Recently Sold Winter Park, FL Homes

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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 $588,674

  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

  Current Estimated Value $2,579,199

  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 $415,112

  Last Listing Agent Melissa Gonzalez LPT REALTY, LLC

  1820 Blaine Terrace, 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 $753,263

  Last Listing Agent Courtney Pelfrey MILLER GRANT AND COMPANY

  1340 Pelham Rd, Winter Park, FL 32789
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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 $559,810

  Last Listing Agent Joseph Sipp KELLER WILLIAMS WINTER PARK

  1561 Nottingham Dr, Winter Park, FL 32792
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  $550,000 Sold Apr 30, 2026

  535 N Interlachen Ave Unit 203, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 986 Sq Ft
  • Built 1972

  Last Sold Summary

  • $558/SF
  • 135 Days On Market

  Current Estimated Value $539,751

  Last Listing Agent Mary Colton FANNIE HILLMAN & ASSOCIATES

  535 N Interlachen Ave Unit 203, Winter Park, FL 32789
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  $850,000 Sold Feb 11, 2026

  1351 Mayfield Ave, Winter Park, FL 32789

  • 3 Beds
  • 2 Baths
  • 1,466 Sq Ft
  • Built 1953

  Last Sold Summary

  • $580/SF
  • 0 Days On Market

  Current Estimated Value $850,450

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

  1351 Mayfield Ave, Winter Park, FL 32789
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  $399,000 Sold Sep 30, 2025

  4959 Ardmore Dr, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,664 Sq Ft
  • Built 1979

  Last Sold Summary

  • 9% Below List Price
  • $240/SF
  • 68 Days On Market

  Current Estimated Value $417,073

  Last Listing Agent Brandon Geers COMPASS FLORIDA LLC

  4959 Ardmore Dr, Winter Park, FL 32792
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  $589,900 Sold Mar 12, 2026

  2492 Brookshire Ave, Winter Park, FL 32792

  • 3 Beds
  • 1.5 Baths
  • 1,352 Sq Ft
  • Built 1959

  Last Sold Summary

  • $436/SF
  • 0 Days On Market

  Current Estimated Value $583,800

  Last Listing Agent Ameer Chaseb COMPASS FLORIDA LLC

  2492 Brookshire Ave, Winter Park, FL 32792
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  $439,000 Sold Jul 17, 2025

  2823 Cady Way, Winter Park, FL 32792

  • 4 Beds
  • 2 Baths
  • 1,688 Sq Ft
  • Built 1965

  Last Sold Summary

  • 25% Below List Price
  • $260/SF
  • 137 Days On Market

  Current Estimated Value $454,860

  Last Listing Agent Ingrid Livingston COLDWELL BANKER REALTY

  2823 Cady Way, Winter Park, FL 32792
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  $460,000 Sold Mar 13, 2026

  714 Denton Rd, Winter Park, FL 32792

  • 3 Beds
  • 3 Baths
  • 1,786 Sq Ft
  • Built 1961

  Last Sold Summary

  • 2% Above List Price
  • $258/SF
  • 67 Days On Market

  Current Estimated Value $439,995

  Last Listing Agent Lauren Lester COLONIALTOWN REALTY

  714 Denton Rd, Winter Park, FL 32792
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  $80,000 Sold Sep 24, 2025

  318 Scottsdale Square Unit 318, Winter Park, FL 32792

  • 2 Beds
  • 2 Baths
  • 1,020 Sq Ft
  • Built 1974

  Last Sold Summary

  • 29% Below List Price
  • $78/SF
  • 209 Days On Market

  Current Estimated Value $83,497

  Last Listing Agent Brittneyann Cover RE/MAX ASSURED

  318 Scottsdale Square Unit 318, Winter Park, FL 32792
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  $1,500,000 Sold Feb 19, 2026

  315 E New England Ave Unit 7, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 1,609 Sq Ft
  • Built 2007

  Last Sold Summary

  • 10% Below List Price
  • $932/SF
  • 33 Days On Market

  Current Estimated Value $1,628,156

  Last Listing Agent Drew Henner PREMIER SOTHEBY'S INTL. REALTY

  315 E New England Ave Unit 7, Winter Park, FL 32789
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  $4,450,000 Sold Dec 23, 2025

  1812 Stonehurst Rd, Winter Park, FL 32789

  • 5 Beds
  • 7 Baths
  • 5,160 Sq Ft
  • Built 2017

  Last Sold Summary

  • $862/SF
  • 0 Days On Market

  Current Estimated Value $4,389,385

  Last Listing Agent Albin Hubscher CENTRAL FLORIDA PRIME REAL ESTATE LLC

  1812 Stonehurst Rd, Winter Park, FL 32789
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  $735,000 Sold Jun 17, 2025

  1312 Golfside Dr, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,867 Sq Ft
  • Built 1979

  Last Sold Summary

  • 6% Below List Price
  • $394/SF
  • 62 Days On Market

  Current Estimated Value $727,549

  Last Listing Agent Uno Sorlie HOPKEY REALTY

  1312 Golfside Dr, Winter Park, FL 32792
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  $920,000 Sold Dec 16, 2025

  2129 Fosgate Dr, Winter Park, FL 32789

  • 3 Beds
  • 3 Baths
  • 2,515 Sq Ft
  • Built 1957

  Last Sold Summary

  • 6% Below List Price
  • $366/SF
  • 34 Days On Market

  Current Estimated Value $915,749

  Last Listing Agent Alison Mosley PREMIER SOTHEBY'S INTL. REALTY

  2129 Fosgate Dr, Winter Park, FL 32789
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  $430,000 Sold Jun 06, 2025

  3420 Arnel Dr, Winter Park, FL 32792

  • 4 Beds
  • 2 Baths
  • 1,998 Sq Ft
  • Built 1967

  Last Sold Summary

  • 2% Below List Price
  • $215/SF
  • 51 Days On Market

  Current Estimated Value $438,643

  Last Listing Agent Brenden Rando NEXTHOME NEIGHBORHOOD REALTY

  3420 Arnel Dr, Winter Park, FL 32792
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  $565,000 Sold May 23, 2025

  230 S Ranger Blvd, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 2,309 Sq Ft
  • Built 1963

  Last Sold Summary

  • 10% Below List Price
  • $245/SF
  • 40 Days On Market

  Current Estimated Value $579,882

  Last Listing Agent Jennifer Sloan COMPASS FLORIDA LLC

  230 S Ranger Blvd, Winter Park, FL 32792
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  $105,000 Sold Apr 24, 2026

  1695 Lee Rd Unit C214, Winter Park, FL 32789

  • 2 Beds
  • 1 Bath
  • 881 Sq Ft
  • Built 1966

  Last Sold Summary

  • 25% Below List Price
  • $119/SF
  • 165 Days On Market

  Last Listing Agent Diana Perez PROFESSIONAL REAL ESTATE TEAM

  1695 Lee Rd Unit C214, Winter Park, FL 32789
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  $343,000 Sold Sep 16, 2025

  657 Overspin Dr, Winter Park, FL 32789

  • 4 Beds
  • 2 Baths
  • 1,349 Sq Ft
  • Built 1955

  Last Sold Summary

  • 12% Below List Price
  • $254/SF
  • 61 Days On Market

  Current Estimated Value $350,913

  Last Listing Agent Abby Nelson RE/MAX 200 REALTY

  657 Overspin Dr, Winter Park, FL 32789

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