Recently Sold Winchester, KY Homes

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  /49

  $390,000

  Sold Jun 30, 2025

  1094 Ford Hampton Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,900 Sq Ft
  • Built 1940

  Last Sold Summary

  • 2% Below List Price
  • $205/SF
  • 26 Days On Market

  Current Estimated Value $388,730

  Last Listing Agent Tom D. Thomas The Real Estate Co.

  1094 Ford Hampton Rd, 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 $435,624

  Last Listing Agent Chelsea Morguson McCallie Real Estate

  870 Pilot View Rd, Winchester, KY 40391
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  /61

  $545,000

  Sold Jul 15, 2025

  1063 Wades Mill Rd, Winchester, KY 40391

  • 4 Beds
  • 3.5 Baths
  • 3,958 Sq Ft
  • Built 2000

  Last Sold Summary

  • 11% Below List Price
  • $138/SF
  • 180 Days On Market

  Current Estimated Value $599,466

  Last Listing Agent Joseph Smallwood Christies International Real Estate Bluegrass

  1063 Wades Mill 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 $245,544

  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 $356,968

  Last Listing Agent Kymberly McCreary eXp Realty, LLC

  418 Skylark Dr, Winchester, KY 40391
• 

  

  /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 $784,818

  Last Listing Agent Alysia Niva Century 21 Advantage Realty - Georgetown

  1700 Cabin Creek Rd, 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 $234,266

  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 $307,988

  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 $247,551

  Last Listing Agent Brooke Martin RO&CO Real Estate

  204 Moss Ct, Winchester, KY 40391
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  /58

  $232,500

  Sold Jul 12, 2025

  114 Holiday Rd, Winchester, KY 40391

  • 3 Beds
  • 1.5 Baths
  • 1,161 Sq Ft
  • Built 1980

  Last Sold Summary

  • 7% Below List Price
  • $200/SF
  • 235 Days On Market

  Current Estimated Value $243,287

  Last Listing Agent Karen Smith Emmerich Muzic Realty

  114 Holiday Rd, Winchester, KY 40391
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  /28

  $234,500

  Sold Jul 29, 2025

  108 Sturbridge Ln, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • Built 2004

  Last Sold Summary

  • 4% Below List Price
  • $195/SF
  • 45 Days On Market

  Current Estimated Value $243,488

  Last Listing Agent Jason Szaks EXIT Town & Country Realtors

  108 Sturbridge Ln, 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 $445,758

  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 $228,566

  Last Listing Agent Josh Wood Freedom Realty & Property Management

  19 Cherokee Ct, Winchester, KY 40391
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  /22

  $334,327

  Sold Jul 01, 2025

  136 Gibson Way, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 1,997 Sq Ft
  • Built 2024

  Last Sold Summary

  • $167/SF
  • 219 Days On Market

  Current Estimated Value $348,029

  Last Listing Agent Neshia Gaines Christies International Real Estate Bluegrass

  136 Gibson 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 $309,443

  Last Listing Agent Chase Pennington Team Pannell Real Estate

  279 Ascot Ave, Winchester, KY 40391
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  /24

  $198,000

  Sold Jul 18, 2025

  113 Colonial Park Dr, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,075 Sq Ft
  • Built 1983

  Last Sold Summary

  • 2% Above List Price
  • $184/SF
  • 0 Days On Market

  Current Estimated Value $211,086

  Last Listing Agent Janet Baldwin Kentucky Land and Home

  113 Colonial Park Dr, 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 $95,878

  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 $413,330

  Last Listing Agent Tracey Goebel Tom Goebel & Company

  220 Spring Valley Dr, Winchester, KY 40391
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  /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 $332,671

  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 $185,117

  Last Listing Agent Ashley Barreto Indigo & Co

  217 Blair Ave, Winchester, KY 40391
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  /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 $227,114

  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 $255,194

  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 $421,284

  Last Listing Agent Joyce Ratliff Tom Goebel & Company

  291 Log Lick Rd, Winchester, KY 40391
• 

  

  /4

  $101,000

  Sold Jul 14, 2025

  2058 Athens Boonesboro Rd, Winchester, KY 40391

  • Land
  • 4.02 Acres
  • $25,124 per Acre

  Last Sold Summary

  • 7% Below List Price
  • 86 Days On Market

  Last Listing Agent Megan McCoy Keller Williams Legacy Group

  2058 Athens Boonesboro Rd, 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 $270,095

  Last Listing Agent Brett Bussell Turf Town Properties

  103 Hampton Ave, Winchester, KY 40391
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  /58

  $460,000

  Sold Jul 11, 2025

  150 Stone Crest Rd, Winchester, KY 40391

  • 4 Beds
  • 4 Baths
  • 4,448 Sq Ft
  • Built 1978

  Last Sold Summary

  • 6% Below List Price
  • $103/SF
  • 18 Days On Market

  Last Listing Agent Brenda Murphy Murphy Realty Group

  150 Stone Crest Rd, 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 $180,564

  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 $394,256

  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 $265,068

  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 $342,394

  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 $196,094

  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 $915,675

  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 $279,509

  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 $285,232

  Last Listing Agent Melissa Brown Keller Williams Legacy Group

  9 Hillcrest Dr, Winchester, KY 40391
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  /24

  $277,000

  Sold Mar 25, 2026

  149 Winn Ave, Winchester, KY 40391

  • 12 Beds
  • 4 Baths
  • 4,010 Sq Ft
  • Built 1940

  Last Sold Summary

  • 4% Below List Price
  • $69/SF
  • 51 Days On Market

  Current Estimated Value $284,727

  Last Listing Agent Libby VanMeter Marshall Lane Real Estate - Lexington

  149 Winn Ave, Winchester, KY 40391
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  /37

  $260,000

  Sold Feb 20, 2026

  313 Carolina Ave, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 1,855 Sq Ft
  • Built 1962

  Last Sold Summary

  • $140/SF
  • 4 Days On Market

  Current Estimated Value $261,675

  Last Listing Agent Kenneth DeGrant High Point Realty & Auction

  313 Carolina Ave, Winchester, KY 40391
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  /38

  $293,000

  Sold Mar 06, 2026

  6261 Ironworks Rd, Winchester, KY 40391

  • Land
  • 15.79 Acres
  • $18,556 per Acre

  Last Sold Summary

  • 2% Below List Price
  • 5 Days On Market

  Last Listing Agent Kyle McPeck Coldwell Banker McMahan

  6261 Ironworks Rd, Winchester, KY 40391
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  /98

  $750,000

  Sold Dec 10, 2025

  3900 (Mt) Mount Sterling Rd, Winchester, KY 40391

  • 6 Beds
  • 5 Baths
  • 4,843 Sq Ft
  • Built 2004

  Last Sold Summary

  • 9% Below List Price
  • $155/SF
  • 42 Days On Market

  Last Listing Agent Teresa Richmond Freedom Realty & Property Management

  3900 (Mt) Mount Sterling Rd, Winchester, KY 40391
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  /39

  $395,000

  Sold Jun 12, 2026

  233 Cunningham Ln, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 2,258 Sq Ft
  • Built 2007

  Last Sold Summary

  • 12% Below List Price
  • $175/SF
  • 116 Days On Market

  Current Estimated Value $429,421

  Last Listing Agent Amanda Marcum Berkshire Hathaway HomeServices Foster Realtors

  233 Cunningham Ln, Winchester, KY 40391
• 

  

  /21

  $225,200

  Sold Apr 28, 2026

  514 Hidden Hills Way, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,120 Sq Ft
  • Built 2001

  Last Sold Summary

  • 2% Below List Price
  • $201/SF
  • 7 Days On Market

  Current Estimated Value $227,224

  Last Listing Agent Mary Layton FC Tucker Bluegrass

  514 Hidden Hills Way, Winchester, KY 40391

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