Recently Sold Winchester, KY Homes

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  /22

  $217,000 Sold Sep 24, 2025

  140 Cherokee Dr, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,134 Sq Ft
  • Built 1968

  Last Sold Summary

  • 3% Below List Price
  • $191/SF
  • 29 Days On Market

  Current Estimated Value $218,470

  Last Listing Agent Serena Cassidy Coldwell Banker McMahan

  140 Cherokee Dr, Winchester, KY 40391
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  /2

  $135,050 Sold Nov 14, 2025

  9999 Sewell Shop Rd, Winchester, KY 40391

  • Land
  • 2 Acres
  • $67,525 per Acre

  Last Sold Summary

  • 20 Days On Market

  Last Listing Agent Joshua Davis The Agency

  9999 Sewell Shop Rd, Winchester, KY 40391
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  /42

  $150,000 Sold Oct 27, 2025

  2317 Muddy Creek Rd, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 1,046 Sq Ft
  • Built 1970

  Last Sold Summary

  • 11% Below List Price
  • $143/SF
  • 4 Days On Market

  Current Estimated Value $156,336

  Last Listing Agent Kathy Burton Coldwell Banker McMahan

  2317 Muddy Creek Rd, Winchester, KY 40391
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  /34

  $300,000 Sold Mar 11, 2025

  421 Skylark Dr, Winchester, KY 40391

  • 3 Beds
  • 3 Baths
  • 1,950 Sq Ft
  • Built 1992

  Last Sold Summary

  • 2% Below List Price
  • $154/SF
  • 45 Days On Market

  Current Estimated Value $342,014

  Last Listing Agent Alyssa M Boley Coldwell Banker McMahan

  421 Skylark Dr, Winchester, KY 40391
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  /39

  $213,900 Sold Sep 10, 2025

  310 Sarah Ct, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,072 Sq Ft
  • Built 1998

  Last Sold Summary

  • $200/SF
  • 3 Days On Market

  Current Estimated Value $213,676

  Last Listing Agent Brooke Otis Mullins RO&CO Real Estate

  310 Sarah Ct, Winchester, KY 40391
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  /37

  $305,000 Sold Jul 22, 2025

  848 Stratton Ln, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 1,936 Sq Ft
  • Built 1984

  Last Sold Summary

  • 2% Above List Price
  • $158/SF
  • 0 Days On Market

  Current Estimated Value $307,979

  Last Listing Agent Joey Hamilton EXP Realty LLC

  848 Stratton Ln, Winchester, KY 40391
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  /13

  $210,000 Sold Apr 24, 2025

  Unlisted Address

  • 3 Beds
  • 1 Bath
  • 1,053 Sq Ft
  • Built 1978

  Last Sold Summary

  • 7% Below List Price
  • $199/SF
  • 15 Days On Market

  Current Estimated Value $216,929

  Last Listing Agent Angela Newby Calumet Realty

  Unlisted Address
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  /2

  $201,000 Sold Apr 18, 2025

  203 Arbor Ct, Winchester, KY 40391

  • 2 Beds
  • 2 Baths
  • 960 Sq Ft
  • Built 1993

  Last Sold Summary

  • 2% Below List Price
  • $209/SF

  Current Estimated Value $201,008

  Last Listing Agent Angie Conley Dixon Dixon Properties

  203 Arbor Ct, Winchester, KY 40391
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  /6

  $20,000 Sold Mar 28, 2025

  231 W Broadway St, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,150 Sq Ft

  Last Sold Summary

  • 60% Below List Price
  • $17/SF
  • 667 Days On Market

  Current Estimated Value $162,432

  Last Listing Agent Will Childers WTC Realty LLC

  231 W Broadway St, Winchester, KY 40391
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  /25

  $248,000 Sold Dec 01, 2025

  331 Newcastle Ln, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,351 Sq Ft
  • Built 2004

  Last Sold Summary

  • $184/SF
  • 3 Days On Market

  Last Listing Agent Sydney Pennington In House Real Estate

  331 Newcastle Ln, Winchester, KY 40391
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  /63

  $616,000 Sold Mar 19, 2025

  291 Sundown Ln, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,356 Sq Ft
  • Built 2004

  Last Sold Summary

  • $261/SF
  • 0 Days On Market

  Current Estimated Value $614,545

  Last Listing Agent Maxine Reyburn RO&CO Real Estate

  291 Sundown Ln, Winchester, KY 40391
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  /28

  $363,000 Sold Apr 07, 2025

  29 Manor Dr, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 2,148 Sq Ft
  • Built 1962

  Last Sold Summary

  • 8% Below List Price
  • $169/SF
  • 247 Days On Market

  Current Estimated Value $362,929

  Last Listing Agent John Patterson Rector Hayden Realtors

  29 Manor Dr, Winchester, KY 40391
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  /24

  $252,500 Sold Dec 23, 2025

  110 Albany Ln, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,306 Sq Ft
  • Built 1987

  Last Sold Summary

  • 6% Below List Price
  • $193/SF
  • 1 Day On Market

  Last Listing Agent Jason Townsend Kentucky Residential Real Estate, LLC

  110 Albany Ln, Winchester, KY 40391
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  /2

  $80,000 Sold Jan 09, 2026

  7244 Ecton Rd, Winchester, KY 40391

  • Land
  • 5.85 Acres
  • $13,675 per Acre

  Last Sold Summary

  • 15 Days On Market

  Last Listing Agent Zella Rosenthal Tom Goebel & Company

  7244 Ecton Rd, Winchester, KY 40391
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  /56

  $241,000 Sold Mar 25, 2025

  725 Estes Dr, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 2,160 Sq Ft
  • Built 1970

  Last Sold Summary

  • $112/SF
  • 3 Days On Market

  Current Estimated Value $245,846

  Last Listing Agent Brenda Sipes Bridgewater Real Estate

  725 Estes Dr, Winchester, KY 40391
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  /55

  $448,000 Sold Jun 09, 2025

  207 Bentbrook Ct, Winchester, KY 40391

  • 3 Beds
  • 3 Baths
  • 4,260 Sq Ft
  • Built 1998

  Last Sold Summary

  • 2% Below List Price
  • $105/SF
  • 12 Days On Market

  Current Estimated Value $456,866

  Last Listing Agent Melodie Lincavage RE/MAX Elite Realty

  207 Bentbrook Ct, Winchester, KY 40391
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  /64

  $260,000 Sold Nov 10, 2025

  113 Olde Potomac Ave, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,928 Sq Ft
  • Built 1942

  Last Sold Summary

  • 3% Below List Price
  • $135/SF
  • 44 Days On Market

  Last Listing Agent Susan Colwell Colwell Realty Professionals, Inc.

  113 Olde Potomac Ave, Winchester, KY 40391
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  /5

  $121,000 Sold Oct 03, 2025

  1200 Craig Crossing, Winchester, KY 40391

  • Land
  • 2.5 Acres
  • $48,400 per Acre

  Last Sold Summary

  • 10% Below List Price
  • 65 Days On Market

  Last Listing Agent N Seth Parker Lifstyl Real Estate

  1200 Craig Crossing, Winchester, KY 40391
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  /22

  $165,000 Sold Jun 23, 2025

  515 Colby Ridge Blvd, Winchester, KY 40391

  • 2 Beds
  • 2.5 Baths
  • 1,134 Sq Ft
  • Built 1999

  Last Sold Summary

  • $146/SF
  • 0 Days On Market

  Current Estimated Value $171,700

  Last Listing Agent Cathleen Gedeon CENTURY 21 Advantage Realty

  515 Colby Ridge Blvd, Winchester, KY 40391
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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

  Current Estimated Value $609,220

  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 $276,720

  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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  /39

  $285,000 Sold Jan 26, 2026

  8 Village Dr, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,979 Sq Ft
  • Built 1970

  Last Sold Summary

  • 3% Below List Price
  • $144/SF
  • 33 Days On Market

  Last Listing Agent Keith Wilson Coldwell Banker McMahan

  8 Village Dr, 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

  Current Estimated Value $248,846

  Last Listing Agent Destiny Darby Keller Williams Commonwealth

  231 Leslie Dr, Winchester, KY 40391
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  /36

  $290,000 Sold Feb 04, 2026

  424 Waycross Dr, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 1,944 Sq Ft
  • Built 2005

  Last Sold Summary

  • $149/SF
  • 3 Days On Market

  Last Listing Agent Kymberly McCreary EXP Realty, LLC

  424 Waycross 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

  Current Estimated Value $206,053

  Last Listing Agent Dale Hatton Dream Maker Realty, LLC

  2858 Ford Hampton Rd, Winchester, KY 40391
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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

  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

  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 $392,104

  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 $307,510

  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 $249,595

  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 $412,015

  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 $351,325

  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 $183,905

  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 $195,796

  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

  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 $292,822

  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 $405,262

  Last Listing Agent Natalie Nohel CENTURY 21 Advantage Realty

  410 Lyon Dr, Winchester, KY 40391

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