Recently Sold Winchester, KY Homes

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  /78

  $660,000 Sold Dec 10, 2025

  420 Alexis Way, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,770 Sq Ft
  • Built 2022

  Last Sold Summary

  • 5% Below List Price
  • $238/SF
  • 26 Days On Market

  Last Listing Agent Edwin Burden McCormick Realty Inc.

  420 Alexis Way, Winchester, KY 40391
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  /49

  $390,000 Sold Jun 30, 2025

  1094 Ford Hampton Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,900 Sq Ft
  • Built 1940

  Last Sold Summary

  • 2% Below List Price
  • $205/SF
  • 26 Days On Market

  Current Estimated Value $390,411

  Last Listing Agent Tom D. Thomas The Real Estate Co.

  1094 Ford Hampton Rd, Winchester, KY 40391
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  /61

  $545,000 Sold Jul 15, 2025

  1063 Wades Mill Rd, Winchester, KY 40391

  • 4 Beds
  • 3.5 Baths
  • 3,958 Sq Ft
  • Built 2000

  Last Sold Summary

  • 11% Below List Price
  • $138/SF
  • 180 Days On Market

  Current Estimated Value $556,382

  Last Listing Agent Joseph Smallwood Christies International Real Estate Bluegrass

  1063 Wades Mill Rd, Winchester, KY 40391
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  /65

  $290,000 Sold Jun 18, 2025

  13 Robyn Dr, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,844 Sq Ft
  • Built 1980

  Last Sold Summary

  • 2% Below List Price
  • $157/SF
  • 1 Day On Market

  Current Estimated Value $293,270

  Last Listing Agent Jason Townsend Kentucky Residential Real Estate, LLC

  13 Robyn Dr, Winchester, KY 40391
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  /32

  $360,000 Sold Aug 14, 2025

  418 Skylark Dr, Winchester, KY 40391

  • 5 Beds
  • 2.5 Baths
  • 2,746 Sq Ft
  • Built 1990

  Last Sold Summary

  • 3% Above List Price
  • $131/SF
  • 12 Days On Market

  Current Estimated Value $354,250

  Last Listing Agent Kymberly McCreary EXP Realty, LLC

  418 Skylark Dr, Winchester, KY 40391
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  /79

  $204,000 Sold Oct 30, 2025

  133 S Burns Ave, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 3,295 Sq Ft
  • Built 1915

  Last Sold Summary

  • 18% Below List Price
  • $62/SF
  • 20 Days On Market

  Current Estimated Value $215,958

  Last Listing Agent Josh Wood Freedom Realty & Property Management

  133 S Burns Ave, Winchester, KY 40391
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  /28

  $246,000 Sold Nov 06, 2025

  204 Moss Ct, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,430 Sq Ft
  • Built 1998

  Last Sold Summary

  • 3% Above List Price
  • $172/SF
  • 1 Day On Market

  Current Estimated Value $245,330

  Last Listing Agent Brooke Martin RO&CO Real Estate

  204 Moss Ct, Winchester, KY 40391
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  /2

  $39,500 Sold Mar 05, 2025

  414 Fairholme Way, Winchester, KY 40391

  • Land
  • 0.37 Acre
  • $106,757 per Acre

  Last Sold Summary

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

  Last Listing Agent Garnett Davis Tom Goebel & Company

  414 Fairholme Way, Winchester, KY 40391
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  /58

  $232,500 Sold Jul 12, 2025

  114 Holiday Rd, Winchester, KY 40391

  • 3 Beds
  • 1.5 Baths
  • 1,161 Sq Ft
  • Built 1980

  Last Sold Summary

  • 7% Below List Price
  • $200/SF
  • 235 Days On Market

  Current Estimated Value $238,360

  Last Listing Agent Karen Smith Emmerich Muzic Realty

  114 Holiday Rd, Winchester, KY 40391
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  /28

  $234,500 Sold Jul 29, 2025

  108 Sturbridge Ln, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • Built 2004

  Last Sold Summary

  • 4% Below List Price
  • $195/SF
  • 45 Days On Market

  Current Estimated Value $241,211

  Last Listing Agent Jason Szaks EXIT TOWN & COUNTRY REALTORS

  108 Sturbridge Ln, Winchester, KY 40391
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  /52

  $230,000 Sold Jan 20, 2026

  19 Cherokee Ct, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,134 Sq Ft
  • Built 1968

  Last Sold Summary

  • 2% Above List Price
  • $203/SF
  • 2 Days On Market

  Last Listing Agent Josh Wood Freedom Realty & Property Management

  19 Cherokee Ct, Winchester, KY 40391
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  /22

  $334,327 Sold Jul 01, 2025

  136 Gibson Way, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 1,997 Sq Ft
  • Built 2024

  Last Sold Summary

  • $167/SF
  • 219 Days On Market

  Current Estimated Value $339,086

  Last Listing Agent Neshia Gaines Christies International Real Estate Bluegrass

  136 Gibson Way, Winchester, KY 40391
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  /6

  $50,000 Sold Mar 17, 2025

  221 Ashton Oak Way, Winchester, KY 40391

  • Land
  • 0.39 Acre
  • $128,205 per Acre

  Last Sold Summary

  • 9% Below List Price
  • 264 Days On Market

  Current Estimated Value $62,110

  Last Listing Agent Melia Hord Keller Williams Legacy Group

  221 Ashton Oak Way, Winchester, KY 40391
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  /37

  $275,000 Sold Sep 10, 2025

  279 Ascot Ave, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,247 Sq Ft
  • Built 2000

  Last Sold Summary

  • 8% Below List Price
  • $122/SF
  • 2 Days On Market

  Current Estimated Value $290,485

  Last Listing Agent Chase Pennington Team Pannell Real Estate

  279 Ascot Ave, Winchester, KY 40391
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  /24

  $198,000 Sold Jul 18, 2025

  113 Colonial Park Dr, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,075 Sq Ft
  • Built 1983

  Last Sold Summary

  • 2% Above List Price
  • $184/SF
  • 0 Days On Market

  Current Estimated Value $204,526

  Last Listing Agent Janet Baldwin Kentucky Land and Home

  113 Colonial Park Dr, Winchester, KY 40391
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  /2

  $415,000 Sold Mar 03, 2025

  1480 White Turley Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 2,470 Sq Ft

  Last Sold Summary

  • $168/SF
  • 0 Days On Market

  Last Listing Agent Hannah Porter DEE'S REAL ESTATE SERVICE

  1480 White Turley Rd, Winchester, KY 40391
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  /28

  $370,000 Sold Sep 03, 2025

  220 Spring Valley Dr, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 3,078 Sq Ft
  • Built 1975

  Last Sold Summary

  • 7% Below List Price
  • $120/SF
  • 3 Days On Market

  Current Estimated Value $380,445

  Last Listing Agent Tracey Goebel Tom Goebel & Company

  220 Spring Valley Dr, Winchester, KY 40391
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  /27

  $335,000 Sold Dec 18, 2025

  2198 Goshen Rd, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,730 Sq Ft
  • Built 1997

  Last Sold Summary

  • 5% Above List Price
  • $194/SF
  • 31 Days On Market

  Last Listing Agent Jason Szaks EXIT TOWN & COUNTRY REALTORS

  2198 Goshen Rd, Winchester, KY 40391
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  /29

  $180,000 Sold Aug 11, 2025

  217 Blair Ave, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,025 Sq Ft
  • Built 1970

  Last Sold Summary

  • 3% Above List Price
  • $176/SF
  • 0 Days On Market

  Current Estimated Value $180,469

  Last Listing Agent Ashley Barreto Indigo & Co

  217 Blair Ave, Winchester, KY 40391
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  /30

  $254,000 Sold Dec 02, 2025

  312 Forest Ave, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,550 Sq Ft
  • Built 1962

  Last Sold Summary

  • 6% Below List Price
  • $164/SF
  • 52 Days On Market

  Last Listing Agent Michelle Blackburn RE/MAX Creative, Winchester

  312 Forest Ave, Winchester, KY 40391
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  /30

  $382,000 Sold Feb 28, 2025

  1186 Lafayette Blvd, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 2,580 Sq Ft
  • Built 1997

  Last Sold Summary

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

  Current Estimated Value $404,125

  Last Listing Agent Jason Caudill RE/MAX Creative Realty

  1186 Lafayette Blvd, Winchester, KY 40391
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  /75

  $410,000 Sold Nov 21, 2025

  291 Log Lick Rd, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,600 Sq Ft
  • Built 2007

  Last Sold Summary

  • 6% Below List Price
  • $158/SF
  • 3 Days On Market

  Last Listing Agent Joyce Ratliff Tom Goebel & Company

  291 Log Lick Rd, Winchester, KY 40391
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  /4

  $101,000 Sold Jul 14, 2025

  2058 Athens Boonesboro Rd, Winchester, KY 40391

  • Land
  • 4.02 Acres
  • $25,124 per Acre

  Last Sold Summary

  • 7% Below List Price
  • 86 Days On Market

  Last Listing Agent Megan McCoy Keller Williams Legacy Group

  2058 Athens Boonesboro Rd, Winchester, KY 40391
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  /16

  $225,000 Sold Apr 25, 2025

  39 Hillcrest Dr, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 943 Sq Ft
  • Built 1968

  Last Sold Summary

  • $239/SF
  • 2 Days On Market

  Current Estimated Value $227,361

  Last Listing Agent Tracey Goebel Tom Goebel & Company

  39 Hillcrest Dr, Winchester, KY 40391
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  /87

  $250,000 Sold Apr 18, 2025

  418 Jameson Way, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,680 Sq Ft
  • Built 1996

  Last Sold Summary

  • 4% Below List Price
  • $149/SF
  • 3 Days On Market

  Current Estimated Value $256,882

  Last Listing Agent Josh Wood Freedom Realty & Property Management

  418 Jameson Way, Winchester, KY 40391
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  /36

  $257,400 Sold Nov 21, 2025

  103 Hampton Ave, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,715 Sq Ft
  • Built 1958

  Last Sold Summary

  • 10% Below List Price
  • $150/SF
  • 4 Days On Market

  Last Listing Agent Brett Bussell Turf Town Properties

  103 Hampton Ave, Winchester, KY 40391
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  /58

  $460,000 Sold Jul 11, 2025

  150 Stone Crest Rd, Winchester, KY 40391

  • 4 Beds
  • 4 Baths
  • 4,448 Sq Ft
  • Built 1978

  Last Sold Summary

  • 6% Below List Price
  • $103/SF
  • 18 Days On Market

  Last Listing Agent Brenda Murphy Murphy Realty Group

  150 Stone Crest Rd, Winchester, KY 40391
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  /32

  $175,000 Sold Dec 29, 2025

  200 Madison Ave, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,124 Sq Ft
  • Built 1996

  Last Sold Summary

  • 2% Below List Price
  • $156/SF
  • 19 Days On Market

  Last Listing Agent Silvia Torres Tru Life Real Estate

  200 Madison Ave, Winchester, KY 40391
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  /3

  $219,000 Sold May 20, 2025

  410 Paisley Ct, Winchester, KY 40391

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

  Last Sold Summary

  • $135/SF
  • 18 Days On Market

  Current Estimated Value $227,344

  Last Listing Agent John Wilson Bluegrass Properties Group

  410 Paisley Ct, Winchester, KY 40391
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  /82

  $392,000 Sold Dec 19, 2025

  397 Calmes Blvd, Winchester, KY 40391

  • 4 Beds
  • 3.5 Baths
  • 2,637 Sq Ft
  • Built 1992

  Last Sold Summary

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

  Last Listing Agent Omar Shalash Tru Life Real Estate

  397 Calmes Blvd, Winchester, KY 40391
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  /27

  $270,000 Sold Aug 25, 2025

  9 Hillcrest Dr, Winchester, KY 40391

  • 3 Beds
  • 3 Baths
  • 1,813 Sq Ft
  • Built 2005

  Last Sold Summary

  • 3% Below List Price
  • $149/SF
  • 13 Days On Market

  Current Estimated Value $275,469

  Last Listing Agent Melissa Brown Keller Williams Legacy Group

  9 Hillcrest Dr, Winchester, KY 40391
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  /15

  $249,900 Sold Jun 09, 2025

  234 Prescott Ln, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,463 Sq Ft
  • Built 2005

  Last Sold Summary

  • $171/SF
  • 17 Days On Market

  Current Estimated Value $257,635

  Last Listing Agent Darrell Tackett Dream Maker Realty, LLC

  234 Prescott Ln, Winchester, KY 40391
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  /98

  $750,000 Sold Dec 10, 2025

  3900 (Mt) Mount Sterling Rd, Winchester, KY 40391

  • 6 Beds
  • 5 Baths
  • 4,843 Sq Ft
  • Built 2004

  Last Sold Summary

  • 9% Below List Price
  • $155/SF
  • 42 Days On Market

  Last Listing Agent Teresa Richmond Freedom Realty & Property Management

  3900 (Mt) Mount Sterling Rd, Winchester, KY 40391
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  /24

  $207,000 Sold May 12, 2025

  411 Pueblo Ct, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,040 Sq Ft
  • Built 2023

  Last Sold Summary

  • 1% Above List Price
  • $199/SF
  • 3 Days On Market

  Current Estimated Value $209,691

  Last Listing Agent Zach Johnson The Brokerage

  411 Pueblo Ct, Winchester, KY 40391
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  /14

  $222,500 Sold Jul 15, 2025

  313 Vanover Way, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,064 Sq Ft
  • Built 1995

  Last Sold Summary

  • 5% Below List Price
  • $209/SF
  • 112 Days On Market

  Current Estimated Value $229,125

  Last Listing Agent Bob Sophiea eXp Realty, LLC

  313 Vanover Way, Winchester, KY 40391
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  /24

  $203,000 Sold Jun 23, 2025

  502 Corley Ln, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,289 Sq Ft
  • Built 1990

  Last Sold Summary

  • 4% Above List Price
  • $157/SF
  • 4 Days On Market

  Current Estimated Value $202,337

  Last Listing Agent Peter doCouto Plum Tree Realty

  502 Corley Ln, Winchester, KY 40391
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  /16

  $168,500 Sold Feb 25, 2025

  142 Spruce Ct, Winchester, KY 40391

  • 4 Beds
  • 1.5 Baths
  • 1,215 Sq Ft
  • Built 1970

  Last Sold Summary

  • 14% Below List Price
  • $139/SF
  • 406 Days On Market

  Current Estimated Value $191,490

  Last Listing Agent Whitney Ensor Ensor Real Estate, LLC

  142 Spruce Ct, Winchester, KY 40391
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  /21

  $525,000 Sold Aug 28, 2025

  Unlisted Address

  • 3 Beds
  • 2 Baths
  • 1,724 Sq Ft
  • Built 2016

  Last Sold Summary

  • $305/SF
  • 0 Days On Market

  Current Estimated Value $521,597

  Last Listing Agent Josh Wood Freedom Realty & Property Management

  Unlisted Address
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  /17

  $278,000 Sold Apr 15, 2025

  218 Bracken Ct, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,292 Sq Ft
  • Built 2005

  Last Sold Summary

  • $215/SF
  • 7 Days On Market

  Current Estimated Value $285,713

  Last Listing Agent Vickie Skeens RE/MAX Elite Lexington

  218 Bracken Ct, Winchester, KY 40391
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  /12

  $65,000 Sold Feb 18, 2025

  123 Magnolia St, Winchester, KY 40391

  • 1,386 Sq Ft
  • Built 1950

  Last Sold Summary

  • 24% Below List Price
  • $47/SF
  • 102 Days On Market

  Current Estimated Value $78,073

  Last Listing Agent Shawna Wever Wever Realty LLC

  123 Magnolia St, Winchester, KY 40391

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