Recently Sold Winchester, KY Homes

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  $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 $188,354

  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 $60,898

  Last Listing Agent Brian Lewis Guide Realty, Inc.

  76 Clay St, Winchester, KY 40391
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  $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 $104,701

  Last Listing Agent Daniel Ellis Metro Max Realty

  27 Oliver St, Winchester, KY 40391
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  $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 $268,446

  Last Listing Agent Jason Townsend Kentucky Residential Real Estate, LLC

  151 Hilltop Dr, Winchester, KY 40391
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  $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 $252,898

  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 $570,045

  Last Listing Agent Shane Underwood Keller Williams Commonwealth

  426 Alexis Way, Winchester, KY 40391
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  $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 $344,096

  Last Listing Agent Geneva Wilder Stewart & Co Realty LLC

  401 Cedar Ct, Winchester, KY 40391
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  $290,000 Sold Mar 12, 2025

  28 Edgewood Dr, Winchester, KY 40391

  • 3 Beds
  • 3 Baths
  • 1,962 Sq Ft
  • Built 1984

  Last Sold Summary

  • 8% Below List Price
  • $148/SF
  • 11 Days On Market

  Current Estimated Value $314,388

  Last Listing Agent Robin Jones Keller Williams Legacy Group

  28 Edgewood Dr, Winchester, KY 40391
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  $39,500 Sold Mar 05, 2025

  418 Fairholme Way, Winchester, KY 40391

  • Land
  • 0.38 Acre
  • $103,947 per Acre

  Last Sold Summary

  • 14% Above List Price
  • 1,594 Days On Market

  Current Estimated Value $96,141

  Last Listing Agent Garnett Davis Tom Goebel & Company

  418 Fairholme Way, 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 $610,684

  Last Listing Agent Natalie Avant Berkshire Hathaway HomeServices Foster Realtors

  4560 Pine Ridge Rd, Winchester, KY 40391
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  $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 $261,967

  Last Listing Agent Ashley Spencer Keller Williams Commonwealth

  2 Chickadee Ln, Winchester, KY 40391
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  $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

  Last Listing Agent Ashley Barreto Indigo & Co

  130 Hibiscus Ln, Winchester, KY 40391
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  $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

  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 $259,896

  Last Listing Agent Destiny Darby Keller Williams Commonwealth

  244 Bay Hill Ct, Winchester, KY 40391
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  $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

  Last Listing Agent Garry Milton Milton and Associates Real Estate

  175 Chatham Place, Winchester, KY 40391
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  $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 $346,812

  Last Listing Agent Elizabeth Hodge Lifstyl Real Estate

  356 Boone Ave, Winchester, KY 40391
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  /3

  $40,000 Sold Feb 11, 2025

  Unlisted Address

  • Land
  • 0.19 Acre
  • $210,526 per Acre

  Last Sold Summary

  Current Estimated Value $362,344

  Last Listing Agent Jo Gawthrop Keller Williams Bluegrass Realty

  Unlisted Address
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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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  $215,000 Sold Feb 21, 2025

  167 E Washington St, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,763 Sq Ft

  Last Sold Summary

  • $122/SF
  • 5 Days On Market

  Current Estimated Value $232,887

  Last Listing Agent Kymberly McCreary EXP Realty, LLC

  167 E Washington St, Winchester, KY 40391
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  $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 $286,062

  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 $170,301

  Last Listing Agent Megan McCoy Keller Williams Legacy Group

  2010 Athens Boonesboro Rd, Winchester, KY 40391
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  $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 $211,090

  Last Listing Agent Mary Layton FC Tucker Bluegrass

  445 Colby Ridge Blvd, Winchester, KY 40391
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  $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 $870,030

  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 $568,375

  Last Listing Agent Robin Jones Keller Williams Legacy Group

  520 Gay Evans Rd, Winchester, KY 40391
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  $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 $108,590

  Last Listing Agent Cathleen Gedeon CENTURY 21 Advantage Realty

  12591 Ironworks Rd, Winchester, KY 40391
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  $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 $278,747

  Last Listing Agent Michelle Blackburn RE/MAX Creative, Winchester

  597 Marseille Blvd, Winchester, KY 40391
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  $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

  Last Listing Agent Tyson Walters Kassie & Associates

  165 Hilltop Dr, Winchester, KY 40391
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  $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 $385,901

  Last Listing Agent Daniel Mullins ERA Select Real Estate

  890 Miller Hunt Rd, Winchester, KY 40391
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  $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 $667,492

  Last Listing Agent Emily Belcher Rector Hayden Realtors

  357 Wades Mill Rd, Winchester, KY 40391
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  $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 $206,504

  Last Listing Agent Aaron Kendall Lifstyl Real Estate

  202 Washington Square, Winchester, KY 40391
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  $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 $212,516

  Last Listing Agent Peggy Baldridge HomeFirst Real Estate

  206 W Clark Dr, 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 $170,444

  Last Listing Agent Null Non-Member Non-Member Office

  Unlisted Address
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  $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 $304,706

  Last Listing Agent Stephanie Hacker Kentucky Residential Real Estate, LLC

  2482 Mina Station Rd, Winchester, KY 40391
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  $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 $922,874

  Last Listing Agent Shane Underwood Keller Williams Commonwealth

  118 Bella Shae Way, Winchester, KY 40391
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  $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 $78,334

  Last Listing Agent Keith Wilson Coldwell Banker McMahan

  120 Jacob Ct, Winchester, KY 40391
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  $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 $423,709

  Last Listing Agent Craig Bridgewater Bridgewater Real Estate

  17 Hampton Ave, Winchester, KY 40391
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  $175,000 Sold Apr 18, 2025

  11 Shelley Dr, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,188 Sq Ft
  • Built 1970

  Last Sold Summary

  • 3% Below List Price
  • $147/SF
  • 5 Days On Market

  Current Estimated Value $191,273

  Last Listing Agent Tonya Morrow KY Local

  11 Shelley Dr, Winchester, KY 40391
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  $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 $241,956

  Last Listing Agent Vickie Skeens RE/MAX Elite Lexington

  129 Bay Hill Dr, Winchester, KY 40391
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  $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

  Last Listing Agent Erin Lewis Christies International Real Estate Bluegrass

  110 Hampton Avenue Exd, Winchester, KY 40391
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  $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 $287,174

  Last Listing Agent Jennifer Parsons RE/MAX Elite Lexington

  223 Bartram Ct, Winchester, KY 40391

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