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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. Photo of 13172 Dendy Way #9, Winter Garden, FL 34787 (MLS # O6255510)
    $628,714
    Photo of 13172 Dendy Way #9, Winter Garden, FL 34787 (MLS # O6255510)
    Photo of 13172 Dendy Way #9, Winter Garden, FL 34787 (MLS # O6255510)
    13172 Dendy Way #9, Winter Garden, FL
    13172 Dendy Way #9
    Winter Garden, FL
    • 3 Beds
    • 3 Baths
    • 2,207 Home (sqft)
    • 3 Baths
    • 5,663 Lot (sqft)
  2. Photo of 3286 Hanging Tide Street, Winter Garden, FL 34787 (MLS # O6254798)
    $600,000
    Photo of 3286 Hanging Tide Street, Winter Garden, FL 34787 (MLS # O6254798)
    Photo of 3286 Hanging Tide Street, Winter Garden, FL 34787 (MLS # O6254798)
    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)
  3. Photo of 17017 Marsh Road, Winter Garden, FL 34787 (MLS # O6254855)
    $12,000,000
    Photo of 17017 Marsh Road, Winter Garden, FL 34787 (MLS # O6254855)
    Photo of 17017 Marsh Road, Winter Garden, FL 34787 (MLS # O6254855)
    17017 Marsh Road, Winter Garden, FL
    17017 Marsh Road
    Winter Garden, FL
    • 6 Beds
    • 6 Baths
    • 6,977 Home (sqft)
    • 6 Baths
    • 17.88 Lot (ac)
  4. Photo of 14739 Glade Hill Park Way, Winter Garden, FL 34787 (MLS # O6255272)
    $850,000
    Photo of 14739 Glade Hill Park Way, Winter Garden, FL 34787 (MLS # O6255272)
    Photo of 14739 Glade Hill Park Way, Winter Garden, FL 34787 (MLS # O6255272)
    14739 Glade Hill Park Way, Winter Garden, FL
    14739 Glade Hill Park Way
    Winter Garden, FL
    • 4 Beds
    • 4 Baths
    • 2,935 Home (sqft)
    • 4 Baths
    • 6,099 Lot (sqft)
  5. Photo of 13412 Fox Glove Street, Winter Garden, FL 34787 (MLS # G5088860)
    $927,900
    Photo of 13412 Fox Glove Street, Winter Garden, FL 34787 (MLS # G5088860)
    Photo of 13412 Fox Glove Street, Winter Garden, FL 34787 (MLS # G5088860)
    13412 Fox Glove Street, Winter Garden, FL
    13412 Fox Glove Street
    Winter Garden, FL
    • 5 Beds
    • 3 Baths
    • 3,954 Home (sqft)
    • 3 Baths
    • 7,841 Lot (sqft)
  6. Photo of 8136 Key West Dove Street, Winter Garden, FL 34787 (MLS # O6248137)
    $750,000
    Photo of 8136 Key West Dove Street, Winter Garden, FL 34787 (MLS # O6248137)
    Photo of 8136 Key West Dove Street, Winter Garden, FL 34787 (MLS # O6248137)
    8136 Key West Dove Street, Winter Garden, FL
    8136 Key West Dove Street
    Winter Garden, FL
    • 4 Beds
    • 3 Baths
    • 2,450 Home (sqft)
    • 3 Baths
    • 9,584 Lot (sqft)
  7. Photo of 13193 Tollcross Way, Winter Garden, FL 34787 (MLS # S5114849)
    $1,100,000
    Photo of 13193 Tollcross Way, Winter Garden, FL 34787 (MLS # S5114849)
    Photo of 13193 Tollcross Way, Winter Garden, FL 34787 (MLS # S5114849)
    13193 Tollcross Way, Winter Garden, FL
    13193 Tollcross Way
    Winter Garden, FL
    • 5 Beds
    • 5 Baths
    • 4,041 Home (sqft)
    • 5 Baths
    • 7,841 Lot (sqft)
  8. Photo of 14867 Ellingsworth Lane, Winter Garden, FL 34787 (MLS # O6254121)
    $749,000
    Photo of 14867 Ellingsworth Lane, Winter Garden, FL 34787 (MLS # O6254121)
    Photo of 14867 Ellingsworth Lane, Winter Garden, FL 34787 (MLS # O6254121)
    14867 Ellingsworth Lane, Winter Garden, FL
    14867 Ellingsworth Lane
    Winter Garden, FL
    • 4 Beds
    • 3 Baths
    • 2,583 Home (sqft)
    • 3 Baths
    • 10,019 Lot (sqft)
  9. Photo of 8794 Eden Cove Drive, Winter Garden, FL 34787 (MLS # O6252903)
    $625,000
    Photo of 8794 Eden Cove Drive, Winter Garden, FL 34787 (MLS # O6252903)
    Photo of 8794 Eden Cove Drive, Winter Garden, FL 34787 (MLS # O6252903)
    8794 Eden Cove Drive, Winter Garden, FL
    8794 Eden Cove Drive
    Winter Garden, FL
    • 4 Beds
    • 4 Baths
    • 2,477 Home (sqft)
    • 4 Baths
    • 7,406 Lot (sqft)
  10. Photo of 15663 Panther Lake Drive, Winter Garden, FL 34787 (MLS # O6251528)
    $2,450,000
    Photo of 15663 Panther Lake Drive, Winter Garden, FL 34787 (MLS # O6251528)
    Photo of 15663 Panther Lake Drive, Winter Garden, FL 34787 (MLS # O6251528)
    15663 Panther Lake Drive, Winter Garden, FL
    15663 Panther Lake Drive
    Winter Garden, FL
    • 5 Beds
    • 6 Baths
    • 4,709 Home (sqft)
    • 6 Baths
    • 1.18 Lot (ac)
  11. Photo of 15217 Farm Stand Court, Winter Garden, FL 34787 (MLS # O6252886)
    $2,469,000
    Photo of 15217 Farm Stand Court, Winter Garden, FL 34787 (MLS # O6252886)
    Photo of 15217 Farm Stand Court, Winter Garden, FL 34787 (MLS # O6252886)
    15217 Farm Stand Court, Winter Garden, FL
    15217 Farm Stand Court
    Winter Garden, FL
    • 4 Beds
    • 5 Baths
    • 4,219 Home (sqft)
    • 5 Baths
    • 13,940 Lot (sqft)
  12. Photo of 854 Lost Grove Circle, Winter Garden, FL 34787 (MLS # O6252133)
    $649,000
    Photo of 854 Lost Grove Circle, Winter Garden, FL 34787 (MLS # O6252133)
    Photo of 854 Lost Grove Circle, Winter Garden, FL 34787 (MLS # O6252133)
    30
     
    854 Lost Grove Circle, Winter Garden, FL
    854 Lost Grove Circle
    Winter Garden, FL
    • 5 Beds
    • 3 Baths
    • 3,382 Home (sqft)
    • 3 Baths
    • 12,197 Lot (sqft)
  13. Photo of 16653 Toccoa Row, Winter Garden, FL 34787 (MLS # O6253807)
    $795,000
    Photo of 16653 Toccoa Row, Winter Garden, FL 34787 (MLS # O6253807)
    Photo of 16653 Toccoa Row, Winter Garden, FL 34787 (MLS # O6253807)
    16653 Toccoa Row, Winter Garden, FL
    16653 Toccoa Row
    Winter Garden, FL
    • 4 Beds
    • 4 Baths
    • 2,806 Home (sqft)
    • 4 Baths
    • 7,841 Lot (sqft)
  14. Photo of 8168 Gray Kingbird Drive, Winter Garden, FL 34787 (MLS # O6249216)
    $715,000
    Photo of 8168 Gray Kingbird Drive, Winter Garden, FL 34787 (MLS # O6249216)
    Photo of 8168 Gray Kingbird Drive, Winter Garden, FL 34787 (MLS # O6249216)
    8168 Gray Kingbird Drive, Winter Garden, FL
    8168 Gray Kingbird Drive
    Winter Garden, FL
    • 4 Beds
    • 3 Baths
    • 2,445 Home (sqft)
    • 3 Baths
    • 5,228 Lot (sqft)
  15. Photo of 14822 Porter Road, Winter Garden, FL 34787 (MLS # S5114405)
    $619,000
    Photo of 14822 Porter Road, Winter Garden, FL 34787 (MLS # S5114405)
    Photo of 14822 Porter Road, Winter Garden, FL 34787 (MLS # S5114405)
    14822 Porter Road, Winter Garden, FL
    14822 Porter Road
    Winter Garden, FL
    • 3 Beds
    • 3 Baths
    • 2,705 Home (sqft)
    • 3 Baths
    • 10,019 Lot (sqft)
  16. Photo of 1404 High Springs Lane, Winter Garden, FL 34787 (MLS # O6253157)
    $825,000
    Photo of 1404 High Springs Lane, Winter Garden, FL 34787 (MLS # O6253157)
    Photo of 1404 High Springs Lane, Winter Garden, FL 34787 (MLS # O6253157)
    1404 High Springs Lane, Winter Garden, FL
    1404 High Springs Lane
    Winter Garden, FL
    • 4 Beds
    • 4 Baths
    • 3,059 Home (sqft)
    • 4 Baths
    • 10,890 Lot (sqft)
  17. Photo of 16294 Honey Harvest Street, Winter Garden, FL 34787 (MLS # S5114649)
    $655,000
    Photo of 16294 Honey Harvest Street, Winter Garden, FL 34787 (MLS # S5114649)
    Photo of 16294 Honey Harvest Street, Winter Garden, FL 34787 (MLS # S5114649)
    16294 Honey Harvest Street, Winter Garden, FL
    16294 Honey Harvest Street
    Winter Garden, FL
    • 5 Beds
    • 5 Baths
    • 2,725 Home (sqft)
    • 5 Baths
    • 3,485 Lot (sqft)
  18. Photo of 557 Lake Cove Pointe Cir, Winter Garden, FL 34787 (MLS # O6252812)
    $1,795,000
    Photo of 557 Lake Cove Pointe Cir, Winter Garden, FL 34787 (MLS # O6252812)
    Photo of 557 Lake Cove Pointe Cir, Winter Garden, FL 34787 (MLS # O6252812)
    73
     
    557 Lake Cove Pointe Cir, Winter Garden, FL
    557 Lake Cove Pointe Cir
    Winter Garden, FL
    • 5 Beds
    • 5 Baths
    • 4,176 Home (sqft)
    • 5 Baths
    • 16,989 Lot (sqft)
  19. Photo of 14616 Avenue Of The Rushes, Winter Garden, FL 34787 (MLS # S5114500)
    $2,300,000
    Photo of 14616 Avenue Of The Rushes, Winter Garden, FL 34787 (MLS # S5114500)
    Photo of 14616 Avenue Of The Rushes, Winter Garden, FL 34787 (MLS # S5114500)
    80
     
    14616 Avenue Of The Rushes, Winter Garden, FL
    14616 Avenue Of The Rushes
    Winter Garden, FL
    • 4 Beds
    • 5 Baths
    • 4,583 Home (sqft)
    • 5 Baths
    • 1.55 Lot (ac)
  20. Photo of 16874 Muskgrass Drive, Winter Garden, FL 34787 (MLS # O6252050)
    $969,990
    Photo of 16874 Muskgrass Drive, Winter Garden, FL 34787 (MLS # O6252050)
    Photo of 16874 Muskgrass Drive, Winter Garden, FL 34787 (MLS # O6252050)
    13
     
    16874 Muskgrass Drive, Winter Garden, FL
    16874 Muskgrass Drive
    Winter Garden, FL
    • 5 Beds
    • 5 Baths
    • 4,728 Home (sqft)
    • 5 Baths
    • 8,712 Lot (sqft)
  21. Photo of 2800 Tropic Court, Winter Garden, FL 34787 (MLS # O6251898)
    $850,000
    Photo of 2800 Tropic Court, Winter Garden, FL 34787 (MLS # O6251898)
    Photo of 2800 Tropic Court, Winter Garden, FL 34787 (MLS # O6251898)
    2800 Tropic Court, Winter Garden, FL
    2800 Tropic Court
    Winter Garden, FL
    • 5 Beds
    • 3 Baths
    • 2,873 Home (sqft)
    • 3 Baths
    • 25,701 Lot (sqft)
  22. Photo of 14547 Black Lake Preserve Street, Winter Garden, FL 34787 (MLS # S5114454)
    $670,000
    Photo of 14547 Black Lake Preserve Street, Winter Garden, FL 34787 (MLS # S5114454)
    Photo of 14547 Black Lake Preserve Street, Winter Garden, FL 34787 (MLS # S5114454)
    14547 Black Lake Preserve Street, Winter Garden, FL
    14547 Black Lake Preserve Street
    Winter Garden, FL
    • 5 Beds
    • 3 Baths
    • 3,638 Home (sqft)
    • 3 Baths
    • 9,584 Lot (sqft)
  23. Photo of 6157 Glory Bower Drive, Winter Garden, FL 34787 (MLS # O6252965)
    $699,900
    Photo of 6157 Glory Bower Drive, Winter Garden, FL 34787 (MLS # O6252965)
    Photo of 6157 Glory Bower Drive, Winter Garden, FL 34787 (MLS # O6252965)
    6157 Glory Bower Drive, Winter Garden, FL
    6157 Glory Bower Drive
    Winter Garden, FL
    • 5 Beds
    • 3 Baths
    • 2,872 Home (sqft)
    • 3 Baths
    • 6,099 Lot (sqft)
  24. Photo of 14969 Winter Stay Drive, Winter Garden, FL 34787 (MLS # O6251569)
    $1,050,000
    Photo of 14969 Winter Stay Drive, Winter Garden, FL 34787 (MLS # O6251569)
    Photo of 14969 Winter Stay Drive, Winter Garden, FL 34787 (MLS # O6251569)
    56
     
    14969 Winter Stay Drive, Winter Garden, FL
    14969 Winter Stay Drive
    Winter Garden, FL
    • 4 Beds
    • 4 Baths
    • 3,443 Home (sqft)
    • 4 Baths
    • 7,406 Lot (sqft)
  25. Photo of 3220 Sailing Pier Avenue, Winter Garden, FL 34787 (MLS # O6251409)
    $939,000
    Photo of 3220 Sailing Pier Avenue, Winter Garden, FL 34787 (MLS # O6251409)
    Photo of 3220 Sailing Pier Avenue, Winter Garden, FL 34787 (MLS # O6251409)
    3220 Sailing Pier Avenue, Winter Garden, FL
    3220 Sailing Pier Avenue
    Winter Garden, FL
    • 4 Beds
    • 3 Baths
    • 2,363 Home (sqft)
    • 3 Baths
    • 10,019 Lot (sqft)
  26. Photo of 9747 Lost Creek Drive, Winter Garden, FL 34787 (MLS # O6251539)
    $1,210,000
    Photo of 9747 Lost Creek Drive, Winter Garden, FL 34787 (MLS # O6251539)
    Photo of 9747 Lost Creek Drive, Winter Garden, FL 34787 (MLS # O6251539)
    9747 Lost Creek Drive, Winter Garden, FL
    9747 Lost Creek Drive
    Winter Garden, FL
    • 5 Beds
    • 4 Baths
    • 3,910 Home (sqft)
    • 4 Baths
    • 9,584 Lot (sqft)
  27. Photo of 28 E Tilden Street, Winter Garden, FL 34787 (MLS # O6251767)
    $795,000
    Photo of 28 E Tilden Street, Winter Garden, FL 34787 (MLS # O6251767)
    Photo of 28 E Tilden Street, Winter Garden, FL 34787 (MLS # O6251767)
    28 E Tilden Street, Winter Garden, FL
    28 E Tilden Street
    Winter Garden, FL
    • 2 Beds
    • 2 Baths
    • 1,300 Home (sqft)
    • 2 Baths
    • 15,246 Lot (sqft)
  28. Photo of 3448 Current Avenue, Winter Garden, FL 34787 (MLS # O6250455)
    $730,000
    Photo of 3448 Current Avenue, Winter Garden, FL 34787 (MLS # O6250455)
    Photo of 3448 Current Avenue, Winter Garden, FL 34787 (MLS # O6250455)
    3448 Current Avenue, Winter Garden, FL
    3448 Current Avenue
    Winter Garden, FL
    • 4 Beds
    • 5 Baths
    • 2,920 Home (sqft)
    • 5 Baths
    • 7,406 Lot (sqft)
  29. Photo of 10386 Atwater Bay Drive, Winter Garden, FL 34787 (MLS # O6251315)
    $669,000
    Photo of 10386 Atwater Bay Drive, Winter Garden, FL 34787 (MLS # O6251315)
    Photo of 10386 Atwater Bay Drive, Winter Garden, FL 34787 (MLS # O6251315)
    10386 Atwater Bay Drive, Winter Garden, FL
    10386 Atwater Bay Drive
    Winter Garden, FL
    • 4 Beds
    • 3 Baths
    • 2,117 Home (sqft)
    • 3 Baths
    • 6,534 Lot (sqft)
  30. Photo of 5308 Golden Apple Drive, Winter Garden, FL 34787 (MLS # O6251346)
    $769,900
    Photo of 5308 Golden Apple Drive, Winter Garden, FL 34787 (MLS # O6251346)
    Photo of 5308 Golden Apple Drive, Winter Garden, FL 34787 (MLS # O6251346)
    5308 Golden Apple Drive, Winter Garden, FL
    5308 Golden Apple Drive
    Winter Garden, FL
    • 4 Beds
    • 4 Baths
    • 2,724 Home (sqft)
    • 4 Baths
    • 6,099 Lot (sqft)
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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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