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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 627 N Interlachen Avenue #B, Winter Park, FL 32789 (MLS # O6221409)
    $1,050,000
    Photo of 627 N Interlachen Avenue #B, Winter Park, FL 32789 (MLS # O6221409)
    Photo of 627 N Interlachen Avenue #B, Winter Park, FL 32789 (MLS # O6221409)
    627 N Interlachen Avenue #B, Winter Park, FL
    627 N Interlachen Avenue #B
    Winter Park, FL
    • 2 Beds
    • 2 Baths
    • 1,610 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
  2. Photo of 1005 Fairway Drive, Winter Park, FL 32792 (MLS # O6219989)
    $799,000
    Photo of 1005 Fairway Drive, Winter Park, FL 32792 (MLS # O6219989)
    Photo of 1005 Fairway Drive, Winter Park, FL 32792 (MLS # O6219989)
    1005 Fairway Drive, Winter Park, FL
    1005 Fairway Drive
    Winter Park, FL
    • 4 Beds
    • 3 Baths
    • 2,584 Home (sqft)
    • 3 Baths
    • 10,890 Lot (sqft)
  3. Photo of 2804 Dike Road, Winter Park, FL 32792 (MLS # O6220247)
    $799,900
    Photo of 2804 Dike Road, Winter Park, FL 32792 (MLS # O6220247)
    Photo of 2804 Dike Road, Winter Park, FL 32792 (MLS # O6220247)
    2804 Dike Road, Winter Park, FL
    2804 Dike Road
    Winter Park, FL
    • 4 Beds
    • 3 Baths
    • 2,503 Home (sqft)
    • 3 Baths
    • 1.87 Lot (ac)
  4. Photo of 1450 Mizell Avenue, Winter Park, FL 32789 (MLS # O6219532)
    $2,795,000
    Photo of 1450 Mizell Avenue, Winter Park, FL 32789 (MLS # O6219532)
    Photo of 1450 Mizell Avenue, Winter Park, FL 32789 (MLS # O6219532)
    1450 Mizell Avenue, Winter Park, FL
    1450 Mizell Avenue
    Winter Park, FL
    • 5 Beds
    • 7 Baths
    • 4,487 Home (sqft)
    • 7 Baths
    • 14,811 Lot (sqft)
  5. Photo of 1618 Holts Grove Circle, Winter Park, FL 32789 (MLS # O6220012)
    $3,225,000
    Photo of 1618 Holts Grove Circle, Winter Park, FL 32789 (MLS # O6220012)
    Photo of 1618 Holts Grove Circle, Winter Park, FL 32789 (MLS # O6220012)
    1618 Holts Grove Circle, Winter Park, FL
    1618 Holts Grove Circle
    Winter Park, FL
    • 5 Beds
    • 8 Baths
    • 4,807 Home (sqft)
    • 8 Baths
    • 15,246 Lot (sqft)
  6. Photo of 1771 Windsor Drive, Winter Park, FL 32789 (MLS # O6218556)
    $950,000
    Photo of 1771 Windsor Drive, Winter Park, FL 32789 (MLS # O6218556)
    Photo of 1771 Windsor Drive, Winter Park, FL 32789 (MLS # O6218556)
    28
     
    1771 Windsor Drive, Winter Park, FL
    1771 Windsor Drive
    Winter Park, FL
    • 3 Beds
    • 3 Baths
    • 2,059 Home (sqft)
    • 3 Baths
    • 11,326 Lot (sqft)
  7. Photo of 1840 Bryan Avenue, Winter Park, FL 32789 (MLS # O6219067)
    $2,200,000
    Photo of 1840 Bryan Avenue, Winter Park, FL 32789 (MLS # O6219067)
    Photo of 1840 Bryan Avenue, Winter Park, FL 32789 (MLS # O6219067)
    1840 Bryan Avenue, Winter Park, FL
    1840 Bryan Avenue
    Winter Park, FL
    • 4 Beds
    • 4 Baths
    • 3,727 Home (sqft)
    • 4 Baths
    • 12,633 Lot (sqft)
  8. Photo of 1932 Temple Drive, Winter Park, FL 32789 (MLS # O6218751)
    $1,295,000
    Photo of 1932 Temple Drive, Winter Park, FL 32789 (MLS # O6218751)
    Photo of 1932 Temple Drive, Winter Park, FL 32789 (MLS # O6218751)
    1932 Temple Drive, Winter Park, FL
    1932 Temple Drive
    Winter Park, FL
    • 3 Beds
    • 3 Baths
    • 2,432 Home (sqft)
    • 3 Baths
    • 10,455 Lot (sqft)
  9. Photo of 675 Overspin Drive, Winter Park, FL 32789 (MLS # O6217949)
    $946,500
    Photo of 675 Overspin Drive, Winter Park, FL 32789 (MLS # O6217949)
    Photo of 675 Overspin Drive, Winter Park, FL 32789 (MLS # O6217949)
    675 Overspin Drive, Winter Park, FL
    675 Overspin Drive
    Winter Park, FL
    • 4 Beds
    • 4 Baths
    • 2,764 Home (sqft)
    • 4 Baths
    • 6,970 Lot (sqft)
  10. Photo of 2234 Via Luna, Winter Park, FL 32789 (MLS # O6217019)
    $2,190,000
    Photo of 2234 Via Luna, Winter Park, FL 32789 (MLS # O6217019)
    Photo of 2234 Via Luna, Winter Park, FL 32789 (MLS # O6217019)
    2234 Via Luna, Winter Park, FL
    2234 Via Luna
    Winter Park, FL
    • 6 Beds
    • 4 Baths
    • 3,554 Home (sqft)
    • 4 Baths
    • 13,068 Lot (sqft)
  11. Photo of 230 S Ranger Boulevard, Winter Park, FL 32792 (MLS # O6216911)
    $675,000
    Photo of 230 S Ranger Boulevard, Winter Park, FL 32792 (MLS # O6216911)
    Photo of 230 S Ranger Boulevard, Winter Park, FL 32792 (MLS # O6216911)
    230 S Ranger Boulevard, Winter Park, FL
    230 S Ranger Boulevard
    Winter Park, FL
    • 3 Beds
    • 2 Baths
    • 2,309 Home (sqft)
    • 2 Baths
    • 8,712 Lot (sqft)
  12. Photo of 2408 Lafayette Avenue, Winter Park, FL 32789 (MLS # O6216221)
    $1,375,000
    Photo of 2408 Lafayette Avenue, Winter Park, FL 32789 (MLS # O6216221)
    Photo of 2408 Lafayette Avenue, Winter Park, FL 32789 (MLS # O6216221)
    2408 Lafayette Avenue, Winter Park, FL
    2408 Lafayette Avenue
    Winter Park, FL
    • 4 Beds
    • 4 Baths
    • 2,838 Home (sqft)
    • 4 Baths
    • 7,406 Lot (sqft)
  13. Photo of 1223 Formosa Avenue, Winter Park, FL 32789 (MLS # O6216744)
    $900,000
    Photo of 1223 Formosa Avenue, Winter Park, FL 32789 (MLS # O6216744)
    Photo of 1223 Formosa Avenue, Winter Park, FL 32789 (MLS # O6216744)
    1223 Formosa Avenue, Winter Park, FL
    1223 Formosa Avenue
    Winter Park, FL
    • 4 Beds
    • 3 Baths
    • 3,834 Home (sqft)
    • 3 Baths
    • 14,811 Lot (sqft)
  14. Photo of 858 Douglas Avenue, Winter Park, FL 32789 (MLS # V4936864)
    $1,400,000
    Photo of 858 Douglas Avenue, Winter Park, FL 32789 (MLS # V4936864)
    Photo of 858 Douglas Avenue, Winter Park, FL 32789 (MLS # V4936864)
    858 Douglas Avenue, Winter Park, FL
    858 Douglas Avenue
    Winter Park, FL
    • 4 Beds
    • 4 Baths
    • 2,334 Home (sqft)
    • 4 Baths
    • 6,970 Lot (sqft)
  15. Photo of 698 N New York Avenue, Winter Park, FL 32789 (MLS # O6211406)
    $5,695,000
    Photo of 698 N New York Avenue, Winter Park, FL 32789 (MLS # O6211406)
    Photo of 698 N New York Avenue, Winter Park, FL 32789 (MLS # O6211406)
    698 N New York Avenue, Winter Park, FL
    698 N New York Avenue
    Winter Park, FL
    • 4 Beds
    • 5 Baths
    • 5,096 Home (sqft)
    • 5 Baths
    • 10,890 Lot (sqft)
  16. Photo of 2105 Fosgate Drive, Winter Park, FL 32789 (MLS # O6212814)
    $1,550,000
    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)
  17. 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)
  18. Photo of 1660 Palmer Avenue, Winter Park, FL 32789 (MLS # O6209613)
    $5,500,000
    Photo of 1660 Palmer Avenue, Winter Park, FL 32789 (MLS # O6209613)
    Photo of 1660 Palmer Avenue, Winter Park, FL 32789 (MLS # O6209613)
    1660 Palmer Avenue, Winter Park, FL
    1660 Palmer Avenue
    Winter Park, FL
    • 5 Beds
    • 7 Baths
    • 5,636 Home (sqft)
    • 7 Baths
    • 15,682 Lot (sqft)
  19. Photo of 1905 S Lakemont Avenue, Winter Park, FL 32792 (MLS # O6210889)
    $899,500
    Photo of 1905 S Lakemont Avenue, Winter Park, FL 32792 (MLS # O6210889)
    Photo of 1905 S Lakemont Avenue, Winter Park, FL 32792 (MLS # O6210889)
    1905 S Lakemont Avenue, Winter Park, FL
    1905 S Lakemont Avenue
    Winter Park, FL
    • 3 Beds
    • 4 Baths
    • 2,066 Home (sqft)
    • 4 Baths
    • 1,743 Lot (sqft)
  20. 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)
  21. Photo of 1250 S Pennsylvania Avenue #8, Winter Park, FL 32789 (MLS # A4611556)
    $809,999
    Photo of 1250 S Pennsylvania Avenue #8, Winter Park, FL 32789 (MLS # A4611556)
    Photo of 1250 S Pennsylvania Avenue #8, Winter Park, FL 32789 (MLS # A4611556)
    1250 S Pennsylvania Avenue #8, Winter Park, FL
    1250 S Pennsylvania Avenue #8
    Winter Park, FL
    • 3 Beds
    • 3 Baths
    • 1,957 Home (sqft)
    • 3 Baths
    • 1,307 Lot (sqft)
  22. 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)
  23. Photo of 1621 Lasbury Avenue, Winter Park, FL 32789 (MLS # O6202020)
    $949,000
    Photo of 1621 Lasbury Avenue, Winter Park, FL 32789 (MLS # O6202020)
    Photo of 1621 Lasbury Avenue, Winter Park, FL 32789 (MLS # O6202020)
    1621 Lasbury Avenue, Winter Park, FL
    1621 Lasbury Avenue
    Winter Park, FL
    • 3 Beds
    • 3 Baths
    • 2,267 Home (sqft)
    • 3 Baths
    • 7,406 Lot (sqft)
  24. Photo of 147 S Interlachen Avenue #400, Winter Park, FL 32789 (MLS # O6201756)
    $2,695,000
    Photo of 147 S Interlachen Avenue #400, Winter Park, FL 32789 (MLS # O6201756)
    Photo of 147 S Interlachen Avenue #400, Winter Park, FL 32789 (MLS # O6201756)
    147 S Interlachen Avenue #400, Winter Park, FL
    147 S Interlachen Avenue #400
    Winter Park, FL
    • 4 Beds
    • 5 Baths
    • 5,159 Home (sqft)
    • 5 Baths
    • 0 Lot (sqft)
  25. 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)
  26. Photo of 508 W Swoope Avenue, Winter Park, FL 32789 (MLS # O6208366)
    $1,795,000
    Photo of 508 W Swoope Avenue, Winter Park, FL 32789 (MLS # O6208366)
    Photo of 508 W Swoope Avenue, Winter Park, FL 32789 (MLS # O6208366)
    508 W Swoope Avenue, Winter Park, FL
    508 W Swoope Avenue
    Winter Park, FL
    • 4 Beds
    • 4 Baths
    • 4,133 Home (sqft)
    • 4 Baths
    • 3,050 Lot (sqft)
  27. Photo of 571 Lake Front Boulevard, Winter Park, FL 32789 (MLS # O6220284)
    $4,200,000
    Photo of 571 Lake Front Boulevard, Winter Park, FL 32789 (MLS # O6220284)
    Photo of 571 Lake Front Boulevard, Winter Park, FL 32789 (MLS # O6220284)
    571 Lake Front Boulevard, Winter Park, FL
    571 Lake Front Boulevard
    Winter Park, FL
    • 7 Beds
    • 5 Baths
    • 5,500 Home (sqft)
    • 5 Baths
    • 20,909 Lot (sqft)
  28. Photo of 985 Lincoln Circle, Winter Park, FL 32789 (MLS # O6193386)
    $4,250,000
    Photo of 985 Lincoln Circle, Winter Park, FL 32789 (MLS # O6193386)
    Photo of 985 Lincoln Circle, Winter Park, FL 32789 (MLS # O6193386)
    985 Lincoln Circle, Winter Park, FL
    985 Lincoln Circle
    Winter Park, FL
    • 5 Beds
    • 7 Baths
    • 3,660 Home (sqft)
    • 7 Baths
    • 10,019 Lot (sqft)
  29. Photo of 1741 Glencoe Road, Winter Park, FL 32789 (MLS # O6190641)
    $2,749,000
    Photo of 1741 Glencoe Road, Winter Park, FL 32789 (MLS # O6190641)
    Photo of 1741 Glencoe Road, Winter Park, FL 32789 (MLS # O6190641)
    1741 Glencoe Road, Winter Park, FL
    1741 Glencoe Road
    Winter Park, FL
    • 4 Beds
    • 5 Baths
    • 4,692 Home (sqft)
    • 5 Baths
    • 11,762 Lot (sqft)
  30. Photo of 106 S Interlachen Avenue #317, Winter Park, FL 32789 (MLS # O6190685)
    $825,000
    Photo of 106 S Interlachen Avenue #317, Winter Park, FL 32789 (MLS # O6190685)
    Photo of 106 S Interlachen Avenue #317, Winter Park, FL 32789 (MLS # O6190685)
    106 S Interlachen Avenue #317, Winter Park, FL
    106 S Interlachen Avenue #317
    Winter Park, FL
    • 2 Beds
    • 2 Baths
    • 1,351 Home (sqft)
    • 2 Baths
    • 1,307 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 11/23/24 6:13 AM PST.

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