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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 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. Photo of 2640 Balforn Tower Way, Winter Garden, FL 34787 (MLS # S5103872)
    $479,000
    Photo of 2640 Balforn Tower Way, Winter Garden, FL 34787 (MLS # S5103872)
    Photo of 2640 Balforn Tower Way, Winter Garden, FL 34787 (MLS # S5103872)
    2640 Balforn Tower Way, Winter Garden, FL
    2640 Balforn Tower Way
    Winter Garden, FL
    • 4 Beds
    • 2 Baths
    • 1,980 Home (sqft)
    • 2 Baths
    • 5,663 Lot (sqft)
  2. Photo of 16417 Parable Way, Winter Garden, FL 34787 (MLS # O6198878)
    $560,000
    Photo of 16417 Parable Way, Winter Garden, FL 34787 (MLS # O6198878)
    Photo of 16417 Parable Way, Winter Garden, FL 34787 (MLS # O6198878)
    16417 Parable Way, Winter Garden, FL
    16417 Parable Way
    Winter Garden, FL
    • 4 Beds
    • 4 Baths
    • 2,494 Home (sqft)
    • 4 Baths
    • 5,228 Lot (sqft)
  3. Photo of 16236 Castelo Lime Alley, Winter Garden, FL 34787 (MLS # G5081277)
    $455,990
    Photo of 16236 Castelo Lime Alley, Winter Garden, FL 34787 (MLS # G5081277)
    Photo of 16236 Castelo Lime Alley, Winter Garden, FL 34787 (MLS # G5081277)
    16236 Castelo Lime Alley, Winter Garden, FL
    16236 Castelo Lime Alley
    Winter Garden, FL
    • 3 Beds
    • 3 Baths
    • 1,729 Home (sqft)
    • 3 Baths
    • 3,050 Lot (sqft)
  4. Photo of 13127 Calming Breeze Way, Winter Garden, FL 34787 (MLS # G5081272)
    $531,001
    Photo of 13127 Calming Breeze Way, Winter Garden, FL 34787 (MLS # G5081272)
    Photo of 13127 Calming Breeze Way, Winter Garden, FL 34787 (MLS # G5081272)
    13127 Calming Breeze Way, Winter Garden, FL
    13127 Calming Breeze Way
    Winter Garden, FL
    • 3 Beds
    • 3 Baths
    • 2,078 Home (sqft)
    • 3 Baths
    • 4,792 Lot (sqft)
  5. Photo of 1769 Morning Sky Drive, Winter Garden, FL 34787 (MLS # O6197859)
    $545,000
    Photo of 1769 Morning Sky Drive, Winter Garden, FL 34787 (MLS # O6197859)
    Photo of 1769 Morning Sky Drive, Winter Garden, FL 34787 (MLS # O6197859)
    1769 Morning Sky Drive, Winter Garden, FL
    1769 Morning Sky Drive
    Winter Garden, FL
    • 4 Beds
    • 3 Baths
    • 2,851 Home (sqft)
    • 3 Baths
    • 6,099 Lot (sqft)
  6. Photo of 751 Bending Oak Trail, Winter Garden, FL 34787 (MLS # G5080601)
    $450,000
    Photo of 751 Bending Oak Trail, Winter Garden, FL 34787 (MLS # G5080601)
    Photo of 751 Bending Oak Trail, Winter Garden, FL 34787 (MLS # G5080601)
    751 Bending Oak Trail, Winter Garden, FL
    751 Bending Oak Trail
    Winter Garden, FL
    • 4 Beds
    • 4 Baths
    • 2,417 Home (sqft)
    • 4 Baths
    • 4,356 Lot (sqft)
  7. Photo of 148 Blue Stone Circle, Winter Garden, FL 34787 (MLS # O6192280)
    $586,000
    Photo of 148 Blue Stone Circle, Winter Garden, FL 34787 (MLS # O6192280)
    Photo of 148 Blue Stone Circle, Winter Garden, FL 34787 (MLS # O6192280)
    148 Blue Stone Circle, Winter Garden, FL
    148 Blue Stone Circle
    Winter Garden, FL
    • 3 Beds
    • 3 Baths
    • 2,323 Home (sqft)
    • 3 Baths
    • 10,019 Lot (sqft)
  8. Photo of 17515 Satsuma Circle, Winter Garden, FL 34787 (MLS # S5101112)
    $465,000
    Photo of 17515 Satsuma Circle, Winter Garden, FL 34787 (MLS # S5101112)
    Photo of 17515 Satsuma Circle, Winter Garden, FL 34787 (MLS # S5101112)
    17515 Satsuma Circle, Winter Garden, FL
    17515 Satsuma Circle
    Winter Garden, FL
    • 3 Beds
    • 3 Baths
    • 1,872 Home (sqft)
    • 3 Baths
    • 18,296 Lot (sqft)
  9. Photo of 14501 Grove Resort Avenue #2627, Winter Garden, FL 34787 (MLS # O6184566)
    $450,000
    Photo of 14501 Grove Resort Avenue #2627, Winter Garden, FL 34787 (MLS # O6184566)
    Photo of 14501 Grove Resort Avenue #2627, Winter Garden, FL 34787 (MLS # O6184566)
    14501 Grove Resort Avenue #2627, Winter Garden, FL
    14501 Grove Resort Avenue #2627
    Winter Garden, FL
    • 3 Beds
    • 3 Baths
    • 1,544 Home (sqft)
    • 3 Baths
    • 1,743 Lot (sqft)
  10. Photo of 14501 Grove Resort Avenue #3327, Winter Garden, FL 34787 (MLS # O6178930)
    $460,000
    Photo of 14501 Grove Resort Avenue #3327, Winter Garden, FL 34787 (MLS # O6178930)
    Photo of 14501 Grove Resort Avenue #3327, Winter Garden, FL 34787 (MLS # O6178930)
    14501 Grove Resort Avenue #3327, Winter Garden, FL
    14501 Grove Resort Avenue #3327
    Winter Garden, FL
    • 3 Beds
    • 3 Baths
    • 1,544 Home (sqft)
    • 3 Baths
    • 1,743 Lot (sqft)
  11. Photo of 8009 Atlantic Puffin Street, Winter Garden, FL 34787 (MLS # O6175971)
    $465,000
    Photo of 8009 Atlantic Puffin Street, Winter Garden, FL 34787 (MLS # O6175971)
    Photo of 8009 Atlantic Puffin Street, Winter Garden, FL 34787 (MLS # O6175971)
    15
     
    8009 Atlantic Puffin Street, Winter Garden, FL
    8009 Atlantic Puffin Street
    Winter Garden, FL
    • 3 Beds
    • 2 Baths
    • 1,801 Home (sqft)
    • 2 Baths
    • 5,228 Lot (sqft)
  12. Photo of 14501 Grove Resort Avenue #2138, Winter Garden, FL 34787 (MLS # O6177763)
    $430,000
    Photo of 14501 Grove Resort Avenue #2138, Winter Garden, FL 34787 (MLS # O6177763)
    Photo of 14501 Grove Resort Avenue #2138, Winter Garden, FL 34787 (MLS # O6177763)
    14501 Grove Resort Avenue #2138, Winter Garden, FL
    14501 Grove Resort Avenue #2138
    Winter Garden, FL
    • 3 Beds
    • 2 Baths
    • 1,396 Home (sqft)
    • 2 Baths
    • 1,307 Lot (sqft)
  13. Photo of 14501 Grove Resort Avenue #2740, Winter Garden, FL 34787 (MLS # O6175624)
    $539,000
    Photo of 14501 Grove Resort Avenue #2740, Winter Garden, FL 34787 (MLS # O6175624)
    Photo of 14501 Grove Resort Avenue #2740, Winter Garden, FL 34787 (MLS # O6175624)
    14501 Grove Resort Avenue #2740, Winter Garden, FL
    14501 Grove Resort Avenue #2740
    Winter Garden, FL
    • 2 Beds
    • 2 Baths
    • 1,265 Home (sqft)
    • 2 Baths
    • 1,743 Lot (sqft)
  14. Photo of 14038 Scarlet Aster Alley, Winter Garden, FL 34787 (MLS # O6170562)
    $459,000
    Photo of 14038 Scarlet Aster Alley, Winter Garden, FL 34787 (MLS # O6170562)
    Photo of 14038 Scarlet Aster Alley, Winter Garden, FL 34787 (MLS # O6170562)
    14038 Scarlet Aster Alley, Winter Garden, FL
    14038 Scarlet Aster Alley
    Winter Garden, FL
    • 3 Beds
    • 3 Baths
    • 1,785 Home (sqft)
    • 3 Baths
    • 2,178 Lot (sqft)
  15. Photo of 13060 Serene Glade Road, Winter Garden, FL 34787 (MLS # G5077114)
    $542,140
    Photo of 13060 Serene Glade Road, Winter Garden, FL 34787 (MLS # G5077114)
    Photo of 13060 Serene Glade Road, Winter Garden, FL 34787 (MLS # G5077114)
    13060 Serene Glade Road, Winter Garden, FL
    13060 Serene Glade Road
    Winter Garden, FL
    • 3 Beds
    • 3 Baths
    • 1,836 Home (sqft)
    • 3 Baths
    • 3,921 Lot (sqft)
  16. Photo of 13054 Serene Glade Road, Winter Garden, FL 34787 (MLS # G5077109)
    $552,500
    Photo of 13054 Serene Glade Road, Winter Garden, FL 34787 (MLS # G5077109)
    Photo of 13054 Serene Glade Road, Winter Garden, FL 34787 (MLS # G5077109)
    13054 Serene Glade Road, Winter Garden, FL
    13054 Serene Glade Road
    Winter Garden, FL
    • 3 Beds
    • 3 Baths
    • 2,078 Home (sqft)
    • 3 Baths
    • 3,921 Lot (sqft)
  17. Photo of 13048 Serene Glade Road, Winter Garden, FL 34787 (MLS # G5077104)
    $565,877
    Photo of 13048 Serene Glade Road, Winter Garden, FL 34787 (MLS # G5077104)
    Photo of 13048 Serene Glade Road, Winter Garden, FL 34787 (MLS # G5077104)
    13048 Serene Glade Road, Winter Garden, FL
    13048 Serene Glade Road
    Winter Garden, FL
    • 3 Beds
    • 3 Baths
    • 2,083 Home (sqft)
    • 3 Baths
    • 3,921 Lot (sqft)
  18. Photo of 14501 Grove Resort Ave #2410, Winter Garden, FL 34787 (MLS # O6168068)
    $449,000
    Photo of 14501 Grove Resort Ave #2410, Winter Garden, FL 34787 (MLS # O6168068)
    Photo of 14501 Grove Resort Ave #2410, Winter Garden, FL 34787 (MLS # O6168068)
    14501 Grove Resort Ave #2410, Winter Garden, FL
    14501 Grove Resort Ave #2410
    Winter Garden, FL
    • 2 Beds
    • 2 Baths
    • 1,434 Home (sqft)
    • 2 Baths
    • 1,743 Lot (sqft)
  19. Photo of 14501 Grove Resort Avenue #2522, Winter Garden, FL 34787 (MLS # O6167655)
    $450,000
    Photo of 14501 Grove Resort Avenue #2522, Winter Garden, FL 34787 (MLS # O6167655)
    Photo of 14501 Grove Resort Avenue #2522, Winter Garden, FL 34787 (MLS # O6167655)
    14501 Grove Resort Avenue #2522, Winter Garden, FL
    14501 Grove Resort Avenue #2522
    Winter Garden, FL
    • 2 Beds
    • 2 Baths
    • 1,265 Home (sqft)
    • 2 Baths
    • 1,743 Lot (sqft)
  20. Photo of 14501 Grove Resort Avenue #2733, Winter Garden, FL 34787 (MLS # O6165808)
    $420,000
    Photo of 14501 Grove Resort Avenue #2733, Winter Garden, FL 34787 (MLS # O6165808)
    Photo of 14501 Grove Resort Avenue #2733, Winter Garden, FL 34787 (MLS # O6165808)
    14501 Grove Resort Avenue #2733, Winter Garden, FL
    14501 Grove Resort Avenue #2733
    Winter Garden, FL
    • 3 Beds
    • 2 Baths
    • 1,396 Home (sqft)
    • 2 Baths
    • 1,743 Lot (sqft)
  21. Photo of 14501 Grove Resort Avenue #2738, Winter Garden, FL 34787 (MLS # O6165813)
    $420,000
    Photo of 14501 Grove Resort Avenue #2738, Winter Garden, FL 34787 (MLS # O6165813)
    Photo of 14501 Grove Resort Avenue #2738, Winter Garden, FL 34787 (MLS # O6165813)
    14501 Grove Resort Avenue #2738, Winter Garden, FL
    14501 Grove Resort Avenue #2738
    Winter Garden, FL
    • 3 Beds
    • 2 Baths
    • 1,396 Home (sqft)
    • 2 Baths
    • 1,743 Lot (sqft)
  22. Photo of 16998 Hamlin Oasis Loop, Winter Garden, FL 34787 (MLS # G5076633)
    $585,429
    Photo of 16998 Hamlin Oasis Loop, Winter Garden, FL 34787 (MLS # G5076633)
    Photo of 16998 Hamlin Oasis Loop, Winter Garden, FL 34787 (MLS # G5076633)
    16998 Hamlin Oasis Loop, Winter Garden, FL
    16998 Hamlin Oasis Loop
    Winter Garden, FL
    • 4 Beds
    • 3 Baths
    • 2,083 Home (sqft)
    • 3 Baths
    • 3,921 Lot (sqft)
  23. Photo of 16980 Hamlin Oasis Loop, Winter Garden, FL 34787 (MLS # G5076629)
    $575,428
    Photo of 16980 Hamlin Oasis Loop, Winter Garden, FL 34787 (MLS # G5076629)
    Photo of 16980 Hamlin Oasis Loop, Winter Garden, FL 34787 (MLS # G5076629)
    16980 Hamlin Oasis Loop, Winter Garden, FL
    16980 Hamlin Oasis Loop
    Winter Garden, FL
    • 3 Beds
    • 3 Baths
    • 1,836 Home (sqft)
    • 3 Baths
    • 3,921 Lot (sqft)
  24. Photo of 14501 Grove Resort Avenue #3716, Winter Garden, FL 34787 (MLS # O6163898)
    $434,900
    Photo of 14501 Grove Resort Avenue #3716, Winter Garden, FL 34787 (MLS # O6163898)
    Photo of 14501 Grove Resort Avenue #3716, Winter Garden, FL 34787 (MLS # O6163898)
    14501 Grove Resort Avenue #3716, Winter Garden, FL
    14501 Grove Resort Avenue #3716
    Winter Garden, FL
    • 3 Beds
    • 2 Baths
    • 1,396 Home (sqft)
    • 2 Baths
    • 1,743 Lot (sqft)
  25. Photo of 1130 Burland Circle, Winter Garden, FL 34787 (MLS # O6160815)
    $579,900
    Photo of 1130 Burland Circle, Winter Garden, FL 34787 (MLS # O6160815)
    Photo of 1130 Burland Circle, Winter Garden, FL 34787 (MLS # O6160815)
    1130 Burland Circle, Winter Garden, FL
    1130 Burland Circle
    Winter Garden, FL
    • 5 Beds
    • 4 Baths
    • 4,046 Home (sqft)
    • 4 Baths
    • 8,712 Lot (sqft)
  26. Photo of 16837 Arrowhead Boulevard, Winter Garden, FL 34787 (MLS # O6158461)
    $599,000
    Photo of 16837 Arrowhead Boulevard, Winter Garden, FL 34787 (MLS # O6158461)
    Photo of 16837 Arrowhead Boulevard, Winter Garden, FL 34787 (MLS # O6158461)
    16837 Arrowhead Boulevard, Winter Garden, FL
    16837 Arrowhead Boulevard
    Winter Garden, FL
    • 3 Beds
    • 2 Baths
    • 1,299 Home (sqft)
    • 2 Baths
    • 1.28 Lot (ac)
  27. Photo of 14501 Grove Resort Avenue #1535, Winter Garden, FL 34787 (MLS # S5094196)
    $419,990
    Photo of 14501 Grove Resort Avenue #1535, Winter Garden, FL 34787 (MLS # S5094196)
    Photo of 14501 Grove Resort Avenue #1535, Winter Garden, FL 34787 (MLS # S5094196)
    14501 Grove Resort Avenue #1535, Winter Garden, FL
    14501 Grove Resort Avenue #1535
    Winter Garden, FL
    • 3 Beds
    • 2 Baths
    • 1,396 Home (sqft)
    • 2 Baths
    • 1,743 Lot (sqft)
  28. Photo of 17055 Wynford Lane, Winter Garden, FL 34787 (MLS # G5074202)
    $549,900
    Photo of 17055 Wynford Lane, Winter Garden, FL 34787 (MLS # G5074202)
    Photo of 17055 Wynford Lane, Winter Garden, FL 34787 (MLS # G5074202)
    17055 Wynford Lane, Winter Garden, FL
    17055 Wynford Lane
    Winter Garden, FL
    • 3 Beds
    • 3 Baths
    • 2,341 Home (sqft)
    • 3 Baths
    • 3,485 Lot (sqft)
  29. Photo of 14501 Grove Resort Avenue #2541, Winter Garden, FL 34787 (MLS # O6128999)
    $415,000
    Photo of 14501 Grove Resort Avenue #2541, Winter Garden, FL 34787 (MLS # O6128999)
    Photo of 14501 Grove Resort Avenue #2541, Winter Garden, FL 34787 (MLS # O6128999)
    18
     
    14501 Grove Resort Avenue #2541, Winter Garden, FL
    14501 Grove Resort Avenue #2541
    Winter Garden, FL
    • 3 Beds
    • 2 Baths
    • 1,396 Home (sqft)
    • 2 Baths
    • 1,743 Lot (sqft)
  30. Photo of 14501 Grove Resort Avenue #3220, Winter Garden, FL 34787 (MLS # O6085058)
    $460,000
    Photo of 14501 Grove Resort Avenue #3220, Winter Garden, FL 34787 (MLS # O6085058)
    Photo of 14501 Grove Resort Avenue #3220, Winter Garden, FL 34787 (MLS # O6085058)
    14501 Grove Resort Avenue #3220, Winter Garden, FL
    14501 Grove Resort Avenue #3220
    Winter Garden, FL
    • 2 Beds
    • 2 Baths
    • 1,265 Home (sqft)
    • 2 Baths
    • 1,307 Lot (sqft)
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