Recently Sold Winter Park, FL Homes

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  $4,599,000 Sold May 28, 2025

  985 Lincoln Cir, Winter Park, FL 32789

  • 5 Beds
  • 7 Baths
  • 3,660 Sq Ft
  • Built 1951

  Last Sold Summary

  • $1,257/SF
  • 0 Days On Market

  Current Estimated Value $4,202,672

  Last Listing Agent Clay Wooten UNITED REAL ESTATE PREFERRED

  985 Lincoln Cir, Winter Park, FL 32789
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  $545,000 Sold Nov 13, 2025

  1123 Fairway Dr, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,772 Sq Ft
  • Built 1979

  Last Sold Summary

  • 5% Below List Price
  • $308/SF
  • 73 Days On Market

  Last Listing Agent Tiffany Licata IRON VALLEY REAL ESTATE OSCEOLA

  1123 Fairway Dr, Winter Park, FL 32792
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  $775,000 Sold Apr 16, 2025

  744 London Rd, Winter Park, FL 32792

  • 5 Beds
  • 3 Baths
  • 2,804 Sq Ft
  • Built 1968

  Last Sold Summary

  • 9% Below List Price
  • $276/SF
  • 73 Days On Market

  Current Estimated Value $780,146

  Last Listing Agent Randall Shirey CHARLES RUTENBERG REALTY ORLANDO

  744 London Rd, Winter Park, FL 32792
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  $372,000 Sold Apr 02, 2025

  5339 Cypress Dr, Winter Park, FL 32792

  • 4 Beds
  • 2 Baths
  • 1,782 Sq Ft
  • Built 1975

  Last Sold Summary

  • $209/SF
  • 19 Days On Market

  Current Estimated Value $381,815

  Last Listing Agent JASON CRAWFORD FUTURE HOME REALTY INC

  5339 Cypress Dr, Winter Park, FL 32792
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  $615,000 Sold Apr 17, 2025

  735 Maryland Ave, Winter Park, FL 32789

  • 3 Beds
  • 2.5 Baths
  • 2,242 Sq Ft
  • Built 1987

  Last Sold Summary

  • 32% Below List Price
  • $274/SF
  • 82 Days On Market

  Current Estimated Value $653,366

  Last Listing Agent Chuck Massab FANNIE HILLMAN & ASSOCIATES

  735 Maryland Ave, Winter Park, FL 32789
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  $956,809 Sold Dec 18, 2025

  Lot #20 Karolina Ave, Winter Park, FL 32789

  • 4 Beds
  • 3.5 Baths
  • 2,662 Sq Ft
  • Built 2025

  Last Sold Summary

  • 4% Above List Price
  • $359/SF
  • 63 Days On Market

  Last Listing Agent Laura Hope COMPASS FLORIDA LLC

  Lot #20 Karolina Ave, Winter Park, FL 32789
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  $1,100,000 Sold Dec 30, 2025

  1701 Palmer Ave, Winter Park, FL 32789

  • 4 Beds
  • 3 Baths
  • 2,841 Sq Ft
  • Built 1953

  Last Sold Summary

  • $387/SF
  • 0 Days On Market

  Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE

  1701 Palmer Ave, Winter Park, FL 32789
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  $430,000 Sold Feb 24, 2025

  2206 Winter Woods Blvd, Winter Park, FL 32792

  • 4 Beds
  • 2 Baths
  • 2,208 Sq Ft
  • Built 1968

  Last Sold Summary

  • $195/SF
  • 6 Days On Market

  Current Estimated Value $435,388

  Last Listing Agent Amy Turner KELLER WILLIAMS WINTER PARK

  2206 Winter Woods Blvd, Winter Park, FL 32792
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  $896,628 Sold Nov 05, 2025

  3870 Tucks Point, Winter Park, FL 32792

  • 4 Beds
  • 4 Baths
  • 3,323 Sq Ft
  • Built 2003

  Last Sold Summary

  • 10% Below List Price
  • $270/SF
  • 31 Days On Market

  Current Estimated Value $889,799

  Last Listing Agent Nicole Dege REDFIN CORPORATION

  3870 Tucks Point, Winter Park, FL 32792
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  $165,000 Sold Jan 26, 2026

  224 Lewfield Cir Unit 224, Winter Park, FL 32792

  • 2 Beds
  • 2 Baths
  • 953 Sq Ft
  • Built 1973

  Last Sold Summary

  • 8% Below List Price
  • $173/SF
  • 124 Days On Market

  Last Listing Agent Chris Creegan CREEGAN GROUP

  224 Lewfield Cir Unit 224, Winter Park, FL 32792
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  $1,475,000 Sold Nov 21, 2025

  1453 Lyndale Blvd, Winter Park, FL 32789

  • 5 Beds
  • 3.5 Baths
  • 3,292 Sq Ft
  • Built 2012

  Last Sold Summary

  • 8% Below List Price
  • $448/SF
  • 54 Days On Market

  Last Listing Agent Tiffany Pantozzi ALIGN REAL ESTATE LLC

  1453 Lyndale Blvd, Winter Park, FL 32789
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  $600,000 Sold Sep 04, 2025

  618 Blairshire Cir, Winter Park, FL 32792

  • 3 Beds
  • 3 Baths
  • 1,876 Sq Ft
  • Built 1964

  Last Sold Summary

  • 14% Below List Price
  • $320/SF
  • 38 Days On Market

  Current Estimated Value $601,247

  Last Listing Agent Nicole Howell FANNIE HILLMAN & ASSOCIATES

  618 Blairshire Cir, Winter Park, FL 32792
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  $2,600,000 Sold Jan 23, 2026

  560 Country Club Dr, Winter Park, FL 32789

  • 6 Beds
  • 7 Baths
  • 3,946 Sq Ft
  • Built 2019

  Last Sold Summary

  • $659/SF
  • 4 Days On Market

  Last Listing Agent MaryStuart Day FANNIE HILLMAN & ASSOCIATES

  560 Country Club Dr, Winter Park, FL 32789
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  $415,000 Sold Aug 05, 2025

  1820 Blaine Terrace, Winter Park, FL 32792

  • 3 Beds
  • 2.5 Baths
  • 1,725 Sq Ft
  • Built 1990

  Last Sold Summary

  • 8% Below List Price
  • $241/SF
  • 230 Days On Market

  Current Estimated Value $418,261

  Last Listing Agent Melissa Gonzalez LPT REALTY, LLC

  1820 Blaine Terrace, Winter Park, FL 32792
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  $545,000 Sold Mar 07, 2025

  2227 King Charles Ct, Winter Park, FL 32792

  • 3 Beds
  • 2.5 Baths
  • 1,754 Sq Ft
  • Built 1970

  Last Sold Summary

  • $311/SF

  Current Estimated Value $532,805

  Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE

  2227 King Charles Ct, Winter Park, FL 32792
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  $485,000 Sold Mar 04, 2025

  1955 Dundee Dr, Winter Park, FL 32792

  • 3 Beds
  • 1.5 Baths
  • 1,144 Sq Ft
  • Built 1955

  Last Sold Summary

  • 25% Below List Price
  • $424/SF
  • 226 Days On Market

  Current Estimated Value $478,792

  Last Listing Agent David Earle CHARLES RUTENBERG REALTY ORLANDO

  1955 Dundee Dr, Winter Park, FL 32792
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  $771,000 Sold Oct 23, 2025

  1340 Pelham Rd, Winter Park, FL 32789

  • 3 Beds
  • 2 Baths
  • 2,042 Sq Ft
  • Built 1946

  Last Sold Summary

  • 1% Above List Price
  • $378/SF
  • 2 Days On Market

  Current Estimated Value $761,462

  Last Listing Agent Courtney Pelfrey MILLER GRANT AND COMPANY

  1340 Pelham Rd, Winter Park, FL 32789
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  $255,000 Sold Apr 18, 2025

  5466 Bracken Ct, Winter Park, FL 32792

  • 3 Beds
  • 2.5 Baths
  • 1,332 Sq Ft
  • Built 1984

  Last Sold Summary

  • 15% Below List Price
  • $191/SF
  • 122 Days On Market

  Current Estimated Value $272,131

  Last Listing Agent Tom Nestor EXP REALTY LLC

  5466 Bracken Ct, Winter Park, FL 32792
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  $569,990 Sold Oct 24, 2025

  1561 Nottingham Dr, Winter Park, FL 32792

  • 4 Beds
  • 2 Baths
  • 1,889 Sq Ft
  • Built 1971

  Last Sold Summary

  • $302/SF
  • 3 Days On Market

  Current Estimated Value $561,481

  Last Listing Agent Joseph Sipp KELLER WILLIAMS WINTER PARK

  1561 Nottingham Dr, Winter Park, FL 32792
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  $610,000 Sold Mar 10, 2025

  2127 Lake Dr, Winter Park, FL 32789

  • 3 Beds
  • 3 Baths
  • 1,732 Sq Ft
  • Built 1955

  Last Sold Summary

  • 1% Below List Price
  • $352/SF
  • 5 Days On Market

  Current Estimated Value $590,821

  Last Listing Agent Heather Frazee FANNIE HILLMAN & ASSOCIATES

  2127 Lake Dr, Winter Park, FL 32789

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