Recently Sold Winchester, KY Homes

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  /34

  $252,000 Sold Jul 30, 2025

  216 Connie Ln, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,248 Sq Ft
  • Built 2017

  Last Sold Summary

  • $202/SF
  • 2 Days On Market

  Current Estimated Value $251,484

  Last Listing Agent Elizabeth Hodge Lifstyl Real Estate

  216 Connie Ln, Winchester, KY 40391
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  /21

  $259,900 Sold Jul 10, 2025

  302 April Way, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,321 Sq Ft
  • Built 2002

  Last Sold Summary

  • $197/SF
  • 12 Days On Market

  Current Estimated Value $262,965

  Last Listing Agent Michael Hilario The Agency

  302 April Way, Winchester, KY 40391
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  /30

  $185,000 Sold Jun 18, 2025

  308 Essex Ct, Winchester, KY 40391

  • 2 Beds
  • 2.5 Baths
  • 1,188 Sq Ft
  • Built 2000

  Last Sold Summary

  • 3% Below List Price
  • $156/SF
  • 3 Days On Market

  Current Estimated Value $200,610

  Last Listing Agent Lisa Sosa Keller Williams Commonwealth

  308 Essex Ct, Winchester, KY 40391
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  /22

  $600,000 Sold Aug 19, 2025

  1203 Irvine Rd, Winchester, KY 40391

  • Land
  • 12.38 Acres
  • $48,465 per Acre

  Last Sold Summary

  • 37% Below List Price
  • 125 Days On Market

  Last Listing Agent Josh Wood Freedom Realty & Property Management

  1203 Irvine Rd, Winchester, KY 40391
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  /17

  $228,500 Sold Feb 06, 2026

  394 S Main St, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 1,858 Sq Ft
  • Built 1900

  Last Sold Summary

  • $123/SF
  • 9 Days On Market

  Current Estimated Value $227,523

  Last Listing Agent Tracey Goebel Tom Goebel & Company

  394 S Main St, Winchester, KY 40391
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  /2

  $75,000 Sold Dec 16, 2025

  1477 Sewell Shop Rd, Winchester, KY 40391

  • Land
  • 4.82 Acres
  • $15,560 per Acre

  Last Sold Summary

  • 3 Days On Market

  Last Listing Agent Zella Rosenthal Tom Goebel & Company

  1477 Sewell Shop Rd, Winchester, KY 40391
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  /48

  $255,000 Sold Apr 30, 2025

  305 Skylark Dr, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 2,358 Sq Ft
  • Built 1965

  Last Sold Summary

  • $108/SF
  • 45 Days On Market

  Current Estimated Value $293,393

  Last Listing Agent Melodie Lincavage RE/MAX Elite Realty

  305 Skylark Dr, Winchester, KY 40391
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  /47

  $350,000 Sold May 01, 2025

  206 Honeysuckle Ln, Winchester, KY 40391

  • 5 Beds
  • 3 Baths
  • 2,117 Sq Ft
  • Built 1999

  Last Sold Summary

  • $165/SF
  • 3 Days On Market

  Current Estimated Value $361,081

  Last Listing Agent Amanda Marcum Berkshire Hathaway HomeServices Foster Realtors

  206 Honeysuckle Ln, Winchester, KY 40391
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  /23

  $197,000 Sold Mar 31, 2025

  42 Park Ave, Winchester, KY 40391

  • 3 Beds
  • 1.5 Baths
  • 1,129 Sq Ft

  Last Sold Summary

  • 14% Below List Price
  • $174/SF
  • 54 Days On Market

  Current Estimated Value $201,641

  Last Listing Agent Jonathan McMahan Coldwell Banker McMahan

  42 Park Ave, Winchester, KY 40391
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  /42

  $249,000 Sold Oct 22, 2025

  9 Apache Trail, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 1,750 Sq Ft
  • Built 1960

  Last Sold Summary

  • 6% Below List Price
  • $142/SF
  • 117 Days On Market

  Current Estimated Value $254,776

  Last Listing Agent Joyce Ratliff Tom Goebel & Company

  9 Apache Trail, Winchester, KY 40391
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  /92

  $364,900 Sold Jul 31, 2025

  31 Mockingbird Valley Rd, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 2,520 Sq Ft
  • Built 1962

  Last Sold Summary

  • 6% Below List Price
  • $145/SF
  • 209 Days On Market

  Current Estimated Value $376,228

  Last Listing Agent Josh Wood Freedom Realty & Property Management

  31 Mockingbird Valley Rd, Winchester, KY 40391
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  /2

  $216,450 Sold Apr 30, 2025

  408 Paisley Ct, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,628 Sq Ft
  • Built 2005

  Last Sold Summary

  • $133/SF
  • 0 Days On Market

  Current Estimated Value $227,018

  Last Listing Agent John Wilson Bluegrass Properties Group

  408 Paisley Ct, Winchester, KY 40391
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  /23

  $335,000 Sold Aug 27, 2025

  413 Lyon Dr, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 2,936 Sq Ft
  • Built 1986

  Last Sold Summary

  • 4% Below List Price
  • $114/SF
  • 8 Days On Market

  Current Estimated Value $331,607

  Last Listing Agent Ray Rush Rush Real Estate

  413 Lyon Dr, Winchester, KY 40391
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  /17

  $390,000 Sold Apr 16, 2025

  3750 Becknerville Rd, Winchester, KY 40391

  • 3 Beds
  • 1.5 Baths
  • 1,854 Sq Ft
  • Built 1983

  Last Sold Summary

  • 9% Below List Price
  • $210/SF
  • 73 Days On Market

  Current Estimated Value $445,994

  Last Listing Agent Holly Goeing The Agency

  3750 Becknerville Rd, Winchester, KY 40391
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  /17

  $86,008 Sold Jul 30, 2025

  977 Muddy Creek Rd, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,030 Sq Ft
  • Built 1940

  Last Sold Summary

  • 28% Below List Price
  • $84/SF
  • 37 Days On Market

  Current Estimated Value $104,113

  Last Listing Agent Jason Szaks EXIT TOWN & COUNTRY REALTORS

  977 Muddy Creek Rd, Winchester, KY 40391
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  /27

  $199,900 Sold Jul 15, 2025

  139 W Hickman St, Winchester, KY 40391

  • 3 Beds
  • 1.5 Baths
  • 1,348 Sq Ft
  • Built 1940

  Last Sold Summary

  • $148/SF
  • 18 Days On Market

  Current Estimated Value $201,584

  Last Listing Agent Clay David Sutherland ERA Select Real Estate

  139 W Hickman St, Winchester, KY 40391
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  /31

  $295,000 Sold Feb 24, 2026

  420 Willowbrook Rd, Winchester, KY 40391

  • 3 Beds
  • 3 Baths
  • 1,738 Sq Ft
  • Built 1980

  Last Sold Summary

  • $170/SF
  • 32 Days On Market

  Current Estimated Value $291,954

  Last Listing Agent Michelle Blackburn RE/MAX Creative, Winchester

  420 Willowbrook Rd, Winchester, KY 40391
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  /82

  $275,000 Sold May 23, 2025

  111 S Burns Ave, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 2,994 Sq Ft
  • Built 1920

  Last Sold Summary

  • 19% Below List Price
  • $92/SF
  • 202 Days On Market

  Current Estimated Value $296,284

  Last Listing Agent Melodie Lincavage RE/MAX Elite Realty

  111 S Burns Ave, Winchester, KY 40391
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  /42

  $247,500 Sold Jan 16, 2026

  125 Summerhill Way, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,333 Sq Ft
  • Built 2003

  Last Sold Summary

  • 5% Below List Price
  • $186/SF
  • 15 Days On Market

  Current Estimated Value $252,467

  Last Listing Agent Gwen Mathews Bluegrass Sotheby's International Realty

  125 Summerhill Way, Winchester, KY 40391
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  /37

  $354,000 Sold Dec 19, 2025

  213 Hood Ave, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,244 Sq Ft
  • Built 1970

  Last Sold Summary

  • 8% Below List Price
  • $158/SF
  • 21 Days On Market

  Current Estimated Value $355,449

  Last Listing Agent Vickie Skeens RE/MAX Elite Lexington

  213 Hood Ave, Winchester, KY 40391
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  /36

  $177,500 Sold May 13, 2025

  406 Pepperwood Ct, Winchester, KY 40391

  • 2 Beds
  • 2.5 Baths
  • 1,259 Sq Ft
  • Built 1998

  Last Sold Summary

  • 1% Below List Price
  • $141/SF
  • 3 Days On Market

  Current Estimated Value $188,665

  Last Listing Agent Peggy Baldridge HomeFirst Real Estate

  406 Pepperwood Ct, Winchester, KY 40391
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  /63

  $1,325,000 Sold May 15, 2025

  6755 Boonesboro Rd, Winchester, KY 40391

  • 5 Beds
  • 8 Baths
  • 5,736 Sq Ft
  • Built 2021

  Last Sold Summary

  • 4% Below List Price
  • $231/SF
  • 72 Days On Market

  Current Estimated Value $1,461,280

  Last Listing Agent Jennifer Ray RE/MAX Elite Lexington

  6755 Boonesboro Rd, Winchester, KY 40391
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  /47

  $396,500 Sold May 19, 2025

  520 Bailey Ln, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 2,400 Sq Ft
  • Built 1980

  Last Sold Summary

  • 12% Below List Price
  • $165/SF
  • 51 Days On Market

  Current Estimated Value $398,900

  Last Listing Agent Paul Waddelow Hand in Hand Realty Central KY

  520 Bailey Ln, Winchester, KY 40391
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  /73

  $799,000 Sold Aug 18, 2025

  1183 the Ridings Rd, Winchester, KY 40391

  • 5 Beds
  • 3 Baths
  • 3,664 Sq Ft
  • Built 1989

  Last Sold Summary

  • 6% Below List Price
  • $218/SF
  • 64 Days On Market

  Current Estimated Value $801,567

  Last Listing Agent Libby VanMeter Marshall Lane Real Estate - Lexington

  1183 the Ridings Rd, Winchester, KY 40391
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  /38

  $258,900 Sold Sep 08, 2025

  313 Geronimo Ct, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 1,678 Sq Ft
  • Built 2000

  Last Sold Summary

  • 4% Above List Price
  • $154/SF
  • 1 Day On Market

  Current Estimated Value $256,865

  Last Listing Agent Shari Frasure Keller Williams Commonwealth

  313 Geronimo Ct, Winchester, KY 40391
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  /23

  $184,900 Sold Jun 20, 2025

  324 Essex Ct, Winchester, KY 40391

  • 2 Beds
  • 1.5 Baths
  • 1,056 Sq Ft
  • Built 2000

  Last Sold Summary

  • $175/SF
  • 2 Days On Market

  Current Estimated Value $189,430

  Last Listing Agent Kymberly McCreary EXP Realty, LLC

  324 Essex Ct, Winchester, KY 40391
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  /21

  $219,500 Sold Jun 20, 2025

  523 Acadia Way, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 1,480 Sq Ft
  • Built 2002

  Last Sold Summary

  • 2% Above List Price
  • $148/SF
  • 6 Days On Market

  Current Estimated Value $231,991

  Last Listing Agent Tyler I Back The Brokerage

  523 Acadia Way, Winchester, KY 40391
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  /24

  $215,000 Sold Apr 24, 2025

  445 Jameson Way, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 1,400 Sq Ft
  • Built 2002

  Last Sold Summary

  • $154/SF
  • 31 Days On Market

  Current Estimated Value $227,801

  Last Listing Agent Tyler I Back The Brokerage

  445 Jameson Way, Winchester, KY 40391
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  /21

  $220,000 Sold Jun 26, 2025

  520 Barlow Dr, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,120 Sq Ft
  • Built 1996

  Last Sold Summary

  • 12% Below List Price
  • $196/SF
  • 72 Days On Market

  Current Estimated Value $227,179

  Last Listing Agent Keith Wilson Coldwell Banker McMahan

  520 Barlow Dr, Winchester, KY 40391
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  /36

  $184,742 Sold Jun 06, 2025

  120 Heather Ln, Winchester, KY 40391

  • 2 Beds
  • 1.5 Baths
  • 1,140 Sq Ft
  • Built 1990

  Last Sold Summary

  • 1% Below List Price
  • $162/SF
  • 3 Days On Market

  Current Estimated Value $194,929

  Last Listing Agent Julie Wiggington RE/MAX Creative, Winchester

  120 Heather Ln, Winchester, KY 40391
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  /34

  $174,000 Sold Apr 25, 2025

  397 College St, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 1,655 Sq Ft
  • Built 1940

  Last Sold Summary

  • 8% Below List Price
  • $105/SF
  • 44 Days On Market

  Current Estimated Value $184,510

  Last Listing Agent Josh Wood Freedom Realty & Property Management

  397 College St, Winchester, KY 40391
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  /46

  $600,000 Sold Dec 04, 2025

  433 Fairholme Way, Winchester, KY 40391

  • 3 Beds
  • 3.5 Baths
  • 2,900 Sq Ft
  • Built 2018

  Last Sold Summary

  • 5% Below List Price
  • $207/SF
  • 28 Days On Market

  Current Estimated Value $603,586

  Last Listing Agent Kathryn Cheuvront Coldwell Banker McMahan

  433 Fairholme Way, Winchester, KY 40391
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  /58

  $290,000 Sold Jul 25, 2025

  19 Valley Ct, Winchester, KY 40391

  • 3 Beds
  • 1.5 Baths
  • 2,240 Sq Ft
  • Built 1968

  Last Sold Summary

  • 14% Below List Price
  • $129/SF
  • 16 Days On Market

  Current Estimated Value $296,397

  Last Listing Agent Dale Hatton Dream Maker Realty, LLC

  19 Valley Ct, Winchester, KY 40391

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