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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 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 8198 Topsail Place, Winter Garden, FL 34787 (MLS # O6245213)
    $1,225,000
    Photo of 8198 Topsail Place, Winter Garden, FL 34787 (MLS # O6245213)
    Photo of 8198 Topsail Place, Winter Garden, FL 34787 (MLS # O6245213)
    8198 Topsail Place, Winter Garden, FL
    8198 Topsail Place
    Winter Garden, FL
    • 5 Beds
    • 5 Baths
    • 3,815 Home (sqft)
    • 5 Baths
    • 8,277 Lot (sqft)
  2. Photo of 3278 Hanging Tide Street, Winter Garden, FL 34787 (MLS # O6244654)
    $1,100,000
    Photo of 3278 Hanging Tide Street, Winter Garden, FL 34787 (MLS # O6244654)
    Photo of 3278 Hanging Tide Street, Winter Garden, FL 34787 (MLS # O6244654)
    3278 Hanging Tide Street, Winter Garden, FL
    3278 Hanging Tide Street
    Winter Garden, FL
    • 5 Beds
    • 5 Baths
    • 3,641 Home (sqft)
    • 5 Baths
    • 6,099 Lot (sqft)
  3. Photo of 15490 Sweet Orange Avenue, Winter Garden, FL 34787 (MLS # A4624706)
    $975,000
    Photo of 15490 Sweet Orange Avenue, Winter Garden, FL 34787 (MLS # A4624706)
    Photo of 15490 Sweet Orange Avenue, Winter Garden, FL 34787 (MLS # A4624706)
    15490 Sweet Orange Avenue, Winter Garden, FL
    15490 Sweet Orange Avenue
    Winter Garden, FL
    • 4 Beds
    • 4 Baths
    • 3,200 Home (sqft)
    • 4 Baths
    • 6,534 Lot (sqft)
  4. Photo of 1125 English Garden Lane SE, Winter Garden, FL 34787 (MLS # O6235713)
    $925,000
    Photo of 1125 English Garden Lane SE, Winter Garden, FL 34787 (MLS # O6235713)
    Photo of 1125 English Garden Lane SE, Winter Garden, FL 34787 (MLS # O6235713)
    1125 English Garden Lane SE, Winter Garden, FL
    1125 English Garden Lane SE
    Winter Garden, FL
    • 5 Beds
    • 4 Baths
    • 3,663 Home (sqft)
    • 4 Baths
    • 15,246 Lot (sqft)
  5. Photo of 16736 Rusty Anchor Road, Winter Garden, FL 34787 (MLS # O6242473)
    $975,000
    Photo of 16736 Rusty Anchor Road, Winter Garden, FL 34787 (MLS # O6242473)
    Photo of 16736 Rusty Anchor Road, Winter Garden, FL 34787 (MLS # O6242473)
    16736 Rusty Anchor Road, Winter Garden, FL
    16736 Rusty Anchor Road
    Winter Garden, FL
    • 4 Beds
    • 3 Baths
    • 2,696 Home (sqft)
    • 3 Baths
    • 8,712 Lot (sqft)
  6. Photo of 13352 Lago Vista Drive, Winter Garden, FL 34787 (MLS # A4623624)
    $3,499,999
    Photo of 13352 Lago Vista Drive, Winter Garden, FL 34787 (MLS # A4623624)
    Photo of 13352 Lago Vista Drive, Winter Garden, FL 34787 (MLS # A4623624)
    13352 Lago Vista Drive, Winter Garden, FL
    13352 Lago Vista Drive
    Winter Garden, FL
    • 5 Beds
    • 6 Baths
    • 7,512 Home (sqft)
    • 6 Baths
    • 5.52 Lot (ac)
  7. Photo of 14126 Fox Glove Street, Winter Garden, FL 34787 (MLS # O6241620)
    $860,000
    Photo of 14126 Fox Glove Street, Winter Garden, FL 34787 (MLS # O6241620)
    Photo of 14126 Fox Glove Street, Winter Garden, FL 34787 (MLS # O6241620)
    14126 Fox Glove Street, Winter Garden, FL
    14126 Fox Glove Street
    Winter Garden, FL
    • 4 Beds
    • 3 Baths
    • 3,807 Home (sqft)
    • 3 Baths
    • 7,406 Lot (sqft)
  8. Photo of 16695 Broadwater Avenue, Winter Garden, FL 34787 (MLS # O6241344)
    $2,200,000
    Photo of 16695 Broadwater Avenue, Winter Garden, FL 34787 (MLS # O6241344)
    Photo of 16695 Broadwater Avenue, Winter Garden, FL 34787 (MLS # O6241344)
    86
     
    16695 Broadwater Avenue, Winter Garden, FL
    16695 Broadwater Avenue
    Winter Garden, FL
    • 5 Beds
    • 6 Baths
    • 5,219 Home (sqft)
    • 6 Baths
    • 19,602 Lot (sqft)
  9. Photo of 17572 Davenport Road, Winter Garden, FL 34787 (MLS # O6238080)
    $1,198,000
    Photo of 17572 Davenport Road, Winter Garden, FL 34787 (MLS # O6238080)
    Photo of 17572 Davenport Road, Winter Garden, FL 34787 (MLS # O6238080)
    17572 Davenport Road, Winter Garden, FL
    17572 Davenport Road
    Winter Garden, FL
    • 4 Beds
    • 4 Baths
    • 2,756 Home (sqft)
    • 4 Baths
    • 1.05 Lot (ac)
  10. Photo of 322 Apopka Street, Winter Garden, FL 34787 (MLS # O6237711)
    $749,000
    Photo of 322 Apopka Street, Winter Garden, FL 34787 (MLS # O6237711)
    Photo of 322 Apopka Street, Winter Garden, FL 34787 (MLS # O6237711)
    322 Apopka Street, Winter Garden, FL
    322 Apopka Street
    Winter Garden, FL
    • 4 Beds
    • 3 Baths
    • 1,579 Home (sqft)
    • 3 Baths
    • 9,148 Lot (sqft)
  11. Photo of 17930 Adrift Road, Winter Garden, FL 34787 (MLS # O6236763)
    $989,000
    Photo of 17930 Adrift Road, Winter Garden, FL 34787 (MLS # O6236763)
    Photo of 17930 Adrift Road, Winter Garden, FL 34787 (MLS # O6236763)
    17930 Adrift Road, Winter Garden, FL
    17930 Adrift Road
    Winter Garden, FL
    • 4 Beds
    • 4 Baths
    • 3,327 Home (sqft)
    • 4 Baths
    • 6,970 Lot (sqft)
  12. Photo of 3228 Sailing Pier Avenue, Winter Garden, FL 34787 (MLS # O6236295)
    $690,000
    Photo of 3228 Sailing Pier Avenue, Winter Garden, FL 34787 (MLS # O6236295)
    Photo of 3228 Sailing Pier Avenue, Winter Garden, FL 34787 (MLS # O6236295)
    3228 Sailing Pier Avenue, Winter Garden, FL
    3228 Sailing Pier Avenue
    Winter Garden, FL
    • 4 Beds
    • 4 Baths
    • 2,894 Home (sqft)
    • 4 Baths
    • 6,534 Lot (sqft)
  13. Photo of 1253 E Fullers Cross Road, Winter Garden, FL 34787 (MLS # G5086247)
    $3,600,000
    Photo of 1253 E Fullers Cross Road, Winter Garden, FL 34787 (MLS # G5086247)
    Photo of 1253 E Fullers Cross Road, Winter Garden, FL 34787 (MLS # G5086247)
    1253 E Fullers Cross Road, Winter Garden, FL
    1253 E Fullers Cross Road
    Winter Garden, FL
    • 4 Beds
    • 5 Baths
    • 3,495 Home (sqft)
    • 5 Baths
    • 12.00 Lot (ac)
  14. Photo of 727 Marsh Reed Drive, Winter Garden, FL 34787 (MLS # O6234291)
    $692,000
    Photo of 727 Marsh Reed Drive, Winter Garden, FL 34787 (MLS # O6234291)
    Photo of 727 Marsh Reed Drive, Winter Garden, FL 34787 (MLS # O6234291)
    727 Marsh Reed Drive, Winter Garden, FL
    727 Marsh Reed Drive
    Winter Garden, FL
    • 5 Beds
    • 4 Baths
    • 3,100 Home (sqft)
    • 4 Baths
    • 4,792 Lot (sqft)
  15. Photo of 13861 Lanyard Way, Winter Garden, FL 34787 (MLS # O6234574)
    $649,900
    Photo of 13861 Lanyard Way, Winter Garden, FL 34787 (MLS # O6234574)
    Photo of 13861 Lanyard Way, Winter Garden, FL 34787 (MLS # O6234574)
    44
     
    13861 Lanyard Way, Winter Garden, FL
    13861 Lanyard Way
    Winter Garden, FL
    • 3 Beds
    • 3 Baths
    • 2,341 Home (sqft)
    • 3 Baths
    • 3,485 Lot (sqft)
  16. Photo of 319 Morning View Drive, Winter Garden, FL 34787 (MLS # O6234576)
    $929,900
    Photo of 319 Morning View Drive, Winter Garden, FL 34787 (MLS # O6234576)
    Photo of 319 Morning View Drive, Winter Garden, FL 34787 (MLS # O6234576)
    319 Morning View Drive, Winter Garden, FL
    319 Morning View Drive
    Winter Garden, FL
    • 7 Beds
    • 5 Baths
    • 4,900 Home (sqft)
    • 5 Baths
    • 8,712 Lot (sqft)
  17. Photo of 15106 Ovation Drive, Winter Garden, FL 34787 (MLS # O6233934)
    $741,000
    Photo of 15106 Ovation Drive, Winter Garden, FL 34787 (MLS # O6233934)
    Photo of 15106 Ovation Drive, Winter Garden, FL 34787 (MLS # O6233934)
    15106 Ovation Drive, Winter Garden, FL
    15106 Ovation Drive
    Winter Garden, FL
    • 6 Beds
    • 4 Baths
    • 2,935 Home (sqft)
    • 4 Baths
    • 11,762 Lot (sqft)
  18. Photo of 15620 Panther Lake Drive, Winter Garden, FL 34787 (MLS # S5110485)
    $2,650,000
    Photo of 15620 Panther Lake Drive, Winter Garden, FL 34787 (MLS # S5110485)
    Photo of 15620 Panther Lake Drive, Winter Garden, FL 34787 (MLS # S5110485)
    15620 Panther Lake Drive, Winter Garden, FL
    15620 Panther Lake Drive
    Winter Garden, FL
    • 6 Beds
    • 5 Baths
    • 4,769 Home (sqft)
    • 5 Baths
    • 12,197 Lot (sqft)
  19. Photo of 15644 Panther Lake Drive, Winter Garden, FL 34787 (MLS # O6234253)
    $1,699,000
    Photo of 15644 Panther Lake Drive, Winter Garden, FL 34787 (MLS # O6234253)
    Photo of 15644 Panther Lake Drive, Winter Garden, FL 34787 (MLS # O6234253)
    15644 Panther Lake Drive, Winter Garden, FL
    15644 Panther Lake Drive
    Winter Garden, FL
    • 5 Beds
    • 6 Baths
    • 4,296 Home (sqft)
    • 6 Baths
    • 10,890 Lot (sqft)
  20. Photo of 10472 Petrillo Way, Winter Garden, FL 34787 (MLS # O6238677)
    $1,179,999
    Photo of 10472 Petrillo Way, Winter Garden, FL 34787 (MLS # O6238677)
    Photo of 10472 Petrillo Way, Winter Garden, FL 34787 (MLS # O6238677)
    10472 Petrillo Way, Winter Garden, FL
    10472 Petrillo Way
    Winter Garden, FL
    • 5 Beds
    • 6 Baths
    • 4,025 Home (sqft)
    • 6 Baths
    • 7,406 Lot (sqft)
  21. Photo of 17000 Red Bird Road, Winter Garden, FL 34787 (MLS # O6231878)
    $1,250,000
    Photo of 17000 Red Bird Road, Winter Garden, FL 34787 (MLS # O6231878)
    Photo of 17000 Red Bird Road, Winter Garden, FL 34787 (MLS # O6231878)
    17000 Red Bird Road, Winter Garden, FL
    17000 Red Bird Road
    Winter Garden, FL
    • 5 Beds
    • 4 Baths
    • 3,370 Home (sqft)
    • 4 Baths
    • 2.25 Lot (ac)
  22. Photo of 15222 Lake Lamonia Street, Winter Garden, FL 34787 (MLS # O6229866)
    $1,084,000
    Photo of 15222 Lake Lamonia Street, Winter Garden, FL 34787 (MLS # O6229866)
    Photo of 15222 Lake Lamonia Street, Winter Garden, FL 34787 (MLS # O6229866)
    15222 Lake Lamonia Street, Winter Garden, FL
    15222 Lake Lamonia Street
    Winter Garden, FL
    • 6 Beds
    • 5 Baths
    • 3,667 Home (sqft)
    • 5 Baths
    • 9,148 Lot (sqft)
  23. Photo of 9306 Holliston Creek Place, Winter Garden, FL 34787 (MLS # O6230271)
    $1,099,000
    Photo of 9306 Holliston Creek Place, Winter Garden, FL 34787 (MLS # O6230271)
    Photo of 9306 Holliston Creek Place, Winter Garden, FL 34787 (MLS # O6230271)
    9306 Holliston Creek Place, Winter Garden, FL
    9306 Holliston Creek Place
    Winter Garden, FL
    • 5 Beds
    • 4 Baths
    • 3,566 Home (sqft)
    • 4 Baths
    • 10,455 Lot (sqft)
  24. Photo of 16061 Sunny Time Avenue, Winter Garden, FL 34787 (MLS # O6230038)
    $813,200
    Photo of 16061 Sunny Time Avenue, Winter Garden, FL 34787 (MLS # O6230038)
    Photo of 16061 Sunny Time Avenue, Winter Garden, FL 34787 (MLS # O6230038)
    16061 Sunny Time Avenue, Winter Garden, FL
    16061 Sunny Time Avenue
    Winter Garden, FL
    • 4 Beds
    • 4 Baths
    • 2,960 Home (sqft)
    • 4 Baths
    • 6,099 Lot (sqft)
  25. Photo of 9313 Quiet Lane, Winter Garden, FL 34787 (MLS # O6226273)
    $1,150,000
    Photo of 9313 Quiet Lane, Winter Garden, FL 34787 (MLS # O6226273)
    Photo of 9313 Quiet Lane, Winter Garden, FL 34787 (MLS # O6226273)
    9313 Quiet Lane, Winter Garden, FL
    9313 Quiet Lane
    Winter Garden, FL
    • 4 Beds
    • 3 Baths
    • 2,854 Home (sqft)
    • 3 Baths
    • 5.28 Lot (ac)
  26. Photo of 14528 Old Thicket Trace, Winter Garden, FL 34787 (MLS # O6226299)
    $780,000
    Photo of 14528 Old Thicket Trace, Winter Garden, FL 34787 (MLS # O6226299)
    Photo of 14528 Old Thicket Trace, Winter Garden, FL 34787 (MLS # O6226299)
    14528 Old Thicket Trace, Winter Garden, FL
    14528 Old Thicket Trace
    Winter Garden, FL
    • 5 Beds
    • 4 Baths
    • 3,179 Home (sqft)
    • 4 Baths
    • 7,406 Lot (sqft)
  27. Photo of 10207 Atwater Bay Drive, Winter Garden, FL 34787 (MLS # O6224829)
    $1,590,000
    Photo of 10207 Atwater Bay Drive, Winter Garden, FL 34787 (MLS # O6224829)
    Photo of 10207 Atwater Bay Drive, Winter Garden, FL 34787 (MLS # O6224829)
    10207 Atwater Bay Drive, Winter Garden, FL
    10207 Atwater Bay Drive
    Winter Garden, FL
    • 5 Beds
    • 5 Baths
    • 3,354 Home (sqft)
    • 5 Baths
    • 33,977 Lot (sqft)
  28. Photo of 15986 Johns Lake Overlook Drive, Winter Garden, FL 34787 (MLS # T3541777)
    $2,175,000
    Photo of 15986 Johns Lake Overlook Drive, Winter Garden, FL 34787 (MLS # T3541777)
    Photo of 15986 Johns Lake Overlook Drive, Winter Garden, FL 34787 (MLS # T3541777)
    15986 Johns Lake Overlook Drive, Winter Garden, FL
    15986 Johns Lake Overlook Drive
    Winter Garden, FL
    • 5 Beds
    • 6 Baths
    • 4,498 Home (sqft)
    • 6 Baths
    • 23,958 Lot (sqft)
  29. Photo of 15144 Shonan Gold Drive, Winter Garden, FL 34787 (MLS # O6219561)
    $1,999,999
    Photo of 15144 Shonan Gold Drive, Winter Garden, FL 34787 (MLS # O6219561)
    Photo of 15144 Shonan Gold Drive, Winter Garden, FL 34787 (MLS # O6219561)
    15144 Shonan Gold Drive, Winter Garden, FL
    15144 Shonan Gold Drive
    Winter Garden, FL
    • 4 Beds
    • 5 Baths
    • 4,056 Home (sqft)
    • 5 Baths
    • 3.59 Lot (ac)
  30. Photo of 515 N Boyd Street, Winter Garden, FL 34787 (MLS # O6222919)
    $1,100,000
    Photo of 515 N Boyd Street, Winter Garden, FL 34787 (MLS # O6222919)
    Photo of 515 N Boyd Street, Winter Garden, FL 34787 (MLS # O6222919)
    40
     
    515 N Boyd Street, Winter Garden, FL
    515 N Boyd Street
    Winter Garden, FL
    • 5 Beds
    • 4 Baths
    • 3,152 Home (sqft)
    • 4 Baths
    • 16,118 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 11/23/24 12:13 AM PST.

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