Recently Sold Homes in 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 $290,057

  Last Listing Agent Zova Rothchild Keller Williams Legacy Group

  115 College St, Winchester, KY 40391
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  /21

  $285,000

  Sold Jul 29, 2025

  219 Bartram Ct, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,696 Sq Ft
  • Built 2004

  Last Sold Summary

  • 1% Below List Price
  • $168/SF
  • 8 Days On Market

  Current Estimated Value $292,035

  Last Listing Agent Nora Williams Keller Williams Commonwealth

  219 Bartram Ct, Winchester, KY 40391
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  /43

  $354,000

  Sold Jul 02, 2025

  485 Mccullough Ln, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 2,120 Sq Ft
  • Built 1950

  Last Sold Summary

  • 21% Below List Price
  • $167/SF
  • 38 Days On Market

  Current Estimated Value $373,158

  Last Listing Agent Dale Hatton Dream Maker Realty, LLC

  485 Mccullough Ln, 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 $681,074

  Last Listing Agent Edwin Burden McCormick Realty Inc.

  420 Alexis Way, Winchester, KY 40391
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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 $402,941

  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 $431,700

  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 $563,739

  Last Listing Agent Joseph Smallwood Christies International Real Estate Bluegrass

  1063 Wades Mill Rd, Winchester, KY 40391
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  /65

  $290,000

  Sold Jun 18, 2025

  13 Robyn Dr, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,844 Sq Ft
  • Built 1980

  Last Sold Summary

  • 2% Below List Price
  • $157/SF
  • 1 Day On Market

  Current Estimated Value $303,529

  Last Listing Agent Jason Townsend Kentucky Residential Real Estate, LLC

  13 Robyn Dr, 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 $239,303

  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 $356,772

  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 $759,500

  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 $224,188

  Last Listing Agent Josh Wood Freedom Realty & Property Management

  133 S Burns 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 $243,058

  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 $227,913

  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 $245,689

  Last Listing Agent Jason Szaks EXIT TOWN & COUNTRY REALTORS

  108 Sturbridge Ln, 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 $227,908

  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 $348,067

  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 $292,933

  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 $211,466

  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 $96,885

  Last Listing Agent Shane Underwood Keller Williams Commonwealth

  701 Williamsburg 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 $330,729

  Last Listing Agent Jason Szaks EXIT TOWN & COUNTRY REALTORS

  2198 Goshen Rd, 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 $406,031

  Last Listing Agent Tracey Goebel Tom Goebel & Company

  220 Spring Valley Dr, 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 $183,291

  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 $235,106

  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 $250,805

  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 $413,647

  Last Listing Agent Joyce Ratliff Tom Goebel & Company

  291 Log Lick Rd, Winchester, KY 40391
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  /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 $265,373

  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 $177,238

  Last Listing Agent Silvia Torres Tru Life Real Estate

  200 Madison Ave, Winchester, KY 40391
• 

  

  /3

  $219,000

  Sold May 20, 2025

  410 Paisley Ct, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,628 Sq Ft
  • Built 2005

  Last Sold Summary

  • $135/SF
  • 18 Days On Market

  Current Estimated Value $235,633

  Last Listing Agent John Wilson Bluegrass Properties Group

  410 Paisley Ct, 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 $388,216

  Last Listing Agent Omar Shalash Tru Life Real Estate

  397 Calmes Blvd, Winchester, KY 40391
• 

  

  /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 $264,884

  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 $342,599

  Last Listing Agent Ashley Spencer Keller Williams Commonwealth

  121 Fitch Ave, 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 $278,677

  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 $287,119

  Last Listing Agent Melissa Brown Keller Williams Legacy Group

  9 Hillcrest Dr, Winchester, KY 40391
• 

  

  /15

  $249,900

  Sold Jun 09, 2025

  234 Prescott Ln, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,463 Sq Ft
  • Built 2005

  Last Sold Summary

  • $171/SF
  • 17 Days On Market

  Current Estimated Value $264,986

  Last Listing Agent Darrell Tackett Dream Maker Realty, LLC

  234 Prescott Ln, Winchester, KY 40391
• 

  

  /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 $283,706

  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 $260,146

  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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