Recently Sold Winchester, KY Homes

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  /30

  $344,000 Sold Feb 06, 2026

  212 Woodbine Ct, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 2,475 Sq Ft
  • Built 1976

  Last Sold Summary

  • 1% Below List Price
  • $139/SF
  • 72 Days On Market

  Current Estimated Value $344,842

  Last Listing Agent Kathy Burton Coldwell Banker McMahan

  212 Woodbine Ct, Winchester, KY 40391
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  /15

  $192,565 Sold Dec 22, 2025

  246 Geronimo Ct, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,092 Sq Ft
  • Built 1998

  Last Sold Summary

  • 12% Below List Price
  • $176/SF
  • 16 Days On Market

  Current Estimated Value $198,237

  Last Listing Agent Devon Ramage The Brokerage

  246 Geronimo Ct, Winchester, KY 40391
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  /61

  $480,000 Sold Feb 09, 2026

  5515 Van Meter Rd, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 2,940 Sq Ft
  • Built 1993

  Last Sold Summary

  • 14% Below List Price
  • $163/SF
  • 175 Days On Market

  Current Estimated Value $500,370

  Last Listing Agent Robyn Bradley Woods Realty Group

  5515 Van Meter Rd, Winchester, KY 40391
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  /2

  $374,738 Sold May 20, 2025

  138 Gibson Way, Winchester, KY 40391

  • 5 Beds
  • 3 Baths
  • 2,519 Sq Ft
  • Built 2024

  Last Sold Summary

  • $149/SF
  • 9 Days On Market

  Current Estimated Value $376,452

  Last Listing Agent Jennifer Sisson Christies International Real Estate Bluegrass

  138 Gibson Way, Winchester, KY 40391
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  /33

  $299,900 Sold Jun 04, 2025

  107 Morning Glory Ct, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 1,876 Sq Ft
  • Built 2002

  Last Sold Summary

  • 5% Below List Price
  • $160/SF
  • 22 Days On Market

  Current Estimated Value $305,745

  Last Listing Agent Jonathan Wood HomeLand Real Estate Inc - Mt Sterling

  107 Morning Glory Ct, Winchester, KY 40391
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  /36

  $390,513 Sold May 19, 2025

  21 Edgewood Dr, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,698 Sq Ft
  • Built 1980

  Last Sold Summary

  • 9% Below List Price
  • $145/SF
  • 32 Days On Market

  Current Estimated Value $415,781

  Last Listing Agent Kelly Nisbet Coldwell Banker McMahan

  21 Edgewood Dr, Winchester, KY 40391
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  /22

  $332,000 Sold Apr 25, 2025

  502 Hewlett Ct, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 2,384 Sq Ft
  • Built 2004

  Last Sold Summary

  • 5% Below List Price
  • $139/SF
  • 203 Days On Market

  Current Estimated Value $356,475

  Last Listing Agent Mila Ensor Ensor Real Estate, LLC

  502 Hewlett Ct, Winchester, KY 40391
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  /36

  $179,000 Sold Jul 23, 2025

  218 Buffalo Trace, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,020 Sq Ft
  • Built 1999

  Last Sold Summary

  • $175/SF
  • 11 Days On Market

  Current Estimated Value $184,850

  Last Listing Agent Sandy Statom Team Realtors

  218 Buffalo Trace, Winchester, KY 40391
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  /46

  $195,000 Sold Jul 29, 2025

  115 Georgia St, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,167 Sq Ft
  • Built 1940

  Last Sold Summary

  • 15% Below List Price
  • $167/SF
  • 66 Days On Market

  Current Estimated Value $198,219

  Last Listing Agent Darrell Tackett Dream Maker Realty, LLC

  115 Georgia St, Winchester, KY 40391
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  /25

  $255,000 Sold Jan 22, 2026

  120 Jackson St, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,342 Sq Ft
  • Built 2022

  Last Sold Summary

  • 3% Above List Price
  • $190/SF
  • 12 Days On Market

  Current Estimated Value $250,674

  Last Listing Agent Hannah Toole Coldwell Banker McMahan

  120 Jackson St, Winchester, KY 40391
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  /36

  $300,000 Sold Jun 23, 2025

  13 Shelley Dr, Winchester, KY 40391

  • 4 Beds
  • 4 Baths
  • 2,019 Sq Ft
  • Built 1969

  Last Sold Summary

  • 2% Above List Price
  • $149/SF
  • 1 Day On Market

  Current Estimated Value $294,700

  Last Listing Agent Melissa Brown Keller Williams Legacy Group

  13 Shelley Dr, Winchester, KY 40391
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  /19

  $413,000 Sold Oct 23, 2025

  410 Lyon Dr, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 3,806 Sq Ft
  • Built 1991

  Last Sold Summary

  • 1% Above List Price
  • $109/SF
  • 7 Days On Market

  Current Estimated Value $405,749

  Last Listing Agent Natalie Nohel CENTURY 21 Advantage Realty

  410 Lyon Dr, Winchester, KY 40391
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  /68

  $850,000 Sold Feb 09, 2026

  2447 Clintonville Rd, Winchester, KY 40391

  • 5 Beds
  • 4 Baths
  • 4,058 Sq Ft
  • Built 1989

  Last Sold Summary

  • 34% Below List Price
  • $209/SF
  • 300 Days On Market

  Current Estimated Value $761,464

  Last Listing Agent Suzanne Elliott Berkshire Hathaway de Movellan Properties

  2447 Clintonville Rd, Winchester, KY 40391
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  /57

  $260,000 Sold Sep 09, 2025

  7934 Ironworks Rd, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,633 Sq Ft
  • Built 1945

  Last Sold Summary

  • 12% Below List Price
  • $159/SF
  • 4 Days On Market

  Current Estimated Value $277,027

  Last Listing Agent Greg Wood Freedom Realty & Property Management

  7934 Ironworks Rd, Winchester, KY 40391
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  /24

  $320,000 Sold Dec 01, 2025

  118 Strawberry Ln, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,008 Sq Ft
  • Built 2022

  Last Sold Summary

  • 2% Below List Price
  • $159/SF
  • 14 Days On Market

  Current Estimated Value $323,670

  Last Listing Agent Susan Baldwin Threshold Real Estate Services

  118 Strawberry Ln, Winchester, KY 40391
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  /27

  $207,500 Sold Jul 11, 2025

  2350 Ironworks Rd, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,385 Sq Ft
  • Built 1970

  Last Sold Summary

  • 3% Below List Price
  • $150/SF
  • 6 Days On Market

  Current Estimated Value $220,329

  Last Listing Agent Dylan Justice GSP Homes

  2350 Ironworks Rd, Winchester, KY 40391
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  /77

  $2,075,000 Sold Aug 15, 2025

  27 Sundown Ln, Winchester, KY 40391

  • 3 Beds
  • 6 Baths
  • 5,984 Sq Ft
  • Built 1994

  Last Sold Summary

  • 3% Below List Price
  • $347/SF
  • 14 Days On Market

  Current Estimated Value $2,179,953

  Last Listing Agent Abby Jones Bluegrass Sotheby's International Realty

  27 Sundown Ln, Winchester, KY 40391
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  /41

  $170,000 Sold Dec 30, 2025

  130 Abbeywood Ct, Winchester, KY 40391

  • 2 Beds
  • 2.5 Baths
  • 1,350 Sq Ft
  • Built 2002

  Last Sold Summary

  • 13% Below List Price
  • $126/SF
  • 18 Days On Market

  Current Estimated Value $176,648

  Last Listing Agent Emily Belcher Rector Hayden Realtors

  130 Abbeywood Ct, Winchester, KY 40391
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  /27

  $229,000 Sold Jun 05, 2025

  13 Fairview Ave, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • Built 2025

  Last Sold Summary

  • 2% Above List Price
  • $191/SF
  • 2 Days On Market

  Current Estimated Value $233,854

  Last Listing Agent Nena Honaker Tom Goebel & Company

  13 Fairview Ave, Winchester, KY 40391
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  /36

  $214,000 Sold May 19, 2025

  509 Hidden Hills Way, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,402 Sq Ft
  • Built 2000

  Last Sold Summary

  • 7% Below List Price
  • $153/SF
  • 38 Days On Market

  Current Estimated Value $221,806

  Last Listing Agent Teresa Richmond Freedom Realty & Property Management

  509 Hidden Hills Way, Winchester, KY 40391
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  /22

  $201,000 Sold Sep 04, 2025

  110 Colonial Park Dr, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,235 Sq Ft
  • Built 1980

  Last Sold Summary

  • 11% Below List Price
  • $163/SF
  • 26 Days On Market

  Current Estimated Value $200,772

  Last Listing Agent Jason Townsend Kentucky Residential Real Estate, LLC

  110 Colonial Park Dr, Winchester, KY 40391
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  /33

  $255,000 Sold Jan 09, 2026

  357 Crescent Ave, Winchester, KY 40391

  • 3 Beds
  • 1.5 Baths
  • 2,188 Sq Ft

  Last Sold Summary

  • $117/SF
  • 44 Days On Market

  Current Estimated Value $253,481

  Last Listing Agent Samantha Gray National Real Estate

  357 Crescent Ave, Winchester, KY 40391
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  /91

  $395,000 Sold Jul 22, 2025

  101 Dorset Ln, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,536 Sq Ft
  • Built 2015

  Last Sold Summary

  • $257/SF
  • 29 Days On Market

  Current Estimated Value $395,903

  Last Listing Agent Josh Wood Freedom Realty & Property Management

  101 Dorset Ln, Winchester, KY 40391
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  /31

  $485,000 Sold Sep 05, 2025

  10 French Ave, Winchester, KY 40391

  • 5 Beds
  • 3 Baths
  • 3,262 Sq Ft
  • Built 1906

  Last Sold Summary

  • 18% Below List Price
  • $149/SF
  • 11 Days On Market

  Current Estimated Value $485,611

  Last Listing Agent Brian England Keller Williams Bluegrass Realty

  10 French Ave, Winchester, KY 40391
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  /39

  $462,000 Sold Nov 21, 2025

  865 Pretty Run Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 2,727 Sq Ft
  • Built 1989

  Last Sold Summary

  • 4% Below List Price
  • $169/SF
  • 6 Days On Market

  Current Estimated Value $457,887

  Last Listing Agent Shane Underwood Keller Williams Commonwealth

  865 Pretty Run Rd, Winchester, KY 40391
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  /40

  $278,500 Sold Jun 06, 2025

  8 Chickadee Ln, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,400 Sq Ft
  • Built 1970

  Last Sold Summary

  • 14% Below List Price
  • $116/SF
  • 130 Days On Market

  Current Estimated Value $289,979

  Last Listing Agent Whitney Ensor Ensor Real Estate, LLC

  8 Chickadee Ln, Winchester, KY 40391
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  /35

  $300,000 Sold Oct 03, 2025

  607 Colby Ridge Blvd, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,948 Sq Ft
  • Built 2020

  Last Sold Summary

  • 4% Below List Price
  • $154/SF
  • 67 Days On Market

  Current Estimated Value $306,926

  Last Listing Agent Suzanne Elliott Berkshire Hathaway de Movellan Properties

  607 Colby Ridge Blvd, Winchester, KY 40391
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  /39

  $450,000 Sold Aug 08, 2025

  600 Ferry Rd, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 2,076 Sq Ft
  • Built 2003

  Last Sold Summary

  • 10% Below List Price
  • $217/SF
  • 32 Days On Market

  Current Estimated Value $476,957

  Last Listing Agent Cathleen Gedeon CENTURY 21 Advantage Realty

  600 Ferry Rd, Winchester, KY 40391
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  /43

  $239,700 Sold Oct 20, 2025

  2413 Log Lick Rd, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,300 Sq Ft
  • Built 1945

  Last Sold Summary

  • $184/SF
  • 19 Days On Market

  Current Estimated Value $234,880

  Last Listing Agent E Anthony Phillips RE/MAX Creative Realty

  2413 Log Lick Rd, Winchester, KY 40391
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  /63

  $430,000 Sold Oct 03, 2025

  259 Hibiscus Ln, Winchester, KY 40391

  • 4 Beds
  • 3.5 Baths
  • 3,921 Sq Ft
  • Built 2003

  Last Sold Summary

  • 2% Below List Price
  • $110/SF
  • 2 Days On Market

  Current Estimated Value $432,009

  Last Listing Agent Janna Chalfant Smith United Real Estate Bluegrass

  259 Hibiscus Ln, Winchester, KY 40391
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  /32

  $349,900 Sold Aug 01, 2025

  275 Cross Brook Ct, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 2,111 Sq Ft
  • Built 1998

  Last Sold Summary

  • $166/SF
  • 2 Days On Market

  Current Estimated Value $349,383

  Last Listing Agent Amanda Stewart Stewart & Co Realty LLC

  275 Cross Brook Ct, Winchester, KY 40391
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  /25

  $270,000 Sold Dec 05, 2025

  102 Ashley Dr, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,132 Sq Ft
  • Built 1994

  Last Sold Summary

  • 2% Above List Price
  • $239/SF
  • 19 Days On Market

  Current Estimated Value $270,164

  Last Listing Agent Kimberli Fister Kentucky Land and Home

  102 Ashley Dr, Winchester, KY 40391
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  /22

  $269,900 Sold Oct 10, 2025

  115 Ashley Dr, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,320 Sq Ft
  • Built 1995

  Last Sold Summary

  • $204/SF
  • 12 Days On Market

  Current Estimated Value $267,394

  Last Listing Agent Jason Townsend Kentucky Residential Real Estate, LLC

  115 Ashley Dr, Winchester, KY 40391
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  /24

  $215,000 Sold May 29, 2025

  13365 Ironworks Rd, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,420 Sq Ft
  • Built 1973

  Last Sold Summary

  • 2% Below List Price
  • $151/SF
  • 10 Days On Market

  Current Estimated Value $227,667

  Last Listing Agent Joshua Davis The Agency

  13365 Ironworks Rd, Winchester, KY 40391
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  /22

  $130,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,232 Sq Ft

  19 Hughes Ave, Winchester, KY 40391

  Investor opportunity in Winchester! This 3-bedroom, 2 full bath brick ranch sits on a spacious 0.67 acre lot and is ready for renovation. Whether you're an investor searching for your next flip, looking to add a rental to your portfolio, or a buyer wanting to build sweat equity, this property offers strong potential. The home needs updates and repairs but features a solid structure and a

  Jaime Daniel Delgado Plum Tree Realty

  19 Hughes Ave, Winchester, KY 40391
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  /25

  $186,500 Sold Dec 08, 2025

  31 Vine St, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,443 Sq Ft
  • Built 1950

  Last Sold Summary

  • 17% Below List Price
  • $129/SF
  • 94 Days On Market

  Current Estimated Value $184,670

  Last Listing Agent Jana Hooten Key 2 Close Realty, LLC

  31 Vine St, Winchester, KY 40391
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  /38

  $220,000 Sold Jun 30, 2025

  212 Southwind Dr, Winchester, KY 40391

  • 3 Beds
  • 1.5 Baths
  • 1,333 Sq Ft
  • Built 1973

  Last Sold Summary

  • 4% Below List Price
  • $165/SF
  • 19 Days On Market

  Current Estimated Value $230,856

  Last Listing Agent Jim Woodrum RE/MAX Creative, Winchester

  212 Southwind Dr, Winchester, KY 40391
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  /3

  $140,000 Sold Apr 09, 2025

  895 Gay Evans Rd, Winchester, KY 40391

  • Land
  • 6.87 Acres
  • $20,378 per Acre

  Last Sold Summary

  • 7% Below List Price
  • 18 Days On Market

  Last Listing Agent Holly Goeing The Agency

  895 Gay Evans Rd, Winchester, KY 40391
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  /48

  $390,000 Sold Nov 21, 2025

  213 Honeysuckle Ln, Winchester, KY 40391

  • 4 Beds
  • 4 Baths
  • 3,087 Sq Ft
  • Built 1999

  Last Sold Summary

  • 2% Below List Price
  • $126/SF
  • 1 Day On Market

  Current Estimated Value $385,755

  Last Listing Agent Shari Frasure Keller Williams Commonwealth

  213 Honeysuckle Ln, Winchester, KY 40391
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  /43

  $399,000 Sold Oct 10, 2025

  7236 Old Boonesboro Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 2,041 Sq Ft
  • Built 2003

  Last Sold Summary

  • $195/SF
  • 3 Days On Market

  Current Estimated Value $399,852

  Last Listing Agent Jason Townsend Kentucky Residential Real Estate, LLC

  7236 Old Boonesboro Rd, Winchester, KY 40391

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