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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 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)
    16
     
     
    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)
    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)
  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)
    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)
  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)
    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)
  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)
    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)
  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)
    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)
  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)
    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)
  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)
    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)
  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)
    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)
  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)
    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)
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