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 - 30 of 86 | Previous Page 1 of 3 Next

1. 

   $375,000

   

   

   50

    

    

   14453 Pleach Street, Winter Garden, FL

   14453 Pleach Street
   Winter Garden, FL

   • 2 Beds
   • 3 Baths
   • 1,448 Home (sqft)
   • 3 Baths
   • 2,614 Lot (sqft)
2. 

   $249,900

   

   

   18

    

    

   1170 Westside Drive, Winter Garden, FL

   1170 Westside Drive
   Winter Garden, FL

   • 2 Beds
   • 2 Baths
   • 814 Home (sqft)
   • 2 Baths
   • 2,178 Lot (sqft)
3. 

   $319,900

   

   

   11

    

    

   577 Maxey Avenue, Winter Garden, FL

   577 Maxey Avenue
   Winter Garden, FL

   • 5 Beds
   • 3 Baths
   • 1,764 Home (sqft)
   • 3 Baths
   • 6,970 Lot (sqft)
4. 

   $345,000

   

   

   19

    

    

   14501 Grove Resort Avenue #3636, Winter Garden, FL

   14501 Grove Resort Avenue #3636
   Winter Garden, FL

   • 2 Beds
   • 2 Baths
   • 1,396 Home (sqft)
   • 2 Baths
   • 1,743 Lot (sqft)
5. 

   $295,000

   

   

   27

    

    

   159 Deepcove Road, Winter Garden, FL

   159 Deepcove Road
   Winter Garden, FL

   • 2 Beds
   • 3 Baths
   • 1,236 Home (sqft)
   • 3 Baths
   • 2,178 Lot (sqft)
6. 

   $280,000

   

   

   40

    

    

   14501 Grove Resort Avenue #2607, Winter Garden, FL

   14501 Grove Resort Avenue #2607
   Winter Garden, FL

   • 3 Beds
   • 2 Baths
   • 1,396 Home (sqft)
   • 2 Baths
   • 1,743 Lot (sqft)
7. 

   $345,000

   

   

   28

    

    

   14501 Grove Resort Avenue #2535, Winter Garden, FL

   14501 Grove Resort Avenue #2535
   Winter Garden, FL

   • 2 Beds
   • 2 Baths
   • 1,434 Home (sqft)
   • 2 Baths
   • 1,743 Lot (sqft)
8. 

   $318,000

   

   

   39

    

    

   13228 Daniels Landing Circle, Winter Garden, FL

   13228 Daniels Landing Circle
   Winter Garden, FL

   • 2 Beds
   • 3 Baths
   • 1,332 Home (sqft)
   • 3 Baths
   • 2,178 Lot (sqft)
9. 

   $325,000

   

   

   49

    

    

   14501 Grove Resort Avenue #1727, Winter Garden, FL

   14501 Grove Resort Avenue #1727
   Winter Garden, FL

   • 2 Beds
   • 2 Baths
   • 1,265 Home (sqft)
   • 2 Baths
   • 1,307 Lot (sqft)
10. 

    $310,000

    

    

    18

     

     

    241 Deepcove Road, Winter Garden, FL

    241 Deepcove Road
    Winter Garden, FL

    • 2 Beds
    • 3 Baths
    • 1,234 Home (sqft)
    • 3 Baths
    • 2,178 Lot (sqft)
11. 

    $370,000

    

    

    16

     

     

    14712 Micah Street, Winter Garden, FL

    14712 Micah Street
    Winter Garden, FL

    • 3 Beds
    • 2 Baths
    • 1,331 Home (sqft)
    • 2 Baths
    • 4,792 Lot (sqft)
12. 

    $305,000

    

    

    26

     

     

    14501 Grove Resort Avenue #2539, Winter Garden, FL

    14501 Grove Resort Avenue #2539
    Winter Garden, FL

    • 2 Beds
    • 2 Baths
    • 1,375 Home (sqft)
    • 2 Baths
    • 1,743 Lot (sqft)
13. 

    $325,000

    

    

    56

     

     

    14501 Grove Resort Avenue #3410, Winter Garden, FL

    14501 Grove Resort Avenue #3410
    Winter Garden, FL

    • 2 Beds
    • 2 Baths
    • 1,434 Home (sqft)
    • 2 Baths
    • 1,743 Lot (sqft)
14. 

    $310,000

    

    

    21

     

     

    14051 Unit 1705 Grove Resort Avenue, Winter Garden, FL

    14051 Unit 1705 Grove Resort Avenue
    Winter Garden, FL

    • 2 Beds
    • 2 Baths
    • 1,265 Home (sqft)
    • 2 Baths
    • 1,307 Lot (sqft)
15. 

    $350,000

    

    

    50

     

     

    14501 Grove Resort Avenue #2423, Winter Garden, FL

    14501 Grove Resort Avenue #2423
    Winter Garden, FL

    • 2 Beds
    • 2 Baths
    • 1,265 Home (sqft)
    • 2 Baths
    • 1,743 Lot (sqft)
16. 

    $330,000

    

    

    24

     

    14501 Grove Resort Avenue #3342, Winter Garden, FL

    14501 Grove Resort Avenue #3342
    Winter Garden, FL

    • 3 Beds
    • 3 Baths
    • 1,544 Home (sqft)
    • 3 Baths
    • 1,743 Lot (sqft)
17. 

    $359,900

    

    

    54

     

     

    1468 Scarlet Oak Loop, Winter Garden, FL

    1468 Scarlet Oak Loop
    Winter Garden, FL

    • 3 Beds
    • 3 Baths
    • 1,592 Home (sqft)
    • 3 Baths
    • 6,534 Lot (sqft)
18. 

    $315,000

    

    

    35

     

     

    14501 Grove Resort Avenue #1618, Winter Garden, FL

    14501 Grove Resort Avenue #1618
    Winter Garden, FL

    • 2 Beds
    • 2 Baths
    • 1,265 Home (sqft)
    • 2 Baths
    • 1,743 Lot (sqft)
19. 

    $269,500

    

    

    26

     

     

    14501 Grove Resort Avenue #1332, Winter Garden, FL

    14501 Grove Resort Avenue #1332
    Winter Garden, FL

    • 2 Beds
    • 2 Baths
    • 1,265 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
20. 

    $325,000

    

    

    38

     

     

    14501 Grove Resort Avenue #3642, Winter Garden, FL

    14501 Grove Resort Avenue #3642
    Winter Garden, FL

    • 3 Beds
    • 3 Baths
    • 1,544 Home (sqft)
    • 3 Baths
    • 1,743 Lot (sqft)
21. 

    $370,000

    

    

    15

     

     

    14501 Grove Resort Avenue #2608, Winter Garden, FL

    14501 Grove Resort Avenue #2608
    Winter Garden, FL

    • 3 Beds
    • 2 Baths
    • 1,396 Home (sqft)
    • 2 Baths
    • 1,743 Lot (sqft)
22. 

    $369,000

    

    

    65

     

    14501 Grove Resort Avenue #1507, Winter Garden, FL

    14501 Grove Resort Avenue #1507
    Winter Garden, FL

    • 3 Beds
    • 3 Baths
    • 1,544 Home (sqft)
    • 3 Baths
    • 1,743 Lot (sqft)
23. 

    $235,000

    

    

    38

     

     

    14200 Avalon Road #219, Winter Garden, FL

    14200 Avalon Road #219
    Winter Garden, FL

    • 2 Beds
    • 2 Baths
    • 1,203 Home (sqft)
    • 2 Baths
    • 1,307 Lot (sqft)
24. 

    $399,000

    

    

    20

     

     

    14501 Grove Resort Avenue #2439, Winter Garden, FL

    14501 Grove Resort Avenue #2439
    Winter Garden, FL

    • 2 Beds
    • 2 Baths
    • 1,375 Home (sqft)
    • 2 Baths
    • 1,743 Lot (sqft)
25. 

    $220,000

    

    

    37

     

     

    1085 Lincoln Terrace, Winter Garden, FL

    1085 Lincoln Terrace
    Winter Garden, FL

    • 4 Beds
    • 2 Baths
    • 1,065 Home (sqft)
    • 2 Baths
    • 6,099 Lot (sqft)
26. 

    $325,000

    

    

    54

     

     

    13962 Daniels Landing Cir, Winter Garden, FL

    13962 Daniels Landing Cir
    Winter Garden, FL

    • 2 Beds
    • 3 Baths
    • 1,236 Home (sqft)
    • 3 Baths
    • 2,178 Lot (sqft)
27. 

    $380,000

    

    

    26

     

     

    14501 Grove Resort Avenue #2704, Winter Garden, FL

    14501 Grove Resort Avenue #2704
    Winter Garden, FL

    • 2 Beds
    • 2 Baths
    • 1,375 Home (sqft)
    • 2 Baths
    • 1,307 Lot (sqft)
28. 

    $365,000

    

    

    15

     

    14177 Avenue Of The Grvs Grvs, Winter Garden, FL

    14177 Avenue Of The Grvs Grvs
    Winter Garden, FL

    • 2 Beds
    • 3 Baths
    • 1,249 Home (sqft)
    • 3 Baths
    • 545.00 Lot (ac)
29. 

    $320,000

    

    

    14

     

     

    14501 Grove Resort Avenue #3439, Winter Garden, FL

    14501 Grove Resort Avenue #3439
    Winter Garden, FL

    • 2 Beds
    • 2 Baths
    • 1,375 Home (sqft)
    • 2 Baths
    • 1,743 Lot (sqft)
30. 

    $399,000

    

    

    31

     

     

    0 Grove Resort Avenue #3209, Winter Garden, FL

    0 Grove Resort Avenue #3209
    Winter Garden, FL

    • 2 Beds
    • 2 Baths
    • 1,434 Home (sqft)
    • 2 Baths
    • 1,743 Lot (sqft)

Previous Page 1 of 3 Next

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 2:20 PM PST.

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