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Winter Park is home to a plethora of world-class museums, high-end boutiques, some of the area's finest restaurants, and is centrally located being only minutes from downtown Orlando. Use our custom search tool to view all pool homes for sale under $400k in Winter Park or click here to return to the list of surrounding towns and cities in the Orlando area. Have questions? Contact us here.

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  1. Photo of 1757 Chilean Lane, Winter Park, FL 32792 (MLS # O6256824)
    $400,000
    Photo of 1757 Chilean Lane, Winter Park, FL 32792 (MLS # O6256824)
    Photo of 1757 Chilean Lane, Winter Park, FL 32792 (MLS # O6256824)
    53
     
     
    1757 Chilean Lane, Winter Park, FL
    1757 Chilean Lane
    Winter Park, FL
    • 4 Beds
    • 2 Baths
    • 1,413 Home (sqft)
    • 2 Baths
    • 8,712 Lot (sqft)
  2. 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)
    21
     
     
    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)
  3. Photo of 151 North Orlando Ave #142, Winter Park, FL 32789 (MLS # O6250765)
    $199,000
    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)
    20
     
     
    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)
  4. 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)
    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)
  5. 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)
    28
     
     
    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)
  6. 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)
  7. Photo of 210 Scottsdale Square #210, Winter Park, FL 32792 (MLS # O6249283)
    $149,900
    Photo of 210 Scottsdale Square #210, Winter Park, FL 32792 (MLS # O6249283)
    Photo of 210 Scottsdale Square #210, Winter Park, FL 32792 (MLS # O6249283)
    10
     
     
    210 Scottsdale Square #210, Winter Park, FL
    210 Scottsdale Square #210
    Winter Park, FL
    • 2 Beds
    • 2 Baths
    • 1,085 Home (sqft)
    • 2 Baths
    • 5,663 Lot (sqft)
  8. Photo of 7794 Country Place #7794, Winter Park, FL 32792 (MLS # O6243737)
    $269,500
    Photo of 7794 Country Place #7794, Winter Park, FL 32792 (MLS # O6243737)
    Photo of 7794 Country Place #7794, Winter Park, FL 32792 (MLS # O6243737)
    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)
  9. Photo of 2434 Barbados Drive, Winter Park, FL 32792 (MLS # O6231911)
    $299,000
    Photo of 2434 Barbados Drive, Winter Park, FL 32792 (MLS # O6231911)
    Photo of 2434 Barbados Drive, Winter Park, FL 32792 (MLS # O6231911)
    28
     
    2434 Barbados Drive, Winter Park, FL
    2434 Barbados Drive
    Winter Park, FL
    • 3 Beds
    • 2 Baths
    • 1,284 Home (sqft)
    • 2 Baths
    • 4,356 Lot (sqft)
  10. 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)
    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)
  11. Photo of 1360 Westdale Avenue, Winter Park, FL 32792 (MLS # O6205879)
    $375,000
    Photo of 1360 Westdale Avenue, Winter Park, FL 32792 (MLS # O6205879)
    Photo of 1360 Westdale Avenue, Winter Park, FL 32792 (MLS # O6205879)
    25
     
     
    1360 Westdale Avenue, Winter Park, FL
    1360 Westdale Avenue
    Winter Park, FL
    • 3 Beds
    • 2 Baths
    • 1,318 Home (sqft)
    • 2 Baths
    • 8,712 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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