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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 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)
  2. 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)
  3. Photo of 1807 Garden Lake Drive #1807, Winter Haven, FL 33884 (MLS # P4932775)
    $260,000
    Photo of 1807 Garden Lake Drive #1807, Winter Haven, FL 33884 (MLS # P4932775)
    Photo of 1807 Garden Lake Drive #1807, Winter Haven, FL 33884 (MLS # P4932775)
    1807 Garden Lake Drive #1807, Winter Haven, FL
    1807 Garden Lake Drive #1807
    Winter Haven, FL
    • 2 Beds
    • 2 Baths
    • 1,103 Home (sqft)
    • 2 Baths
    • 436 Lot (sqft)
  4. Photo of 2203 Starboard, Winter Haven, FL 33881 (MLS # L4948476)
    $220,000
    Photo of 2203 Starboard, Winter Haven, FL 33881 (MLS # L4948476)
    Photo of 2203 Starboard, Winter Haven, FL 33881 (MLS # L4948476)
    2203 Starboard, Winter Haven, FL
    2203 Starboard
    Winter Haven, FL
    • 2 Beds
    • 2 Baths
    • 1,260 Home (sqft)
    • 2 Baths
    • 3,050 Lot (sqft)
  5. Photo of 3400 Costello Circle, Winter Haven, FL 33884 (MLS # O6259105)
    $322,990
    Photo of 3400 Costello Circle, Winter Haven, FL 33884 (MLS # O6259105)
    Photo of 3400 Costello Circle, Winter Haven, FL 33884 (MLS # O6259105)
    3400 Costello Circle, Winter Haven, FL
    3400 Costello Circle
    Winter Haven, FL
    • 5 Beds
    • 3 Baths
    • 2,447 Home (sqft)
    • 3 Baths
    • 4,356 Lot (sqft)
  6. Photo of 807 Avenue M SE, Winter Haven, FL 33880 (MLS # P4932797)
    $285,000
    Photo of 807 Avenue M SE, Winter Haven, FL 33880 (MLS # P4932797)
    Photo of 807 Avenue M SE, Winter Haven, FL 33880 (MLS # P4932797)
    807 Avenue M SE, Winter Haven, FL
    807 Avenue M SE
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,590 Home (sqft)
    • 2 Baths
    • 11,326 Lot (sqft)
  7. Photo of 157 Browning Circle, Winter Haven, FL 33884 (MLS # L4948926)
    $250,000
    Photo of 157 Browning Circle, Winter Haven, FL 33884 (MLS # L4948926)
    Photo of 157 Browning Circle, Winter Haven, FL 33884 (MLS # L4948926)
    157 Browning Circle, Winter Haven, FL
    157 Browning Circle
    Winter Haven, FL
    • 2 Beds
    • 2 Baths
    • 1,134 Home (sqft)
    • 2 Baths
    • 9,148 Lot (sqft)
  8. Photo of 2725 Attwater Loop, Winter Haven, FL 33884 (MLS # P4932811)
    $310,000
    Photo of 2725 Attwater Loop, Winter Haven, FL 33884 (MLS # P4932811)
    Photo of 2725 Attwater Loop, Winter Haven, FL 33884 (MLS # P4932811)
    2725 Attwater Loop, Winter Haven, FL
    2725 Attwater Loop
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,841 Home (sqft)
    • 2 Baths
    • 8,712 Lot (sqft)
  9. Photo of 3166 Laurel Oak Lane, Winter Haven, FL 33884 (MLS # L4948982)
    $330,375
    Photo of 3166 Laurel Oak Lane, Winter Haven, FL 33884 (MLS # L4948982)
    Photo of 3166 Laurel Oak Lane, Winter Haven, FL 33884 (MLS # L4948982)
    3166 Laurel Oak Lane, Winter Haven, FL
    3166 Laurel Oak Lane
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,646 Home (sqft)
    • 2 Baths
    • 6,534 Lot (sqft)
  10. Photo of 5108 Sylas Jax Avenue, Winter Haven, FL 33884 (MLS # L4948981)
    $291,730
    Photo of 5108 Sylas Jax Avenue, Winter Haven, FL 33884 (MLS # L4948981)
    Photo of 5108 Sylas Jax Avenue, Winter Haven, FL 33884 (MLS # L4948981)
    5108 Sylas Jax Avenue, Winter Haven, FL
    5108 Sylas Jax Avenue
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,358 Home (sqft)
    • 2 Baths
    • 4,356 Lot (sqft)
  11. Photo of 317 Hamilton Shores Drive NE, Winter Haven, FL 33881 (MLS # P4932720)
    $1,650,000
    Photo of 317 Hamilton Shores Drive NE, Winter Haven, FL 33881 (MLS # P4932720)
    Photo of 317 Hamilton Shores Drive NE, Winter Haven, FL 33881 (MLS # P4932720)
    317 Hamilton Shores Drive NE, Winter Haven, FL
    317 Hamilton Shores Drive NE
    Winter Haven, FL
    • 5 Beds
    • 5 Baths
    • 5,168 Home (sqft)
    • 5 Baths
    • 40,947 Lot (sqft)
  12. Photo of 1345 Daisy Field Drive, Winter Haven, FL 33884 (MLS # O6258807)
    $329,990
    Photo of 1345 Daisy Field Drive, Winter Haven, FL 33884 (MLS # O6258807)
    Photo of 1345 Daisy Field Drive, Winter Haven, FL 33884 (MLS # O6258807)
    1345 Daisy Field Drive, Winter Haven, FL
    1345 Daisy Field Drive
    Winter Haven, FL
    • 4 Beds
    • 2 Baths
    • 1,828 Home (sqft)
    • 2 Baths
    • 16,989 Lot (sqft)
  13. Photo of 217 W Lake Ina Drive, Winter Haven, FL 33884 (MLS # P4932805)
    $289,000
    Photo of 217 W Lake Ina Drive, Winter Haven, FL 33884 (MLS # P4932805)
    Photo of 217 W Lake Ina Drive, Winter Haven, FL 33884 (MLS # P4932805)
    217 W Lake Ina Drive, Winter Haven, FL
    217 W Lake Ina Drive
    Winter Haven, FL
    • 4 Beds
    • 3 Baths
    • 2,360 Home (sqft)
    • 3 Baths
    • 12,197 Lot (sqft)
  14. Photo of 1429 Wallace Manor Pass, Winter Haven, FL 33880 (MLS # L4948388)
    $285,000
    Photo of 1429 Wallace Manor Pass, Winter Haven, FL 33880 (MLS # L4948388)
    Photo of 1429 Wallace Manor Pass, Winter Haven, FL 33880 (MLS # L4948388)
    1429 Wallace Manor Pass, Winter Haven, FL
    1429 Wallace Manor Pass
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,750 Home (sqft)
    • 2 Baths
    • 5,663 Lot (sqft)
  15. Photo of 3029 Pinetree, Winter Haven, FL 33884 (MLS # P4932801)
    $285,000
    Photo of 3029 Pinetree, Winter Haven, FL 33884 (MLS # P4932801)
    Photo of 3029 Pinetree, Winter Haven, FL 33884 (MLS # P4932801)
    3029 Pinetree, Winter Haven, FL
    3029 Pinetree
    Winter Haven, FL
    • 3 Beds
    • 3 Baths
    • 1,942 Home (sqft)
    • 3 Baths
    • 8,712 Lot (sqft)
  16. 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)
  17. Photo of 569 Drayton Road, Winter Haven, FL 33884 (MLS # S5115822)
    $329,900
    Photo of 569 Drayton Road, Winter Haven, FL 33884 (MLS # S5115822)
    Photo of 569 Drayton Road, Winter Haven, FL 33884 (MLS # S5115822)
    569 Drayton Road, Winter Haven, FL
    569 Drayton Road
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,867 Home (sqft)
    • 2 Baths
    • 10,890 Lot (sqft)
  18. Photo of 497 Mckenna Drive, Winter Haven, FL 33881 (MLS # P4932735)
    $299,900
    Photo of 497 Mckenna Drive, Winter Haven, FL 33881 (MLS # P4932735)
    Photo of 497 Mckenna Drive, Winter Haven, FL 33881 (MLS # P4932735)
    497 Mckenna Drive, Winter Haven, FL
    497 Mckenna Drive
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,461 Home (sqft)
    • 2 Baths
    • 5,663 Lot (sqft)
  19. Photo of 1905 16th Street NW, Winter Haven, FL 33881 (MLS # P4932783)
    $300,000
    Photo of 1905 16th Street NW, Winter Haven, FL 33881 (MLS # P4932783)
    Photo of 1905 16th Street NW, Winter Haven, FL 33881 (MLS # P4932783)
    1905 16th Street NW, Winter Haven, FL
    1905 16th Street NW
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,418 Home (sqft)
    • 2 Baths
    • 11,326 Lot (sqft)
  20. 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)
  21. Photo of 147 Krenson Bay Loop, Winter Haven, FL 33881 (MLS # L4948880)
    $299,900
    Photo of 147 Krenson Bay Loop, Winter Haven, FL 33881 (MLS # L4948880)
    Photo of 147 Krenson Bay Loop, Winter Haven, FL 33881 (MLS # L4948880)
    147 Krenson Bay Loop, Winter Haven, FL
    147 Krenson Bay Loop
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,413 Home (sqft)
    • 2 Baths
    • 5,228 Lot (sqft)
  22. Photo of 1109 Normandy Heights Circle, Winter Haven, FL 33880 (MLS # P4932751)
    $299,900
    Photo of 1109 Normandy Heights Circle, Winter Haven, FL 33880 (MLS # P4932751)
    Photo of 1109 Normandy Heights Circle, Winter Haven, FL 33880 (MLS # P4932751)
    1109 Normandy Heights Circle, Winter Haven, FL
    1109 Normandy Heights Circle
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,582 Home (sqft)
    • 2 Baths
    • 8,277 Lot (sqft)
  23. Photo of 1561 Vienna Square Drive, Winter Haven, FL 33884 (MLS # P4932767)
    $237,000
    Photo of 1561 Vienna Square Drive, Winter Haven, FL 33884 (MLS # P4932767)
    Photo of 1561 Vienna Square Drive, Winter Haven, FL 33884 (MLS # P4932767)
    1561 Vienna Square Drive, Winter Haven, FL
    1561 Vienna Square Drive
    Winter Haven, FL
    • 2 Beds
    • 2 Baths
    • 1,231 Home (sqft)
    • 2 Baths
    • 3,050 Lot (sqft)
  24. Photo of 863 Reflections Loop E, Winter Haven, FL 33884 (MLS # P4932723)
    $259,000
    Photo of 863 Reflections Loop E, Winter Haven, FL 33884 (MLS # P4932723)
    Photo of 863 Reflections Loop E, Winter Haven, FL 33884 (MLS # P4932723)
    30
     
    863 Reflections Loop E, Winter Haven, FL
    863 Reflections Loop E
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,329 Home (sqft)
    • 2 Baths
    • 7,841 Lot (sqft)
  25. Photo of 444 Archaic Drive, Winter Haven, FL 33880 (MLS # O6257676)
    $385,000
    Photo of 444 Archaic Drive, Winter Haven, FL 33880 (MLS # O6257676)
    Photo of 444 Archaic Drive, Winter Haven, FL 33880 (MLS # O6257676)
    444 Archaic Drive, Winter Haven, FL
    444 Archaic Drive
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 2,003 Home (sqft)
    • 2 Baths
    • 10,890 Lot (sqft)
  26. Photo of 236 Hernando Road, Winter Haven, FL 33884 (MLS # P4932757)
    $399,000
    Photo of 236 Hernando Road, Winter Haven, FL 33884 (MLS # P4932757)
    Photo of 236 Hernando Road, Winter Haven, FL 33884 (MLS # P4932757)
    236 Hernando Road, Winter Haven, FL
    236 Hernando Road
    Winter Haven, FL
    • 4 Beds
    • 3 Baths
    • 2,197 Home (sqft)
    • 3 Baths
    • 25,701 Lot (sqft)
  27. Photo of 5844 Royal Hills Circle, Winter Haven, FL 33881 (MLS # P4932762)
    $325,000
    Photo of 5844 Royal Hills Circle, Winter Haven, FL 33881 (MLS # P4932762)
    Photo of 5844 Royal Hills Circle, Winter Haven, FL 33881 (MLS # P4932762)
    5844 Royal Hills Circle, Winter Haven, FL
    5844 Royal Hills Circle
    Winter Haven, FL
    • 4 Beds
    • 4 Baths
    • 3,004 Home (sqft)
    • 4 Baths
    • 8,277 Lot (sqft)
  28. Photo of 672 Wakulla Drive, Winter Haven, FL 33884 (MLS # P4932592)
    $325,000
    Photo of 672 Wakulla Drive, Winter Haven, FL 33884 (MLS # P4932592)
    Photo of 672 Wakulla Drive, Winter Haven, FL 33884 (MLS # P4932592)
    672 Wakulla Drive, Winter Haven, FL
    672 Wakulla Drive
    Winter Haven, FL
    • 3 Beds
    • 2 Baths
    • 1,628 Home (sqft)
    • 2 Baths
    • 10,455 Lot (sqft)
  29. Photo of 3484 Julius Estates Boulevard, Winter Haven, FL 33881 (MLS # L4948836)
    $329,000
    Photo of 3484 Julius Estates Boulevard, Winter Haven, FL 33881 (MLS # L4948836)
    Photo of 3484 Julius Estates Boulevard, Winter Haven, FL 33881 (MLS # L4948836)
    3484 Julius Estates Boulevard, Winter Haven, FL
    3484 Julius Estates Boulevard
    Winter Haven, FL
    • 4 Beds
    • 3 Baths
    • 2,900 Home (sqft)
    • 3 Baths
    • 6,534 Lot (sqft)
  30. Photo of 2065 Isle Royale Court SE #143, Winter Haven, FL 33880 (MLS # P4932653)
    $119,900
    Photo of 2065 Isle Royale Court SE #143, Winter Haven, FL 33880 (MLS # P4932653)
    Photo of 2065 Isle Royale Court SE #143, Winter Haven, FL 33880 (MLS # P4932653)
    2065 Isle Royale Court SE #143, Winter Haven, FL
    2065 Isle Royale Court SE #143
    Winter Haven, FL
    • 1 Bed
    • 1 Bath
    • 648 Home (sqft)
    • 1 Bath
    • 436 Lot (sqft)
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