Recently Sold Winchester, KY Homes

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  /30

  $185,000

  Sold Feb 06, 2026

  40 Garner St, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,354 Sq Ft
  • Built 1950

  Last Sold Summary

  • 16% Below List Price
  • $137/SF
  • 217 Days On Market

  Current Estimated Value $191,930

  Last Listing Agent Nicole Seals Guide Realty, Inc.

  40 Garner St, Winchester, KY 40391
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  /36

  $435,000

  Sold May 22, 2026

  3886 Jackson Ferry Rd, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 1,692 Sq Ft
  • Built 1992

  Last Sold Summary

  • $257/SF
  • 21 Days On Market

  Current Estimated Value $423,237

  Last Listing Agent Whitney Ensor Ensor Real Estate, LLC

  3886 Jackson Ferry Rd, Winchester, KY 40391
• 

  

  

  /19

  $189,000

  Sold Mar 03, 2026

  111 Quail Ridge Rd, Winchester, KY 40391

  • 2 Beds
  • 2.5 Baths
  • 1,197 Sq Ft
  • Built 1994

  Last Sold Summary

  • $158/SF
  • 5 Days On Market

  Current Estimated Value $191,472

  Last Listing Agent Kim Dice eXp Realty, LLC

  111 Quail Ridge Rd, Winchester, KY 40391
• 

  

  

  /35

  $244,000

  Sold Mar 09, 2026

  426 Paisley Ct, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,641 Sq Ft
  • Built 2004

  Last Sold Summary

  • $149/SF
  • 2 Days On Market

  Current Estimated Value $245,612

  Last Listing Agent Lura Justice Rector Hayden Realtors

  426 Paisley Ct, Winchester, KY 40391
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  /39

  $315,000

  Sold Aug 07, 2026

  13 Lakeview Dr, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,932 Sq Ft
  • Built 1980

  Last Sold Summary

  • $163/SF
  • 5 Days On Market

  Current Estimated Value $314,962

  Last Listing Agent Michelle Blackburn RE/MAX Creative, Winchester

  13 Lakeview Dr, Winchester, KY 40391
• 

  

  /22

  $220,000

  Sold Mar 31, 2026

  443 Jameson Way, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 1,400 Sq Ft
  • Built 2002

  Last Sold Summary

  • 1% Below List Price
  • $157/SF
  • 64 Days On Market

  Current Estimated Value $222,297

  Last Listing Agent Tyler I Back The Brokerage

  443 Jameson Way, Winchester, KY 40391
• 

  /2

  $160,000

  Sold Sep 19, 2025

  8 Village Dr, Winchester, KY 40391

  • 3 Beds
  • 1.5 Baths
  • 1,414 Sq Ft
  • Built 1970

  Last Sold Summary

  • 9% Below List Price
  • $113/SF
  • 0 Days On Market

  Current Estimated Value $283,126

  Last Listing Agent Joyce Ratliff Tom Goebel & Company

  8 Village Dr, Winchester, KY 40391
• 

  

  /28

  $290,000

  Sold Apr 17, 2026

  24 N Burns Ave, Winchester, KY 40391

  • 3 Beds
  • 3.5 Baths
  • 2,526 Sq Ft
  • Built 1920

  Last Sold Summary

  • 6% Below List Price
  • $115/SF
  • 92 Days On Market

  Current Estimated Value $286,659

  Last Listing Agent Sarah Hess Keller Williams Commonwealth

  24 N Burns Ave, Winchester, KY 40391
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  /101

  $1,050,000

  Sold Jun 01, 2026

  3760 Old Boonesboro Rd, Winchester, KY 40391

  • 5 Beds
  • 5 Baths
  • 5,666 Sq Ft
  • Built 1985

  Last Sold Summary

  • 19% Below List Price
  • $185/SF
  • 15 Days On Market

  Current Estimated Value $672,000

  Last Listing Agent Josh Wood Freedom Realty & Property Management

  3760 Old Boonesboro Rd, Winchester, KY 40391
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  /42

  $339,500

  Sold Jul 15, 2026

  221 W Hickman St, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 2,800 Sq Ft
  • Built 1940

  Last Sold Summary

  • 3% Below List Price
  • $121/SF
  • 4 Days On Market

  Current Estimated Value $345,306

  Last Listing Agent Brandon Hedinger Keller Williams Bluegrass Realty

  221 W Hickman St, Winchester, KY 40391
• 

  /2

  $85,000

  Sold Dec 12, 2025

  1385 Sewell Shop Rd, Winchester, KY 40391

  • Land
  • 6.43 Acres
  • $13,219 per Acre

  Last Sold Summary

  • 6% Below List Price
  • 6 Days On Market

  Last Listing Agent Zella Rosenthal Tom Goebel & Company

  1385 Sewell Shop Rd, Winchester, KY 40391
• 

  

  /34

  $349,000

  Sold Jul 16, 2026

  405 Tremont Ln, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,274 Sq Ft
  • Built 2005

  Last Sold Summary

  • $153/SF
  • 6 Days On Market

  Current Estimated Value $351,826

  Last Listing Agent Darryl Bond Guide Realty, Inc.

  405 Tremont Ln, Winchester, KY 40391
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  /36

  $420,000

  Sold Feb 25, 2026

  134 Fontaine Blvd, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,747 Sq Ft
  • Built 1994

  Last Sold Summary

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

  Current Estimated Value $420,852

  Last Listing Agent Craig Bridgewater Bridgewater Real Estate

  134 Fontaine Blvd, Winchester, KY 40391
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  /59

  $277,500

  Sold Jun 30, 2026

  403 Pueblo Ct, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,311 Sq Ft
  • Built 2020

  Last Sold Summary

  • 1% Above List Price
  • $212/SF
  • 8 Days On Market

  Current Estimated Value $273,917

  Last Listing Agent Josh Wood Freedom Realty & Property Management

  403 Pueblo Ct, Winchester, KY 40391
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  /41

  $310,000

  Sold Dec 29, 2025

  1996 White Conkwright Rd, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 1,055 Sq Ft
  • Built 1966

  Last Sold Summary

  • 9% Below List Price
  • $294/SF
  • 45 Days On Market

  Current Estimated Value $338,478

  Last Listing Agent Lucy Martin Jenkins United Real Estate Bluegrass

  1996 White Conkwright Rd, Winchester, KY 40391
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  /43

  $299,900

  Sold Jul 14, 2026

  3622 Stamper Dr, Winchester, KY 40391

  • 3 Beds
  • 3 Baths
  • 2,821 Sq Ft
  • Built 1983

  Last Sold Summary

  • $106/SF
  • 12 Days On Market

  Current Estimated Value $305,088

  Last Listing Agent Josh Wood Freedom Realty & Property Management

  3622 Stamper Dr, Winchester, KY 40391
• 

  

  /38

  $599,500

  Sold Sep 08, 2025

  102 Bella Shae Way, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 2,204 Sq Ft
  • Built 2025

  Last Sold Summary

  • $272/SF
  • 72 Days On Market

  Current Estimated Value $599,255

  Last Listing Agent Shane Underwood Keller Williams Commonwealth

  102 Bella Shae Way, Winchester, KY 40391
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  /10

  $100,000

  Sold Feb 20, 2026

  17 Waveland Ave, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 1,061 Sq Ft
  • Built 1950

  Last Sold Summary

  • 9% Below List Price
  • $94/SF
  • 4 Days On Market

  Current Estimated Value $136,209

  Last Listing Agent Darrell Lewis DIY Realty

  17 Waveland Ave, Winchester, KY 40391
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  /37

  $220,000

  Sold Sep 23, 2025

  213 Blair Ave, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,025 Sq Ft
  • Built 1979

  Last Sold Summary

  • 2% Below List Price
  • $215/SF
  • 4 Days On Market

  Current Estimated Value $217,503

  Last Listing Agent Elizabeth Hodge Lifstyl Real Estate

  213 Blair Ave, Winchester, KY 40391
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  /54

  $649,900

  Sold Aug 06, 2026

  1480 Irvine Rd, Winchester, KY 40391

  • 3 Beds
  • 3.5 Baths
  • 3,388 Sq Ft
  • Built 1920

  Last Sold Summary

  • 13% Below List Price
  • $192/SF
  • 87 Days On Market

  Current Estimated Value $642,559

  Last Listing Agent Ivanna Barko National Real Estate

  1480 Irvine Rd, Winchester, KY 40391
• 

  

  /20

  $339,000

  Sold Aug 04, 2026

  107 Gibson Way, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 2,266 Sq Ft
  • Built 2020

  Last Sold Summary

  • 8% Below List Price
  • $150/SF
  • 26 Days On Market

  Current Estimated Value $356,467

  Last Listing Agent Vanessa Highland Stewart & Co Realty LLC

  107 Gibson Way, Winchester, KY 40391
• 

  

  /33

  $208,000

  Sold May 15, 2026

  59 Holiday Rd, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,050 Sq Ft
  • Built 1985

  Last Sold Summary

  • 1% Below List Price
  • $198/SF
  • 6 Days On Market

  Current Estimated Value $207,702

  Last Listing Agent Kathy Burton Coldwell Banker McMahan

  59 Holiday Rd, Winchester, KY 40391
• 

  

  /14

  $200,000

  Sold Sep 19, 2025

  9711 Ironworks Rd, Winchester, KY 40391

  Last Sold Summary

  • 11% Below List Price
  • 19 Days On Market

  Last Listing Agent Jessica Maloney Denniston Realty

  9711 Ironworks Rd, Winchester, KY 40391
• 

  

  /75

  $490,000

  Sold Sep 26, 2025

  497 Goose Creek Rd, Winchester, KY 40391

  • 4 Beds
  • 3.5 Baths
  • 2,972 Sq Ft
  • Built 1993

  Last Sold Summary

  • 1% Below List Price
  • $165/SF
  • 2 Days On Market

  Current Estimated Value $478,133

  Last Listing Agent O Eve Stern Threshold Real Estate Services

  497 Goose Creek Rd, Winchester, KY 40391
• 

  

  /25

  $287,000

  Sold Aug 20, 2025

  220 Mcdowell Dr, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,402 Sq Ft
  • Built 1987

  Last Sold Summary

  • 12% Below List Price
  • $205/SF
  • 36 Days On Market

  Current Estimated Value $296,368

  Last Listing Agent Alyssa M Boley Coldwell Banker McMahan

  220 Mcdowell Dr, Winchester, KY 40391
• 

  

  /33

  $240,000

  Sold Sep 10, 2025

  752 Wayland Dr, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 2,472 Sq Ft
  • Built 1969

  Last Sold Summary

  • 11% Below List Price
  • $97/SF
  • 18 Days On Market

  Current Estimated Value $266,196

  Last Listing Agent Craig Bridgewater Bridgewater Real Estate

  752 Wayland Dr, Winchester, KY 40391
• 

  

  /24

  $275,000

  Sold Mar 02, 2026

  434 Paisley Ct, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,678 Sq Ft
  • Built 2012

  Last Sold Summary

  • $164/SF
  • 1 Day On Market

  Current Estimated Value $275,764

  Last Listing Agent Joshua Davis The Agency

  434 Paisley Ct, Winchester, KY 40391
• 

  

  /27

  $185,000

  Sold Mar 23, 2026

  616 Boone Ave, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 1,223 Sq Ft
  • Built 1955

  Last Sold Summary

  • 7% Below List Price
  • $151/SF
  • 16 Days On Market

  Current Estimated Value $187,391

  Last Listing Agent Garnett Davis Tom Goebel & Company

  616 Boone Ave, Winchester, KY 40391
• 

  

  /29

  $262,500

  Sold Feb 18, 2026

  410 Wellington Way, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,192 Sq Ft
  • Built 2007

  Last Sold Summary

  • 2% Below List Price
  • $220/SF
  • 69 Days On Market

  Current Estimated Value $263,461

  Last Listing Agent Monica Marcum Century 21 Pinnacle

  410 Wellington Way, Winchester, KY 40391
• 

  

  /15

  $241,500

  Sold May 01, 2026

  318 Buffalo Trace, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • Built 2026

  Last Sold Summary

  • 3% Above List Price
  • $201/SF
  • 1 Day On Market

  Current Estimated Value $236,474

  Last Listing Agent Nena Honaker Tom Goebel & Company

  318 Buffalo Trace, Winchester, KY 40391
• 

  

  /32

  $310,000

  Sold May 01, 2026

  113 Strawberry Ln, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,780 Sq Ft
  • Built 2023

  Last Sold Summary

  • 2% Below List Price
  • $174/SF
  • 1 Day On Market

  Current Estimated Value $309,962

  Last Listing Agent Rob Bolton Christies International Real Estate Bluegrass

  113 Strawberry Ln, Winchester, KY 40391
• 

  

  /31

  $240,200

  Sold Oct 28, 2025

  203 Inverness Ln, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,935 Sq Ft
  • Built 2004

  Last Sold Summary

  • 2% Below List Price
  • $124/SF
  • 16 Days On Market

  Current Estimated Value $255,864

  Last Listing Agent Kymberly McCreary eXp Realty, LLC

  203 Inverness Ln, Winchester, KY 40391
• 

  

  /19

  $221,000

  Sold Jun 16, 2026

  357 Silverton Way, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,502 Sq Ft
  • Built 1999

  Last Sold Summary

  • 90,847% Above List Price
  • $147/SF
  • 64 Days On Market

  Current Estimated Value $225,015

  Last Listing Agent Frank Mulder Tru Life Real Estate

  357 Silverton Way, Winchester, KY 40391
• 

  

  /44

  $847,000

  Sold Apr 22, 2026

  7075 Ecton Rd, Winchester, KY 40391

  • Land
  • 83.71 Acres
  • $10,118 per Acre

  Last Sold Summary

  • 39 Days On Market

  Current Estimated Value $850,390

  Last Listing Agent Jonathan Noel Noel Auctioneers and Real Estate Advisors

  7075 Ecton Rd, Winchester, KY 40391
• 

  

  /43

  $339,000

  Sold Feb 12, 2026

  106 Gibson Way, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 2,064 Sq Ft
  • Built 2021

  Last Sold Summary

  • $164/SF
  • 1 Day On Market

  Current Estimated Value $337,444

  Last Listing Agent Brittany Nester RO&CO Real Estate

  106 Gibson Way, Winchester, KY 40391
• 

  

  /36

  $472,500

  Sold Sep 09, 2025

  208 Royal Oak Dr, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,593 Sq Ft
  • Built 2007

  Last Sold Summary

  • 1% Above List Price
  • $182/SF
  • 1 Day On Market

  Current Estimated Value $489,207

  Last Listing Agent Megan McCoy Keller Williams Legacy Group

  208 Royal Oak Dr, Winchester, KY 40391
• 

  

  /32

  $259,000

  Sold Apr 30, 2026

  414 Wellington Way, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,251 Sq Ft
  • Built 2007

  Last Sold Summary

  • $207/SF
  • 53 Days On Market

  Current Estimated Value $257,208

  Last Listing Agent Amy Diamond ERA Select Real Estate

  414 Wellington Way, Winchester, KY 40391
• 

  

  /15

  $139,000

  Sold May 29, 2026

  37 Ashland Ave, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 904 Sq Ft
  • Built 1940

  Last Sold Summary

  • $154/SF
  • 5 Days On Market

  Current Estimated Value $139,441

  Last Listing Agent Samantha Gray National Real Estate

  37 Ashland Ave, Winchester, KY 40391
• 

  

  /20

  $217,500

  Sold Sep 30, 2025

  511 Acadia Way, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 1,400 Sq Ft
  • Built 2001

  Last Sold Summary

  • 3% Below List Price
  • $155/SF
  • 28 Days On Market

  Current Estimated Value $219,838

  Last Listing Agent Tyler I Back The Brokerage

  511 Acadia Way, Winchester, KY 40391
• 

  

  /35

  $290,000

  Sold Jul 17, 2026

  110 Buckingham Ln, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,240 Sq Ft
  • Built 2001

  Last Sold Summary

  • $234/SF
  • 3 Days On Market

  Current Estimated Value $289,894

  Last Listing Agent Jeremy Perryman United Real Estate Bluegrass

  110 Buckingham Ln, Winchester, KY 40391

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