Recently Sold Winter Park, FL Homes

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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 $2,647,421

  Last Listing Agent MaryStuart Day FANNIE HILLMAN & ASSOCIATES

  560 Country Club Dr, Winter Park, FL 32789
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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 $791,417

  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 $571,023

  Last Listing Agent Joseph Sipp KELLER WILLIAMS WINTER PARK

  1561 Nottingham Dr, Winter Park, FL 32792
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  $370,000

  Sold Jul 02, 2026

  1617 Chilean Ln, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,359 Sq Ft
  • Built 1960

  Last Sold Summary

  • $272/SF
  • 119 Days On Market

  Current Estimated Value $360,353

  Last Listing Agent Brenda Feliciani CHARLES RUTENBERG REALTY ORLANDO

  1617 Chilean Ln, Winter Park, FL 32792
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  $390,000

  Sold Jun 12, 2026

  2225 Winter Woods Blvd, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,473 Sq Ft
  • Built 1968

  Last Sold Summary

  • 4% Above List Price
  • $265/SF
  • 4 Days On Market

  Current Estimated Value $387,121

  Last Listing Agent Amy Turner KELLER WILLIAMS WINTER PARK

  2225 Winter Woods Blvd, 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 $546,919

  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 $855,550

  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 $420,459

  Last Listing Agent Brandon Geers COMPASS FLORIDA LLC

  4959 Ardmore Dr, Winter Park, FL 32792
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  $450,000

  Sold Jun 16, 2026

  1205 Valley Creek Run, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,815 Sq Ft
  • Built 1997

  Last Sold Summary

  • $248/SF
  • 18 Days On Market

  Current Estimated Value $453,134

  Last Listing Agent Amy Turner KELLER WILLIAMS WINTER PARK

  1205 Valley Creek Run, 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 $589,820

  Last Listing Agent Ameer Chaseb COMPASS FLORIDA LLC

  2492 Brookshire Ave, 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 $454,973

  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 $89,319

  Last Listing Agent Brittneyann Cover RE/MAX ASSURED

  318 Scottsdale Square Unit 318, Winter Park, FL 32792
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  $470,000

  Sold Jun 16, 2026

  7120 Brookside Trail, Winter Park, FL 32792

  • 4 Beds
  • 2 Baths
  • 1,753 Sq Ft
  • Built 1976

  Last Sold Summary

  • 8% Below List Price
  • $268/SF
  • 7 Days On Market

  Current Estimated Value $478,085

  Last Listing Agent Teresa Jones-Cintron KELLY PRICE & COMPANY LLC

  7120 Brookside Trail, 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 $1,465,392

  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 $4,544,816

  Last Listing Agent Albin Hubscher CENTRAL FLORIDA PRIME REAL ESTATE LLC

  1812 Stonehurst Rd, Winter Park, FL 32789
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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 $948,508

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

  2129 Fosgate Dr, Winter Park, FL 32789
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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

  Current Estimated Value $112,511

  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 $364,852

  Last Listing Agent Abby Nelson RE/MAX 200 REALTY

  657 Overspin Dr, Winter Park, FL 32789
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  $795,000

  Sold Sep 30, 2025

  1773 Walnut Ave, Winter Park, FL 32789

  • 4 Beds
  • 2 Baths
  • 2,146 Sq Ft
  • Built 1957

  Last Sold Summary

  • 23% Above List Price
  • $370/SF
  • 6 Days On Market

  Current Estimated Value $836,771

  Last Listing Agent Vincent Scarlatos CORCORAN PREMIER REALTY

  1773 Walnut Ave, Winter Park, FL 32789
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  $100,000

  Sold Dec 22, 2025

  7449 Daniel Webster Dr Unit 3, Winter Park, FL 32792

  • 2 Beds
  • 2.5 Baths
  • 1,085 Sq Ft
  • Built 1974

  Last Sold Summary

  • 29% Below List Price
  • $92/SF
  • 140 Days On Market

  Last Listing Agent Chris Creegan CREEGAN GROUP

  7449 Daniel Webster Dr Unit 3, Winter Park, FL 32792

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