Recently Sold Winchester, KY Homes

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  /57

  $260,000 Sold Sep 09, 2025

  7934 Ironworks Rd, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,633 Sq Ft
  • Built 1945

  Last Sold Summary

  • 12% Below List Price
  • $159/SF
  • 4 Days On Market

  Current Estimated Value $269,185

  Last Listing Agent Greg Wood Freedom Realty & Property Management

  7934 Ironworks Rd, Winchester, KY 40391
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  /24

  $320,000 Sold Dec 01, 2025

  118 Strawberry Ln, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,008 Sq Ft
  • Built 2022

  Last Sold Summary

  • 2% Below List Price
  • $159/SF
  • 14 Days On Market

  Last Listing Agent Susan Baldwin Threshold Real Estate Services

  118 Strawberry Ln, Winchester, KY 40391
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  /27

  $207,500 Sold Jul 11, 2025

  2350 Ironworks Rd, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,385 Sq Ft
  • Built 1970

  Last Sold Summary

  • 3% Below List Price
  • $150/SF
  • 6 Days On Market

  Current Estimated Value $219,033

  Last Listing Agent Dylan Justice GSP Homes

  2350 Ironworks Rd, Winchester, KY 40391
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  /77

  $2,075,000 Sold Aug 15, 2025

  27 Sundown Ln, Winchester, KY 40391

  • 3 Beds
  • 6 Baths
  • 5,984 Sq Ft
  • Built 1994

  Last Sold Summary

  • 3% Below List Price
  • $347/SF
  • 14 Days On Market

  Current Estimated Value $2,057,135

  Last Listing Agent Abby Jones Bluegrass Sotheby's International Realty

  27 Sundown Ln, Winchester, KY 40391
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  /41

  $170,000 Sold Dec 30, 2025

  130 Abbeywood Ct, Winchester, KY 40391

  • 2 Beds
  • 2.5 Baths
  • 1,350 Sq Ft
  • Built 2002

  Last Sold Summary

  • 13% Below List Price
  • $126/SF
  • 18 Days On Market

  Last Listing Agent Emily Belcher Rector Hayden Realtors

  130 Abbeywood Ct, Winchester, KY 40391
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  /27

  $229,000 Sold Jun 05, 2025

  13 Fairview Ave, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • Built 2025

  Last Sold Summary

  • 2% Above List Price
  • $191/SF
  • 2 Days On Market

  Current Estimated Value $226,472

  Last Listing Agent Nena Honaker Tom Goebel & Company

  13 Fairview Ave, Winchester, KY 40391
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  /36

  $214,000 Sold May 19, 2025

  509 Hidden Hills Way, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,402 Sq Ft
  • Built 2000

  Last Sold Summary

  • 7% Below List Price
  • $153/SF
  • 38 Days On Market

  Current Estimated Value $222,220

  Last Listing Agent Teresa Richmond Freedom Realty & Property Management

  509 Hidden Hills Way, Winchester, KY 40391
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  /22

  $201,000 Sold Sep 04, 2025

  110 Colonial Park Dr, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,235 Sq Ft
  • Built 1980

  Last Sold Summary

  • 11% Below List Price
  • $163/SF
  • 26 Days On Market

  Current Estimated Value $204,009

  Last Listing Agent Jason Townsend Kentucky Residential Real Estate, LLC

  110 Colonial Park Dr, Winchester, KY 40391
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  /33

  $255,000 Sold Jan 09, 2026

  357 Crescent Ave, Winchester, KY 40391

  • 3 Beds
  • 1.5 Baths
  • 2,188 Sq Ft

  Last Sold Summary

  • $117/SF
  • 44 Days On Market

  Last Listing Agent Samantha Gray National Real Estate

  357 Crescent Ave, Winchester, KY 40391
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  /91

  $395,000 Sold Jul 22, 2025

  101 Dorset Ln, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,536 Sq Ft
  • Built 2015

  Last Sold Summary

  • $257/SF
  • 29 Days On Market

  Current Estimated Value $388,934

  Last Listing Agent Josh Wood Freedom Realty & Property Management

  101 Dorset Ln, Winchester, KY 40391
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  /31

  $485,000 Sold Sep 05, 2025

  10 French Ave, Winchester, KY 40391

  • 5 Beds
  • 3 Baths
  • 3,262 Sq Ft
  • Built 1906

  Last Sold Summary

  • 18% Below List Price
  • $149/SF
  • 11 Days On Market

  Current Estimated Value $478,871

  Last Listing Agent Brian England Keller Williams Bluegrass Realty

  10 French Ave, Winchester, KY 40391
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  /39

  $462,000 Sold Nov 21, 2025

  865 Pretty Run Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 2,727 Sq Ft
  • Built 1989

  Last Sold Summary

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

  Last Listing Agent Shane Underwood Keller Williams Commonwealth

  865 Pretty Run Rd, Winchester, KY 40391
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  /2

  $39,500 Sold Mar 05, 2025

  416 Fairholme Way, Winchester, KY 40391

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

  Last Sold Summary

  • 14% Above List Price
  • 1,596 Days On Market

  Current Estimated Value $98,487

  Last Listing Agent Garnett Davis Tom Goebel & Company

  416 Fairholme Way, Winchester, KY 40391
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  /40

  $278,500 Sold Jun 06, 2025

  8 Chickadee Ln, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,400 Sq Ft
  • Built 1970

  Last Sold Summary

  • 14% Below List Price
  • $116/SF
  • 130 Days On Market

  Current Estimated Value $286,329

  Last Listing Agent Whitney Ensor Ensor Real Estate, LLC

  8 Chickadee Ln, Winchester, KY 40391
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  /35

  $300,000 Sold Oct 03, 2025

  607 Colby Ridge Blvd, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,948 Sq Ft
  • Built 2020

  Last Sold Summary

  • 4% Below List Price
  • $154/SF
  • 67 Days On Market

  Current Estimated Value $309,699

  Last Listing Agent Suzanne Elliott Berkshire Hathaway de Movellan Properties

  607 Colby Ridge Blvd, Winchester, KY 40391
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  /39

  $450,000 Sold Aug 08, 2025

  600 Ferry Rd, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 2,076 Sq Ft
  • Built 2003

  Last Sold Summary

  • 10% Below List Price
  • $217/SF
  • 32 Days On Market

  Current Estimated Value $465,447

  Last Listing Agent Cathleen Gedeon CENTURY 21 Advantage Realty

  600 Ferry Rd, Winchester, KY 40391
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  /43

  $239,700 Sold Oct 20, 2025

  2413 Log Lick Rd, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,300 Sq Ft
  • Built 1945

  Last Sold Summary

  • $184/SF
  • 19 Days On Market

  Current Estimated Value $239,557

  Last Listing Agent E Anthony Phillips RE/MAX Creative Realty

  2413 Log Lick Rd, Winchester, KY 40391
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  /63

  $430,000 Sold Oct 03, 2025

  259 Hibiscus Ln, Winchester, KY 40391

  • 4 Beds
  • 3.5 Baths
  • 3,921 Sq Ft
  • Built 2003

  Last Sold Summary

  • 2% Below List Price
  • $110/SF
  • 2 Days On Market

  Current Estimated Value $438,619

  Last Listing Agent Janna Smith United Real Estate Bluegrass

  259 Hibiscus Ln, Winchester, KY 40391
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  /32

  $349,900 Sold Aug 01, 2025

  275 Cross Brook Ct, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 2,111 Sq Ft
  • Built 1998

  Last Sold Summary

  • $166/SF
  • 2 Days On Market

  Current Estimated Value $349,109

  Last Listing Agent Amanda Stewart Stewart & Co Realty LLC

  275 Cross Brook Ct, Winchester, KY 40391
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  /25

  $270,000 Sold Dec 05, 2025

  102 Ashley Dr, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,132 Sq Ft
  • Built 1994

  Last Sold Summary

  • 2% Above List Price
  • $239/SF
  • 19 Days On Market

  Last Listing Agent Kimberli Fister Kentucky Land and Home

  102 Ashley Dr, Winchester, KY 40391
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  /22

  $269,900 Sold Oct 10, 2025

  115 Ashley Dr, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,320 Sq Ft
  • Built 1995

  Last Sold Summary

  • $204/SF
  • 12 Days On Market

  Current Estimated Value $267,784

  Last Listing Agent Jason Townsend Kentucky Residential Real Estate, LLC

  115 Ashley Dr, Winchester, KY 40391
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  /24

  $215,000 Sold May 29, 2025

  13365 Ironworks Rd, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,420 Sq Ft
  • Built 1973

  Last Sold Summary

  • 2% Below List Price
  • $151/SF
  • 10 Days On Market

  Current Estimated Value $226,215

  Last Listing Agent Joshua Davis The Agency

  13365 Ironworks Rd, Winchester, KY 40391
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  /25

  $186,500 Sold Dec 08, 2025

  31 Vine St, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,443 Sq Ft
  • Built 1950

  Last Sold Summary

  • 17% Below List Price
  • $129/SF
  • 94 Days On Market

  Last Listing Agent Jana Hooten Key 2 Close Realty, LLC

  31 Vine St, Winchester, KY 40391
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  /38

  $220,000 Sold Jun 30, 2025

  212 Southwind Dr, Winchester, KY 40391

  • 3 Beds
  • 1.5 Baths
  • 1,333 Sq Ft
  • Built 1973

  Last Sold Summary

  • 4% Below List Price
  • $165/SF
  • 19 Days On Market

  Current Estimated Value $231,167

  Last Listing Agent Jim Woodrum RE/MAX Creative, Winchester

  212 Southwind Dr, Winchester, KY 40391
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  /3

  $140,000 Sold Apr 09, 2025

  895 Gay Evans Rd, Winchester, KY 40391

  • Land
  • 6.87 Acres
  • $20,378 per Acre

  Last Sold Summary

  • 7% Below List Price
  • 18 Days On Market

  Last Listing Agent Holly Goeing The Agency

  895 Gay Evans Rd, Winchester, KY 40391
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  /48

  $390,000 Sold Nov 21, 2025

  213 Honeysuckle Ln, Winchester, KY 40391

  • 4 Beds
  • 4 Baths
  • 3,087 Sq Ft
  • Built 1999

  Last Sold Summary

  • 2% Below List Price
  • $126/SF
  • 1 Day On Market

  Last Listing Agent Shari Frasure Keller Williams Commonwealth

  213 Honeysuckle Ln, Winchester, KY 40391
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  /43

  $399,000 Sold Oct 10, 2025

  7236 Old Boonesboro Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 2,041 Sq Ft
  • Built 2003

  Last Sold Summary

  • $195/SF
  • 3 Days On Market

  Current Estimated Value $401,482

  Last Listing Agent Jason Townsend Kentucky Residential Real Estate, LLC

  7236 Old Boonesboro Rd, Winchester, KY 40391
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  /2

  $260,000 Sold May 01, 2025

  Unlisted Address

  • 4 Beds
  • 3.5 Baths
  • 2,766 Sq Ft
  • Built 1993

  Last Sold Summary

  • $94/SF

  Current Estimated Value $473,261

  Last Listing Agent Shari Frasure Keller Williams Commonwealth

  Unlisted Address
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  /2

  $59,000 Sold Dec 16, 2025

  7340 Ecton Rd, Winchester, KY 40391

  • Land
  • 1.69 Acres
  • $34,911 per Acre

  Last Sold Summary

  • 2% Below List Price
  • 3 Days On Market

  Last Listing Agent Zella Rosenthal Tom Goebel & Company

  7340 Ecton Rd, Winchester, KY 40391
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  /27

  $190,000 Sold Apr 18, 2025

  7 Pocahontas Trail, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 1,550 Sq Ft
  • Built 1969

  Last Sold Summary

  • 3% Below List Price
  • $123/SF
  • 7 Days On Market

  Current Estimated Value $205,477

  Last Listing Agent Mila Ensor Ensor Real Estate, LLC

  7 Pocahontas Trail, Winchester, KY 40391
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  /30

  $300,000 Sold Apr 04, 2025

  302 Ascot Cir, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 1,758 Sq Ft
  • Built 1995

  Last Sold Summary

  • 14% Below List Price
  • $171/SF
  • 19 Days On Market

  Current Estimated Value $319,729

  Last Listing Agent Amy Mills Keys To Kentucky Realty

  302 Ascot Cir, Winchester, KY 40391
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  /40

  $215,000 Sold Dec 08, 2025

  5620 Ironworks Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,699 Sq Ft
  • Built 1960

  Last Sold Summary

  • 4% Below List Price
  • $127/SF
  • 13 Days On Market

  Last Listing Agent Michelle Blackburn RE/MAX Creative, Winchester

  5620 Ironworks Rd, Winchester, KY 40391
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  /36

  $320,000 Sold Oct 02, 2025

  510 Kimberly Dr, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 2,430 Sq Ft
  • Built 1970

  Last Sold Summary

  • 2% Below List Price
  • $132/SF
  • 3 Days On Market

  Current Estimated Value $325,690

  Last Listing Agent Ashley Barreto Indigo & Co

  510 Kimberly Dr, Winchester, KY 40391
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  /19

  $281,000 Sold Aug 22, 2025

  223 Cross Brook Ln, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,708 Sq Ft
  • Built 1999

  Last Sold Summary

  • 1% Below List Price
  • $165/SF
  • 11 Days On Market

  Current Estimated Value $285,838

  Last Listing Agent Dwight Donaldson Murphy Realty Group

  223 Cross Brook Ln, Winchester, KY 40391
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  /24

  $249,900 Sold Jul 21, 2025

  114 Bayberry Ln, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,644 Sq Ft
  • Built 1991

  Last Sold Summary

  • $152/SF
  • 2 Days On Market

  Current Estimated Value $253,779

  Last Listing Agent Debra Ward Coldwell Banker McMahan

  114 Bayberry Ln, Winchester, KY 40391
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  /14

  $240,000 Sold Oct 24, 2025

  3020 Dry Fork Creek Rd, Winchester, KY 40391

  Last Sold Summary

  • 9% Below List Price
  • 14 Days On Market

  Current Estimated Value $240,672

  Last Listing Agent Ellie Hatton The Brokerage

  3020 Dry Fork Creek Rd, Winchester, KY 40391
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  /23

  $250,000 Sold Jan 23, 2026

  208 Watercrest Way, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,416 Sq Ft
  • Built 1999

  Last Sold Summary

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

  Last Listing Agent Chad Bowman The Brokerage

  208 Watercrest Way, Winchester, KY 40391
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  /16

  $221,000 Sold Apr 10, 2025

  717 Estes Dr, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,053 Sq Ft
  • Built 1970

  Last Sold Summary

  • $210/SF
  • 0 Days On Market

  Current Estimated Value $225,310

  Last Listing Agent Rebecca Worth Redfin

  717 Estes Dr, Winchester, KY 40391
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  /27

  $199,500 Sold Apr 30, 2025

  374 S Main St, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 972 Sq Ft
  • Built 1940

  Last Sold Summary

  • 11% Below List Price
  • $205/SF
  • 206 Days On Market

  Current Estimated Value $200,629

  Last Listing Agent Mila Ensor Ensor Real Estate, LLC

  374 S Main St, Winchester, KY 40391
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  /31

  $235,000 Sold Sep 26, 2025

  210 Moss Ct, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,201 Sq Ft
  • Built 1998

  Last Sold Summary

  • 4% Below List Price
  • $196/SF
  • 48 Days On Market

  Current Estimated Value $236,439

  Last Listing Agent Jason Townsend Kentucky Residential Real Estate, LLC

  210 Moss Ct, Winchester, KY 40391

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