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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 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 311 E Morse Boulevard #7-15, Winter Park, FL 32789 (MLS # O6265966)
    $329,900
    Photo of 311 E Morse Boulevard #7-15, Winter Park, FL 32789 (MLS # O6265966)
    Photo of 311 E Morse Boulevard #7-15, Winter Park, FL 32789 (MLS # O6265966)
    311 E Morse Boulevard #7-15, Winter Park, FL
    311 E Morse Boulevard #7-15
    Winter Park, FL
    • 1 Bed
    • 1 Bath
    • 482 Home (sqft)
    • 1 Bath
    • 2.77 Lot (ac)
  2. Photo of 108 Scottsdale Square #108, Winter Park, FL 32792 (MLS # O6265811)
    $169,999
    Photo of 108 Scottsdale Square #108, Winter Park, FL 32792 (MLS # O6265811)
    Photo of 108 Scottsdale Square #108, Winter Park, FL 32792 (MLS # O6265811)
    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)
  3. Photo of 7707 Country Place, Winter Park, FL 32792 (MLS # O6260326)
    $275,000
    Photo of 7707 Country Place, Winter Park, FL 32792 (MLS # O6260326)
    Photo of 7707 Country Place, Winter Park, FL 32792 (MLS # O6260326)
    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)
  4. Photo of 163 Lewfield Circle, Winter Park, FL 32792 (MLS # S5116141)
    $187,000
    Photo of 163 Lewfield Circle, Winter Park, FL 32792 (MLS # S5116141)
    Photo of 163 Lewfield Circle, Winter Park, FL 32792 (MLS # S5116141)
    163 Lewfield Circle, Winter Park, FL
    163 Lewfield Circle
    Winter Park, FL
    • 1 Bed
    • 1 Bath
    • 678 Home (sqft)
    • 1 Bath
    • 872 Lot (sqft)
  5. Photo of 145 Scottsdale Square #145, Winter Park, FL 32792 (MLS # S5114886)
    $160,000
    Photo of 145 Scottsdale Square #145, Winter Park, FL 32792 (MLS # S5114886)
    Photo of 145 Scottsdale Square #145, Winter Park, FL 32792 (MLS # S5114886)
    145 Scottsdale Square #145, Winter Park, FL
    145 Scottsdale Square #145
    Winter Park, FL
    • 2 Beds
    • 2 Baths
    • 1,020 Home (sqft)
    • 2 Baths
    • 8,712 Lot (sqft)
  6. Photo of 151 North Orlando Ave #142, Winter Park, FL 32789 (MLS # O6250765)
    $179,000
    Photo of 151 North Orlando Ave #142, Winter Park, FL 32789 (MLS # O6250765)
    Photo of 151 North Orlando Ave #142, Winter Park, FL 32789 (MLS # O6250765)
    151 North Orlando Ave #142, Winter Park, FL
    151 North Orlando Ave #142
    Winter Park, FL
    • 1 Bed
    • 1 Bath
    • 582 Home (sqft)
    • 1 Bath
    • 8,712 Lot (sqft)
  7. Photo of 3651 N Goldenrod Road E #102, Winter Park, FL 32792 (MLS # W7869224)
    $199,999
    Photo of 3651 N Goldenrod Road E #102, Winter Park, FL 32792 (MLS # W7869224)
    Photo of 3651 N Goldenrod Road E #102, Winter Park, FL 32792 (MLS # W7869224)
    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)
  8. Photo of 740 #3 Killarney Bay Ct, Winter Park, FL 32789 (MLS # O6249823)
    $384,400
    Photo of 740 #3 Killarney Bay Ct, Winter Park, FL 32789 (MLS # O6249823)
    Photo of 740 #3 Killarney Bay Ct, Winter Park, FL 32789 (MLS # O6249823)
    740 #3 Killarney Bay Ct, Winter Park, FL
    740 #3 Killarney Bay Ct
    Winter Park, FL
    • 2 Beds
    • 3 Baths
    • 1,536 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
  9. Photo of 5418 S Bracken Court, Winter Park, FL 32792 (MLS # O6251052)
    $399,900
    Photo of 5418 S Bracken Court, Winter Park, FL 32792 (MLS # O6251052)
    Photo of 5418 S Bracken Court, Winter Park, FL 32792 (MLS # O6251052)
    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)
  10. Photo of 7794 Country Place #7794, Winter Park, FL 32792 (MLS # O6243737)
    $269,900
    Photo of 7794 Country Place #7794, Winter Park, FL 32792 (MLS # O6243737)
    Photo of 7794 Country Place #7794, Winter Park, FL 32792 (MLS # O6243737)
    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)
  11. Photo of 1000 S Semoran Boulevard #608, Winter Park, FL 32792 (MLS # O6213242)
    $195,000
    Photo of 1000 S Semoran Boulevard #608, Winter Park, FL 32792 (MLS # O6213242)
    Photo of 1000 S Semoran Boulevard #608, Winter Park, FL 32792 (MLS # O6213242)
    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)
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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 12/22/24 6:20 PM PST.

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