Recently Sold Winchester, KY Homes

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  /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 $242,717

  Last Listing Agent Lura Justice Rector Hayden Realtors

  426 Paisley Ct, Winchester, KY 40391
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  /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 $222,350

  Last Listing Agent Tyler I Back The Brokerage

  443 Jameson Way, Winchester, KY 40391
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  /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 $277,556

  Last Listing Agent Joyce Ratliff Tom Goebel & Company

  8 Village Dr, Winchester, KY 40391
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  /22

  $193,000 Sold Jun 06, 2025

  116 Linden Ave, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,164 Sq Ft
  • Built 1945

  Last Sold Summary

  • 2% Below List Price
  • $166/SF
  • 3 Days On Market

  Current Estimated Value $198,739

  Last Listing Agent Jeremy Perryman United Real Estate Bluegrass

  116 Linden Ave, Winchester, KY 40391
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  /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 $295,524

  Last Listing Agent Sarah Hess Keller Williams Commonwealth

  24 N Burns Ave, Winchester, KY 40391
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  /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
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  /53

  $867,500 Sold Aug 01, 2025

  511 Boone Ave, Winchester, KY 40391

  • 4 Beds
  • 4.5 Baths
  • 4,698 Sq Ft
  • Built 1885

  Last Sold Summary

  • 11% Below List Price
  • $185/SF
  • 318 Days On Market

  Current Estimated Value $908,797

  Last Listing Agent Greg Leveridge Block + Lot Real Estate

  511 Boone Ave, 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 $419,447

  Last Listing Agent Craig Bridgewater Bridgewater Real Estate

  134 Fontaine Blvd, 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 $315,826

  Last Listing Agent Lucy Martin Jenkins United Real Estate Bluegrass

  1996 White Conkwright Rd, Winchester, KY 40391
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  /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 $595,217

  Last Listing Agent Shane Underwood Keller Williams Commonwealth

  102 Bella Shae Way, Winchester, KY 40391
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  /34

  $333,900 Sold Jul 28, 2025

  366 Hanover Dr, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,162 Sq Ft
  • Built 2001

  Last Sold Summary

  • $154/SF
  • 2 Days On Market

  Current Estimated Value $337,731

  Last Listing Agent Melissa Brown Keller Williams Legacy Group

  366 Hanover Dr, 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 $217,583

  Last Listing Agent Elizabeth Hodge Lifstyl Real Estate

  213 Blair Ave, Winchester, KY 40391
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  $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 $140,984

  Last Listing Agent Darrell Lewis DIY Realty Flat Fee MLS

  17 Waveland Ave, Winchester, KY 40391
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  /2

  $110,000 Sold May 13, 2025

  140 Duclair Dr, Winchester, KY 40391

  • Land
  • 18,295 Sq Ft
  • $261,905 per Acre

  Last Sold Summary

  • 900 Days On Market

  Last Listing Agent John Wilson Bluegrass Properties Group

  140 Duclair Dr, Winchester, KY 40391
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  /44

  $515,000 Sold May 19, 2025

  31 Bonnie Brook Ln, Winchester, KY 40391

  • 5 Beds
  • 3.5 Baths
  • 4,091 Sq Ft
  • Built 1958

  Last Sold Summary

  • 10% Below List Price
  • $126/SF
  • 294 Days On Market

  Current Estimated Value $559,000

  Last Listing Agent Kelly Nisbet Coldwell Banker McMahan

  31 Bonnie Brook Ln, Winchester, KY 40391
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  /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
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  /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 $465,493

  Last Listing Agent O Eve Stern Threshold Real Estate Services

  497 Goose Creek Rd, Winchester, KY 40391
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  /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 $297,768

  Last Listing Agent Alyssa M Boley Coldwell Banker McMahan

  220 Mcdowell Dr, Winchester, KY 40391
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  /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 $258,178

  Last Listing Agent Craig Bridgewater Bridgewater Real Estate

  752 Wayland Dr, Winchester, KY 40391
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  /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 $270,493

  Last Listing Agent Joshua Davis The Agency

  434 Paisley Ct, Winchester, KY 40391
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  /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 $197,049

  Last Listing Agent Garnett Davis Tom Goebel & Company

  616 Boone Ave, Winchester, KY 40391
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  /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 $259,652

  Last Listing Agent Monica Marcum Century 21 Pinnacle

  410 Wellington Way, Winchester, KY 40391
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  /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 $180,330

  Last Listing Agent Nena Honaker Tom Goebel & Company

  318 Buffalo Trace, Winchester, KY 40391
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  /27

  $245,000 Sold Jun 13, 2025

  8 Seneca Dr, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,728 Sq Ft
  • Built 1968

  Last Sold Summary

  • 2% Above List Price
  • $142/SF
  • 8 Days On Market

  Current Estimated Value $251,514

  Last Listing Agent Michael Hilario The Agency

  8 Seneca Dr, Winchester, KY 40391
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  /26

  $239,900 Sold Jun 23, 2025

  134 Boone Ave, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,878 Sq Ft
  • Built 1920

  Last Sold Summary

  • 3% Below List Price
  • $128/SF
  • 74 Days On Market

  Current Estimated Value $256,164

  Last Listing Agent Steve Lindsey CENTURY 21 Commonwealth Real Estate

  134 Boone Ave, Winchester, KY 40391
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  /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 $314,130

  Last Listing Agent Rob Bolton Christies International Real Estate Bluegrass

  113 Strawberry Ln, Winchester, KY 40391
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  /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 $245,499

  Last Listing Agent Kymberly McCreary EXP Realty, LLC

  203 Inverness Ln, Winchester, KY 40391
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  /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 $833,000

  Last Listing Agent Jonathan Noel Noel Auctioneers and Real Estate Advisors

  7075 Ecton Rd, Winchester, KY 40391
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  /13

  $38,700 Sold May 20, 2025

  11 Spring St, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 1,100 Sq Ft
  • Built 1945

  Last Sold Summary

  • 3% Below List Price
  • $35/SF
  • 33 Days On Market

  Current Estimated Value $45,000

  Last Listing Agent Jason Szaks EXIT TOWN & COUNTRY REALTORS

  11 Spring St, Winchester, KY 40391
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  /36

  $345,000 Sold Jun 02, 2025

  1173 Lafayette Blvd, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,910 Sq Ft
  • Built 1996

  Last Sold Summary

  • 3% Below List Price
  • $181/SF
  • 36 Days On Market

  Current Estimated Value $356,501

  Last Listing Agent Janna Chalfant Smith United Real Estate Bluegrass

  1173 Lafayette Blvd, Winchester, KY 40391
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  /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 $340,731

  Last Listing Agent Brittany Nester RO&CO Real Estate

  106 Gibson Way, Winchester, KY 40391
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  /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 $469,830

  Last Listing Agent Megan McCoy Keller Williams Legacy Group

  208 Royal Oak Dr, Winchester, KY 40391
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  /6

  $51,000 Sold May 14, 2025

  214 Ashton Oak Way, Winchester, KY 40391

  • Land
  • 10,890 Sq Ft
  • $204,000 per Acre

  Last Sold Summary

  • 7% Below List Price
  • 325 Days On Market

  Current Estimated Value $54,792

  Last Listing Agent Melia Hord Keller Williams Legacy Group

  214 Ashton Oak Way, Winchester, KY 40391
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  /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 $254,943

  Last Listing Agent Amy Diamond ERA Select Real Estate

  414 Wellington Way, Winchester, KY 40391
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  /23

  $135,000 Sold Jul 02, 2025

  2100 Old Log Lick Rd, Winchester, KY 40391

  • Land
  • 5 Acres
  • $27,000 per Acre

  Last Sold Summary

  • 10% Below List Price
  • 69 Days On Market

  Current Estimated Value $142,767

  Last Listing Agent Michelle Blackburn RE/MAX Creative, Winchester

  2100 Old Log Lick Rd, Winchester, KY 40391
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  /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 $217,211

  Last Listing Agent Tyler I Back The Brokerage

  511 Acadia Way, Winchester, KY 40391
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  /2

  $99,500 Sold Dec 01, 2025

  1295 Sewell Shop Rd, Winchester, KY 40391

  • Land
  • 8.39 Acres
  • $11,859 per Acre

  Last Sold Summary

  • 10 Days On Market

  Last Listing Agent Zella Rosenthal Tom Goebel & Company

  1295 Sewell Shop Rd, Winchester, KY 40391
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  /13

  $140,000 Sold Nov 24, 2025

  220 Pendleton St, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 902 Sq Ft

  Last Sold Summary

  • 24% Below List Price
  • $155/SF
  • 37 Days On Market

  Current Estimated Value $137,854

  Last Listing Agent Steve Adams Steven D Adams Real Estate Services, LLC

  220 Pendleton St, Winchester, KY 40391
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  /21

  $195,000 Sold Apr 10, 2026

  319 Essex Ct, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,224 Sq Ft
  • Built 2000

  Last Sold Summary

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

  Current Estimated Value $201,635

  Last Listing Agent Michelle Blackburn RE/MAX Creative, Winchester

  319 Essex Ct, Winchester, KY 40391
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  /2

  $59,000 Sold Dec 16, 2025

  1515 Sewell Shop Rd, Winchester, KY 40391

  • Land
  • 2.83 Acres
  • $20,848 per Acre

  Last Sold Summary

  • 2% Below List Price
  • 3 Days On Market

  Last Listing Agent Zella Rosenthal Tom Goebel & Company

  1515 Sewell Shop Rd, Winchester, KY 40391

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