, Winter Haven, FL 33884 (MLS # P4933073)
    Photo of 9 Skidmore Road, Winter Haven, FL 33884 (MLS # P4933073)
    9 Skidmore Road, Winter Haven, FL
    9 Skidmore Road
    Winter Haven, FL
    • 5 Beds
    • 4 Baths
    • 5,028 Home (sqft)
    • 4 Baths
    • 40,076 Lot (sqft)
  2. Photo of 3206 Heron Cove, Winter Haven, FL 33884 (MLS # L4949141)
    $699,900
    Photo of 3206 Heron Cove, Winter Haven, FL 33884 (MLS # L4949141)
    Photo of 3206 Heron Cove, Winter Haven, FL 33884 (MLS # L4949141)
    3206 Heron Cove, Winter Haven, FL
    3206 Heron Cove
    Winter Haven, FL
    • 3 Beds
    • 3 Baths
    • 3,050 Home (sqft)
    • 3 Baths
    • 20,038 Lot (sqft)
  3. Photo of 1324 Mirror Terrace NW, Winter Haven, FL 33881 (MLS # P4932730)
    $1,199,000
    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)
  4. Photo of 4040 Palma Ceia Circle, Winter Haven, FL 33884 (MLS # O6255663)
    $799,000
    Photo of 4040 Palma Ceia Circle, Winter Haven, FL 33884 (MLS # O6255663)
    Photo of 4040 Palma Ceia Circle, Winter Haven, FL 33884 (MLS # O6255663)
    4040 Palma Ceia Circle, Winter Haven, FL
    4040 Palma Ceia Circle
    Winter Haven, FL
    • 3 Beds
    • 4 Baths
    • 2,493 Home (sqft)
    • 4 Baths
    • 13,068 Lot (sqft)
  5. Photo of 123 Old Spanish Way, Winter Haven, FL 33884 (MLS # P4932665)
    $629,000
    Photo of 123 Old Spanish Way, Winter Haven, FL 33884 (MLS # P4932665)
    Photo of 123 Old Spanish Way, Winter Haven, FL 33884 (MLS # P4932665)
    123 Old Spanish Way, Winter Haven, FL
    123 Old Spanish Way
    Winter Haven, FL
    • 4 Beds
    • 3 Baths
    • 2,916 Home (sqft)
    • 3 Baths
    • 3.10 Lot (ac)
  6. Photo of 1935 Austin Terrace, Winter Haven, FL 33884 (MLS # L4948611)
    $650,000
    Photo of 1935 Austin Terrace, Winter Haven, FL 33884 (MLS # L4948611)
    Photo of 1935 Austin Terrace, Winter Haven, FL 33884 (MLS # L4948611)
    1935 Austin Terrace, Winter Haven, FL
    1935 Austin Terrace
    Winter Haven, FL
    • 3 Beds
    • 3 Baths
    • 2,494 Home (sqft)
    • 3 Baths
    • 13,940 Lot (sqft)
  7. Photo of 1957 Rifle Range Road, Winter Haven, FL 33880 (MLS # P4932639)
    $1,650,000
    Photo of 1957 Rifle Range Road, Winter Haven, FL 33880 (MLS # P4932639)
    Photo of 1957 Rifle Range Road, Winter Haven, FL 33880 (MLS # P4932639)
    1957 Rifle Range Road, Winter Haven, FL
    1957 Rifle Range Road
    Winter Haven, FL
    • 8 Beds
    • 6 Baths
    • 5,194 Home (sqft)
    • 6 Baths
    • 14.22 Lot (ac)
  8. Photo of 3041 Eagle Haven Drive, Winter Haven, FL 33880 (MLS # L4948486)
    $740,000
    Photo of 3041 Eagle Haven Drive, Winter Haven, FL 33880 (MLS # L4948486)
    Photo of 3041 Eagle Haven Drive, Winter Haven, FL 33880 (MLS # L4948486)
    3041 Eagle Haven Drive, Winter Haven, FL
    3041 Eagle Haven Drive
    Winter Haven, FL
    • 3 Beds
    • 4 Baths
    • 3,456 Home (sqft)
    • 4 Baths
    • 1.10 Lot (ac)
  9. Photo of 2609 Wyndsor Oaks Court, Winter Haven, FL 33884 (MLS # P4932561)
    $749,900
    Photo of 2609 Wyndsor Oaks Court, Winter Haven, FL 33884 (MLS # P4932561)
    Photo of 2609 Wyndsor Oaks Court, Winter Haven, FL 33884 (MLS # P4932561)
    2609 Wyndsor Oaks Court, Winter Haven, FL
    2609 Wyndsor Oaks Court
    Winter Haven, FL
    • 4 Beds
    • 3 Baths
    • 3,322 Home (sqft)
    • 3 Baths
    • 22,652 Lot (sqft)
  10. Photo of 999 Oleander Drive SE, Winter Haven, FL 33880 (MLS # P4932432)
    $1,650,000
    Photo of 999 Oleander Drive SE, Winter Haven, FL 33880 (MLS # P4932432)
    Photo of 999 Oleander Drive SE, Winter Haven, FL 33880 (MLS # P4932432)
    999 Oleander Drive SE, Winter Haven, FL
    999 Oleander Drive SE
    Winter Haven, FL
    • 5 Beds
    • 8 Baths
    • 8,505 Home (sqft)
    • 8 Baths
    • 3.22 Lot (ac)
  11. Photo of 2418 Berkshire Drive, Winter Haven, FL 33884 (MLS # B4901738)
    $859,000
    Photo of 2418 Berkshire Drive, Winter Haven, FL 33884 (MLS # B4901738)
    Photo of 2418 Berkshire Drive, Winter Haven, FL 33884 (MLS # B4901738)
    2418 Berkshire Drive, Winter Haven, FL
    2418 Berkshire Drive
    Winter Haven, FL
    • 4 Beds
    • 3 Baths
    • 3,790 Home (sqft)
    • 3 Baths
    • 32,670 Lot (sqft)
  12. Photo of 6261 Pinehurst Loop, Winter Haven, FL 33884 (MLS # P4932152)
    $650,000
    Photo of 6261 Pinehurst Loop, Winter Haven, FL 33884 (MLS # P4932152)
    Photo of 6261 Pinehurst Loop, Winter Haven, FL 33884 (MLS # P4932152)
    6261 Pinehurst Loop, Winter Haven, FL
    6261 Pinehurst Loop
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 2,512 Home (sqft)
    • 2 Baths
    • 8,277 Lot (sqft)
  13. Photo of 3047 Eagle Haven Drive, Winter Haven, FL 33880 (MLS # P4932157)
    $699,000
    Photo of 3047 Eagle Haven Drive, Winter Haven, FL 33880 (MLS # P4932157)
    Photo of 3047 Eagle Haven Drive, Winter Haven, FL 33880 (MLS # P4932157)
    3047 Eagle Haven Drive, Winter Haven, FL
    3047 Eagle Haven Drive
    Winter Haven, FL
    • 4 Beds
    • 3 Baths
    • 2,496 Home (sqft)
    • 3 Baths
    • 43,125 Lot (sqft)
  14. Photo of 3350 Crump Road, Winter Haven, FL 33881 (MLS # P4931966)
    $675,000
    Photo of 3350 Crump Road, Winter Haven, FL 33881 (MLS # P4931966)
    Photo of 3350 Crump Road, Winter Haven, FL 33881 (MLS # P4931966)
    3350 Crump Road, Winter Haven, FL
    3350 Crump Road
    Winter Haven, FL
    • 2 Beds
    • 4 Baths
    • 2,387 Home (sqft)
    • 4 Baths
    • 36,155 Lot (sqft)
  15. Photo of 856 Twin Oaks Lane, Winter Haven, FL 33880 (MLS # P4931707)
    $1,190,000
    Photo of 856 Twin Oaks Lane, Winter Haven, FL 33880 (MLS # P4931707)
    Photo of 856 Twin Oaks Lane, Winter Haven, FL 33880 (MLS # P4931707)
    856 Twin Oaks Lane, Winter Haven, FL
    856 Twin Oaks Lane
    Winter Haven, FL
    • 4 Beds
    • 3 Baths
    • 3,237 Home (sqft)
    • 3 Baths
    • 2.93 Lot (ac)
  16. Photo of 121 E Lake Summit Drive, Winter Haven, FL 33884 (MLS # P4931785)
    $1,300,000
    Photo of 121 E Lake Summit Drive, Winter Haven, FL 33884 (MLS # P4931785)
    Photo of 121 E Lake Summit Drive, Winter Haven, FL 33884 (MLS # P4931785)
    121 E Lake Summit Drive, Winter Haven, FL
    121 E Lake Summit Drive
    Winter Haven, FL
    • 5 Beds
    • 4 Baths
    • 4,591 Home (sqft)
    • 4 Baths
    • 29,186 Lot (sqft)
  17. Photo of 3824 Gaines Drive, Winter Haven, FL 33884 (MLS # P4931341)
    $1,500,000
    Photo of 3824 Gaines Drive, Winter Haven, FL 33884 (MLS # P4931341)
    Photo of 3824 Gaines Drive, Winter Haven, FL 33884 (MLS # P4931341)
    3824 Gaines Drive, Winter Haven, FL
    3824 Gaines Drive
    Winter Haven, FL
    • 7 Beds
    • 7 Baths
    • 7,448 Home (sqft)
    • 7 Baths
    • 27,879 Lot (sqft)
  18. Photo of 341 Hamilton Shores Dr. NE, Winter Haven, FL 33881 (MLS # L4946733)
    $1,070,000
    Photo of 341 Hamilton Shores Dr. NE, Winter Haven, FL 33881 (MLS # L4946733)
    Photo of 341 Hamilton Shores Dr. NE, Winter Haven, FL 33881 (MLS # L4946733)
    341 Hamilton Shores Dr. NE, Winter Haven, FL
    341 Hamilton Shores Dr. NE
    Winter Haven, FL
    • 3 Beds
    • 3 Baths
    • 3,233 Home (sqft)
    • 3 Baths
    • 40,076 Lot (sqft)
  19. Photo of 2606 Wyndsor Oaks Court, Winter Haven, FL 33884 (MLS # P4931552)
    $734,000
    Photo of 2606 Wyndsor Oaks Court, Winter Haven, FL 33884 (MLS # P4931552)
    Photo of 2606 Wyndsor Oaks Court, Winter Haven, FL 33884 (MLS # P4931552)
    2606 Wyndsor Oaks Court, Winter Haven, FL
    2606 Wyndsor Oaks Court
    Winter Haven, FL
    • 5 Beds
    • 4 Baths
    • 3,233 Home (sqft)
    • 4 Baths
    • 23,958 Lot (sqft)
  20. Photo of 108 Campbell Drive, Winter Haven, FL 33884 (MLS # P4931279)
    $1,399,000
    Photo of 108 Campbell Drive, Winter Haven, FL 33884 (MLS # P4931279)
    Photo of 108 Campbell Drive, Winter Haven, FL 33884 (MLS # P4931279)
    108 Campbell Drive, Winter Haven, FL
    108 Campbell Drive
    Winter Haven, FL
    • 4 Beds
    • 5 Baths
    • 5,861 Home (sqft)
    • 5 Baths
    • 1.06 Lot (ac)
  21. Photo of 1441 S Lake Roy Drive, Winter Haven, FL 33884 (MLS # P4931110)
    $1,350,000
    Photo of 1441 S Lake Roy Drive, Winter Haven, FL 33884 (MLS # P4931110)
    Photo of 1441 S Lake Roy Drive, Winter Haven, FL 33884 (MLS # P4931110)
    1441 S Lake Roy Drive, Winter Haven, FL
    1441 S Lake Roy Drive
    Winter Haven, FL
    • 5 Beds
    • 5 Baths
    • 4,513 Home (sqft)
    • 5 Baths
    • 22,652 Lot (sqft)
  22. Photo of 1793 Lakehill Drive, Winter Haven, FL 33884 (MLS # P4931194)
    $799,000
    Photo of 1793 Lakehill Drive, Winter Haven, FL 33884 (MLS # P4931194)
    Photo of 1793 Lakehill Drive, Winter Haven, FL 33884 (MLS # P4931194)
    51
     
    1793 Lakehill Drive, Winter Haven, FL
    1793 Lakehill Drive
    Winter Haven, FL
    • 4 Beds
    • 3 Baths
    • 2,549 Home (sqft)
    • 3 Baths
    • 13,940 Lot (sqft)
  23. Photo of 1955 W Lake Hamilton Drive, Winter Haven, FL 33881 (MLS # P4931088)
    $2,000,000
    Photo of 1955 W Lake Hamilton Drive, Winter Haven, FL 33881 (MLS # P4931088)
    Photo of 1955 W Lake Hamilton Drive, Winter Haven, FL 33881 (MLS # P4931088)
    1955 W Lake Hamilton Drive, Winter Haven, FL
    1955 W Lake Hamilton Drive
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 2,814 Home (sqft)
    • 2 Baths
    • 19.39 Lot (ac)
  24. Photo of 2841 Country Club Road N, Winter Haven, FL 33881 (MLS # L4945839)
    $1,499,995
    Photo of 2841 Country Club Road N, Winter Haven, FL 33881 (MLS # L4945839)
    Photo of 2841 Country Club Road N, Winter Haven, FL 33881 (MLS # L4945839)
    2841 Country Club Road N, Winter Haven, FL
    2841 Country Club Road N
    Winter Haven, FL
    • 5 Beds
    • 6 Baths
    • 5,448 Home (sqft)
    • 6 Baths
    • 2.96 Lot (ac)
  25. Photo of 4225 Shadow Wood Court, Winter Haven, FL 33880 (MLS # L4945398)
    $690,000
    Photo of 4225 Shadow Wood Court, Winter Haven, FL 33880 (MLS # L4945398)
    Photo of 4225 Shadow Wood Court, Winter Haven, FL 33880 (MLS # L4945398)
    4225 Shadow Wood Court, Winter Haven, FL
    4225 Shadow Wood Court
    Winter Haven, FL
    • 5 Beds
    • 3 Baths
    • 3,680 Home (sqft)
    • 3 Baths
    • 17,424 Lot (sqft)
  26. Photo of 6265 Pinehurst Loop, Winter Haven, FL 33884 (MLS # L4944406)
    $650,000
    Photo of 6265 Pinehurst Loop, Winter Haven, FL 33884 (MLS # L4944406)
    Photo of 6265 Pinehurst Loop, Winter Haven, FL 33884 (MLS # L4944406)
    6265 Pinehurst Loop, Winter Haven, FL
    6265 Pinehurst Loop
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 2,521 Home (sqft)
    • 2 Baths
    • 7,841 Lot (sqft)
  27. Photo of 2412 Berkshire Drive, Winter Haven, FL 33884 (MLS # P4930184)
    $879,000
    Photo of 2412 Berkshire Drive, Winter Haven, FL 33884 (MLS # P4930184)
    Photo of 2412 Berkshire Drive, Winter Haven, FL 33884 (MLS # P4930184)
    2412 Berkshire Drive, Winter Haven, FL
    2412 Berkshire Drive
    Winter Haven, FL
    • 4 Beds
    • 4 Baths
    • 4,272 Home (sqft)
    • 4 Baths
    • 25,265 Lot (sqft)
  28. Photo of 103 Eagle Lake Loop Road, Winter Haven, FL 33884 (MLS # B4901530)
    $1,000,000
    Photo of 103 Eagle Lake Loop Road, Winter Haven, FL 33884 (MLS # B4901530)
    Photo of 103 Eagle Lake Loop Road, Winter Haven, FL 33884 (MLS # B4901530)
    103 Eagle Lake Loop Road, Winter Haven, FL
    103 Eagle Lake Loop Road
    Winter Haven, FL
    • 2 Beds
    • 1 Bath
    • 840 Home (sqft)
    • 1 Bath
    • 40,511 Lot (sqft)
  29. Photo of 1242 11th Street NE, Winter Haven, FL 33881 (MLS # P4930071)
    $695,000
    Photo of 1242 11th Street NE, Winter Haven, FL 33881 (MLS # P4930071)
    Photo of 1242 11th Street NE, Winter Haven, FL 33881 (MLS # P4930071)
    1242 11th Street NE, Winter Haven, FL
    1242 11th Street NE
    Winter Haven, FL
    • 3 Beds
    • 3 Baths
    • 2,935 Home (sqft)
    • 3 Baths
    • 1.93 Lot (ac)
  30. Photo of 256 Golf Aire Boulevard, Winter Haven, FL 33884 (MLS # T3512327)
    $628,000
    Photo of 256 Golf Aire Boulevard, Winter Haven, FL 33884 (MLS # T3512327)
    Photo of 256 Golf Aire Boulevard, Winter Haven, FL 33884 (MLS # T3512327)
    256 Golf Aire Boulevard, Winter Haven, FL
    256 Golf Aire Boulevard
    Winter Haven, FL
    • 3 Beds
    • 3 Baths
    • 3,928 Home (sqft)
    • 3 Baths
    • 12,633 Lot (sqft)
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