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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 homes for sale above $600k 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 or schedule your FREE consultation here.


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  1. Photo of 1833 Loch Berry Road, Winter Park, FL 32789 (MLS # O6185001)
    $3,150,000
    Photo of 1833 Loch Berry Road, Winter Park, FL 32789 (MLS # O6185001)
    Photo of 1833 Loch Berry Road, Winter Park, FL 32789 (MLS # O6185001)
    1833 Loch Berry Road, Winter Park, FL
    1833 Loch Berry Road
    Winter Park, FL
    • 5 Beds
    • 5 Baths
    • 4,770 Home (sqft)
    • 5 Baths
    • 11,762 Lot (sqft)
  2. Photo of 1907 S Lakemont Avenue, Winter Park, FL 32792 (MLS # O6185675)
    $919,000
    Photo of 1907 S Lakemont Avenue, Winter Park, FL 32792 (MLS # O6185675)
    Photo of 1907 S Lakemont Avenue, Winter Park, FL 32792 (MLS # O6185675)
    1907 S Lakemont Avenue, Winter Park, FL
    1907 S Lakemont Avenue
    Winter Park, FL
    • 3 Beds
    • 4 Baths
    • 2,063 Home (sqft)
    • 4 Baths
    • 1,743 Lot (sqft)
  3. Photo of 336 Saint Dunstan Way, Winter Park, FL 32792 (MLS # O6185776)
    $659,000
    Photo of 336 Saint Dunstan Way, Winter Park, FL 32792 (MLS # O6185776)
    Photo of 336 Saint Dunstan Way, Winter Park, FL 32792 (MLS # O6185776)
    336 Saint Dunstan Way, Winter Park, FL
    336 Saint Dunstan Way
    Winter Park, FL
    • 3 Beds
    • 2 Baths
    • 1,715 Home (sqft)
    • 2 Baths
    • 8,277 Lot (sqft)
  4. Photo of 2612 Lafayette Avenue, Winter Park, FL 32789 (MLS # O6183345)
    $749,900
    Photo of 2612 Lafayette Avenue, Winter Park, FL 32789 (MLS # O6183345)
    Photo of 2612 Lafayette Avenue, Winter Park, FL 32789 (MLS # O6183345)
    2612 Lafayette Avenue, Winter Park, FL
    2612 Lafayette Avenue
    Winter Park, FL
    • 3 Beds
    • 3 Baths
    • 2,447 Home (sqft)
    • 3 Baths
    • 7,841 Lot (sqft)
  5. Photo of 2955 Sanbina Street, Winter Park, FL 32789 (MLS # O6183727)
    $649,900
    Photo of 2955 Sanbina Street, Winter Park, FL 32789 (MLS # O6183727)
    Photo of 2955 Sanbina Street, Winter Park, FL 32789 (MLS # O6183727)
    2955 Sanbina Street, Winter Park, FL
    2955 Sanbina Street
    Winter Park, FL
    • 3 Beds
    • 2 Baths
    • 1,553 Home (sqft)
    • 2 Baths
    • 10,019 Lot (sqft)
  6. Photo of 2955 Lolissa Lane, Winter Park, FL 32789 (MLS # O6202663)
    $889,000
    Photo of 2955 Lolissa Lane, Winter Park, FL 32789 (MLS # O6202663)
    Photo of 2955 Lolissa Lane, Winter Park, FL 32789 (MLS # O6202663)
    2955 Lolissa Lane, Winter Park, FL
    2955 Lolissa Lane
    Winter Park, FL
    • 4 Beds
    • 3 Baths
    • 3,902 Home (sqft)
    • 3 Baths
    • 8,712 Lot (sqft)
  7. Photo of 1340 Chestnut Avenue, Winter Park, FL 32789 (MLS # O6176048)
    $1,977,000
    Photo of 1340 Chestnut Avenue, Winter Park, FL 32789 (MLS # O6176048)
    Photo of 1340 Chestnut Avenue, Winter Park, FL 32789 (MLS # O6176048)
    1340 Chestnut Avenue, Winter Park, FL
    1340 Chestnut Avenue
    Winter Park, FL
    • 6 Beds
    • 6 Baths
    • 4,182 Home (sqft)
    • 6 Baths
    • 10,890 Lot (sqft)
  8. Photo of 1101 Kenwood Avenue, Winter Park, FL 32789 (MLS # O6172852)
    $1,625,000
    Photo of 1101 Kenwood Avenue, Winter Park, FL 32789 (MLS # O6172852)
    Photo of 1101 Kenwood Avenue, Winter Park, FL 32789 (MLS # O6172852)
    1101 Kenwood Avenue, Winter Park, FL
    1101 Kenwood Avenue
    Winter Park, FL
    • 3 Beds
    • 3 Baths
    • 2,955 Home (sqft)
    • 3 Baths
    • 7,841 Lot (sqft)
  9. Photo of 2009 Oglesby Avenue, Winter Park, FL 32789 (MLS # O6130245)
    $750,000
    Photo of 2009 Oglesby Avenue, Winter Park, FL 32789 (MLS # O6130245)
    Photo of 2009 Oglesby Avenue, Winter Park, FL 32789 (MLS # O6130245)
    2009 Oglesby Avenue, Winter Park, FL
    2009 Oglesby Avenue
    Winter Park, FL
    • 3 Beds
    • 1 Bath
    • 1,400 Home (sqft)
    • 1 Bath
    • 13,940 Lot (sqft)
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