Recently Sold Winchester, KY Homes

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  /21

  $240,000

  Sold Jun 09, 2026

  720 Estes Dr, Winchester, KY 40391

  • 3 Beds
  • 1.5 Baths
  • 1,494 Sq Ft
  • Built 1970

  Last Sold Summary

  • 2% Below List Price
  • $161/SF
  • 28 Days On Market

  Current Estimated Value $247,014

  Last Listing Agent Jonathan Wood HomeLand Real Estate Inc - Mt Sterling

  720 Estes Dr, Winchester, KY 40391
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  /10

  $325,000

  Sold Aug 29, 2025

  210 Cabin Creek Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,584 Sq Ft
  • Built 1999

  Last Sold Summary

  • $205/SF

  Current Estimated Value $339,994

  Last Listing Agent Janine Shackelford LPT Realty

  210 Cabin Creek Rd, Winchester, KY 40391
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  /36

  $261,000

  Sold Feb 04, 2026

  433 Wellington Way, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,234 Sq Ft
  • Built 2010

  Last Sold Summary

  • 2% Below List Price
  • $212/SF
  • 60 Days On Market

  Current Estimated Value $261,328

  Last Listing Agent Nick Ratliff Realty Team - Nicholas Ratliff Real Broker, LLC - Lexington

  433 Wellington Way, Winchester, KY 40391
• 

  

  /2

  $180,000

  Sold Jul 01, 2025

  23 Meadowbrook Dr, Winchester, KY 40391

  • 4 Beds
  • 4 Baths
  • 2,250 Sq Ft
  • Built 1953

  Last Sold Summary

  • $80/SF

  Current Estimated Value $257,493

  Last Listing Agent A. Rebecca Woods Woods Realty Group

  23 Meadowbrook Dr, Winchester, KY 40391
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  /7

  $55,000

  Sold Nov 06, 2025

  76 Clay St, Winchester, KY 40391

  • 1,768 Sq Ft
  • Built 1945

  Last Sold Summary

  • $31/SF
  • 2 Days On Market

  Current Estimated Value $61,167

  Last Listing Agent Brian Lewis Guide Realty, Inc.

  76 Clay St, Winchester, KY 40391
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  /65

  $275,000

  Sold Aug 15, 2025

  151 Hilltop Dr, Winchester, KY 40391

  • 4 Beds
  • 1.5 Baths
  • 1,873 Sq Ft
  • Built 1960

  Last Sold Summary

  • 1% Below List Price
  • $147/SF
  • 130 Days On Market

  Current Estimated Value $277,282

  Last Listing Agent Jason Townsend Kentucky Residential Real Estate, LLC

  151 Hilltop Dr, Winchester, KY 40391
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  /3

  $554,651

  Sold Jul 10, 2025

  426 Alexis Way, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 2,400 Sq Ft
  • Built 2024

  Last Sold Summary

  • 4% Above List Price
  • $231/SF
  • 21 Days On Market

  Current Estimated Value $566,921

  Last Listing Agent Shane Underwood Keller Williams Commonwealth

  426 Alexis Way, Winchester, KY 40391
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  /63

  $445,000

  Sold May 22, 2026

  1911 Trapp-Goffs Corner Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,288 Sq Ft
  • Built 2000

  Last Sold Summary

  • 3% Below List Price
  • $345/SF
  • 51 Days On Market

  Last Listing Agent Cheri Shaffer Lifstyl Real Estate

  1911 Trapp-Goffs Corner Rd, Winchester, KY 40391
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  /48

  $341,500

  Sold Jun 27, 2025

  401 Cedar Ct, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,834 Sq Ft
  • Built 1996

  Last Sold Summary

  • 1% Above List Price
  • $186/SF
  • 2 Days On Market

  Current Estimated Value $350,317

  Last Listing Agent Geneva Wilder Stewart & Co Realty LLC

  401 Cedar Ct, Winchester, KY 40391
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  /2

  $610,000

  Sold Aug 29, 2025

  4560 Pine Ridge Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,848 Sq Ft
  • Built 1905

  Last Sold Summary

  • $330/SF
  • 1 Day On Market

  Current Estimated Value $630,348

  Last Listing Agent Natalie Avant Berkshire Hathaway HomeServices Foster Realtors

  4560 Pine Ridge Rd, Winchester, KY 40391
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  /32

  $263,000

  Sold Sep 05, 2025

  2 Chickadee Ln, Winchester, KY 40391

  • 3 Beds
  • 1.5 Baths
  • 1,397 Sq Ft
  • Built 1960

  Last Sold Summary

  • 1% Above List Price
  • $188/SF
  • 2 Days On Market

  Current Estimated Value $266,968

  Last Listing Agent Ashley Spencer Keller Williams Commonwealth

  2 Chickadee Ln, Winchester, KY 40391
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  /31

  $292,500

  Sold May 22, 2026

  306 Trapp-Goffs Corner Rd, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 1,840 Sq Ft
  • Built 1974

  Last Sold Summary

  • 2% Below List Price
  • $159/SF
  • 1 Day On Market

  Current Estimated Value $299,774

  Last Listing Agent Patrick Arvin Keller Williams Commonwealth

  306 Trapp-Goffs Corner Rd, Winchester, KY 40391
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  /35

  $325,000

  Sold Nov 21, 2025

  130 Hibiscus Ln, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 1,900 Sq Ft
  • Built 2000

  Last Sold Summary

  • 7% Below List Price
  • $171/SF
  • 19 Days On Market

  Current Estimated Value $341,455

  Last Listing Agent Ashley Barreto Indigo & Co

  130 Hibiscus Ln, Winchester, KY 40391
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  /22

  $255,000

  Sold May 26, 2026

  35 Cherokee Ct, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 2,332 Sq Ft
  • Built 1968

  Last Sold Summary

  • 6% Below List Price
  • $109/SF
  • 123 Days On Market

  Current Estimated Value $259,838

  Last Listing Agent Brenda Rue Keller Williams Bluegrass Realty

  35 Cherokee Ct, Winchester, KY 40391
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  /51

  $303,000

  Sold Jan 16, 2026

  22 N Bloomfield Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,913 Sq Ft
  • Built 1919

  Last Sold Summary

  • 5% Below List Price
  • $158/SF
  • 16 Days On Market

  Current Estimated Value $307,297

  Last Listing Agent Libby VanMeter Marshall Lane Real Estate - Lexington

  22 N Bloomfield Rd, Winchester, KY 40391
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  /2

  $89,000

  Sold Dec 18, 2025

  13067 Irvine Rd, Winchester, KY 40391

  • Land
  • 7.86 Acres
  • $11,323 per Acre

  Last Sold Summary

  • 78 Days On Market

  Last Listing Agent Mendel Tipton Natural Bridge Realty

  13067 Irvine Rd, Winchester, KY 40391
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  /2

  $4,900,000

  Sold Dec 23, 2025

  175 Chatham Place, Winchester, KY 40391

  • 2 Beds
  • 3 Baths
  • 37,192 Sq Ft
  • Built 2007

  Last Sold Summary

  • 13% Below List Price
  • $132/SF
  • 111 Days On Market

  Current Estimated Value $5,022,391

  Last Listing Agent Garry Milton Milton and Associates Real Estate

  175 Chatham Place, Winchester, KY 40391
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  /51

  $340,000

  Sold Oct 30, 2025

  356 Boone Ave, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 3,200 Sq Ft
  • Built 1940

  Last Sold Summary

  • 5% Below List Price
  • $106/SF
  • 30 Days On Market

  Current Estimated Value $352,551

  Last Listing Agent Elizabeth Hodge Lifstyl Real Estate

  356 Boone Ave, Winchester, KY 40391
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  /28

  $131,000

  Sold Mar 12, 2026

  46 Judy Ann Ct, Winchester, KY 40391

  • 2 Beds
  • 1.5 Baths
  • 960 Sq Ft

  Last Sold Summary

  • 3% Below List Price
  • $136/SF
  • 0 Days On Market

  Current Estimated Value $136,182

  Last Listing Agent Lukas Owens The Brokerage

  46 Judy Ann Ct, Winchester, KY 40391
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  /4

  $315,000

  Sold Jun 30, 2025

  4550 Schollsville Rd Unit 40391, Winchester, KY 40391

  Last Sold Summary

  • 2 Days On Market

  Last Listing Agent Mila Ensor Ensor Real Estate, LLC

  4550 Schollsville Rd Unit 40391, Winchester, KY 40391
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  /38

  $375,750

  Sold Apr 01, 2026

  6239 Old Boonesboro Rd, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 2,659 Sq Ft
  • Built 1960

  Last Sold Summary

  • 6% Below List Price
  • $141/SF
  • 121 Days On Market

  Current Estimated Value $384,036

  Last Listing Agent Kenya Woods United Real Estate Bluegrass

  6239 Old Boonesboro Rd, Winchester, KY 40391
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  /3

  $94,000

  Sold Aug 22, 2025

  2010 Athens Boonesboro Rd, Winchester, KY 40391

  • Land
  • 4.02 Acres
  • $23,383 per Acre

  Last Sold Summary

  • 14% Below List Price
  • 140 Days On Market

  Current Estimated Value $180,352

  Last Listing Agent Megan McCoy Keller Williams Legacy Group

  2010 Athens Boonesboro Rd, Winchester, KY 40391
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  /26

  $178,000

  Sold Apr 30, 2026

  356 Colby Ridge Blvd, Winchester, KY 40391

  • 2 Beds
  • 1.5 Baths
  • 1,102 Sq Ft
  • Built 2003

  Last Sold Summary

  • 3% Below List Price
  • $162/SF
  • 51 Days On Market

  Current Estimated Value $184,519

  Last Listing Agent Nena Honaker Tom Goebel & Company

  356 Colby Ridge Blvd, Winchester, KY 40391
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  /43

  $253,000

  Sold Jun 22, 2026

  564 Trapp-Goffs Corner Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,960 Sq Ft
  • Built 2000

  Last Sold Summary

  • 6% Below List Price
  • $129/SF
  • 54 Days On Market

  Current Estimated Value $267,810

  Last Listing Agent Felicia Mayes The Real Estate Co.

  564 Trapp-Goffs Corner Rd, Winchester, KY 40391
• 

  /2

  $85,000

  Sold Apr 15, 2026

  2465 Flanagan Station Rd, Winchester, KY 40391

  • Land
  • 3.68 Acres
  • $23,098 per Acre

  Last Sold Summary

  • 9 Days On Market

  Current Estimated Value $85,805

  Last Listing Agent Shari Frasure Keller Williams Commonwealth

  2465 Flanagan Station Rd, Winchester, KY 40391
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  /17

  $30,000

  Sold Jun 30, 2025

  12591 Ironworks Rd, Winchester, KY 40391

  • Land
  • 1.72 Acres
  • $17,442 per Acre

  Last Sold Summary

  • 14% Below List Price
  • 51 Days On Market

  Current Estimated Value $188,245

  Last Listing Agent Cathleen Gedeon CENTURY 21 Advantage Realty

  12591 Ironworks Rd, Winchester, KY 40391
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  /46

  $282,900

  Sold Jan 02, 2026

  165 Hilltop Dr, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,454 Sq Ft
  • Built 2020

  Last Sold Summary

  • 1% Below List Price
  • $195/SF
  • 6 Days On Market

  Current Estimated Value $284,465

  Last Listing Agent Tyson Walters Kassie & Associates

  165 Hilltop Dr, Winchester, KY 40391
• 

  

  /25

  $262,500

  Sold May 22, 2026

  398 Pine Ridge Rd, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 1,170 Sq Ft
  • Built 1977

  Last Sold Summary

  • 15% Below List Price
  • $224/SF
  • 97 Days On Market

  Current Estimated Value $292,244

  Last Listing Agent Amie Hieneman ERA Select Real Estate

  398 Pine Ridge Rd, Winchester, KY 40391
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  /26

  $250,000

  Sold Feb 20, 2026

  21 Virginia Ave, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,749 Sq Ft
  • Built 1962

  Last Sold Summary

  • 4% Below List Price
  • $143/SF
  • 40 Days On Market

  Current Estimated Value $249,389

  Last Listing Agent Emily Crump eXp Realty, LLC

  21 Virginia Ave, Winchester, KY 40391
• 

  

  /19

  $199,900

  Sold Feb 12, 2026

  117 Buffalo Trace, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,072 Sq Ft
  • Built 1998

  Last Sold Summary

  • $186/SF
  • 49 Days On Market

  Current Estimated Value $201,380

  Last Listing Agent Nena Honaker Tom Goebel & Company

  117 Buffalo Trace, Winchester, KY 40391
• 

  

  /31

  $205,000

  Sold Jun 12, 2026

  34 Hays St, Winchester, KY 40391

  • 4 Beds
  • 1.5 Baths
  • 2,450 Sq Ft
  • Built 1950

  Last Sold Summary

  • 8% Below List Price
  • $84/SF
  • 18 Days On Market

  Current Estimated Value $211,366

  Last Listing Agent Vickie Skeens RE/MAX Elite Lexington

  34 Hays St, Winchester, KY 40391
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  /44

  $310,000

  Sold Jun 27, 2025

  2482 Mina Station Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,756 Sq Ft
  • Built 1962

  Last Sold Summary

  • $177/SF
  • 24 Days On Market

  Current Estimated Value $321,654

  Last Listing Agent Stephanie Hacker Kentucky Residential Real Estate, LLC

  2482 Mina Station Rd, Winchester, KY 40391
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  /51

  $428,000

  Sold Sep 04, 2025

  17 Hampton Ave, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 3,181 Sq Ft
  • Built 1960

  Last Sold Summary

  • 4% Below List Price
  • $135/SF
  • 34 Days On Market

  Current Estimated Value $443,724

  Last Listing Agent Craig Bridgewater Bridgewater Real Estate

  17 Hampton Ave, Winchester, KY 40391
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  /33

  $275,000

  Sold May 18, 2026

  402 Harney Dr, Winchester, KY 40391

  • 3 Beds
  • 1.5 Baths
  • 1,634 Sq Ft
  • Built 1979

  Last Sold Summary

  • $168/SF
  • 5 Days On Market

  Current Estimated Value $275,539

  Last Listing Agent Michelle Blackburn RE/MAX Creative, Winchester

  402 Harney Dr, Winchester, KY 40391
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  /26

  $239,500

  Sold Jul 15, 2025

  129 Bay Hill Dr, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 2,017 Sq Ft
  • Built 1998

  Last Sold Summary

  • 2% Below List Price
  • $119/SF
  • 26 Days On Market

  Current Estimated Value $247,589

  Last Listing Agent Vickie Skeens RE/MAX Elite Lexington

  129 Bay Hill Dr, Winchester, KY 40391
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  /34

  $380,000

  Sold Nov 21, 2025

  110 Hampton Avenue Exd, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 2,516 Sq Ft

  Last Sold Summary

  • 1% Above List Price
  • $151/SF
  • 5 Days On Market

  Current Estimated Value $376,127

  Last Listing Agent Erin Lewis Christies International Real Estate Bluegrass

  110 Hampton Avenue Exd, Winchester, KY 40391
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  /30

  $289,100

  Sold Nov 03, 2025

  223 Bartram Ct, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,606 Sq Ft
  • Built 2004

  Last Sold Summary

  • $180/SF
  • 46 Days On Market

  Current Estimated Value $291,397

  Last Listing Agent Jennifer Parsons RE/MAX Elite Lexington

  223 Bartram Ct, Winchester, KY 40391
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  /42

  $400,000

  Sold Dec 05, 2025

  210 College St, Winchester, KY 40391

  • 4 Beds
  • 3.5 Baths
  • 2,718 Sq Ft
  • Built 1895

  Last Sold Summary

  • 5% Below List Price
  • $147/SF
  • 59 Days On Market

  Current Estimated Value $401,339

  Last Listing Agent Erin Lewis Christies International Real Estate Bluegrass

  210 College St, Winchester, KY 40391
• 

  

  /15

  $286,000

  Sold Jun 12, 2026

  110 Buckingham Ln, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,240 Sq Ft
  • Built 2001

  Last Sold Summary

  • 4% Above List Price
  • $231/SF
  • 3 Days On Market

  Current Estimated Value $275,479

  Last Listing Agent Oliver Winn ERA Select Real Estate

  110 Buckingham Ln, Winchester, KY 40391
• 

  

  /31

  $379,717

  Sold Mar 27, 2026

  300 Calmes Blvd, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 2,636 Sq Ft
  • Built 1989

  Last Sold Summary

  • 5% Below List Price
  • $144/SF
  • 111 Days On Market

  Current Estimated Value $386,517

  Last Listing Agent Darrell Tackett Dream Maker Realty, LLC

  300 Calmes Blvd, Winchester, KY 40391

Showing Results 81 - 120, Page 3 of 12