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 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 - 13 of 13 | Previous Page 1 of 1 Next

1. 

   $310,000

   

   

   10

    

    

   2465 Grand Teton Circle #2465, Winter Park, FL

   2465 Grand Teton Circle #2465
   Winter Park, FL

   • 2 Beds
   • 2 Baths
   • 1,457 Home (sqft)
   • 2 Baths
   • 2,178 Lot (sqft)
2. 

   $260,500

   

   

   39

    

    

   7474 Canford Court #13, Winter Park, FL

   7474 Canford Court #13
   Winter Park, FL

   • 2 Beds
   • 3 Baths
   • 1,611 Home (sqft)
   • 3 Baths
   • 6.71 Lot (ac)
3. 

   $124,500

   

   

   21

    

    

   257 Scottsdale Square #257, Winter Park, FL

   257 Scottsdale Square #257
   Winter Park, FL

   • 2 Beds
   • 2 Baths
   • 1,020 Home (sqft)
   • 2 Baths
   • 8,712 Lot (sqft)
4. 

   $113,000

   

   

   37

    

    

   337 Scottsdale Square #337, Winter Park, FL

   337 Scottsdale Square #337
   Winter Park, FL

   • 1 Bed
   • 1 Bath
   • 785 Home (sqft)
   • 1 Bath
   • 8,712 Lot (sqft)
5. 

   $220,000

   

   

   31

    

    

   3358 Cedar Springs Place #159, Winter Park, FL

   3358 Cedar Springs Place #159
   Winter Park, FL

   • 2 Beds
   • 3 Baths
   • 1,031 Home (sqft)
   • 3 Baths
   • 5.93 Lot (ac)
6. 

   $169,000

   

   

   15

    

    

   108 Scottsdale Square #108, Winter Park, FL

   108 Scottsdale Square #108
   Winter Park, FL

   • 3 Beds
   • 2 Baths
   • 1,300 Home (sqft)
   • 2 Baths
   • 8,712 Lot (sqft)
7. 

   $275,000

   

   

   26

    

    

   7707 Country Place, Winter Park, FL

   7707 Country Place
   Winter Park, FL

   • 2 Beds
   • 2 Baths
   • 1,068 Home (sqft)
   • 2 Baths
   • 872 Lot (sqft)
8. 

   $187,000

   

   

   17

    

    

   163 Lewfield Circle, Winter Park, FL

   163 Lewfield Circle
   Winter Park, FL

   • 1 Bed
   • 1 Bath
   • 678 Home (sqft)
   • 1 Bath
   • 872 Lot (sqft)
9. 

   $198,000

   

   

   20

    

    

   3651 N Goldenrod Road E #102, Winter Park, FL

   3651 N Goldenrod Road E #102
   Winter Park, FL

   • 2 Beds
   • 2 Baths
   • 840 Home (sqft)
   • 2 Baths
   • 9,584 Lot (sqft)
10. 

    $384,400

    

    

    28

     

     

    740 Killarney Bay Ct #7-3, Winter Park, FL

    740 Killarney Bay Ct #7-3
    Winter Park, FL

    • 2 Beds
    • 3 Baths
    • 1,536 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
11. 

    $399,900

    

    

    30

     

    5418 S Bracken Court, Winter Park, FL

    5418 S Bracken Court
    Winter Park, FL

    • 3 Beds
    • 2 Baths
    • 1,301 Home (sqft)
    • 2 Baths
    • 5,663 Lot (sqft)
12. 

    $265,000

    

    

    41

     

     

    7794 Country Place #7794, Winter Park, FL

    7794 Country Place #7794
    Winter Park, FL

    • 2 Beds
    • 2 Baths
    • 1,068 Home (sqft)
    • 2 Baths
    • 872 Lot (sqft)
13. 

    $189,000

    

    

    17

     

     

    1000 S Semoran Boulevard #608, Winter Park, FL

    1000 S Semoran Boulevard #608
    Winter Park, FL

    • 2 Beds
    • 2 Baths
    • 1,049 Home (sqft)
    • 2 Baths
    • 6.04 Lot (ac)

Previous Page 1 of 1 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 1/28/25 2:30 PM PST.

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