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 95 | Previous Page 1 of 4 Next

1. 

   $225,000

   

   

   15

    

    

   28 Windtree Lane #202, Winter Garden, FL

   28 Windtree Lane #202
   Winter Garden, FL

   • 2 Beds
   • 2 Baths
   • 918 Home (sqft)
   • 2 Baths
   • 4,356 Lot (sqft)
2. 

   $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)
3. 

   $116,900

   

   

   8

    

    

   418 Eron Way #40, Winter Garden, FL

   418 Eron Way #40
   Winter Garden, FL

   • 1 Bed
   • 1 Bath
   • 420 Home (sqft)
   • 1 Bath
   • 436 Lot (sqft)
4. 

   $325,000

   

   

   15

    

    

   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)
5. 

   $310,000

   

   

   20

    

    

   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)
6. 

   $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)
7. 

   $295,000

   

   

   37

    

    

   1308 Eagle Lane, Winter Garden, FL

   1308 Eagle Lane
   Winter Garden, FL

   • 3 Beds
   • 2 Baths
   • 1,260 Home (sqft)
   • 2 Baths
   • 2,178 Lot (sqft)
8. 

   $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)
9. 

   $315,000

   

   

   21

    

    

   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)
10. 

    $300,000

    

    

    28

     

     

    1670 Scarlet Oak Loop #A, Winter Garden, FL

    1670 Scarlet Oak Loop #A
    Winter Garden, FL

    • 2 Beds
    • 2 Baths
    • 1,216 Home (sqft)
    • 2 Baths
    • 3,050 Lot (sqft)
11. 

    $290,000

    

    

    27

     

     

    14878 Astrolyn Street, Winter Garden, FL

    14878 Astrolyn Street
    Winter Garden, FL

    • 3 Beds
    • 2 Baths
    • 1,260 Home (sqft)
    • 2 Baths
    • 6,099 Lot (sqft)
12. 

    $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)
13. 

    $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)
14. 

    $324,900

    

    

    21

     

     

    143 Southern Pecan Circle #105, Winter Garden, FL

    143 Southern Pecan Circle #105
    Winter Garden, FL

    • 3 Beds
    • 2 Baths
    • 1,340 Home (sqft)
    • 2 Baths
    • 11,326 Lot (sqft)
15. 

    $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)
16. 

    $339,900

    

    

    10

     

    206 Regal Downs Circle, Winter Garden, FL

    206 Regal Downs Circle
    Winter Garden, FL

    • 3 Beds
    • 2 Baths
    • 1,456 Home (sqft)
    • 2 Baths
    • 7,406 Lot (sqft)
17. 

    $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)
18. 

    $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)
19. 

    $399,000

    

    

    33

     

     

    139 W Story Road, Winter Garden, FL

    139 W Story Road
    Winter Garden, FL

    • 3 Beds
    • 2 Baths
    • 1,502 Home (sqft)
    • 2 Baths
    • 6,534 Lot (sqft)
20. 

    $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)
21. 

    $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)
22. 

    $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)
23. 

    $400,000

    

    

    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)
24. 

    $365,000

    

    

    20

     

    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)
25. 

    $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)
26. 

    $355,000

    

    

    35

     

     

    13633 Daniels Landing Circle, Winter Garden, FL

    13633 Daniels Landing Circle
    Winter Garden, FL

    • 3 Beds
    • 3 Baths
    • 1,455 Home (sqft)
    • 3 Baths
    • 3,050 Lot (sqft)
27. 

    $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)
28. 

    $318,000

    

    

    23

     

     

    236 Deepcove Road, Winter Garden, FL

    236 Deepcove Road
    Winter Garden, FL

    • 2 Beds
    • 3 Baths
    • 1,236 Home (sqft)
    • 3 Baths
    • 2,178 Lot (sqft)
29. 

    $365,000

    

    

    25

     

     

    14501 Grove Resort Avenue #3230, Winter Garden, FL

    14501 Grove Resort Avenue #3230
    Winter Garden, FL

    • 2 Beds
    • 2 Baths
    • 1,265 Home (sqft)
    • 2 Baths
    • 1,307 Lot (sqft)
30. 

    $369,000

    

    

    35

     

     

    14501 Grove Resort Avenue #3128, Winter Garden, FL

    14501 Grove Resort Avenue #3128
    Winter Garden, FL

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

Previous Page 1 of 4 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 11/21/24 2:12 AM PST.

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