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 above $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 244 | Previous Page 1 of 9 Next

1. 

   $649,900

   

   

   39

    

   1850 Jean Marie Drive, Winter Garden, FL

   1850 Jean Marie Drive
   Winter Garden, FL

   • 4 Beds
   • 3 Baths
   • 2,833 Home (sqft)
   • 3 Baths
   • 9,148 Lot (sqft)
2. 

   $674,500

   

   

   36

    

    

   8066 Bowery Drive, Winter Garden, FL

   8066 Bowery Drive
   Winter Garden, FL

   • 4 Beds
   • 3 Baths
   • 2,579 Home (sqft)
   • 3 Baths
   • 6,534 Lot (sqft)
3. 

   $740,000

   

   

   62

    

    

   15583 Hamlin Blossom Avenue, Winter Garden, FL

   15583 Hamlin Blossom Avenue
   Winter Garden, FL

   • 4 Beds
   • 3 Baths
   • 2,817 Home (sqft)
   • 3 Baths
   • 6,534 Lot (sqft)
4. 

   $620,000

   

   

   32

    

    

   523 Cascading Creek Lane, Winter Garden, FL

   523 Cascading Creek Lane
   Winter Garden, FL

   • 4 Beds
   • 2 Baths
   • 2,365 Home (sqft)
   • 2 Baths
   • 10,019 Lot (sqft)
5. 

   $4,500,000

   

   

   5

    

   15614 Espalier Way, Winter Garden, FL

   15614 Espalier Way
   Winter Garden, FL

   • 5 Beds
   • 7 Baths
   • 6,601 Home (sqft)
   • 7 Baths
   • 2.19 Lot (ac)
6. 

   $605,000

   

   

   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)
7. 

   $760,000

   

   

   32

    

    

   658 Lake Cove Pointe Circle, Winter Garden, FL

   658 Lake Cove Pointe Circle
   Winter Garden, FL

   • 4 Beds
   • 2 Baths
   • 2,463 Home (sqft)
   • 2 Baths
   • 10,019 Lot (sqft)
8. 

   $770,000

   

   

   30

    

    

   1349 Castleport Road, Winter Garden, FL

   1349 Castleport Road
   Winter Garden, FL

   • 5 Beds
   • 4 Baths
   • 3,673 Home (sqft)
   • 4 Baths
   • 7,406 Lot (sqft)
9. 

   $1,150,000

   

   

   58

    

    

   15049 Canopy Cover Dr, Winter Garden, FL

   15049 Canopy Cover Dr
   Winter Garden, FL

   • 2 Beds
   • 3 Baths
   • 2,282 Home (sqft)
   • 3 Baths
   • 8,277 Lot (sqft)
10. 

    $605,000

    

    

    23

     

     

    15121 Pigeon Plum Lane, Winter Garden, FL

    15121 Pigeon Plum Lane
    Winter Garden, FL

    • 3 Beds
    • 3 Baths
    • 2,004 Home (sqft)
    • 3 Baths
    • 5,228 Lot (sqft)
11. 

    $903,875

    

    

    10

     

     

    16409 Silver Grove Boulevard, Winter Garden, FL

    16409 Silver Grove Boulevard
    Winter Garden, FL

    • 5 Beds
    • 5 Baths
    • 3,871 Home (sqft)
    • 5 Baths
    • 10,890 Lot (sqft)
12. 

    $875,000

    

    

    60

     

     

    663 Caterpillar Run, Winter Garden, FL

    663 Caterpillar Run
    Winter Garden, FL

    • 5 Beds
    • 4 Baths
    • 4,258 Home (sqft)
    • 4 Baths
    • 8,712 Lot (sqft)
13. 

    $789,000

    

    

    33

     

     

    8325 Topsail Place, Winter Garden, FL

    8325 Topsail Place
    Winter Garden, FL

    • 3 Beds
    • 2 Baths
    • 2,170 Home (sqft)
    • 2 Baths
    • 6,534 Lot (sqft)
14. 

    $1,199,995

    

    

    43

     

     

    16556 Olive Hill Drive, Winter Garden, FL

    16556 Olive Hill Drive
    Winter Garden, FL

    • 5 Beds
    • 4 Baths
    • 3,752 Home (sqft)
    • 4 Baths
    • 9,148 Lot (sqft)
15. 

    $2,200,000

    

    

    78

     

     

    7645 Green Mountain Way, Winter Garden, FL

    7645 Green Mountain Way
    Winter Garden, FL

    • 4 Beds
    • 4 Baths
    • 3,296 Home (sqft)
    • 4 Baths
    • 33,977 Lot (sqft)
16. 

    $809,685

    

    

    1

     

    16397 Silver Grove Boulevard, Winter Garden, FL

    16397 Silver Grove Boulevard
    Winter Garden, FL

    • 4 Beds
    • 4 Baths
    • 2,950 Home (sqft)
    • 4 Baths
    • 8,712 Lot (sqft)
17. 

    $1,850,000

    

    

    63

     

    7573 Green Mountain Way, Winter Garden, FL

    7573 Green Mountain Way
    Winter Garden, FL

    • 4 Beds
    • 4 Baths
    • 3,388 Home (sqft)
    • 4 Baths
    • 1.26 Lot (ac)
18. 

    $800,000

    

    

    65

     

     

    1249 Selbydon Way, Winter Garden, FL

    1249 Selbydon Way
    Winter Garden, FL

    • 5 Beds
    • 3 Baths
    • 3,492 Home (sqft)
    • 3 Baths
    • 11,762 Lot (sqft)
19. 

    $2,175,000

    

    

    85

     

     

    15687 Panther Lake Drive, Winter Garden, FL

    15687 Panther Lake Drive
    Winter Garden, FL

    • 4 Beds
    • 5 Baths
    • 4,276 Home (sqft)
    • 5 Baths
    • 20,909 Lot (sqft)
20. 

    $897,730

    

    

    12

     

    16862 Muskgrass Drive, Winter Garden, FL

    16862 Muskgrass Drive
    Winter Garden, FL

    • 5 Beds
    • 5 Baths
    • 4,340 Home (sqft)
    • 5 Baths
    • 8,712 Lot (sqft)
21. 

    $1,250,000

    

    

    34

     

     

    128 N Highland Avenue, Winter Garden, FL

    128 N Highland Avenue
    Winter Garden, FL

    • 4 Beds
    • 3 Baths
    • 2,332 Home (sqft)
    • 3 Baths
    • 14,811 Lot (sqft)
22. 

    $669,000

    

    

    51

     

     

    2019 Wintermere Pointe Drive, Winter Garden, FL

    2019 Wintermere Pointe Drive
    Winter Garden, FL

    • 4 Beds
    • 3 Baths
    • 2,455 Home (sqft)
    • 3 Baths
    • 13,068 Lot (sqft)
23. 

    $1,200,000

    

    

    14

     

     

    1669 Markel Drive, Winter Garden, FL

    1669 Markel Drive
    Winter Garden, FL

    • 4 Beds
    • 4 Baths
    • 2,965 Home (sqft)
    • 4 Baths
    • 20,909 Lot (sqft)
24. 

    $639,900

    

    

    50

     

     

    15503 Marina Bay Drive, Winter Garden, FL

    15503 Marina Bay Drive
    Winter Garden, FL

    • 4 Beds
    • 4 Baths
    • 2,477 Home (sqft)
    • 4 Baths
    • 8,712 Lot (sqft)
25. 

    $680,000

    

    

    50

     

     

    15542 Gwinnett Drive, Winter Garden, FL

    15542 Gwinnett Drive
    Winter Garden, FL

    • 5 Beds
    • 4 Baths
    • 3,157 Home (sqft)
    • 4 Baths
    • 4,356 Lot (sqft)
26. 

    $650,000

    

    

    67

     

     

    18 Cooledge Street, Winter Garden, FL

    18 Cooledge Street
    Winter Garden, FL

    • 4 Beds
    • 2 Baths
    • 2,128 Home (sqft)
    • 2 Baths
    • 9,584 Lot (sqft)
27. 

    $625,000

    

    

    24

     

     

    1849 Burdock Drive, Winter Garden, FL

    1849 Burdock Drive
    Winter Garden, FL

    • 4 Beds
    • 3 Baths
    • 2,683 Home (sqft)
    • 3 Baths
    • 10,455 Lot (sqft)
28. 

    $930,000

    

    

    55

     

     

    15356 Heron Hideaway Circle, Winter Garden, FL

    15356 Heron Hideaway Circle
    Winter Garden, FL

    • 5 Beds
    • 4 Baths
    • 4,084 Home (sqft)
    • 4 Baths
    • 7,841 Lot (sqft)
29. 

    $690,811

    

    

    31

     

     

    12614 Clear Sapphire Drive #137, Winter Garden, FL

    12614 Clear Sapphire Drive #137
    Winter Garden, FL

    • 4 Beds
    • 3 Baths
    • 2,743 Home (sqft)
    • 3 Baths
    • 3,921 Lot (sqft)
30. 

    $680,587

    

    

    2

     

     

    13184 Dendy Way #7, Winter Garden, FL

    13184 Dendy Way #7
    Winter Garden, FL

    • 3 Beds
    • 3 Baths
    • 2,207 Home (sqft)
    • 3 Baths
    • 5,663 Lot (sqft)

Previous Page 1 of 9 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 12:12 AM PST.

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