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 208 | Previous Page 1 of 7 Next

1. 

   $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)
2. 

   $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)
3. 

   $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)
4. 

   $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)
5. 

   $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)
6. 

   $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)
7. 

   $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)
8. 

   $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)
9. 

   $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)
10. 

    $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)
11. 

    $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)
12. 

    $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)
13. 

    $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)
14. 

    $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)
15. 

    $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)
16. 

    $535,000

    

    

    53

     

     

    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)
17. 

    $534,900

    

    

    100

     

     

    1124 Brandy Creek Drive, Winter Garden, FL

    1124 Brandy Creek Drive
    Winter Garden, FL

    • 3 Beds
    • 2 Baths
    • 1,856 Home (sqft)
    • 2 Baths
    • 9,148 Lot (sqft)
18. 

    $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)
19. 

    $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)
20. 

    $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)
21. 

    $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)
22. 

    $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)
23. 

    $600,000

    

    

    48

     

     

    3286 Hanging Tide Street, Winter Garden, FL

    3286 Hanging Tide Street
    Winter Garden, FL

    • 3 Beds
    • 2 Baths
    • 2,175 Home (sqft)
    • 2 Baths
    • 6,099 Lot (sqft)
24. 

    $479,990

    

    

    22

     

    15877 Tollington Alley, Winter Garden, FL

    15877 Tollington Alley
    Winter Garden, FL

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

    $480,000

    

    

    52

     

     

    14501 Grove Resort Avenue #2122, Winter Garden, FL

    14501 Grove Resort Avenue #2122
    Winter Garden, FL

    • 2 Beds
    • 2 Baths
    • 1,265 Home (sqft)
    • 2 Baths
    • 1,743 Lot (sqft)
26. 

    $475,000

    

    

    31

     

     

    1533 Loch Avich Road, Winter Garden, FL

    1533 Loch Avich Road
    Winter Garden, FL

    • 3 Beds
    • 2 Baths
    • 1,384 Home (sqft)
    • 2 Baths
    • 4,792 Lot (sqft)
27. 

    $589,000

    

    

    40

     

     

    7119 Spring Park Drive, Winter Garden, FL

    7119 Spring Park Drive
    Winter Garden, FL

    • 4 Beds
    • 3 Baths
    • 2,119 Home (sqft)
    • 3 Baths
    • 3,485 Lot (sqft)
28. 

    $479,990

    

    

    11

     

    15076 Grove Lake Drive, Winter Garden, FL

    15076 Grove Lake Drive
    Winter Garden, FL

    • 3 Beds
    • 3 Baths
    • 1,881 Home (sqft)
    • 3 Baths
    • 1,743 Lot (sqft)
29. 

    $539,900

    

    

    29

     

     

    7910 Winter Wren Street, Winter Garden, FL

    7910 Winter Wren Street
    Winter Garden, FL

    • 3 Beds
    • 2 Baths
    • 1,901 Home (sqft)
    • 2 Baths
    • 5,663 Lot (sqft)
30. 

    $520,000

    

    

    25

     

     

    15914 Moonlight Bay Street, Winter Garden, FL

    15914 Moonlight Bay Street
    Winter Garden, FL

    • 3 Beds
    • 2 Baths
    • 1,685 Home (sqft)
    • 2 Baths
    • 5,228 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 11/21/24 2:12 AM PST.

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