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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 14014 Lanyard Way, Winter Garden, FL 34787 (MLS # G5077123)
    $831,707
    Photo of 14014 Lanyard Way, Winter Garden, FL 34787 (MLS # G5077123)
    Photo of 14014 Lanyard Way, Winter Garden, FL 34787 (MLS # G5077123)
    14014 Lanyard Way, Winter Garden, FL
    14014 Lanyard Way
    Winter Garden, FL
    • 5 Beds
    • 4 Baths
    • 3,076 Home (sqft)
    • 4 Baths
    • 4,792 Lot (sqft)
  2. Photo of 3394 Buoy Circle, Winter Garden, FL 34787 (MLS # O6168229)
    $740,000
    Photo of 3394 Buoy Circle, Winter Garden, FL 34787 (MLS # O6168229)
    Photo of 3394 Buoy Circle, Winter Garden, FL 34787 (MLS # O6168229)
    3394 Buoy Circle, Winter Garden, FL
    3394 Buoy Circle
    Winter Garden, FL
    • 5 Beds
    • 5 Baths
    • 3,747 Home (sqft)
    • 5 Baths
    • 7,841 Lot (sqft)
  3. Photo of 14372 Sunbridge Circle, Winter Garden, FL 34787 (MLS # O6166589)
    $835,000
    Photo of 14372 Sunbridge Circle, Winter Garden, FL 34787 (MLS # O6166589)
    Photo of 14372 Sunbridge Circle, Winter Garden, FL 34787 (MLS # O6166589)
    45
     
    14372 Sunbridge Circle, Winter Garden, FL
    14372 Sunbridge Circle
    Winter Garden, FL
    • 4 Beds
    • 5 Baths
    • 4,166 Home (sqft)
    • 5 Baths
    • 9,148 Lot (sqft)
  4. Photo of 13978 Lanyard Way, Winter Garden, FL 34787 (MLS # O6159176)
    $977,990
    Photo of 13978 Lanyard Way, Winter Garden, FL 34787 (MLS # O6159176)
    Photo of 13978 Lanyard Way, Winter Garden, FL 34787 (MLS # O6159176)
    13978 Lanyard Way, Winter Garden, FL
    13978 Lanyard Way
    Winter Garden, FL
    • 5 Beds
    • 4 Baths
    • 4,883 Home (sqft)
    • 4 Baths
    • 6,970 Lot (sqft)
  5. Photo of 17814 Hither Hills Circle, Winter Garden, FL 34787 (MLS # O6150118)
    $1,316,990
    Photo of 17814 Hither Hills Circle, Winter Garden, FL 34787 (MLS # O6150118)
    Photo of 17814 Hither Hills Circle, Winter Garden, FL 34787 (MLS # O6150118)
    17814 Hither Hills Circle, Winter Garden, FL
    17814 Hither Hills Circle
    Winter Garden, FL
    • 4 Beds
    • 4 Baths
    • 4,328 Home (sqft)
    • 4 Baths
    • 5,663 Lot (sqft)
  6. Photo of 260 Deer Isle Drive, Winter Garden, FL 34787 (MLS # O6135342)
    $2,195,000
    Photo of 260 Deer Isle Drive, Winter Garden, FL 34787 (MLS # O6135342)
    Photo of 260 Deer Isle Drive, Winter Garden, FL 34787 (MLS # O6135342)
    260 Deer Isle Drive, Winter Garden, FL
    260 Deer Isle Drive
    Winter Garden, FL
    • 4 Beds
    • 5 Baths
    • 4,714 Home (sqft)
    • 5 Baths
    • 2.01 Lot (ac)
  7. Photo of 3470 Buoy Circle, Winter Garden, FL 34787 (MLS # O6127373)
    $729,000
    Photo of 3470 Buoy Circle, Winter Garden, FL 34787 (MLS # O6127373)
    Photo of 3470 Buoy Circle, Winter Garden, FL 34787 (MLS # O6127373)
    3470 Buoy Circle, Winter Garden, FL
    3470 Buoy Circle
    Winter Garden, FL
    • 4 Beds
    • 3 Baths
    • 3,268 Home (sqft)
    • 3 Baths
    • 6,099 Lot (sqft)
  8. Photo of 13900 Fox Glove Street, Winter Garden, FL 34787 (MLS # S5087198)
    $699,000
    Photo of 13900 Fox Glove Street, Winter Garden, FL 34787 (MLS # S5087198)
    Photo of 13900 Fox Glove Street, Winter Garden, FL 34787 (MLS # S5087198)
    13900 Fox Glove Street, Winter Garden, FL
    13900 Fox Glove Street
    Winter Garden, FL
    • 5 Beds
    • 3 Baths
    • 3,887 Home (sqft)
    • 3 Baths
    • 7,406 Lot (sqft)
  9. Photo of 13377 Lake Butler Boulevard, Winter Garden, FL 34787 (MLS # O6100391)
    $5,997,000
    Photo of 13377 Lake Butler Boulevard, Winter Garden, FL 34787 (MLS # O6100391)
    Photo of 13377 Lake Butler Boulevard, Winter Garden, FL 34787 (MLS # O6100391)
    13377 Lake Butler Boulevard, Winter Garden, FL
    13377 Lake Butler Boulevard
    Winter Garden, FL
    • 5 Beds
    • 5 Baths
    • 6,210 Home (sqft)
    • 5 Baths
    • 4.99 Lot (ac)
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