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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 pool 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 16354 Grey Pine Drive, Winter Garden, FL 34787 (MLS # O6259632)
    $531,990
    Photo of 16354 Grey Pine Drive, Winter Garden, FL 34787 (MLS # O6259632)
    Photo of 16354 Grey Pine Drive, Winter Garden, FL 34787 (MLS # O6259632)
    16354 Grey Pine Drive, Winter Garden, FL
    16354 Grey Pine Drive
    Winter Garden, FL
    • 3 Beds
    • 3 Baths
    • 1,628 Home (sqft)
    • 3 Baths
    • 6,099 Lot (sqft)
  2. Photo of 714 Home Grove Drive, Winter Garden, FL 34787 (MLS # S5115534)
    $587,000
    Photo of 714 Home Grove Drive, Winter Garden, FL 34787 (MLS # S5115534)
    Photo of 714 Home Grove Drive, Winter Garden, FL 34787 (MLS # S5115534)
    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)
  3. Photo of 1533 Loch Avich Road, Winter Garden, FL 34787 (MLS # O6254633)
    $455,000
    Photo of 1533 Loch Avich Road, Winter Garden, FL 34787 (MLS # O6254633)
    Photo of 1533 Loch Avich Road, Winter Garden, FL 34787 (MLS # O6254633)
    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)
  4. Photo of 14501 Grove Resort Avenue #2532, Winter Garden, FL 34787 (MLS # S5114233)
    $420,000
    Photo of 14501 Grove Resort Avenue #2532, Winter Garden, FL 34787 (MLS # S5114233)
    Photo of 14501 Grove Resort Avenue #2532, Winter Garden, FL 34787 (MLS # S5114233)
    14501 Grove Resort Avenue #2532, Winter Garden, FL
    14501 Grove Resort Avenue #2532
    Winter Garden, FL
    • 2 Beds
    • 2 Baths
    • 1,265 Home (sqft)
    • 2 Baths
    • 1,307 Lot (sqft)
  5. Photo of 14501 Grove Resort Avenue #2530, Winter Garden, FL 34787 (MLS # S5114231)
    $420,000
    Photo of 14501 Grove Resort Avenue #2530, Winter Garden, FL 34787 (MLS # S5114231)
    Photo of 14501 Grove Resort Avenue #2530, Winter Garden, FL 34787 (MLS # S5114231)
    14501 Grove Resort Avenue #2530, Winter Garden, FL
    14501 Grove Resort Avenue #2530
    Winter Garden, FL
    • 2 Beds
    • 2 Baths
    • 1,265 Home (sqft)
    • 2 Baths
    • 1,307 Lot (sqft)
  6. Photo of 17019 Seville Orange Road, Winter Garden, FL 34787 (MLS # O6252124)
    $589,900
    Photo of 17019 Seville Orange Road, Winter Garden, FL 34787 (MLS # O6252124)
    Photo of 17019 Seville Orange Road, Winter Garden, FL 34787 (MLS # O6252124)
    17019 Seville Orange Road, Winter Garden, FL
    17019 Seville Orange Road
    Winter Garden, FL
    • 4 Beds
    • 3 Baths
    • 2,048 Home (sqft)
    • 3 Baths
    • 4,792 Lot (sqft)
  7. Photo of 16269 Admirals Cove Lane, Winter Garden, FL 34787 (MLS # O6250117)
    $405,000
    Photo of 16269 Admirals Cove Lane, Winter Garden, FL 34787 (MLS # O6250117)
    Photo of 16269 Admirals Cove Lane, Winter Garden, FL 34787 (MLS # O6250117)
    16269 Admirals Cove Lane, Winter Garden, FL
    16269 Admirals Cove Lane
    Winter Garden, FL
    • 3 Beds
    • 3 Baths
    • 1,568 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
  8. Photo of 13418 Princess Street, Winter Garden, FL 34787 (MLS # O6249192)
    $449,990
    Photo of 13418 Princess Street, Winter Garden, FL 34787 (MLS # O6249192)
    Photo of 13418 Princess Street, Winter Garden, FL 34787 (MLS # O6249192)
    13418 Princess Street, Winter Garden, FL
    13418 Princess Street
    Winter Garden, FL
    • 2 Beds
    • 2 Baths
    • 1,579 Home (sqft)
    • 2 Baths
    • 3,921 Lot (sqft)
  9. Photo of 434 Millwood Place, Winter Garden, FL 34787 (MLS # O6235644)
    $510,000
    Photo of 434 Millwood Place, Winter Garden, FL 34787 (MLS # O6235644)
    Photo of 434 Millwood Place, Winter Garden, FL 34787 (MLS # O6235644)
    434 Millwood Place, Winter Garden, FL
    434 Millwood Place
    Winter Garden, FL
    • 3 Beds
    • 2 Baths
    • 1,696 Home (sqft)
    • 2 Baths
    • 6,970 Lot (sqft)
  10. Photo of 344 E Maple Street, Winter Garden, FL 34787 (MLS # O6233175)
    $439,990
    Photo of 344 E Maple Street, Winter Garden, FL 34787 (MLS # O6233175)
    Photo of 344 E Maple Street, Winter Garden, FL 34787 (MLS # O6233175)
    344 E Maple Street, Winter Garden, FL
    344 E Maple Street
    Winter Garden, FL
    • 3 Beds
    • 3 Baths
    • 1,678 Home (sqft)
    • 3 Baths
    • 10,890 Lot (sqft)
  11. Photo of 16944 Arrowhead Boulevard, Winter Garden, FL 34787 (MLS # O6229034)
    $520,000
    Photo of 16944 Arrowhead Boulevard, Winter Garden, FL 34787 (MLS # O6229034)
    Photo of 16944 Arrowhead Boulevard, Winter Garden, FL 34787 (MLS # O6229034)
    16944 Arrowhead Boulevard, Winter Garden, FL
    16944 Arrowhead Boulevard
    Winter Garden, FL
    • 3 Beds
    • 2 Baths
    • 1,008 Home (sqft)
    • 2 Baths
    • 1.23 Lot (ac)
  12. Photo of 13460 Princess Street, Winter Garden, FL 34787 (MLS # O6227746)
    $478,000
    Photo of 13460 Princess Street, Winter Garden, FL 34787 (MLS # O6227746)
    Photo of 13460 Princess Street, Winter Garden, FL 34787 (MLS # O6227746)
    13460 Princess Street, Winter Garden, FL
    13460 Princess Street
    Winter Garden, FL
    • 2 Beds
    • 2 Baths
    • 1,579 Home (sqft)
    • 2 Baths
    • 3,921 Lot (sqft)
  13. Photo of 470 Regal Downs Circle, Winter Garden, FL 34787 (MLS # O6217239)
    $585,000
    Photo of 470 Regal Downs Circle, Winter Garden, FL 34787 (MLS # O6217239)
    Photo of 470 Regal Downs Circle, Winter Garden, FL 34787 (MLS # O6217239)
    470 Regal Downs Circle, Winter Garden, FL
    470 Regal Downs Circle
    Winter Garden, FL
    • 4 Beds
    • 3 Baths
    • 2,316 Home (sqft)
    • 3 Baths
    • 13,940 Lot (sqft)
  14. Photo of 14278 Murcott Blossom Boulevard, Winter Garden, FL 34787 (MLS # O6214707)
    $574,000
    Photo of 14278 Murcott Blossom Boulevard, Winter Garden, FL 34787 (MLS # O6214707)
    Photo of 14278 Murcott Blossom Boulevard, Winter Garden, FL 34787 (MLS # O6214707)
    14278 Murcott Blossom Boulevard, Winter Garden, FL
    14278 Murcott Blossom Boulevard
    Winter Garden, FL
    • 5 Beds
    • 3 Baths
    • 2,110 Home (sqft)
    • 3 Baths
    • 4,356 Lot (sqft)
  15. Photo of 15240 Chapter Way, Winter Garden, FL 34787 (MLS # O6207683)
    $520,000
    Photo of 15240 Chapter Way, Winter Garden, FL 34787 (MLS # O6207683)
    Photo of 15240 Chapter Way, Winter Garden, FL 34787 (MLS # O6207683)
    15240 Chapter Way, Winter Garden, FL
    15240 Chapter Way
    Winter Garden, FL
    • 4 Beds
    • 4 Baths
    • 2,500 Home (sqft)
    • 4 Baths
    • 3,921 Lot (sqft)
  16. Photo of 13406 Princess Street, Winter Garden, FL 34787 (MLS # O6201549)
    $422,000
    Photo of 13406 Princess Street, Winter Garden, FL 34787 (MLS # O6201549)
    Photo of 13406 Princess Street, Winter Garden, FL 34787 (MLS # O6201549)
    13406 Princess Street, Winter Garden, FL
    13406 Princess Street
    Winter Garden, FL
    • 2 Beds
    • 2 Baths
    • 1,579 Home (sqft)
    • 2 Baths
    • 3,921 Lot (sqft)
  17. 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)
  18. 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)
  19. Photo of 14501 Grove Resort Avenue #1430, Winter Garden, FL 34787 (MLS # O6070878)
    $450,000
    Photo of 14501 Grove Resort Avenue #1430, Winter Garden, FL 34787 (MLS # O6070878)
    Photo of 14501 Grove Resort Avenue #1430, Winter Garden, FL 34787 (MLS # O6070878)
    14501 Grove Resort Avenue #1430, Winter Garden, FL
    14501 Grove Resort Avenue #1430
    Winter Garden, FL
    • 3 Beds
    • 3 Baths
    • 1,544 Home (sqft)
    • 3 Baths
    • 1,743 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 12/22/24 12:20 PM PST.

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