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 under $400k 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 - 30 of 500+ | Previous Page 1 of 17 Next

1. 

   $355,000

   

   

   42

    

    

   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. 

   $260,000

   

   

   63

    

    

   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)
3. 

   $220,000

   

   

   42

    

    

   2203 Starboard, Winter Haven, FL

   2203 Starboard
   Winter Haven, FL

   • 2 Beds
   • 2 Baths
   • 1,260 Home (sqft)
   • 2 Baths
   • 3,050 Lot (sqft)
4. 

   $322,990

   

   

   26

    

    

   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)
5. 

   $285,000

   

   

   57

    

    

   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)
6. 

   $250,000

   

   

   25

    

    

   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)
7. 

   $310,000

   

   

   44

    

    

   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)
8. 

   $330,375

   

   

   3

    

   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)
9. 

   $291,730

   

   

   15

    

    

   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)
10. 

    $329,990

    

    

    30

     

     

    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)
11. 

    $289,000

    

    

    35

     

     

    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)
12. 

    $285,000

    

    

    22

     

     

    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)
13. 

    $285,000

    

    

    11

     

     

    3029 Pinetree, Winter Haven, FL

    3029 Pinetree
    Winter Haven, FL

    • 3 Beds
    • 3 Baths
    • 1,942 Home (sqft)
    • 3 Baths
    • 8,712 Lot (sqft)
14. 

    $329,900

    

    

    36

     

     

    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)
15. 

    $299,900

    

    

    39

     

     

    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)
16. 

    $300,000

    

    

    28

     

     

    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)
17. 

    $299,900

    

    

    32

     

     

    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)
18. 

    $299,900

    

    

    41

     

     

    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)
19. 

    $237,000

    

    

    44

     

     

    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)
20. 

    $259,000

    

    

    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)
21. 

    $385,000

    

    

    25

     

     

    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)
22. 

    $399,000

    

    

    42

     

     

    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)
23. 

    $325,000

    

    

    41

     

     

    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)
24. 

    $325,000

    

    

    39

     

     

    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)
25. 

    $329,000

    

    

    29

     

     

    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)
26. 

    $119,900

    

    

    29

     

     

    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)
27. 

    $314,995

    

    

    34

     

     

    1802 Emily Drive, Winter Haven, FL

    1802 Emily Drive
    Winter Haven, FL

    • 4 Beds
    • 3 Baths
    • 2,200 Home (sqft)
    • 3 Baths
    • 8,712 Lot (sqft)
28. 

    $280,000

    

    

    30

     

     

    1210 Tangerine Parkway NE, Winter Haven, FL

    1210 Tangerine Parkway NE
    Winter Haven, FL

    • 4 Beds
    • 2 Baths
    • 1,444 Home (sqft)
    • 2 Baths
    • 12,197 Lot (sqft)
29. 

    $314,900

    

    

    16

     

     

    4066 Island Lakes Drive, Winter Haven, FL

    4066 Island Lakes Drive
    Winter Haven, FL

    • 4 Beds
    • 2 Baths
    • 2,046 Home (sqft)
    • 2 Baths
    • 6,970 Lot (sqft)
30. 

    $375,000

    

    

    56

     

     

    2741 Attwater Loop, Winter Haven, FL

    2741 Attwater Loop
    Winter Haven, FL

    • 3 Beds
    • 2 Baths
    • 1,841 Home (sqft)
    • 2 Baths
    • 5,228 Lot (sqft)

Previous Page 1 of 17 Next

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 11/21/24 2:12 AM PST.

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