Recently Sold Winchester, KY Homes

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  /92

  $1,075,000

  Sold Mar 18, 2026

  6237 Bybee Rd, Winchester, KY 40391

  • 5 Beds
  • 7 Baths
  • 8,236 Sq Ft
  • Built 2000

  Last Sold Summary

  • 10% Below List Price
  • $131/SF
  • 212 Days On Market

  Current Estimated Value $1,111,666

  Last Listing Agent Amanda Marcum Berkshire Hathaway HomeServices Foster Realtors

  6237 Bybee Rd, Winchester, KY 40391
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  /42

  $390,000

  Sold Oct 21, 2025

  19 Snowfall Dr, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,625 Sq Ft
  • Built 1950

  Last Sold Summary

  • 11% Above List Price
  • $240/SF
  • 2 Days On Market

  Current Estimated Value $379,580

  Last Listing Agent Bradford Queen Bluegrass Sotheby's International Realty

  19 Snowfall Dr, Winchester, KY 40391
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  /34

  $369,500

  Sold Aug 22, 2025

  148 Gibson Way, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,456 Sq Ft
  • Built 2022

  Last Sold Summary

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

  Current Estimated Value $380,780

  Last Listing Agent Patrick Arvin Keller Williams Commonwealth

  148 Gibson Way, Winchester, KY 40391
• 

  

  

  /26

  $200,000

  Sold Oct 02, 2025

  34 N Burns Ave, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,500 Sq Ft
  • Built 1945

  Last Sold Summary

  • 11% Below List Price
  • $133/SF
  • 8 Days On Market

  Current Estimated Value $214,473

  Last Listing Agent Ashley Barreto Indigo & Co

  34 N Burns Ave, Winchester, KY 40391
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  /16

  $214,900

  Sold Dec 05, 2025

  15 Holly Ave, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • Built 2025

  Last Sold Summary

  • 4% Below List Price
  • $179/SF
  • 52 Days On Market

  Current Estimated Value $217,595

  Last Listing Agent Nena Honaker Tom Goebel & Company

  15 Holly Ave, Winchester, KY 40391
• 

  

  /57

  $264,000

  Sold Jul 27, 2026

  720 Terry Dr, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,779 Sq Ft
  • Built 1990

  Last Sold Summary

  • 4% Below List Price
  • $148/SF
  • 28 Days On Market

  Current Estimated Value $272,136

  Last Listing Agent Christa Joynt Keller Williams Commonwealth

  720 Terry Dr, Winchester, KY 40391
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  /54

  $410,000

  Sold Apr 10, 2026

  204 Delaplain Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 3,563 Sq Ft
  • Built 1979

  Last Sold Summary

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

  Current Estimated Value $410,321

  Last Listing Agent Sam Watkins COLOR Real Estate

  204 Delaplain Rd, Winchester, KY 40391
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  /48

  $550,000

  Sold Sep 04, 2025

  594 Earlymeade Dr, Winchester, KY 40391

  • 5 Beds
  • 3 Baths
  • 3,489 Sq Ft
  • Built 2007

  Last Sold Summary

  • 4% Below List Price
  • $158/SF
  • 43 Days On Market

  Current Estimated Value $565,206

  Last Listing Agent Alyssa M Boley Coldwell Banker McMahan

  594 Earlymeade Dr, Winchester, KY 40391
• 

  

  /26

  $259,000

  Sold Jun 22, 2026

  86 Bon-Haven Ave, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 2,295 Sq Ft
  • Built 1960

  Last Sold Summary

  • 4% Below List Price
  • $113/SF
  • 1 Day On Market

  Current Estimated Value $263,355

  Last Listing Agent Tracey Goebel Tom Goebel & Company

  86 Bon-Haven Ave, Winchester, KY 40391
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  /75

  $600,000

  Sold May 29, 2026

  905 Pretty Run Rd, Winchester, KY 40391

  • 3 Beds
  • 3.5 Baths
  • 3,391 Sq Ft
  • Built 1997

  Last Sold Summary

  • $177/SF
  • 3 Days On Market

  Current Estimated Value $595,025

  Last Listing Agent Niki Wiley Bluegrass Sotheby's International Realty

  905 Pretty Run Rd, Winchester, KY 40391
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  /64

  $490,000

  Sold Aug 05, 2026

  182 Chardonnay Ct, Winchester, KY 40391

  • 5 Beds
  • 2.5 Baths
  • 3,097 Sq Ft
  • Built 1994

  Last Sold Summary

  • 2% Below List Price
  • $158/SF
  • 10 Days On Market

  Current Estimated Value $497,650

  Last Listing Agent Kathryn Cheuvront Coldwell Banker McMahan

  182 Chardonnay Ct, Winchester, KY 40391
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  /44

  $267,000

  Sold Mar 24, 2026

  146 W Lexington Ave, Winchester, KY 40391

  • 8 Beds
  • 3 Baths
  • 3,393 Sq Ft
  • Built 1940

  Last Sold Summary

  • 1% Below List Price
  • $79/SF
  • 54 Days On Market

  Current Estimated Value $273,739

  Last Listing Agent KB Realty Group -Kevin Bradley KB Realty Group

  146 W Lexington Ave, Winchester, KY 40391
• 

  

  /22

  $156,000

  Sold Jan 16, 2026

  146 Cook Ave, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,274 Sq Ft
  • Built 1940

  Last Sold Summary

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

  Current Estimated Value $164,871

  Last Listing Agent Autumn Johannes National Real Estate

  146 Cook Ave, Winchester, KY 40391
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  /71

  $410,000

  Sold Nov 07, 2025

  188 Big Stoner Rd, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,388 Sq Ft
  • Built 2001

  Last Sold Summary

  • 2% Below List Price
  • $172/SF
  • 9 Days On Market

  Current Estimated Value $430,473

  Last Listing Agent Trina Penn RE/MAX Creative Realty

  188 Big Stoner Rd, Winchester, KY 40391
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  /73

  $325,000

  Sold Sep 23, 2025

  407 Fairholme Way, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,805 Sq Ft
  • Built 2021

  Last Sold Summary

  • 4% Below List Price
  • $180/SF
  • 123 Days On Market

  Current Estimated Value $339,136

  Last Listing Agent Josh Wood Freedom Realty & Property Management

  407 Fairholme Way, Winchester, KY 40391
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  /40

  $210,000

  Sold Sep 11, 2025

  635 Lisletown Ln, Winchester, KY 40391

  • 2 Beds
  • 2 Baths
  • 1,628 Sq Ft
  • Built 1981

  Last Sold Summary

  • 12% Below List Price
  • $129/SF
  • 31 Days On Market

  Current Estimated Value $222,356

  Last Listing Agent Robin Jones Keller Williams Legacy Group

  635 Lisletown Ln, Winchester, KY 40391
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  /74

  $350,000

  Sold Mar 06, 2026

  4611 Colby Rd, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 3,712 Sq Ft
  • Built 1980

  Last Sold Summary

  • $94/SF
  • 2 Days On Market

  Current Estimated Value $359,577

  Last Listing Agent Nancy Smith Rector Hayden Realtors

  4611 Colby Rd, Winchester, KY 40391
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  /33

  $340,000

  Sold May 12, 2026

  1270 Sewell Shop Rd, Winchester, KY 40391

  • 5 Beds
  • 2 Baths
  • 1,952 Sq Ft
  • Built 2020

  Last Sold Summary

  • 7% Below List Price
  • $174/SF
  • 73 Days On Market

  Current Estimated Value $342,910

  Last Listing Agent Meggan Batey Keller Williams Legacy Group

  1270 Sewell Shop Rd, Winchester, KY 40391
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  /30

  $310,900

  Sold Sep 12, 2025

  115 Hampton Ave, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 3,042 Sq Ft
  • Built 1960

  Last Sold Summary

  • 4% Below List Price
  • $102/SF
  • 2 Days On Market

  Current Estimated Value $346,790

  Last Listing Agent Lauren Ball Deborah Ball Realty

  115 Hampton Ave, Winchester, KY 40391
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  /82

  $385,000

  Sold Nov 07, 2025

  1138 Lafayette Blvd, Winchester, KY 40391

  • 3 Beds
  • 3 Baths
  • 2,300 Sq Ft
  • Built 1995

  Last Sold Summary

  • 4% Above List Price
  • $167/SF
  • 1 Day On Market

  Current Estimated Value $371,391

  Last Listing Agent Josh Wood Freedom Realty & Property Management

  1138 Lafayette Blvd, Winchester, KY 40391
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  /50

  $220,000

  Sold Jun 18, 2026

  314 Snowden Dr, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,196 Sq Ft
  • Built 1960

  Last Sold Summary

  • 2% Below List Price
  • $184/SF
  • 1 Day On Market

  Current Estimated Value $223,189

  Last Listing Agent Josh Wood Freedom Realty & Property Management

  314 Snowden Dr, Winchester, KY 40391
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  /17

  $190,000

  Sold Sep 10, 2025

  114 Sunset Heights, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,059 Sq Ft
  • Built 1960

  Last Sold Summary

  • 3% Below List Price
  • $179/SF
  • 50 Days On Market

  Current Estimated Value $191,407

  Last Listing Agent Susan Baldwin Threshold Real Estate Services

  114 Sunset Heights, Winchester, KY 40391
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  /35

  $355,000

  Sold Aug 06, 2026

  411 Skylark Dr, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,591 Sq Ft
  • Built 1989

  Last Sold Summary

  • 1% Above List Price
  • $137/SF
  • 0 Days On Market

  Current Estimated Value $344,192

  Last Listing Agent Jennifer Hickman Keller Williams Commonwealth

  411 Skylark Dr, Winchester, KY 40391
• 

  

  /34

  $342,000

  Sold Sep 16, 2025

  3560 Wades Mill Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,305 Sq Ft
  • Built 1950

  Last Sold Summary

  • 10% Below List Price
  • $262/SF
  • 37 Days On Market

  Current Estimated Value $343,742

  Last Listing Agent Sarah MacHarg Kentucky Land and Home

  3560 Wades Mill Rd, Winchester, KY 40391
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  /5

  $41,500

  Sold Sep 15, 2025

  434 Fairholme Way, Winchester, KY 40391

  • Land
  • 15,681 Sq Ft
  • $115,278 per Acre

  Last Sold Summary

  • 8% Below List Price
  • 6 Days On Market

  Current Estimated Value $134,516

  Last Listing Agent Justin Lee JL Realty Group, LLC

  434 Fairholme Way, Winchester, KY 40391
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  /58

  $239,900

  Sold Jun 08, 2026

  3610 Stamper Dr, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,148 Sq Ft
  • Built 1986

  Last Sold Summary

  • $209/SF
  • 4 Days On Market

  Current Estimated Value $240,558

  Last Listing Agent Pete doCouto Plum Tree Realty

  3610 Stamper Dr, Winchester, KY 40391
• 

  

  /58

  $830,000

  Sold Feb 27, 2026

  2395 Becknerville Rd, Winchester, KY 40391

  • 4 Beds
  • 3.5 Baths
  • 3,234 Sq Ft
  • Built 2012

  Last Sold Summary

  • 2% Below List Price
  • $257/SF
  • 8 Days On Market

  Current Estimated Value $807,230

  Last Listing Agent Crystal Towe The Real Estate Group

  2395 Becknerville Rd, Winchester, KY 40391
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  /33

  $364,900

  Sold Feb 06, 2026

  446 Tremont Ln, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,811 Sq Ft
  • Built 2005

  Last Sold Summary

  • 1% Below List Price
  • $130/SF
  • 15 Days On Market

  Current Estimated Value $362,404

  Last Listing Agent Dylan Langdon The Agency

  446 Tremont Ln, Winchester, KY 40391
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  /60

  $249,900

  Sold Jul 22, 2026

  17 Holiday Rd, Winchester, KY 40391

  • 3 Beds
  • 1.5 Baths
  • 1,161 Sq Ft
  • Built 1992

  Last Sold Summary

  • $215/SF
  • 8 Days On Market

  Current Estimated Value $250,763

  Last Listing Agent Josh Wood Freedom Realty & Property Management

  17 Holiday Rd, Winchester, KY 40391
• 

  

  /38

  $173,000

  Sold Sep 22, 2025

  44 5th St, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,270 Sq Ft
  • Built 1952

  Last Sold Summary

  • 2% Above List Price
  • $136/SF
  • 2 Days On Market

  Current Estimated Value $181,397

  Last Listing Agent Tirza Howard The Howard Realty Co

  44 5th St, Winchester, KY 40391
• 

  

  /18

  $200,000

  Sold Jan 14, 2026

  245 Ecton Rd, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,074 Sq Ft
  • Built 1940

  Last Sold Summary

  • 9% Below List Price
  • $186/SF
  • 2 Days On Market

  Current Estimated Value $201,682

  Last Listing Agent Anthony Gigilo ListWithFreedom.com

  245 Ecton Rd, Winchester, KY 40391
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  /52

  $500,000

  Sold Aug 25, 2025

  1778 Elkin Rd, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 2,020 Sq Ft
  • Built 2015

  Last Sold Summary

  • 7% Below List Price
  • $248/SF
  • 103 Days On Market

  Last Listing Agent Vicki VanWinkle ERA Select Real Estate

  1778 Elkin Rd, Winchester, KY 40391
• 

  

  /28

  $203,900

  Sold Dec 10, 2025

  25 Hiawatha Trail, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 925 Sq Ft
  • Built 1968

  Last Sold Summary

  • 3% Below List Price
  • $220/SF
  • 35 Days On Market

  Current Estimated Value $204,810

  Last Listing Agent Sarah Hess Keller Williams Commonwealth

  25 Hiawatha Trail, Winchester, KY 40391
• 

  

  /80

  $524,000

  Sold Dec 16, 2025

  160 Agawam Rd, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 4,933 Sq Ft
  • Built 1978

  Last Sold Summary

  • 9% Below List Price
  • $106/SF
  • 51 Days On Market

  Current Estimated Value $520,291

  Last Listing Agent Megan McCoy Keller Williams Legacy Group

  160 Agawam Rd, Winchester, KY 40391
• 

  

  /90

  $650,000

  Sold Jun 17, 2026

  142 Clubhouse Dr, Winchester, KY 40391

  • 6 Beds
  • 4 Baths
  • 4,351 Sq Ft
  • Built 2001

  Last Sold Summary

  • $149/SF
  • 10 Days On Market

  Current Estimated Value $642,627

  Last Listing Agent Timothy Saylor Threshold Real Estate Services

  142 Clubhouse Dr, Winchester, KY 40391
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  /57

  $350,000

  Sold May 20, 2026

  220 Hibiscus Ln, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,640 Sq Ft
  • Built 2001

  Last Sold Summary

  • $213/SF
  • 4 Days On Market

  Current Estimated Value $346,038

  Last Listing Agent Timothy Saylor Threshold Real Estate Services

  220 Hibiscus Ln, Winchester, KY 40391
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  /41

  $300,300

  Sold Nov 07, 2025

  37 Lynnway Dr, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 3,220 Sq Ft
  • Built 1976

  Last Sold Summary

  • $93/SF
  • 58 Days On Market

  Current Estimated Value $331,506

  Last Listing Agent Donna Thwaites Thwaites Realtors LLC

  37 Lynnway Dr, Winchester, KY 40391
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  /41

  $247,000

  Sold Sep 19, 2025

  3588 Stamper Dr, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,530 Sq Ft
  • Built 1987

  Last Sold Summary

  • 1% Below List Price
  • $161/SF
  • 4 Days On Market

  Current Estimated Value $251,494

  Last Listing Agent Zach Johnson The Brokerage

  3588 Stamper Dr, Winchester, KY 40391
• 

  

  /20

  $205,000

  Sold Aug 19, 2025

  202 Custer Ct, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,113 Sq Ft
  • Built 1999

  Last Sold Summary

  • 8% Above List Price
  • $184/SF
  • 2 Days On Market

  Current Estimated Value $197,740

  Last Listing Agent Brittany Beer eXp Realty, LLC

  202 Custer Ct, Winchester, KY 40391
• 

  

  /15

  $176,000

  Sold Oct 17, 2025

  7575 Irvine Rd, Winchester, KY 40391

  Last Sold Summary

  • 6% Below List Price
  • 2 Days On Market

  Current Estimated Value $188,054

  Last Listing Agent Jason Townsend Kentucky Residential Real Estate, LLC

  7575 Irvine Rd, Winchester, KY 40391

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