Recently Sold Winchester, KY Homes

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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 $136,323

  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 $194,296

  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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  /53

  $439,000

  Sold Dec 29, 2025

  129 Lana Ln, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 2,844 Sq Ft
  • Built 1968

  Last Sold Summary

  • 7% Below List Price
  • $154/SF
  • 110 Days On Market

  Current Estimated Value $440,198

  Last Listing Agent Jo Gawthrop Keller Williams Bluegrass Realty

  129 Lana Ln, Winchester, KY 40391
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  /37

  $295,000

  Sold Dec 27, 2025

  115 College St, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,839 Sq Ft
  • Built 1940

  Last Sold Summary

  • 2% Below List Price
  • $160/SF
  • 0 Days On Market

  Current Estimated Value $296,456

  Last Listing Agent Zova Rothchild Keller Williams Legacy Group

  115 College St, Winchester, KY 40391
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  /78

  $660,000

  Sold Dec 10, 2025

  420 Alexis Way, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,770 Sq Ft
  • Built 2022

  Last Sold Summary

  • 5% Below List Price
  • $238/SF
  • 26 Days On Market

  Current Estimated Value $676,289

  Last Listing Agent Edwin Burden McCormick Realty Inc.

  420 Alexis Way, Winchester, KY 40391
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  /21

  $430,000

  Sold Mar 09, 2026

  870 Pilot View Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,568 Sq Ft
  • Built 2022

  Last Sold Summary

  • 2% Below List Price
  • $274/SF
  • 31 Days On Market

  Current Estimated Value $464,230

  Last Listing Agent Chelsea Morguson McCallie Real Estate

  870 Pilot View Rd, Winchester, KY 40391
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  /29

  $235,000

  Sold Feb 09, 2026

  142 Sturbridge Ln, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,220 Sq Ft
  • Built 2005

  Last Sold Summary

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

  Current Estimated Value $245,874

  Last Listing Agent Donna Mink Mink Realty

  142 Sturbridge Ln, Winchester, KY 40391
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  /32

  $360,000

  Sold Aug 14, 2025

  418 Skylark Dr, Winchester, KY 40391

  • 5 Beds
  • 2.5 Baths
  • 2,746 Sq Ft
  • Built 1990

  Last Sold Summary

  • 3% Above List Price
  • $131/SF
  • 12 Days On Market

  Current Estimated Value $358,398

  Last Listing Agent Kymberly McCreary eXp Realty, LLC

  418 Skylark Dr, Winchester, KY 40391
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  /57

  $775,000

  Sold Mar 02, 2026

  1700 Cabin Creek Rd, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 2,695 Sq Ft
  • Built 1994

  Last Sold Summary

  • $288/SF
  • 33 Days On Market

  Current Estimated Value $773,511

  Last Listing Agent Alysia Niva Century 21 Advantage Realty - Georgetown

  1700 Cabin Creek Rd, Winchester, KY 40391
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  /32

  $217,500

  Sold Jul 13, 2026

  525 Colby Ridge Blvd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,197 Sq Ft
  • Built 2001

  Last Sold Summary

  • 1% Below List Price
  • $182/SF
  • 11 Days On Market

  Current Estimated Value $220,426

  Last Listing Agent Craig Bridgewater Bridgewater Real Estate

  525 Colby Ridge Blvd, Winchester, KY 40391
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  /79

  $204,000

  Sold Oct 30, 2025

  133 S Burns Ave, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 3,295 Sq Ft
  • Built 1915

  Last Sold Summary

  • 18% Below List Price
  • $62/SF
  • 20 Days On Market

  Current Estimated Value $240,082

  Last Listing Agent Josh Wood Freedom Realty & Property Management

  133 S Burns Ave, Winchester, KY 40391
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  /62

  $260,000

  Sold Jun 09, 2026

  144 Holly Ave, Winchester, KY 40391

  • 8 Beds
  • 5 Baths
  • 3,637 Sq Ft
  • Built 2001

  Last Sold Summary

  • 19% Below List Price
  • $71/SF
  • 69 Days On Market

  Current Estimated Value $270,427

  Last Listing Agent Shane Underwood Keller Williams Commonwealth

  144 Holly Ave, Winchester, KY 40391
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  /28

  $246,000

  Sold Nov 06, 2025

  204 Moss Ct, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,430 Sq Ft
  • Built 1998

  Last Sold Summary

  • 3% Above List Price
  • $172/SF
  • 1 Day On Market

  Current Estimated Value $251,127

  Last Listing Agent Brooke Martin RO&CO Real Estate

  204 Moss Ct, Winchester, KY 40391
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  /26

  $390,000

  Sold Jul 22, 2026

  178 Hawthorne Dr, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 2,156 Sq Ft
  • Built 2018

  Last Sold Summary

  • $181/SF
  • 6 Days On Market

  Current Estimated Value $392,941

  Last Listing Agent Tiffani Casey Waizenhofer Real Estate

  178 Hawthorne Dr, Winchester, KY 40391
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  /43

  $450,000

  Sold May 26, 2026

  222 Ashton Oak Way, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 3,444 Sq Ft
  • Built 2006

  Last Sold Summary

  • $131/SF
  • 4 Days On Market

  Current Estimated Value $439,079

  Last Listing Agent Mila Ensor Ensor Real Estate, LLC

  222 Ashton Oak Way, Winchester, KY 40391
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  /52

  $230,000

  Sold Jan 20, 2026

  19 Cherokee Ct, Winchester, KY 40391

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

  Last Sold Summary

  • 2% Above List Price
  • $203/SF
  • 2 Days On Market

  Current Estimated Value $229,579

  Last Listing Agent Josh Wood Freedom Realty & Property Management

  19 Cherokee Ct, Winchester, KY 40391
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  /36

  $202,000

  Sold Mar 18, 2026

  58 Hughes Ave, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,456 Sq Ft

  Last Sold Summary

  • 6% Below List Price
  • $139/SF
  • 15 Days On Market

  Current Estimated Value $193,219

  Last Listing Agent E Anthony Phillips RE/MAX Creative Realty

  58 Hughes Ave, Winchester, KY 40391
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  /39

  $395,000

  Sold Jun 18, 2026

  18 Casa Landa Way, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,883 Sq Ft
  • Built 1975

  Last Sold Summary

  • $210/SF
  • 0 Days On Market

  Current Estimated Value $395,130

  Last Listing Agent Steve Charles Freedom Realty & Property Management

  18 Casa Landa Way, Winchester, KY 40391
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  /37

  $275,000

  Sold Sep 10, 2025

  279 Ascot Ave, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,247 Sq Ft
  • Built 2000

  Last Sold Summary

  • 8% Below List Price
  • $122/SF
  • 2 Days On Market

  Current Estimated Value $312,438

  Last Listing Agent Chase Pennington Team Pannell Real Estate

  279 Ascot Ave, Winchester, KY 40391
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  /24

  $90,000

  Sold Mar 23, 2026

  701 Williamsburg Dr, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 996 Sq Ft
  • Built 1971

  Last Sold Summary

  • 7% Below List Price
  • $90/SF
  • 2 Days On Market

  Current Estimated Value $94,208

  Last Listing Agent Shane Underwood Keller Williams Commonwealth

  701 Williamsburg Dr, Winchester, KY 40391
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  /28

  $370,000

  Sold Sep 03, 2025

  220 Spring Valley Dr, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 3,078 Sq Ft
  • Built 1975

  Last Sold Summary

  • 7% Below List Price
  • $120/SF
  • 3 Days On Market

  Current Estimated Value $409,740

  Last Listing Agent Tracey Goebel Tom Goebel & Company

  220 Spring Valley Dr, Winchester, KY 40391
• 

  

  /27

  $335,000

  Sold Dec 18, 2025

  2198 Goshen Rd, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,730 Sq Ft
  • Built 1997

  Last Sold Summary

  • 5% Above List Price
  • $194/SF
  • 31 Days On Market

  Current Estimated Value $334,859

  Last Listing Agent Jason Szaks EXIT Town & Country Realtors

  2198 Goshen Rd, Winchester, KY 40391
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  /29

  $180,000

  Sold Aug 11, 2025

  217 Blair Ave, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,025 Sq Ft
  • Built 1970

  Last Sold Summary

  • 3% Above List Price
  • $176/SF
  • 0 Days On Market

  Current Estimated Value $184,013

  Last Listing Agent Ashley Barreto Indigo & Co

  217 Blair Ave, Winchester, KY 40391
• 

  /2

  $224,900

  Sold May 08, 2026

  11 Shelley Dr, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,188 Sq Ft
  • Built 1970

  Last Sold Summary

  • $189/SF

  Current Estimated Value $225,046

  Last Listing Agent Mark Wallace Transactionbroker.com

  11 Shelley Dr, Winchester, KY 40391
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  /30

  $254,000

  Sold Dec 02, 2025

  312 Forest Ave, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,550 Sq Ft
  • Built 1962

  Last Sold Summary

  • 6% Below List Price
  • $164/SF
  • 52 Days On Market

  Current Estimated Value $255,742

  Last Listing Agent Michelle Blackburn RE/MAX Creative, Winchester

  312 Forest Ave, Winchester, KY 40391
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  /75

  $410,000

  Sold Nov 21, 2025

  291 Log Lick Rd, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,600 Sq Ft
  • Built 2007

  Last Sold Summary

  • 6% Below List Price
  • $158/SF
  • 3 Days On Market

  Current Estimated Value $420,513

  Last Listing Agent Joyce Ratliff Tom Goebel & Company

  291 Log Lick Rd, Winchester, KY 40391
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  /34

  $200,000

  Sold Aug 03, 2026

  190 Privacy Ln, Winchester, KY 40391

  • Land
  • 6.08 Acres
  • $32,895 per Acre

  Last Sold Summary

  • 27% Below List Price
  • 136 Days On Market

  Current Estimated Value $242,250

  Last Listing Agent Jason Joseph Keller Williams Commonwealth

  190 Privacy Ln, Winchester, KY 40391
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  /36

  $257,400

  Sold Nov 21, 2025

  103 Hampton Ave, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,715 Sq Ft
  • Built 1958

  Last Sold Summary

  • 10% Below List Price
  • $150/SF
  • 4 Days On Market

  Current Estimated Value $273,553

  Last Listing Agent Brett Bussell Turf Town Properties

  103 Hampton Ave, Winchester, KY 40391
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  /32

  $175,000

  Sold Dec 29, 2025

  200 Madison Ave, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,124 Sq Ft
  • Built 1996

  Last Sold Summary

  • 2% Below List Price
  • $156/SF
  • 19 Days On Market

  Current Estimated Value $180,403

  Last Listing Agent Silvia Torres Tru Life Real Estate

  200 Madison Ave, Winchester, KY 40391
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  /82

  $392,000

  Sold Dec 19, 2025

  397 Calmes Blvd, Winchester, KY 40391

  • 4 Beds
  • 3.5 Baths
  • 2,637 Sq Ft
  • Built 1992

  Last Sold Summary

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

  Current Estimated Value $400,468

  Last Listing Agent Omar Shalash Tru Life Real Estate

  397 Calmes Blvd, Winchester, KY 40391
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  /24

  $265,000

  Sold Feb 25, 2026

  120 Sunset Heights, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,440 Sq Ft
  • Built 1999

  Last Sold Summary

  • 4% Below List Price
  • $184/SF
  • 32 Days On Market

  Current Estimated Value $262,240

  Last Listing Agent Keith Wilson Coldwell Banker McMahan

  120 Sunset Heights, Winchester, KY 40391
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  /35

  $349,000

  Sold Feb 13, 2026

  121 Fitch Ave, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 2,100 Sq Ft
  • Built 1955

  Last Sold Summary

  • 8% Below List Price
  • $166/SF
  • 3 Days On Market

  Current Estimated Value $337,664

  Last Listing Agent Ashley Spencer Keller Williams Commonwealth

  121 Fitch Ave, Winchester, KY 40391
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  /31

  $175,000

  Sold Jun 18, 2026

  5434 Pine Ridge Rd, Winchester, KY 40391

  • 2 Beds
  • 2 Baths
  • 1,000 Sq Ft
  • Built 2024

  Last Sold Summary

  • 7% Below List Price
  • $175/SF
  • 23 Days On Market

  Current Estimated Value $180,347

  Last Listing Agent Jim Woodrum RE/MAX Creative, Winchester

  5434 Pine Ridge Rd, Winchester, KY 40391
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  /34

  $800,000

  Sold Jun 03, 2026

  1150 Craig Crossing, Winchester, KY 40391

  • 5 Beds
  • 3.5 Baths
  • 2,842 Sq Ft
  • Built 2025

  Last Sold Summary

  • 14% Below List Price
  • $281/SF
  • 82 Days On Market

  Current Estimated Value $797,932

  Last Listing Agent Stephanie Hacker Kentucky Residential Real Estate, LLC

  1150 Craig Crossing, Winchester, KY 40391
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  /45

  $271,000

  Sold Feb 26, 2026

  4180 Bybee Rd, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,523 Sq Ft
  • Built 1978

  Last Sold Summary

  • 7% Below List Price
  • $178/SF
  • 5 Days On Market

  Current Estimated Value $274,383

  Last Listing Agent Craig Bridgewater Bridgewater Real Estate

  4180 Bybee Rd, Winchester, KY 40391
• 

  

  /27

  $270,000

  Sold Aug 25, 2025

  9 Hillcrest Dr, Winchester, KY 40391

  • 3 Beds
  • 3 Baths
  • 1,813 Sq Ft
  • Built 2005

  Last Sold Summary

  • 3% Below List Price
  • $149/SF
  • 13 Days On Market

  Current Estimated Value $278,995

  Last Listing Agent Melissa Brown Keller Williams Legacy Group

  9 Hillcrest Dr, Winchester, KY 40391
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  /40

  $310,000

  Sold Jul 06, 2026

  305 Abbeywood Dr, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,899 Sq Ft
  • Built 2003

  Last Sold Summary

  • 2% Below List Price
  • $163/SF
  • 2 Days On Market

  Current Estimated Value $316,589

  Last Listing Agent Shevawn Akers Firefly Realty & Investments

  305 Abbeywood Dr, Winchester, KY 40391
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  /64

  $349,000

  Sold Jul 28, 2026

  411 Boone Ave, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 3,405 Sq Ft
  • Built 1945

  Last Sold Summary

  • $102/SF
  • 3 Days On Market

  Current Estimated Value $398,103

  Last Listing Agent Cathy Mattingly Indigo & Co

  411 Boone Ave, Winchester, KY 40391

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