Recently Sold Winchester, KY Homes

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  /83

  $850,000

  Sold Mar 25, 2026

  4755 Combs Ferry Rd, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 2,768 Sq Ft
  • Built 1993

  Last Sold Summary

  • $307/SF
  • 13 Days On Market

  Current Estimated Value $838,643

  Last Listing Agent Craig Bridgewater Bridgewater Real Estate

  4755 Combs Ferry Rd, Winchester, KY 40391
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  /27

  $199,900

  Sold May 15, 2026

  215 Short St, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,036 Sq Ft
  • Built 1955

  Last Sold Summary

  • $193/SF
  • 1 Day On Market

  Current Estimated Value $197,491

  Last Listing Agent Amanda Marcum Berkshire Hathaway HomeServices Foster Realtors

  215 Short St, Winchester, KY 40391
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  /67

  $307,900

  Sold May 29, 2026

  118 Windridge Dr, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,617 Sq Ft
  • Built 1978

  Last Sold Summary

  • 2% Below List Price
  • $190/SF
  • 3 Days On Market

  Current Estimated Value $303,855

  Last Listing Agent Amber Hunt Whalen & Company

  118 Windridge Dr, Winchester, KY 40391
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  /42

  $249,000

  Sold Oct 22, 2025

  9 Apache Trail, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 1,750 Sq Ft
  • Built 1960

  Last Sold Summary

  • 6% Below List Price
  • $142/SF
  • 117 Days On Market

  Current Estimated Value $259,683

  Last Listing Agent Joyce Ratliff Tom Goebel & Company

  9 Apache Trail, Winchester, KY 40391
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  /34

  $405,000

  Sold May 26, 2026

  505 Lasalle Ct, Winchester, KY 40391

  • 5 Beds
  • 3 Baths
  • 2,944 Sq Ft
  • Built 1995

  Last Sold Summary

  • $138/SF
  • 1 Day On Market

  Current Estimated Value $401,750

  Last Listing Agent Amanda Thomas The Agency

  505 Lasalle Ct, Winchester, KY 40391
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  /23

  $335,000

  Sold Aug 27, 2025

  413 Lyon Dr, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 2,936 Sq Ft
  • Built 1986

  Last Sold Summary

  • 4% Below List Price
  • $114/SF
  • 8 Days On Market

  Current Estimated Value $327,605

  Last Listing Agent Ray Rush Rush Real Estate

  413 Lyon Dr, Winchester, KY 40391
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  /31

  $295,000

  Sold Feb 24, 2026

  420 Willowbrook Rd, Winchester, KY 40391

  • 3 Beds
  • 3 Baths
  • 1,738 Sq Ft
  • Built 1980

  Last Sold Summary

  • $170/SF
  • 32 Days On Market

  Current Estimated Value $295,628

  Last Listing Agent Michelle Blackburn RE/MAX Creative, Winchester

  420 Willowbrook Rd, Winchester, KY 40391
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  /42

  $247,500

  Sold Jan 16, 2026

  125 Summerhill Way, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,333 Sq Ft
  • Built 2003

  Last Sold Summary

  • 5% Below List Price
  • $186/SF
  • 15 Days On Market

  Current Estimated Value $256,562

  Last Listing Agent Gwen Mathews Bluegrass Sotheby's International Realty

  125 Summerhill Way, Winchester, KY 40391
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  /39

  $265,000

  Sold Apr 03, 2026

  543 Cunningham Ln, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,404 Sq Ft
  • Built 2019

  Last Sold Summary

  • 8% Below List Price
  • $189/SF
  • 10 Days On Market

  Current Estimated Value $266,450

  Last Listing Agent Dale Hatton Dream Maker Realty, LLC

  543 Cunningham Ln, Winchester, KY 40391
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  /37

  $354,000

  Sold Dec 19, 2025

  213 Hood Ave, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,244 Sq Ft
  • Built 1970

  Last Sold Summary

  • 8% Below List Price
  • $158/SF
  • 21 Days On Market

  Current Estimated Value $354,409

  Last Listing Agent Vickie Skeens RE/MAX Elite Lexington

  213 Hood Ave, Winchester, KY 40391
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  /10

  $370,000

  Sold Mar 31, 2026

  395 Croxton Way, Winchester, KY 40391

  • Land
  • 1.29 Acres
  • $286,822 per Acre

  Last Sold Summary

  • 18% Below List Price
  • 793 Days On Market

  Current Estimated Value $440,902

  Last Listing Agent Rich Decker Rector Hayden Realtors

  395 Croxton Way, Winchester, KY 40391
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  /15

  $212,000

  Sold Apr 13, 2026

  707 Estes Dr, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,053 Sq Ft
  • Built 1960

  Last Sold Summary

  • $201/SF
  • 9 Days On Market

  Current Estimated Value $208,291

  Last Listing Agent Tracey Goebel Tom Goebel & Company

  707 Estes Dr, Winchester, KY 40391
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  /73

  $799,000

  Sold Aug 18, 2025

  1183 the Ridings Rd, Winchester, KY 40391

  • 5 Beds
  • 3 Baths
  • 3,664 Sq Ft
  • Built 1989

  Last Sold Summary

  • 6% Below List Price
  • $218/SF
  • 64 Days On Market

  Current Estimated Value $779,886

  Last Listing Agent Libby VanMeter Marshall Lane Real Estate - Lexington

  1183 the Ridings Rd, Winchester, KY 40391
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  /38

  $258,900

  Sold Sep 08, 2025

  313 Geronimo Ct, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 1,678 Sq Ft
  • Built 2000

  Last Sold Summary

  • 4% Above List Price
  • $154/SF
  • 1 Day On Market

  Current Estimated Value $265,042

  Last Listing Agent Shari Frasure Keller Williams Commonwealth

  313 Geronimo Ct, Winchester, KY 40391
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  /29

  $287,000

  Sold Jun 18, 2026

  207 Abbeywood Dr, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,894 Sq Ft
  • Built 2011

  Last Sold Summary

  • 1% Above List Price
  • $152/SF
  • 4 Days On Market

  Current Estimated Value $291,503

  Last Listing Agent Carlos Elliott Tru Life Real Estate

  207 Abbeywood Dr, Winchester, KY 40391
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  /22

  $233,000

  Sold Jul 21, 2026

  108 Spruce Ct, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 2,106 Sq Ft
  • Built 1970

  Last Sold Summary

  • 1% Above List Price
  • $111/SF
  • 19 Days On Market

  Current Estimated Value $230,276

  Last Listing Agent Tierra Newkirk Keller Williams Commonwealth

  108 Spruce Ct, Winchester, KY 40391
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  /34

  $293,000

  Sold May 01, 2026

  1508 Ford Hampton Rd, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 1,531 Sq Ft
  • Built 1950

  Last Sold Summary

  • 10% Below List Price
  • $191/SF
  • 162 Days On Market

  Current Estimated Value $288,818

  Last Listing Agent Michelle Blackburn RE/MAX Creative, Winchester

  1508 Ford Hampton Rd, Winchester, KY 40391
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  /46

  $600,000

  Sold Dec 04, 2025

  433 Fairholme Way, Winchester, KY 40391

  • 3 Beds
  • 3.5 Baths
  • 2,900 Sq Ft
  • Built 2018

  Last Sold Summary

  • 5% Below List Price
  • $207/SF
  • 28 Days On Market

  Current Estimated Value $603,538

  Last Listing Agent Kathryn Cheuvront Coldwell Banker McMahan

  433 Fairholme Way, Winchester, KY 40391

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