Recently Sold Winchester, KY Homes

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  /27

  $274,900 Sold May 23, 2025

  707 Terry Dr, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,770 Sq Ft
  • Built 1978

  Last Sold Summary

  • 5% Below List Price
  • $155/SF
  • 40 Days On Market

  Current Estimated Value $290,446

  Last Listing Agent Kymberly McCreary EXP Realty, LLC

  707 Terry Dr, Winchester, KY 40391
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  /39

  $549,000 Sold Jul 30, 2025

  154 Hawthorne Dr, Winchester, KY 40391

  • 5 Beds
  • 3.5 Baths
  • 3,478 Sq Ft
  • Built 2020

  Last Sold Summary

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

  Current Estimated Value $554,375

  Last Listing Agent Jarran Thomas The Agency

  154 Hawthorne Dr, Winchester, KY 40391
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  /47

  $374,900 Sold Sep 19, 2025

  714 Concord Ave, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,750 Sq Ft
  • Built 2017

  Last Sold Summary

  • $214/SF
  • 23 Days On Market

  Current Estimated Value $374,817

  Last Listing Agent Josh Wood Freedom Realty & Property Management

  714 Concord Ave, Winchester, KY 40391
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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 $1,182,344

  Last Listing Agent Amanda Marcum Berkshire Hathaway HomeServices Foster Realtors

  6237 Bybee Rd, Winchester, KY 40391
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  /36

  $309,000 Sold May 21, 2025

  172 Buckingham Ln, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,958 Sq Ft
  • Built 1999

  Last Sold Summary

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

  Current Estimated Value $322,707

  Last Listing Agent Mila Ensor Ensor Real Estate, LLC

  172 Buckingham Ln, 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 $358,158

  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 $363,753

  Last Listing Agent Patrick Arvin Keller Williams Commonwealth

  148 Gibson Way, Winchester, KY 40391
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  /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 $210,220

  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 $214,856

  Last Listing Agent Nena Honaker Tom Goebel & Company

  15 Holly Ave, 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 $560,380

  Last Listing Agent Alyssa M Boley Coldwell Banker McMahan

  594 Earlymeade Dr, Winchester, KY 40391
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  /28

  $359,900 Sold Jul 30, 2025

  210 Jett Dr, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,600 Sq Ft
  • Built 2024

  Last Sold Summary

  • $225/SF
  • 311 Days On Market

  Last Listing Agent Mila Ensor Ensor Real Estate, LLC

  210 Jett Dr, Winchester, KY 40391
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  /47

  $330,000 Sold Mar 31, 2025

  150 Privacy Ln, Winchester, KY 40391

  • 3 Beds
  • 3 Baths
  • 2,784 Sq Ft
  • Built 1987

  Last Sold Summary

  • 6% Below List Price
  • $119/SF
  • 103 Days On Market

  Current Estimated Value $348,277

  Last Listing Agent Jason Joseph Keller Williams Commonwealth

  150 Privacy Ln, 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 $269,171

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

  146 W Lexington Ave, Winchester, KY 40391
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  /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 $164,074

  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 $419,825

  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 $326,371

  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 $213,540

  Last Listing Agent Robin Jones Keller Williams Legacy Group

  635 Lisletown Ln, Winchester, KY 40391
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  /43

  $485,000 Sold Jun 23, 2025

  430 Fairholme Way, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 2,414 Sq Ft
  • Built 2017

  Last Sold Summary

  • 4% Below List Price
  • $201/SF
  • 55 Days On Market

  Current Estimated Value $495,956

  Last Listing Agent Robyn Bradley Woods Realty Group

  430 Fairholme Way, 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 $362,884

  Last Listing Agent Nancy Smith Rector Hayden Realtors

  4611 Colby Rd, Winchester, KY 40391
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  /24

  $186,000 Sold May 14, 2025

  205 Arbor Ct, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,188 Sq Ft
  • Built 1994

  Last Sold Summary

  • 3% Above List Price
  • $157/SF
  • 77 Days On Market

  Current Estimated Value $196,999

  Last Listing Agent Kathryn Cheuvront Coldwell Banker McMahan

  205 Arbor Ct, 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 $315,688

  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 $381,413

  Last Listing Agent Josh Wood Freedom Realty & Property Management

  1138 Lafayette Blvd, 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 $194,153

  Last Listing Agent Susan Baldwin Threshold Real Estate Services

  114 Sunset Heights, Winchester, KY 40391
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  /48

  $222,500 Sold Jul 28, 2025

  217 Locust Grove Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 2,055 Sq Ft
  • Built 1955

  Last Sold Summary

  • 1% Above List Price
  • $108/SF
  • 2 Days On Market

  Current Estimated Value $226,140

  Last Listing Agent Robin Murray The Agency

  217 Locust Grove Rd, Winchester, KY 40391
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  /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 $343,389

  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
  • 0.36 Acre
  • $115,278 per Acre

  Last Sold Summary

  • 8% Below List Price
  • 6 Days On Market

  Current Estimated Value $51,486

  Last Listing Agent Justin Lee JL Realty Group, LLC

  434 Fairholme Way, Winchester, KY 40391
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  /48

  $330,000 Sold May 23, 2025

  113 Holiday Rd, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 2,090 Sq Ft
  • Built 1970

  Last Sold Summary

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

  Current Estimated Value $306,118

  Last Listing Agent Jason Townsend Kentucky Residential Real Estate, LLC

  113 Holiday Rd, Winchester, KY 40391
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  /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 $834,586

  Last Listing Agent Crystal Towe The Real Estate Group

  2395 Becknerville Rd, Winchester, KY 40391
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  /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 $170,890

  Last Listing Agent Tirza Cooper The Howard Realty Co

  44 5th St, Winchester, KY 40391
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  /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 $199,174

  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
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  /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 $525,452

  Last Listing Agent Megan McCoy Keller Williams Legacy Group

  160 Agawam Rd, Winchester, KY 40391
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  /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 $200,325

  Last Listing Agent Sarah Hess Keller Williams Commonwealth

  25 Hiawatha Trail, Winchester, KY 40391
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  /3

  $220,000 Sold Jul 30, 2025

  412 Paisley Ct, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,300 Sq Ft
  • Built 2005

  Last Sold Summary

  • 4% Below List Price
  • $169/SF
  • 38 Days On Market

  Current Estimated Value $224,004

  Last Listing Agent John Wilson Bluegrass Properties Group

  412 Paisley Ct, Winchester, KY 40391
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  /37

  $228,000 Sold May 02, 2025

  102 E Clark Dr, Winchester, KY 40391

  • 3 Beds
  • 1.5 Baths
  • 1,247 Sq Ft
  • Built 1962

  Last Sold Summary

  • 1% Below List Price
  • $183/SF
  • 6 Days On Market

  Current Estimated Value $229,046

  Last Listing Agent Jim Woodrum RE/MAX Creative, Winchester

  102 E Clark Dr, Winchester, KY 40391
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  /35

  $185,000 Sold Apr 02, 2025

  125 Magnolia St, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,251 Sq Ft
  • Built 1945

  Last Sold Summary

  • 2% Below List Price
  • $148/SF
  • 31 Days On Market

  Current Estimated Value $211,438

  Last Listing Agent Dale Hatton Dream Maker Realty, LLC

  125 Magnolia St, Winchester, KY 40391
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  /61

  $372,500 Sold Mar 28, 2025

  521 Lasalle Ct, Winchester, KY 40391

  • 3 Beds
  • 3 Baths
  • 2,101 Sq Ft
  • Built 1979

  Last Sold Summary

  • 2% Below List Price
  • $177/SF
  • 15 Days On Market

  Current Estimated Value $366,413

  Last Listing Agent Keith Wilson Coldwell Banker McMahan

  521 Lasalle Ct, 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 $306,802

  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 $246,480

  Last Listing Agent Zach Johnson The Brokerage

  3588 Stamper Dr, Winchester, KY 40391
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  /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 $198,827

  Last Listing Agent Brittany Beer EXP Realty, LLC

  202 Custer Ct, Winchester, KY 40391

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