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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 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 2105 Fosgate Drive, Winter Park, FL 32789 (MLS # O6212814)
    $1,450,999
    Photo of 2105 Fosgate Drive, Winter Park, FL 32789 (MLS # O6212814)
    Photo of 2105 Fosgate Drive, Winter Park, FL 32789 (MLS # O6212814)
    2105 Fosgate Drive, Winter Park, FL
    2105 Fosgate Drive
    Winter Park, FL
    • 5 Beds
    • 4 Baths
    • 3,068 Home (sqft)
    • 4 Baths
    • 11,762 Lot (sqft)
  2. Photo of 1400 Alabama Drive, Winter Park, FL 32789 (MLS # O6212012)
    $6,950,000
    Photo of 1400 Alabama Drive, Winter Park, FL 32789 (MLS # O6212012)
    Photo of 1400 Alabama Drive, Winter Park, FL 32789 (MLS # O6212012)
    1400 Alabama Drive, Winter Park, FL
    1400 Alabama Drive
    Winter Park, FL
    • 5 Beds
    • 9 Baths
    • 7,916 Home (sqft)
    • 9 Baths
    • 30,492 Lot (sqft)
  3. Photo of 850 Juanita Rael, Winter Park, FL 32789 (MLS # O6209075)
    $1,175,000
    Photo of 850 Juanita Rael, Winter Park, FL 32789 (MLS # O6209075)
    Photo of 850 Juanita Rael, Winter Park, FL 32789 (MLS # O6209075)
    850 Juanita Rael, Winter Park, FL
    850 Juanita Rael
    Winter Park, FL
    • 4 Beds
    • 3 Baths
    • 2,306 Home (sqft)
    • 3 Baths
    • 14,811 Lot (sqft)
  4. Photo of 2412 Chantilly Avenue, Winter Park, FL 32789 (MLS # O6206511)
    $2,495,000
    Photo of 2412 Chantilly Avenue, Winter Park, FL 32789 (MLS # O6206511)
    Photo of 2412 Chantilly Avenue, Winter Park, FL 32789 (MLS # O6206511)
    63
     
    2412 Chantilly Avenue, Winter Park, FL
    2412 Chantilly Avenue
    Winter Park, FL
    • 5 Beds
    • 7 Baths
    • 4,500 Home (sqft)
    • 7 Baths
    • 11,762 Lot (sqft)
  5. Photo of 1350 Lyndale Boulevard, Winter Park, FL 32789 (MLS # O6200787)
    $1,750,000
    Photo of 1350 Lyndale Boulevard, Winter Park, FL 32789 (MLS # O6200787)
    Photo of 1350 Lyndale Boulevard, Winter Park, FL 32789 (MLS # O6200787)
    1350 Lyndale Boulevard, Winter Park, FL
    1350 Lyndale Boulevard
    Winter Park, FL
    • 4 Beds
    • 5 Baths
    • 3,478 Home (sqft)
    • 5 Baths
    • 10,019 Lot (sqft)
  6. Photo of 220 Blossom Lane, Winter Park, FL 32789 (MLS # O6187877)
    $615,000
    Photo of 220 Blossom Lane, Winter Park, FL 32789 (MLS # O6187877)
    Photo of 220 Blossom Lane, Winter Park, FL 32789 (MLS # O6187877)
    220 Blossom Lane, Winter Park, FL
    220 Blossom Lane
    Winter Park, FL
    • 3 Beds
    • 2 Baths
    • 2,193 Home (sqft)
    • 2 Baths
    • 10,890 Lot (sqft)
  7. 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)
  8. 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)
  9. 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)
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