Winter Garden is located 14 miles west of downtown Orlando in the western part of Orange County. Nestled alongside beautiful Lake Apopka, it is a former citrus town incorporated in 1908 and is home to more than 40,000 residents. Its historic downtown is listed on the National Registry of Historic Places and is a favorite destination for residents due to its shops, restaurants, and award-winning West Orange Trail, part of the 250-mile Coast-to-Coast Connector Trail across Central Florida. Use our custom search tool to view all homes for sale between $400k - $600k in Winter Garden 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 214 | Previous Page 1 of 8 Next

1. 

   $474,999

   

   

   42

    

    

   15241 Sunrise Grove Court, Winter Garden, FL

   15241 Sunrise Grove Court
   Winter Garden, FL

   • 3 Beds
   • 3 Baths
   • 1,902 Home (sqft)
   • 3 Baths
   • 3,050 Lot (sqft)
2. 

   $492,500

   

   

   46

    

   6572 Calamondin Drive, Winter Garden, FL

   6572 Calamondin Drive
   Winter Garden, FL

   • 3 Beds
   • 3 Baths
   • 1,908 Home (sqft)
   • 3 Baths
   • 3,050 Lot (sqft)
3. 

   $531,990

   

   

   7

    

    

   16354 Grey Pine Drive, Winter Garden, FL

   16354 Grey Pine Drive
   Winter Garden, FL

   • 3 Beds
   • 3 Baths
   • 1,628 Home (sqft)
   • 3 Baths
   • 6,099 Lot (sqft)
4. 

   $599,000

   

   

   53

    

    

   1212 Hunterman Lane, Winter Garden, FL

   1212 Hunterman Lane
   Winter Garden, FL

   • 4 Beds
   • 2 Baths
   • 2,176 Home (sqft)
   • 2 Baths
   • 13,504 Lot (sqft)
5. 

   $509,000

   

   

   38

    

    

   10414 Austrina Oak Loop, Winter Garden, FL

   10414 Austrina Oak Loop
   Winter Garden, FL

   • 4 Beds
   • 3 Baths
   • 2,204 Home (sqft)
   • 3 Baths
   • 3,921 Lot (sqft)
6. 

   $474,900

   

   

   16

    

   14012 Earlsmede Court, Winter Garden, FL

   14012 Earlsmede Court
   Winter Garden, FL

   • 4 Beds
   • 2 Baths
   • 2,101 Home (sqft)
   • 2 Baths
   • 5,663 Lot (sqft)
7. 

   $425,000

   

   

   48

    

    

   17646 Washington Street, Winter Garden, FL

   17646 Washington Street
   Winter Garden, FL

   • 4 Beds
   • 2 Baths
   • 1,536 Home (sqft)
   • 2 Baths
   • 15,246 Lot (sqft)
8. 

   $578,000

   

   

   38

    

    

   4718 Abbeywood Alley, Winter Garden, FL

   4718 Abbeywood Alley
   Winter Garden, FL

   • 4 Beds
   • 3 Baths
   • 2,114 Home (sqft)
   • 3 Baths
   • 0 Lot (sqft)
9. 

   $465,000

   

   

   31

    

    

   990 Glenview Circle, Winter Garden, FL

   990 Glenview Circle
   Winter Garden, FL

   • 3 Beds
   • 2 Baths
   • 1,444 Home (sqft)
   • 2 Baths
   • 20,038 Lot (sqft)
10. 

    $599,000

    

    

    50

     

     

    15609 Signature Drive, Winter Garden, FL

    15609 Signature Drive
    Winter Garden, FL

    • 6 Beds
    • 3 Baths
    • 2,714 Home (sqft)
    • 3 Baths
    • 6,099 Lot (sqft)
11. 

    $445,900

    

    

    53

     

     

    684 Cascading Creek Lane, Winter Garden, FL

    684 Cascading Creek Lane
    Winter Garden, FL

    • 3 Beds
    • 2 Baths
    • 1,695 Home (sqft)
    • 2 Baths
    • 10,455 Lot (sqft)
12. 

    $570,000

    

    

    27

     

     

    5027 Lake Hamlin Trail, Winter Garden, FL

    5027 Lake Hamlin Trail
    Winter Garden, FL

    • 4 Beds
    • 3 Baths
    • 2,038 Home (sqft)
    • 3 Baths
    • 5,663 Lot (sqft)
13. 

    $579,900

    

    

    22

     

     

    12122 Bracco Street, Winter Garden, FL

    12122 Bracco Street
    Winter Garden, FL

    • 4 Beds
    • 3 Baths
    • 2,114 Home (sqft)
    • 3 Baths
    • 4,356 Lot (sqft)
14. 

    $544,900

    

    

    30

     

     

    930 Butter Oaks Court, Winter Garden, FL

    930 Butter Oaks Court
    Winter Garden, FL

    • 4 Beds
    • 3 Baths
    • 2,098 Home (sqft)
    • 3 Baths
    • 13,068 Lot (sqft)
15. 

    $524,900

    

    

    40

     

     

    11024 Folklore Street, Winter Garden, FL

    11024 Folklore Street
    Winter Garden, FL

    • 3 Beds
    • 3 Baths
    • 2,138 Home (sqft)
    • 3 Baths
    • 5,228 Lot (sqft)
16. 

    $440,000

    

    

    30

     

     

    15588 Blackbead Street, Winter Garden, FL

    15588 Blackbead Street
    Winter Garden, FL

    • 3 Beds
    • 3 Baths
    • 1,559 Home (sqft)
    • 3 Baths
    • 4,792 Lot (sqft)
17. 

    $529,900

    

    

    63

     

     

    9344 Tyrella Pine Trail, Winter Garden, FL

    9344 Tyrella Pine Trail
    Winter Garden, FL

    • 3 Beds
    • 3 Baths
    • 1,838 Home (sqft)
    • 3 Baths
    • 3,050 Lot (sqft)
18. 

    $445,000

    

    

    96

     

     

    16133 Pebble Bluff Loop, Winter Garden, FL

    16133 Pebble Bluff Loop
    Winter Garden, FL

    • 3 Beds
    • 3 Baths
    • 1,568 Home (sqft)
    • 3 Baths
    • 2,614 Lot (sqft)
19. 

    $495,000

    

    

    35

     

     

    15523 Camp Dubois Crescent, Winter Garden, FL

    15523 Camp Dubois Crescent
    Winter Garden, FL

    • 3 Beds
    • 2 Baths
    • 1,720 Home (sqft)
    • 2 Baths
    • 5,663 Lot (sqft)
20. 

    $595,000

    

    

    39

     

     

    5548 Thomas Square Drive, Winter Garden, FL

    5548 Thomas Square Drive
    Winter Garden, FL

    • 3 Beds
    • 4 Baths
    • 2,342 Home (sqft)
    • 4 Baths
    • 4,356 Lot (sqft)
21. 

    $587,000

    

    

    43

     

     

    714 Home Grove Drive, Winter Garden, FL

    714 Home Grove Drive
    Winter Garden, FL

    • 4 Beds
    • 2 Baths
    • 1,992 Home (sqft)
    • 2 Baths
    • 8,712 Lot (sqft)
22. 

    $537,080

    

    

    1

     

    11928 Bracco Street, Winter Garden, FL

    11928 Bracco Street
    Winter Garden, FL

    • 3 Beds
    • 3 Baths
    • 1,788 Home (sqft)
    • 3 Baths
    • 4,356 Lot (sqft)
23. 

    $546,040

    

    

    1

     

    11932 Bracco Street, Winter Garden, FL

    11932 Bracco Street
    Winter Garden, FL

    • 3 Beds
    • 3 Baths
    • 1,985 Home (sqft)
    • 3 Baths
    • 4,356 Lot (sqft)
24. 

    $501,530

    

    

    13

     

    9332 Bolshoi Alley, Winter Garden, FL

    9332 Bolshoi Alley
    Winter Garden, FL

    • 3 Beds
    • 3 Baths
    • 1,835 Home (sqft)
    • 3 Baths
    • 3,485 Lot (sqft)
25. 

    $535,000

    

    

    54

     

     

    6317 Hamlin Reserve Boulevard, Winter Garden, FL

    6317 Hamlin Reserve Boulevard
    Winter Garden, FL

    • 3 Beds
    • 3 Baths
    • 1,990 Home (sqft)
    • 3 Baths
    • 6,970 Lot (sqft)
26. 

    $474,142

    

    

    12

     

     

    9350 Bolshoi Alley, Winter Garden, FL

    9350 Bolshoi Alley
    Winter Garden, FL

    • 3 Beds
    • 3 Baths
    • 1,693 Home (sqft)
    • 3 Baths
    • 2,614 Lot (sqft)
27. 

    $467,990

    

    

    13

     

     

    15375 Burgtheater Drive, Winter Garden, FL

    15375 Burgtheater Drive
    Winter Garden, FL

    • 3 Beds
    • 3 Baths
    • 1,693 Home (sqft)
    • 3 Baths
    • 2,614 Lot (sqft)
28. 

    $499,988

    

    

    12

     

     

    14667 Bahama Swallow Boulevard, Winter Garden, FL

    14667 Bahama Swallow Boulevard
    Winter Garden, FL

    • 3 Beds
    • 2 Baths
    • 1,794 Home (sqft)
    • 2 Baths
    • 5,228 Lot (sqft)
29. 

    $450,000

    

    

    54

     

    15501 Avenue Of The Arbors, Winter Garden, FL

    15501 Avenue Of The Arbors
    Winter Garden, FL

    • 3 Beds
    • 3 Baths
    • 2,146 Home (sqft)
    • 3 Baths
    • 3,485 Lot (sqft)
30. 

    $488,000

    

    

    25

     

     

    6560 Candied Peel Alley, Winter Garden, FL

    6560 Candied Peel Alley
    Winter Garden, FL

    • 4 Beds
    • 4 Baths
    • 1,902 Home (sqft)
    • 4 Baths
    • 5,228 Lot (sqft)

Previous Page 1 of 8 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 11/23/24 2:13 AM PST.

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