Recently Sold Winchester, KY Homes

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  /42

  $610,000 Sold Oct 07, 2025

  439 Lynnway Dr, Winchester, KY 40391

  • 6 Beds
  • 3.5 Baths
  • 5,227 Sq Ft
  • Built 1993

  Last Sold Summary

  • 5% Below List Price
  • $117/SF
  • 219 Days On Market

  Last Listing Agent Reagan Rainey Dream Maker Realty, LLC

  439 Lynnway Dr, Winchester, KY 40391
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  /37

  $345,000 Sold Nov 12, 2025

  103 Mayfair Ct, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,485 Sq Ft
  • Built 2019

  Last Sold Summary

  • 1% Below List Price
  • $232/SF
  • 8 Days On Market

  Last Listing Agent Carlos Elliott Tru Life Real Estate

  103 Mayfair Ct, Winchester, KY 40391
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  /2

  $110,000 Sold Apr 18, 2025

  210 Duclair Dr, Winchester, KY 40391

  • Land
  • 0.59 Acre
  • $186,441 per Acre

  Last Sold Summary

  • 847 Days On Market

  Last Listing Agent John Wilson Bluegrass Properties Group

  210 Duclair Dr, Winchester, KY 40391
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  /9

  $240,000 Sold Mar 24, 2025

  2417 Old Boonesboro Rd, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,732 Sq Ft
  • Built 1960

  Last Sold Summary

  • 14% Below List Price
  • $139/SF
  • 76 Days On Market

  Current Estimated Value $275,659

  Last Listing Agent Dale Hatton Dream Maker Realty, LLC

  2417 Old Boonesboro Rd, Winchester, KY 40391
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  /10

  $811,910 Sold Oct 10, 2025

  3505 Basin Springs Rd, Winchester, KY 40391

  Last Sold Summary

  • 46% Below List Price
  • 165 Days On Market

  Last Listing Agent Kathryn Cheuvront Coldwell Banker McMahan

  3505 Basin Springs Rd, Winchester, KY 40391
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  /25

  $245,000 Sold Oct 24, 2025

  231 Leslie Dr, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,438 Sq Ft
  • Built 2008

  Last Sold Summary

  • 2% Below List Price
  • $170/SF
  • 15 Days On Market

  Last Listing Agent Destiny Darby Keller Williams Commonwealth

  231 Leslie Dr, Winchester, KY 40391
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  /32

  $200,000 Sold Oct 02, 2025

  2858 Ford Hampton Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,294 Sq Ft
  • Built 1997

  Last Sold Summary

  • 5% Below List Price
  • $155/SF
  • 42 Days On Market

  Last Listing Agent Dale Hatton Dream Maker Realty, LLC

  2858 Ford Hampton Rd, 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

  Last Listing Agent Devon Ramage The Brokerage

  246 Geronimo Ct, 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 $383,109

  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 $306,273

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

  107 Morning Glory Ct, Winchester, KY 40391
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  /26

  $220,000 Sold Feb 28, 2025

  636 Laura Dr, Winchester, KY 40391

  • 3 Beds
  • 1.5 Baths
  • 1,108 Sq Ft
  • Built 1978

  Last Sold Summary

  • 4% Below List Price
  • $199/SF
  • 3 Days On Market

  Current Estimated Value $248,178

  Last Listing Agent Mila Ensor Ensor Real Estate, LLC

  636 Laura Dr, 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 $410,457

  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 $349,826

  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 $184,884

  Last Listing Agent Sandy Statom ERA 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 $195,410

  Last Listing Agent Darrell Tackett Dream Maker Realty, LLC

  115 Georgia 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 $293,225

  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

  Last Listing Agent Natalie Nohel CENTURY 21 Advantage Realty

  410 Lyon Dr, 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 $266,831

  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

  Last Listing Agent Susan Baldwin Threshold Real Estate Services

  118 Strawberry Ln, Winchester, KY 40391
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  /46

  $302,500 Sold Jun 11, 2025

  1740 Oil Springs Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,475 Sq Ft
  • Built 2020

  Last Sold Summary

  • 1% Above List Price
  • $205/SF
  • 4 Days On Market

  Current Estimated Value $301,339

  Last Listing Agent Libby VanMeter Marshall Lane Real Estate - Lexington

  1740 Oil Springs Rd, 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 $219,787

  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 $2,082,267

  Last Listing Agent Abby Jones Bluegrass Sotheby's International Realty

  27 Sundown Ln, 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 $222,472

  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 $219,149

  Last Listing Agent Teresa Richmond Freedom Realty & Property Management

  509 Hidden Hills Way, Winchester, KY 40391
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  /19

  $166,000 Sold Jan 24, 2025

  125 Buffalo Trace, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 932 Sq Ft
  • Built 1997

  Last Sold Summary

  • 2% Below List Price
  • $178/SF
  • 43 Days On Market

  Current Estimated Value $177,983

  Last Listing Agent Elizabeth Herrington Bluegrass Sotheby's International Realty

  125 Buffalo Trace, 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 $202,263

  Last Listing Agent Jason Townsend Kentucky Residential Real Estate, LLC

  110 Colonial Park Dr, 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 $390,094

  Last Listing Agent Josh Wood Freedom Realty & Property Management

  101 Dorset Ln, Winchester, KY 40391
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  /2

  $110,750 Sold Feb 07, 2025

  Unlisted Address

  • 3 Beds
  • 2 Baths
  • 1,150 Sq Ft
  • Built 1985

  Last Sold Summary

  • $96/SF

  Current Estimated Value $168,045

  Last Listing Agent Jo Gawthrop Keller Williams Bluegrass Realty

  Unlisted Address
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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 $485,560

  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

  Last Listing Agent Shane Underwood Keller Williams Commonwealth

  865 Pretty Run Rd, Winchester, KY 40391
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  /2

  $110,750 Sold Feb 07, 2025

  Unlisted Address

  • 2 Beds
  • 2 Baths
  • 906 Sq Ft
  • Built 1995

  Last Sold Summary

  • $122/SF

  Current Estimated Value $159,890

  Last Listing Agent Jo Gawthrop Keller Williams Bluegrass Realty

  Unlisted Address
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  /2

  $39,500 Sold Mar 05, 2025

  416 Fairholme Way, Winchester, KY 40391

  • Land
  • 0.38 Acre
  • $103,947 per Acre

  Last Sold Summary

  • 14% Above List Price
  • 1,596 Days On Market

  Current Estimated Value $90,378

  Last Listing Agent Garnett Davis Tom Goebel & Company

  416 Fairholme Way, 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 $285,704

  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

  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 $452,063

  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

  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

  Last Listing Agent Janna 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 $348,540

  Last Listing Agent Amanda Stewart Selling the South Realty

  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

  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

  Last Listing Agent Jason Townsend Kentucky Residential Real Estate, LLC

  115 Ashley Dr, Winchester, KY 40391

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