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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 under $400k 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 14501 Grove Resort Avenue #1219, Winter Garden, FL 34787 (MLS # O6239993)
    $330,000
    Photo of 14501 Grove Resort Avenue #1219, Winter Garden, FL 34787 (MLS # O6239993)
    Photo of 14501 Grove Resort Avenue #1219, Winter Garden, FL 34787 (MLS # O6239993)
    14501 Grove Resort Avenue #1219, Winter Garden, FL
    14501 Grove Resort Avenue #1219
    Winter Garden, FL
    • 2 Beds
    • 2 Baths
    • 1,265 Home (sqft)
    • 2 Baths
    • 1,743 Lot (sqft)
  2. Photo of 350 Winter Nellis Circle, Winter Garden, FL 34787 (MLS # O6244519)
    $355,000
    Photo of 350 Winter Nellis Circle, Winter Garden, FL 34787 (MLS # O6244519)
    Photo of 350 Winter Nellis Circle, Winter Garden, FL 34787 (MLS # O6244519)
    350 Winter Nellis Circle, Winter Garden, FL
    350 Winter Nellis Circle
    Winter Garden, FL
    • 3 Beds
    • 3 Baths
    • 1,554 Home (sqft)
    • 3 Baths
    • 2,178 Lot (sqft)
  3. Photo of 447 Winter Nellis Circle, Winter Garden, FL 34787 (MLS # O6236985)
    $355,000
    Photo of 447 Winter Nellis Circle, Winter Garden, FL 34787 (MLS # O6236985)
    Photo of 447 Winter Nellis Circle, Winter Garden, FL 34787 (MLS # O6236985)
    447 Winter Nellis Circle, Winter Garden, FL
    447 Winter Nellis Circle
    Winter Garden, FL
    • 2 Beds
    • 3 Baths
    • 1,606 Home (sqft)
    • 3 Baths
    • 2,614 Lot (sqft)
  4. Photo of 14501 Grove Resort Ave #1303, Winter Garden, FL 34787 (MLS # O6236753)
    $365,000
    Photo of 14501 Grove Resort Ave #1303, Winter Garden, FL 34787 (MLS # O6236753)
    Photo of 14501 Grove Resort Ave #1303, Winter Garden, FL 34787 (MLS # O6236753)
    14501 Grove Resort Ave #1303, Winter Garden, FL
    14501 Grove Resort Ave #1303
    Winter Garden, FL
    • 3 Beds
    • 2 Baths
    • 1,396 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  5. Photo of 14501 Grove Resort Avenue #3329, Winter Garden, FL 34787 (MLS # O6236603)
    $329,000
    Photo of 14501 Grove Resort Avenue #3329, Winter Garden, FL 34787 (MLS # O6236603)
    Photo of 14501 Grove Resort Avenue #3329, Winter Garden, FL 34787 (MLS # O6236603)
    14501 Grove Resort Avenue #3329, Winter Garden, FL
    14501 Grove Resort Avenue #3329
    Winter Garden, FL
    • 3 Beds
    • 2 Baths
    • 1,396 Home (sqft)
    • 2 Baths
    • 1,743 Lot (sqft)
  6. Photo of 14501 Grove Resort Avenue #3229, Winter Garden, FL 34787 (MLS # O6236600)
    $329,000
    Photo of 14501 Grove Resort Avenue #3229, Winter Garden, FL 34787 (MLS # O6236600)
    Photo of 14501 Grove Resort Avenue #3229, Winter Garden, FL 34787 (MLS # O6236600)
    14501 Grove Resort Avenue #3229, Winter Garden, FL
    14501 Grove Resort Avenue #3229
    Winter Garden, FL
    • 3 Beds
    • 2 Baths
    • 1,396 Home (sqft)
    • 2 Baths
    • 1,743 Lot (sqft)
  7. Photo of 14501 Grove Resort Avenue #3137, Winter Garden, FL 34787 (MLS # O6236595)
    $329,000
    Photo of 14501 Grove Resort Avenue #3137, Winter Garden, FL 34787 (MLS # O6236595)
    Photo of 14501 Grove Resort Avenue #3137, Winter Garden, FL 34787 (MLS # O6236595)
    14501 Grove Resort Avenue #3137, Winter Garden, FL
    14501 Grove Resort Avenue #3137
    Winter Garden, FL
    • 3 Beds
    • 2 Baths
    • 1,396 Home (sqft)
    • 2 Baths
    • 1,743 Lot (sqft)
  8. Photo of 14501 Grove Resort Avenue #3134, Winter Garden, FL 34787 (MLS # O6235590)
    $329,000
    Photo of 14501 Grove Resort Avenue #3134, Winter Garden, FL 34787 (MLS # O6235590)
    Photo of 14501 Grove Resort Avenue #3134, Winter Garden, FL 34787 (MLS # O6235590)
    14501 Grove Resort Avenue #3134, Winter Garden, FL
    14501 Grove Resort Avenue #3134
    Winter Garden, FL
    • 3 Beds
    • 2 Baths
    • 1,396 Home (sqft)
    • 2 Baths
    • 1,743 Lot (sqft)
  9. Photo of 14501 Grove Resort Avenue #1746, Winter Garden, FL 34787 (MLS # S5110719)
    $272,000
    Photo of 14501 Grove Resort Avenue #1746, Winter Garden, FL 34787 (MLS # S5110719)
    Photo of 14501 Grove Resort Avenue #1746, Winter Garden, FL 34787 (MLS # S5110719)
    14501 Grove Resort Avenue #1746, Winter Garden, FL
    14501 Grove Resort Avenue #1746
    Winter Garden, FL
    • 2 Beds
    • 2 Baths
    • 1,375 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  10. Photo of 14501 Grove Resort Avenue, Winter Garden, FL 34787 (MLS # O6231739)
    $375,000
    Photo of 14501 Grove Resort Avenue, Winter Garden, FL 34787 (MLS # O6231739)
    Photo of 14501 Grove Resort Avenue, Winter Garden, FL 34787 (MLS # O6231739)
    14501 Grove Resort Avenue, Winter Garden, FL
    14501 Grove Resort Avenue
    Winter Garden, FL
    • 3 Beds
    • 2 Baths
    • 1,396 Home (sqft)
    • 2 Baths
    • 1,743 Lot (sqft)
  11. Photo of 14501 Grove Resort Avenue #2411, Winter Garden, FL 34787 (MLS # S5110881)
    $322,500
    Photo of 14501 Grove Resort Avenue #2411, Winter Garden, FL 34787 (MLS # S5110881)
    Photo of 14501 Grove Resort Avenue #2411, Winter Garden, FL 34787 (MLS # S5110881)
    14501 Grove Resort Avenue #2411, Winter Garden, FL
    14501 Grove Resort Avenue #2411
    Winter Garden, FL
    • 3 Beds
    • 2 Baths
    • 1,396 Home (sqft)
    • 2 Baths
    • 1,743 Lot (sqft)
  12. Photo of 14501 Grove Resort Avenue #3132, Winter Garden, FL 34787 (MLS # O6233619)
    $297,999
    Photo of 14501 Grove Resort Avenue #3132, Winter Garden, FL 34787 (MLS # O6233619)
    Photo of 14501 Grove Resort Avenue #3132, Winter Garden, FL 34787 (MLS # O6233619)
    14501 Grove Resort Avenue #3132, Winter Garden, FL
    14501 Grove Resort Avenue #3132
    Winter Garden, FL
    • 2 Beds
    • 2 Baths
    • 1,265 Home (sqft)
    • 2 Baths
    • 1,307 Lot (sqft)
  13. Photo of 14501 Grove Resort Avenue #1529, Winter Garden, FL 34787 (MLS # O6233782)
    $334,900
    Photo of 14501 Grove Resort Avenue #1529, Winter Garden, FL 34787 (MLS # O6233782)
    Photo of 14501 Grove Resort Avenue #1529, Winter Garden, FL 34787 (MLS # O6233782)
    14501 Grove Resort Avenue #1529, Winter Garden, FL
    14501 Grove Resort Avenue #1529
    Winter Garden, FL
    • 3 Beds
    • 3 Baths
    • 1,544 Home (sqft)
    • 3 Baths
    • 1,743 Lot (sqft)
  14. Photo of 1422 Basin Street, Winter Garden, FL 34787 (MLS # O6230190)
    $199,900
    Photo of 1422 Basin Street, Winter Garden, FL 34787 (MLS # O6230190)
    Photo of 1422 Basin Street, Winter Garden, FL 34787 (MLS # O6230190)
    1422 Basin Street, Winter Garden, FL
    1422 Basin Street
    Winter Garden, FL
    • 4 Beds
    • 1 Bath
    • 880 Home (sqft)
    • 1 Bath
    • 6,534 Lot (sqft)
  15. Photo of 14501 Grove Resort Avenue #3201, Winter Garden, FL 34787 (MLS # O6230305)
    $328,900
    Photo of 14501 Grove Resort Avenue #3201, Winter Garden, FL 34787 (MLS # O6230305)
    Photo of 14501 Grove Resort Avenue #3201, Winter Garden, FL 34787 (MLS # O6230305)
    14501 Grove Resort Avenue #3201, Winter Garden, FL
    14501 Grove Resort Avenue #3201
    Winter Garden, FL
    • 3 Beds
    • 3 Baths
    • 1,544 Home (sqft)
    • 3 Baths
    • 1,743 Lot (sqft)
  16. Photo of 1118 Priory Circle, Winter Garden, FL 34787 (MLS # O6227722)
    $375,000
    Photo of 1118 Priory Circle, Winter Garden, FL 34787 (MLS # O6227722)
    Photo of 1118 Priory Circle, Winter Garden, FL 34787 (MLS # O6227722)
    1118 Priory Circle, Winter Garden, FL
    1118 Priory Circle
    Winter Garden, FL
    • 3 Beds
    • 3 Baths
    • 1,625 Home (sqft)
    • 3 Baths
    • 2,614 Lot (sqft)
  17. Photo of 515 9th Street, Winter Garden, FL 34787 (MLS # T3545395)
    $280,000
    Photo of 515 9th Street, Winter Garden, FL 34787 (MLS # T3545395)
    Photo of 515 9th Street, Winter Garden, FL 34787 (MLS # T3545395)
    515 9th Street, Winter Garden, FL
    515 9th Street
    Winter Garden, FL
    • 3 Beds
    • 1 Bath
    • 672 Home (sqft)
    • 1 Bath
    • 4,792 Lot (sqft)
  18. Photo of 913 Butterfly Boulevard, Winter Garden, FL 34787 (MLS # O6225759)
    $200,000
    Photo of 913 Butterfly Boulevard, Winter Garden, FL 34787 (MLS # O6225759)
    Photo of 913 Butterfly Boulevard, Winter Garden, FL 34787 (MLS # O6225759)
    913 Butterfly Boulevard, Winter Garden, FL
    913 Butterfly Boulevard
    Winter Garden, FL
    • 2 Beds
    • 2 Baths
    • 938 Home (sqft)
    • 2 Baths
    • 2,178 Lot (sqft)
  19. Photo of 14501 Grove Resort Avenue #3337, Winter Garden, FL 34787 (MLS # O6223627)
    $369,900
    Photo of 14501 Grove Resort Avenue #3337, Winter Garden, FL 34787 (MLS # O6223627)
    Photo of 14501 Grove Resort Avenue #3337, Winter Garden, FL 34787 (MLS # O6223627)
    14501 Grove Resort Avenue #3337, Winter Garden, FL
    14501 Grove Resort Avenue #3337
    Winter Garden, FL
    • 3 Beds
    • 2 Baths
    • 1,396 Home (sqft)
    • 2 Baths
    • 1,743 Lot (sqft)
  20. Photo of 13329 Harbor Shore Lane, Winter Garden, FL 34787 (MLS # G5083767)
    $319,900
    Photo of 13329 Harbor Shore Lane, Winter Garden, FL 34787 (MLS # G5083767)
    Photo of 13329 Harbor Shore Lane, Winter Garden, FL 34787 (MLS # G5083767)
    13329 Harbor Shore Lane, Winter Garden, FL
    13329 Harbor Shore Lane
    Winter Garden, FL
    • 2 Beds
    • 3 Baths
    • 1,236 Home (sqft)
    • 3 Baths
    • 2,178 Lot (sqft)
  21. Photo of 14501 Grove Resort Avenue #3706, Winter Garden, FL 34787 (MLS # O6210138)
    $369,000
    Photo of 14501 Grove Resort Avenue #3706, Winter Garden, FL 34787 (MLS # O6210138)
    Photo of 14501 Grove Resort Avenue #3706, Winter Garden, FL 34787 (MLS # O6210138)
    14501 Grove Resort Avenue #3706, Winter Garden, FL
    14501 Grove Resort Avenue #3706
    Winter Garden, FL
    • 2 Beds
    • 2 Baths
    • 1,265 Home (sqft)
    • 2 Baths
    • 1,307 Lot (sqft)
  22. Photo of 14501 Grove Resort Avenue #1440, Winter Garden, FL 34787 (MLS # O6208787)
    $298,000
    Photo of 14501 Grove Resort Avenue #1440, Winter Garden, FL 34787 (MLS # O6208787)
    Photo of 14501 Grove Resort Avenue #1440, Winter Garden, FL 34787 (MLS # O6208787)
    14501 Grove Resort Avenue #1440, Winter Garden, FL
    14501 Grove Resort Avenue #1440
    Winter Garden, FL
    • 2 Beds
    • 2 Baths
    • 1,375 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  23. Photo of 14501 Grove Resort Avenue #3514, Winter Garden, FL 34787 (MLS # O6208428)
    $305,000
    Photo of 14501 Grove Resort Avenue #3514, Winter Garden, FL 34787 (MLS # O6208428)
    Photo of 14501 Grove Resort Avenue #3514, Winter Garden, FL 34787 (MLS # O6208428)
    14501 Grove Resort Avenue #3514, Winter Garden, FL
    14501 Grove Resort Avenue #3514
    Winter Garden, FL
    • 2 Beds
    • 2 Baths
    • 1,375 Home (sqft)
    • 2 Baths
    • 1,743 Lot (sqft)
  24. Photo of Winter Garden, FL 34787 (MLS # O6205774)
    $380,000
    Photo of Winter Garden, FL 34787 (MLS # O6205774)
    Photo of Winter Garden, FL 34787 (MLS # O6205774)
    MLS # O6205774, Winter Garden, FL
    MLS # O6205774
    Winter Garden, FL
    • 3 Beds
    • 2 Baths
    • 1,396 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  25. Photo of 200 Southern Pecan Circle #105, Winter Garden, FL 34787 (MLS # O6205722)
    $319,000
    Photo of 200 Southern Pecan Circle #105, Winter Garden, FL 34787 (MLS # O6205722)
    Photo of 200 Southern Pecan Circle #105, Winter Garden, FL 34787 (MLS # O6205722)
    200 Southern Pecan Circle #105, Winter Garden, FL
    200 Southern Pecan Circle #105
    Winter Garden, FL
    • 3 Beds
    • 2 Baths
    • 1,340 Home (sqft)
    • 2 Baths
    • 11,326 Lot (sqft)
  26. Photo of 14090 Avenue Of The Groves, Winter Garden, FL 34787 (MLS # O6205434)
    $372,000
    Photo of 14090 Avenue Of The Groves, Winter Garden, FL 34787 (MLS # O6205434)
    Photo of 14090 Avenue Of The Groves, Winter Garden, FL 34787 (MLS # O6205434)
    14090 Avenue Of The Groves, Winter Garden, FL
    14090 Avenue Of The Groves
    Winter Garden, FL
    • 2 Beds
    • 3 Baths
    • 1,076 Home (sqft)
    • 3 Baths
    • 2,178 Lot (sqft)
  27. Photo of 14501 Grove Resort Avenue #1635, Winter Garden, FL 34787 (MLS # S5104046)
    $349,000
    Photo of 14501 Grove Resort Avenue #1635, Winter Garden, FL 34787 (MLS # S5104046)
    Photo of 14501 Grove Resort Avenue #1635, Winter Garden, FL 34787 (MLS # S5104046)
    14501 Grove Resort Avenue #1635, Winter Garden, FL
    14501 Grove Resort Avenue #1635
    Winter Garden, FL
    • 3 Beds
    • 2 Baths
    • 1,396 Home (sqft)
    • 2 Baths
    • 1,743 Lot (sqft)
  28. Photo of . Grove Resort Avenue #2709, Winter Garden, FL 34787 (MLS # O6197673)
    $280,000
    Photo of . Grove Resort Avenue #2709, Winter Garden, FL 34787 (MLS # O6197673)
    Photo of . Grove Resort Avenue #2709, Winter Garden, FL 34787 (MLS # O6197673)
    . Grove Resort Avenue #2709, Winter Garden, FL
    . Grove Resort Avenue #2709
    Winter Garden, FL
    • 2 Beds
    • 2 Baths
    • 1,434 Home (sqft)
    • 2 Baths
    • 1,743 Lot (sqft)
  29. Photo of 14501 Grove Resort Avenue #3332, Winter Garden, FL 34787 (MLS # O6199910)
    $360,000
    Photo of 14501 Grove Resort Avenue #3332, Winter Garden, FL 34787 (MLS # O6199910)
    Photo of 14501 Grove Resort Avenue #3332, Winter Garden, FL 34787 (MLS # O6199910)
    14501 Grove Resort Avenue #3332, Winter Garden, FL
    14501 Grove Resort Avenue #3332
    Winter Garden, FL
    • 2 Beds
    • 2 Baths
    • 1,434 Home (sqft)
    • 2 Baths
    • 1,307 Lot (sqft)
  30. Photo of 14501 Grove Resort Avenue #3438, Winter Garden, FL 34787 (MLS # O6199583)
    $390,000
    Photo of 14501 Grove Resort Avenue #3438, Winter Garden, FL 34787 (MLS # O6199583)
    Photo of 14501 Grove Resort Avenue #3438, Winter Garden, FL 34787 (MLS # O6199583)
    14501 Grove Resort Avenue #3438, Winter Garden, FL
    14501 Grove Resort Avenue #3438
    Winter Garden, FL
    • 3 Beds
    • 2 Baths
    • 1,396 Home (sqft)
    • 2 Baths
    • 0 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 4:12 AM PST.

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