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 184 | Previous Page 1 of 7 Next

1. 

   $587,960

   

   

   1

    

   4996 Railroad Vine Alley, Winter Garden, FL

   4996 Railroad Vine Alley
   Winter Garden, FL

   • 3 Beds
   • 3 Baths
   • 1,985 Home (sqft)
   • 3 Baths
   • 4,792 Lot (sqft)
2. 

   $568,255

   

   

   1

    

   5008 Railroad Vine Alley, Winter Garden, FL

   5008 Railroad Vine Alley
   Winter Garden, FL

   • 3 Beds
   • 3 Baths
   • 1,788 Home (sqft)
   • 3 Baths
   • 4,792 Lot (sqft)
3. 

   $438,700

   

   

   33

    

    

   14778 Peekskill Drive, Winter Garden, FL

   14778 Peekskill Drive
   Winter Garden, FL

   • 3 Beds
   • 3 Baths
   • 1,831 Home (sqft)
   • 3 Baths
   • 6,970 Lot (sqft)
4. 

   $425,000

   

   

   44

    

   522 S Woodland Street, Winter Garden, FL

   522 S Woodland Street
   Winter Garden, FL

   • 3 Beds
   • 2 Baths
   • 1,412 Home (sqft)
   • 2 Baths
   • 8,712 Lot (sqft)
5. 

   $535,000

   

   

   6

    

    

   15084 Stuttgart Alley, Winter Garden, FL

   15084 Stuttgart Alley
   Winter Garden, FL

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

   $425,000

   

   

   52

    

    

   6185 Elfin Herb Way, Winter Garden, FL

   6185 Elfin Herb Way
   Winter Garden, FL

   • 3 Beds
   • 3 Baths
   • 1,560 Home (sqft)
   • 3 Baths
   • 2,614 Lot (sqft)
7. 

   $560,000

   

   

   31

    

    

   6414 Flat Lemon Drive, Winter Garden, FL

   6414 Flat Lemon Drive
   Winter Garden, FL

   • 3 Beds
   • 2 Baths
   • 1,979 Home (sqft)
   • 2 Baths
   • 5,663 Lot (sqft)
8. 

   $485,000

   

   

   4

    

   16478 Angel Fish Road, Winter Garden, FL

   16478 Angel Fish Road
   Winter Garden, FL

   • 3 Beds
   • 2 Baths
   • 1,685 Home (sqft)
   • 2 Baths
   • 5,663 Lot (sqft)
9. 

   $565,000

   

   

   38

    

    

   14043 Lochend Way, Winter Garden, FL

   14043 Lochend Way
   Winter Garden, FL

   • 4 Beds
   • 4 Baths
   • 2,290 Home (sqft)
   • 4 Baths
   • 2,178 Lot (sqft)
10. 

    $499,900

    

    

    30

     

     

    1021 Jilliam Way, Winter Garden, FL

    1021 Jilliam Way
    Winter Garden, FL

    • 4 Beds
    • 2 Baths
    • 2,047 Home (sqft)
    • 2 Baths
    • 10,890 Lot (sqft)
11. 

    $516,990

    

    

    33

     

     

    15142 Grove Lake Drive, Winter Garden, FL

    15142 Grove Lake Drive
    Winter Garden, FL

    • 3 Beds
    • 3 Baths
    • 1,846 Home (sqft)
    • 3 Baths
    • 2,614 Lot (sqft)
12. 

    $592,695

    

    

    1

     

    11940 Bracco Street, Winter Garden, FL

    11940 Bracco Street
    Winter Garden, FL

    • 3 Beds
    • 3 Baths
    • 2,088 Home (sqft)
    • 3 Baths
    • 4,792 Lot (sqft)
13. 

    $525,000

    

    

    40

     

     

    14035 Lochend Way, Winter Garden, FL

    14035 Lochend Way
    Winter Garden, FL

    • 3 Beds
    • 4 Baths
    • 2,290 Home (sqft)
    • 4 Baths
    • 2,178 Lot (sqft)
14. 

    $530,000

    

    

    49

     

     

    1455 Williams Road, Winter Garden, FL

    1455 Williams Road
    Winter Garden, FL

    • 4 Beds
    • 3 Baths
    • 2,030 Home (sqft)
    • 3 Baths
    • 4,792 Lot (sqft)
15. 

    $450,000

    

    

    37

     

     

    8013 Basilica Lane, Winter Garden, FL

    8013 Basilica Lane
    Winter Garden, FL

    • 3 Beds
    • 3 Baths
    • 1,723 Home (sqft)
    • 3 Baths
    • 3,050 Lot (sqft)
16. 

    $582,000

    

    

    34

     

     

    15554 Gwinnett Drive, Winter Garden, FL

    15554 Gwinnett Drive
    Winter Garden, FL

    • 3 Beds
    • 4 Baths
    • 2,304 Home (sqft)
    • 4 Baths
    • 4,356 Lot (sqft)
17. 

    $424,999

    

    

    30

     

     

    159 9th Street, Winter Garden, FL

    159 9th Street
    Winter Garden, FL

    • 3 Beds
    • 2 Baths
    • 1,188 Home (sqft)
    • 2 Baths
    • 4,792 Lot (sqft)
18. 

    $474,999

    

    

    27

     

     

    16019 Pebble Bluff Loop, Winter Garden, FL

    16019 Pebble Bluff Loop
    Winter Garden, FL

    • 3 Beds
    • 2 Baths
    • 1,685 Home (sqft)
    • 2 Baths
    • 5,228 Lot (sqft)
19. 

    $460,000

    

    

    54

     

     

    6719 Marmalade Alley, Winter Garden, FL

    6719 Marmalade Alley
    Winter Garden, FL

    • 3 Beds
    • 3 Baths
    • 1,936 Home (sqft)
    • 3 Baths
    • 3,050 Lot (sqft)
20. 

    $599,000

    

    

    73

     

     

    267 Doe Run Drive, Winter Garden, FL

    267 Doe Run Drive
    Winter Garden, FL

    • 4 Beds
    • 2 Baths
    • 1,972 Home (sqft)
    • 2 Baths
    • 7,406 Lot (sqft)
21. 

    $459,999

    

    

    29

     

     

    16878 Arrowhead Boulevard, Winter Garden, FL

    16878 Arrowhead Boulevard
    Winter Garden, FL

    • 3 Beds
    • 2 Baths
    • 1,152 Home (sqft)
    • 2 Baths
    • 1.07 Lot (ac)
22. 

    $582,475

    

    

    1

     

    5015 Railroad Vine Alley, Winter Garden, FL

    5015 Railroad Vine Alley
    Winter Garden, FL

    • 3 Beds
    • 3 Baths
    • 2,011 Home (sqft)
    • 3 Baths
    • 4,792 Lot (sqft)
23. 

    $469,000

    

    

    42

     

     

    556 Home Grove Drive, Winter Garden, FL

    556 Home Grove Drive
    Winter Garden, FL

    • 4 Beds
    • 2 Baths
    • 1,705 Home (sqft)
    • 2 Baths
    • 6,534 Lot (sqft)
24. 

    $579,000

    

    

    48

     

    11063 Bostwick Alley, Winter Garden, FL

    11063 Bostwick Alley
    Winter Garden, FL

    • 3 Beds
    • 2 Baths
    • 1,685 Home (sqft)
    • 2 Baths
    • 5,228 Lot (sqft)
25. 

    $485,000

    

    

    38

     

     

    15321 Beamleigh Road, Winter Garden, FL

    15321 Beamleigh Road
    Winter Garden, FL

    • 3 Beds
    • 3 Baths
    • 1,645 Home (sqft)
    • 3 Baths
    • 4,356 Lot (sqft)
26. 

    $435,000

    

    

    45

     

     

    5613 New Independence Parkway, Winter Garden, FL

    5613 New Independence Parkway
    Winter Garden, FL

    • 3 Beds
    • 3 Baths
    • 1,766 Home (sqft)
    • 3 Baths
    • 5,663 Lot (sqft)
27. 

    $415,000

    

    

    8

     

     

    14501 Grove Resort Avenue #2438, Winter Garden, FL

    14501 Grove Resort Avenue #2438
    Winter Garden, FL

    • 3 Beds
    • 2 Baths
    • 1,396 Home (sqft)
    • 2 Baths
    • 1,743 Lot (sqft)
28. 

    $570,000

    

    

    20

     

     

    15542 Sunquat Drive, Winter Garden, FL

    15542 Sunquat Drive
    Winter Garden, FL

    • 3 Beds
    • 2 Baths
    • 1,979 Home (sqft)
    • 2 Baths
    • 7,406 Lot (sqft)
29. 

    $468,000

    

    

    27

     

     

    9658 Amber Chestnut Way, Winter Garden, FL

    9658 Amber Chestnut Way
    Winter Garden, FL

    • 3 Beds
    • 3 Baths
    • 1,503 Home (sqft)
    • 3 Baths
    • 2,614 Lot (sqft)
30. 

    $449,000

    

    

    26

     

     

    133 Agnes Street, Winter Garden, FL

    133 Agnes Street
    Winter Garden, FL

    • 2 Beds
    • 1 Bath
    • 1,287 Home (sqft)
    • 1 Bath
    • 8,712 Lot (sqft)

Previous Page 1 of 7 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 12/22/24 12:20 PM PST.

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