Recently Sold Winchester, KY Homes

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  /31

  $379,717

  Sold Mar 27, 2026

  300 Calmes Blvd, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 2,636 Sq Ft
  • Built 1989

  Last Sold Summary

  • 5% Below List Price
  • $144/SF
  • 111 Days On Market

  Current Estimated Value $381,770

  Last Listing Agent Darrell Tackett Dream Maker Realty, LLC

  300 Calmes Blvd, Winchester, KY 40391
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  /64

  $360,000

  Sold Oct 17, 2025

  309 Gallahadion Ct, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,920 Sq Ft
  • Built 2024

  Last Sold Summary

  • 3% Below List Price
  • $188/SF
  • 60 Days On Market

  Current Estimated Value $385,013

  Last Listing Agent Josh Wood Freedom Realty & Property Management

  309 Gallahadion Ct, Winchester, KY 40391
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  /64

  $415,000

  Sold Feb 25, 2026

  1857 Ironworks Rd, Winchester, KY 40391

  • 5 Beds
  • 2.5 Baths
  • 2,924 Sq Ft
  • Built 1865

  Last Sold Summary

  • 3% Below List Price
  • $142/SF
  • 70 Days On Market

  Current Estimated Value $421,834

  Last Listing Agent Meredith Walker Bluegrass Sotheby's International Realty

  1857 Ironworks Rd, Winchester, KY 40391
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  /23

  $225,000

  Sold Aug 21, 2025

  26 Stefanie Ct, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,080 Sq Ft
  • Built 1972

  Last Sold Summary

  • $208/SF
  • 12 Days On Market

  Current Estimated Value $222,687

  Last Listing Agent Alyssa M Boley Coldwell Banker McMahan

  26 Stefanie Ct, Winchester, KY 40391
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  /47

  $365,000

  Sold Apr 20, 2026

  114 Mallard Ln, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 2,105 Sq Ft
  • Built 1970

  Last Sold Summary

  • 4% Below List Price
  • $173/SF
  • 162 Days On Market

  Current Estimated Value $358,863

  Last Listing Agent Robin Jones Keller Williams Legacy Group

  114 Mallard Ln, Winchester, KY 40391
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  /50

  $465,000

  Sold Aug 11, 2025

  701 Lisletown Ln, Winchester, KY 40391

  • 2 Beds
  • 2.5 Baths
  • 2,784 Sq Ft
  • Built 2008

  Last Sold Summary

  • $167/SF
  • 2 Days On Market

  Current Estimated Value $481,107

  Last Listing Agent Robin Jones Keller Williams Legacy Group

  701 Lisletown Ln, Winchester, KY 40391
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  /2

  $75,000

  Sold Jan 05, 2026

  1341 Sewell Shop Rd, Winchester, KY 40391

  • Land
  • 5.75 Acres
  • $13,043 per Acre

  Last Sold Summary

  • 6% Below List Price
  • 10 Days On Market

  Last Listing Agent Zella Rosenthal Tom Goebel & Company

  1341 Sewell Shop Rd, Winchester, KY 40391
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  /29

  $408,000

  Sold Sep 12, 2025

  4732 Old Boonesboro Rd, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 2,361 Sq Ft
  • Built 1945

  Last Sold Summary

  • 18% Below List Price
  • $173/SF
  • 285 Days On Market

  Current Estimated Value $425,011

  Last Listing Agent Patrick Arvin Keller Williams Commonwealth

  4732 Old Boonesboro Rd, Winchester, KY 40391
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  /2

  $555,000

  Sold Jan 16, 2026

  184 Casa Landa Way, Winchester, KY 40391

  • 4 Beds
  • 3.5 Baths
  • 3,585 Sq Ft
  • Built 1998

  Last Sold Summary

  • 6% Below List Price
  • $155/SF

  Current Estimated Value $575,126

  Last Listing Agent Jim Woodrum RE/MAX Creative, Winchester

  184 Casa Landa Way, Winchester, KY 40391
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  /38

  $239,000

  Sold Aug 07, 2026

  210 Shannon Ct, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,164 Sq Ft
  • Built 2003

  Last Sold Summary

  • $205/SF
  • 4 Days On Market

  Current Estimated Value $219,606

  Last Listing Agent ROBIN TRIMBLE HomeFirst Real Estate

  210 Shannon Ct, Winchester, KY 40391
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  /30

  $292,000

  Sold Aug 07, 2026

  872 Stratton Ln, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 2,285 Sq Ft
  • Built 1984

  Last Sold Summary

  • 6% Below List Price
  • $128/SF
  • 15 Days On Market

  Current Estimated Value $306,709

  Last Listing Agent Kathryn Cheuvront Coldwell Banker McMahan

  872 Stratton Ln, Winchester, KY 40391
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  /12

  $9,000

  Sold Sep 18, 2025

  406 W Washington St, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 1,428 Sq Ft
  • Built 1945

  Last Sold Summary

  • 10% Below List Price
  • $6/SF
  • 19 Days On Market

  Current Estimated Value $144,199

  Last Listing Agent Jack Rookard Rookard Real Estate Consultants

  406 W Washington St, Winchester, KY 40391
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  /26

  $175,000

  Sold Apr 22, 2026

  10 Pocahontas Trail, Winchester, KY 40391

  • 2 Beds
  • 1.5 Baths
  • 924 Sq Ft
  • Built 1988

  Last Sold Summary

  • $189/SF
  • 7 Days On Market

  Current Estimated Value $177,717

  Last Listing Agent Libby VanMeter Marshall Lane Real Estate - Lexington

  10 Pocahontas Trail, Winchester, KY 40391
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  /79

  $425,000

  Sold Feb 23, 2026

  1410 Dry Fork Creek Rd, Winchester, KY 40391

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

  Last Sold Summary

  • 15% Below List Price
  • $399/SF
  • 78 Days On Market

  Last Listing Agent Skyler Lewis Dream Maker Realty, LLC

  1410 Dry Fork Creek Rd, Winchester, KY 40391
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  /53

  $268,000

  Sold Jul 31, 2026

  311 Geronimo Ct, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 1,510 Sq Ft
  • Built 1999

  Last Sold Summary

  • $177/SF
  • 14 Days On Market

  Current Estimated Value $268,713

  Last Listing Agent Brenda Sipes WEICHERT REALTORS - ABG Properties

  311 Geronimo Ct, Winchester, KY 40391
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  /24

  $188,000

  Sold Jan 29, 2026

  27 Ashland Ave, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,653 Sq Ft
  • Built 1950

  Last Sold Summary

  • 6% Below List Price
  • $114/SF
  • 112 Days On Market

  Current Estimated Value $188,085

  Last Listing Agent Robin Mobley-Mosher Marshall Lane Real Estate - Lexington

  27 Ashland Ave, Winchester, KY 40391
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  /52

  $448,000

  Sold Jul 10, 2026

  207 Hibiscus Ln, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 3,126 Sq Ft
  • Built 1999

  Last Sold Summary

  • $143/SF
  • 2 Days On Market

  Current Estimated Value $448,899

  Last Listing Agent Jonathan Wood HomeLand Real Estate Inc - Mt Sterling

  207 Hibiscus Ln, Winchester, KY 40391
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  /62

  $453,200

  Sold Jul 23, 2026

  1661 Waterworks Rd, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,793 Sq Ft
  • Built 1983

  Last Sold Summary

  • 6% Above List Price
  • $162/SF
  • 3 Days On Market

  Current Estimated Value $443,506

  Last Listing Agent Jim Woodrum RE/MAX Creative, Winchester

  1661 Waterworks Rd, Winchester, KY 40391
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  /26

  $165,000

  Sold Apr 23, 2026

  52 Judy Ann Ct, Winchester, KY 40391

  • 3 Beds
  • 1.5 Baths
  • 1,312 Sq Ft
  • Built 1981

  Last Sold Summary

  • $126/SF
  • 0 Days On Market

  Current Estimated Value $167,887

  Last Listing Agent Cathleen Gedeon CENTURY 21 Advantage Realty

  52 Judy Ann Ct, Winchester, KY 40391
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  /20

  $230,000

  Sold Jul 23, 2026

  86 Brink Ave, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,136 Sq Ft
  • Built 2000

  Last Sold Summary

  • $202/SF
  • 12 Days On Market

  Current Estimated Value $216,409

  Last Listing Agent Jennifer Hukill RE/MAX Elite Lexington

  86 Brink Ave, Winchester, KY 40391
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  /25

  $375,000

  Sold Aug 29, 2025

  317 Hanover Dr, Winchester, KY 40391

  • 5 Beds
  • 3.5 Baths
  • 3,111 Sq Ft
  • Built 2001

  Last Sold Summary

  • 1% Below List Price
  • $121/SF
  • 8 Days On Market

  Current Estimated Value $382,439

  Last Listing Agent Mike Wheatley Bluegrass Properties Group

  317 Hanover Dr, Winchester, KY 40391
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  /60

  $545,000

  Sold Oct 31, 2025

  445 Lynnway Dr, Winchester, KY 40391

  • 4 Beds
  • 3.5 Baths
  • 3,649 Sq Ft
  • Built 1993

  Last Sold Summary

  • $149/SF
  • 4 Days On Market

  Current Estimated Value $555,129

  Last Listing Agent Janna Chalfant Smith United Real Estate Bluegrass

  445 Lynnway Dr, Winchester, KY 40391
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  /27

  $263,500

  Sold Apr 10, 2026

  222 Bracken Ct, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,456 Sq Ft
  • Built 2006

  Last Sold Summary

  • 2% Below List Price
  • $181/SF
  • 121 Days On Market

  Current Estimated Value $263,130

  Last Listing Agent Jim Woodrum RE/MAX Creative, Winchester

  222 Bracken Ct, Winchester, KY 40391
• 

  

  /27

  $380,000

  Sold Nov 10, 2025

  5705 Mount Sterling Rd, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,980 Sq Ft
  • Built 1971

  Last Sold Summary

  • 5% Below List Price
  • $128/SF
  • 50 Days On Market

  Current Estimated Value $391,349

  Last Listing Agent Dale Hatton Dream Maker Realty, LLC

  5705 Mount Sterling Rd, Winchester, KY 40391
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  /102

  $525,000

  Sold Dec 22, 2025

  1953 Cabin Creek Rd, Winchester, KY 40391

  • 6 Beds
  • 4.5 Baths
  • 3,846 Sq Ft
  • Built 1980

  Last Sold Summary

  • 4% Below List Price
  • $137/SF
  • 9 Days On Market

  Current Estimated Value $546,377

  Last Listing Agent Josh Wood Freedom Realty & Property Management

  1953 Cabin Creek Rd, Winchester, KY 40391
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  /114

  $635,000

  Sold Sep 30, 2025

  315 The Woods Ln, Winchester, KY 40391

  • 5 Beds
  • 4.5 Baths
  • 5,524 Sq Ft
  • Built 1995

  Last Sold Summary

  • 2% Below List Price
  • $115/SF
  • 63 Days On Market

  Current Estimated Value $615,502

  Last Listing Agent Terri McGraw FC Tucker Bluegrass

  315 The Woods Ln, Winchester, KY 40391
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  /30

  $189,900

  Sold Mar 16, 2026

  357 E Washington St, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,328 Sq Ft
  • Built 1940

  Last Sold Summary

  • 5% Below List Price
  • $143/SF
  • 26 Days On Market

  Current Estimated Value $186,864

  Last Listing Agent Dylan Justice Bluegrass Commercial Real Estate

  357 E Washington St, Winchester, KY 40391
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  /33

  $159,200

  Sold Oct 09, 2025

  646 Laura Dr, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 1,534 Sq Ft
  • Built 1980

  Last Sold Summary

  • 6% Below List Price
  • $104/SF
  • 16 Days On Market

  Current Estimated Value $230,992

  Last Listing Agent Kimberly Brunson Hunter Real Estate

  646 Laura Dr, Winchester, KY 40391
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  /31

  $145,000

  Sold May 11, 2026

  730 Byrd Ave, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,160 Sq Ft
  • Built 1960

  Last Sold Summary

  • 6% Below List Price
  • $125/SF
  • 11 Days On Market

  Current Estimated Value $147,268

  Last Listing Agent Patricia Weiderman Kentucky Land and Home

  730 Byrd Ave, Winchester, KY 40391
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  /61

  $220,000

  Sold Nov 10, 2025

  313 Snowden Dr, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,232 Sq Ft
  • Built 1960

  Last Sold Summary

  • 12% Below List Price
  • $179/SF
  • 51 Days On Market

  Current Estimated Value $230,857

  Last Listing Agent Josh Wood Freedom Realty & Property Management

  313 Snowden Dr, Winchester, KY 40391
• 

  

  /17

  $595,000

  Sold Nov 17, 2025

  304 Winterberry Dr, Winchester, KY 40391

  • 7 Beds
  • 4 Baths
  • 4,386 Sq Ft
  • Built 1999

  Last Sold Summary

  • 1% Below List Price
  • $136/SF
  • 10 Days On Market

  Current Estimated Value $598,334

  Last Listing Agent Beckie Moore Bluegrass Properties Group

  304 Winterberry Dr, Winchester, KY 40391
• 

  /2

  $185,000

  Sold Nov 28, 2025

  23 Hillcrest Dr, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 1,557 Sq Ft
  • Built 1962

  Last Sold Summary

  • 12% Below List Price
  • $119/SF
  • 18 Days On Market

  Current Estimated Value $205,013

  Last Listing Agent Samantha Gray National Real Estate

  23 Hillcrest Dr, Winchester, KY 40391
• 

  

  /25

  $222,000

  Sold Jun 11, 2026

  213 Short St, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,068 Sq Ft
  • Built 1955

  Last Sold Summary

  • 3% Below List Price
  • $208/SF
  • 2 Days On Market

  Current Estimated Value $223,859

  Last Listing Agent Jason Townsend Kentucky Residential Real Estate, LLC

  213 Short St, Winchester, KY 40391
• 

  

  /22

  $216,000

  Sold Feb 27, 2026

  521 Acadia Way, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 1,370 Sq Ft
  • Built 2001

  Last Sold Summary

  • 2% Below List Price
  • $158/SF
  • 17 Days On Market

  Current Estimated Value $215,450

  Last Listing Agent Tyler I Back The Brokerage

  521 Acadia Way, Winchester, KY 40391
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  /86

  $515,000

  Sold Apr 17, 2026

  125 Casa Landa Way, Winchester, KY 40391

  • 4 Beds
  • 3.5 Baths
  • 3,848 Sq Ft
  • Built 1999

  Last Sold Summary

  • 6% Below List Price
  • $134/SF
  • 88 Days On Market

  Current Estimated Value $520,628

  Last Listing Agent Maggie Napier Napier Realtors

  125 Casa Landa Way, Winchester, KY 40391
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  /65

  $385,000

  Sold Dec 11, 2025

  1731 Ford Hampton Rd, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 2,111 Sq Ft
  • Built 2001

  Last Sold Summary

  • 27% Below List Price
  • $182/SF
  • 157 Days On Market

  Current Estimated Value $409,389

  Last Listing Agent Julie Wiggington RE/MAX Creative, Winchester

  1731 Ford Hampton Rd, Winchester, KY 40391
• 

  

  /27

  $269,000

  Sold Apr 20, 2026

  916 Stratton Ln, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,400 Sq Ft
  • Built 1988

  Last Sold Summary

  • $192/SF
  • 0 Days On Market

  Current Estimated Value $267,870

  Last Listing Agent Joshua Davis The Agency

  916 Stratton Ln, Winchester, KY 40391
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  /79

  $584,900

  Sold Feb 17, 2026

  180 Casa Landa Way, Winchester, KY 40391

  • 4 Beds
  • 3.5 Baths
  • 4,779 Sq Ft
  • Built 2000

  Last Sold Summary

  • 10% Below List Price
  • $122/SF
  • 46 Days On Market

  Current Estimated Value $594,971

  Last Listing Agent Janna Chalfant Smith United Real Estate Bluegrass

  180 Casa Landa Way, Winchester, KY 40391
• 

  

  /31

  $249,900

  Sold Jul 17, 2026

  123 Sunset Heights, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,446 Sq Ft
  • Built 1956

  Last Sold Summary

  • 2% Below List Price
  • $173/SF
  • 52 Days On Market

  Current Estimated Value $247,714

  Last Listing Agent Keith Wilson Coldwell Banker McMahan

  123 Sunset Heights, Winchester, KY 40391
• 

  

  /15

  $110,000

  Sold Sep 04, 2025

  706 Williamsburg Dr, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 924 Sq Ft
  • Built 2024

  Last Sold Summary

  • 21% Below List Price
  • $119/SF

  Current Estimated Value $119,745

  Last Listing Agent Andrew Fugitt KY Property Hunters

  706 Williamsburg Dr, Winchester, KY 40391

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