Recently Sold Winchester, KY Homes

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  /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 $179,509

  Last Listing Agent Jason Townsend Kentucky Residential Real Estate, LLC

  7575 Irvine Rd, Winchester, KY 40391
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  /40

  $400,000 Sold May 23, 2025

  109 Monet Blvd, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,432 Sq Ft
  • Built 1995

  Last Sold Summary

  • 5% Below List Price
  • $164/SF
  • 26 Days On Market

  Current Estimated Value $422,996

  Last Listing Agent Melissa Brown Keller Williams Legacy Group

  109 Monet Blvd, 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 $326,181

  Last Listing Agent Janine Shackelford LPT Realty

  210 Cabin Creek Rd, Winchester, KY 40391
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  /77

  $464,900 Sold Jun 09, 2025

  275 Runnymeade Dr, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 2,495 Sq Ft
  • Built 2017

  Last Sold Summary

  • $186/SF
  • 21 Days On Market

  Current Estimated Value $475,002

  Last Listing Agent Tyson Walters Kassie & Associates

  275 Runnymeade Dr, 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 $258,718

  Last Listing Agent Stephen Brashear Real Broker LLC

  433 Wellington Way, Winchester, KY 40391
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  /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 $197,400

  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 $60,530

  Last Listing Agent Brian Lewis Guide Realty, Inc.

  76 Clay St, Winchester, KY 40391
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  /18

  $99,000 Sold Jun 17, 2025

  27 Oliver St, Winchester, KY 40391

  • 2 Beds
  • 2 Baths
  • 1,242 Sq Ft
  • Built 1940

  Last Sold Summary

  • 7% Below List Price
  • $80/SF
  • 8 Days On Market

  Current Estimated Value $108,271

  Last Listing Agent Daniel Ellis Metro Max Realty

  27 Oliver 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 $271,186

  Last Listing Agent Jason Townsend Kentucky Residential Real Estate, LLC

  151 Hilltop Dr, Winchester, KY 40391
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  /35

  $248,000 Sold May 22, 2025

  206 Moss Cir, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,773 Sq Ft
  • Built 1997

  Last Sold Summary

  • 6% Below List Price
  • $140/SF
  • 20 Days On Market

  Current Estimated Value $259,201

  Last Listing Agent David Baesler Kentucky Dreams Realty

  206 Moss Cir, 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 $548,631

  Last Listing Agent Shane Underwood Keller Williams Commonwealth

  426 Alexis Way, 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 $348,268

  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 $618,608

  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 $256,602

  Last Listing Agent Ashley Spencer Keller Williams Commonwealth

  2 Chickadee Ln, 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 $334,469

  Last Listing Agent Ashley Barreto Indigo & Co

  130 Hibiscus Ln, 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 $302,839

  Last Listing Agent Libby VanMeter Marshall Lane Real Estate - Lexington

  22 N Bloomfield Rd, Winchester, KY 40391
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  /23

  $244,895 Sold Jun 10, 2025

  244 Bay Hill Ct, Winchester, KY 40391

  • 3 Beds
  • 3 Baths
  • 2,536 Sq Ft
  • Built 2006

  Last Sold Summary

  • 2% Below List Price
  • $97/SF
  • 10 Days On Market

  Current Estimated Value $267,697

  Last Listing Agent Destiny Darby Keller Williams Commonwealth

  244 Bay Hill Ct, 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 $4,910,294

  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 $344,847

  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 $148,072

  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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  /33

  $270,000 Sold Mar 28, 2025

  129 Ashley Dr, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,884 Sq Ft
  • Built 1993

  Last Sold Summary

  • $143/SF
  • 8 Days On Market

  Current Estimated Value $305,185

  Last Listing Agent Audra Tate National Real Estate

  129 Ashley Dr, 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 $175,774

  Last Listing Agent Megan McCoy Keller Williams Legacy Group

  2010 Athens Boonesboro Rd, Winchester, KY 40391
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  /21

  $199,500 Sold May 09, 2025

  445 Colby Ridge Blvd, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,539 Sq Ft
  • Built 1998

  Last Sold Summary

  • $130/SF
  • 3 Days On Market

  Current Estimated Value $214,214

  Last Listing Agent Mary Layton FC Tucker Bluegrass

  445 Colby Ridge Blvd, Winchester, KY 40391
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  /79

  $849,900 Sold May 23, 2025

  3714 Wades Mill Rd, Winchester, KY 40391

  • 5 Beds
  • 3.5 Baths
  • 3,818 Sq Ft
  • Built 2001

  Last Sold Summary

  • $223/SF
  • 55 Days On Market

  Current Estimated Value $899,392

  Last Listing Agent Nora Williams Keller Williams Commonwealth

  3714 Wades Mill Rd, Winchester, KY 40391
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  /51

  $560,000 Sold Jun 10, 2025

  520 Gay Evans Rd, Winchester, KY 40391

  • 3 Beds
  • 4 Baths
  • 3,160 Sq Ft
  • Built 2012

  Last Sold Summary

  • 3% Below List Price
  • $177/SF
  • 11 Days On Market

  Current Estimated Value $566,354

  Last Listing Agent Robin Jones Keller Williams Legacy Group

  520 Gay Evans 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 $132,227

  Last Listing Agent Cathleen Gedeon CENTURY 21 Advantage Realty

  12591 Ironworks Rd, Winchester, KY 40391
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  /34

  $260,000 Sold Apr 17, 2025

  597 Marseille Blvd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,565 Sq Ft
  • Built 1993

  Last Sold Summary

  • 5% Below List Price
  • $166/SF
  • 63 Days On Market

  Current Estimated Value $283,290

  Last Listing Agent Michelle Blackburn RE/MAX Creative, Winchester

  597 Marseille Blvd, 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 $280,883

  Last Listing Agent Tyson Walters Kassie & Associates

  165 Hilltop Dr, Winchester, KY 40391
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  /62

  $384,000 Sold Apr 10, 2025

  890 Miller Hunt Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,425 Sq Ft
  • Built 1965

  Last Sold Summary

  • $269/SF
  • 5 Days On Market

  Current Estimated Value $400,241

  Last Listing Agent Daniel Mullins ERA Select Real Estate

  890 Miller Hunt Rd, Winchester, KY 40391
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  /41

  $650,000 Sold Jun 23, 2025

  357 Wades Mill Rd, Winchester, KY 40391

  • 4 Beds
  • 3.5 Baths
  • 3,007 Sq Ft
  • Built 2002

  Last Sold Summary

  • 6% Below List Price
  • $216/SF
  • 15 Days On Market

  Current Estimated Value $668,993

  Last Listing Agent Emily Belcher Rector Hayden Realtors

  357 Wades Mill Rd, Winchester, KY 40391
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  /23

  $210,000 Sold May 12, 2025

  202 Washington Square, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • Built 1998

  Last Sold Summary

  • 11% Above List Price
  • $175/SF
  • 1 Day On Market

  Current Estimated Value $210,916

  Last Listing Agent Aaron Kendall Lifstyl Real Estate

  202 Washington Square, 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 $252,766

  Last Listing Agent Emily Crump EXP Realty, LLC

  21 Virginia Ave, Winchester, KY 40391
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  /44

  $206,500 Sold May 21, 2025

  206 W Clark Dr, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,107 Sq Ft
  • Built 1962

  Last Sold Summary

  • 6% Below List Price
  • $187/SF
  • 23 Days On Market

  Current Estimated Value $212,820

  Last Listing Agent Peggy Baldridge HomeFirst Real Estate

  206 W Clark Dr, Winchester, KY 40391
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  /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 $198,126

  Last Listing Agent Nena Honaker Tom Goebel & Company

  117 Buffalo Trace, Winchester, KY 40391
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  /2

  $165,000 Sold May 30, 2025

  Unlisted Address

  • 3 Beds
  • 1.5 Baths
  • 1,200 Sq Ft
  • Built 1988

  Last Sold Summary

  • $138/SF

  Current Estimated Value $173,092

  Last Listing Agent Null Non-Member Non-Member Office

  Unlisted Address
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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 $313,620

  Last Listing Agent Stephanie Hacker Kentucky Residential Real Estate, LLC

  2482 Mina Station Rd, Winchester, KY 40391
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  /54

  $1,546,482 Sold Apr 02, 2025

  118 Bella Shae Way, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 3,220 Sq Ft
  • Built 2024

  Last Sold Summary

  • 62% Above List Price
  • $480/SF
  • 0 Days On Market

  Current Estimated Value $1,009,643

  Last Listing Agent Shane Underwood Keller Williams Commonwealth

  118 Bella Shae Way, Winchester, KY 40391
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  /12

  $75,000 Sold Jun 17, 2025

  120 Jacob Ct, Winchester, KY 40391

  • Land
  • 0.55 Acre
  • $136,364 per Acre

  Last Sold Summary

  • 32% Below List Price
  • 210 Days On Market

  Current Estimated Value $77,257

  Last Listing Agent Keith Wilson Coldwell Banker McMahan

  120 Jacob Ct, Winchester, KY 40391

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