Recently Sold Winchester, KY Homes

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  /24

  $277,000

  Sold Mar 25, 2026

  149 Winn Ave, Winchester, KY 40391

  • 12 Beds
  • 4 Baths
  • 4,010 Sq Ft
  • Built 1940

  Last Sold Summary

  • 4% Below List Price
  • $69/SF
  • 51 Days On Market

  Current Estimated Value $280,145

  Last Listing Agent Libby VanMeter Marshall Lane Real Estate - Lexington

  149 Winn Ave, Winchester, KY 40391
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  /37

  $260,000

  Sold Feb 20, 2026

  313 Carolina Ave, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 1,855 Sq Ft
  • Built 1962

  Last Sold Summary

  • $140/SF
  • 4 Days On Market

  Current Estimated Value $263,460

  Last Listing Agent Kenneth DeGrant High Point Realty & Auction

  313 Carolina Ave, Winchester, KY 40391
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  /38

  $293,000

  Sold Mar 06, 2026

  6261 Ironworks Rd, Winchester, KY 40391

  • Land
  • 15.79 Acres
  • $18,556 per Acre

  Last Sold Summary

  • 2% Below List Price
  • 5 Days On Market

  Last Listing Agent Kyle McPeck Coldwell Banker McMahan

  6261 Ironworks Rd, 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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  /39

  $395,000

  Sold Jun 12, 2026

  233 Cunningham Ln, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 2,258 Sq Ft
  • Built 2007

  Last Sold Summary

  • 12% Below List Price
  • $175/SF
  • 116 Days On Market

  Current Estimated Value $426,703

  Last Listing Agent Amanda Marcum Berkshire Hathaway HomeServices Foster Realtors

  233 Cunningham Ln, Winchester, KY 40391
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  /21

  $199,900

  Sold Jul 02, 2026

  265 Cunningham Ln, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,140 Sq Ft
  • Built 2024

  Last Sold Summary

  • $175/SF
  • 14 Days On Market

  Current Estimated Value $201,071

  Last Listing Agent Kierstin Shaffer Berkshire Hathaway HomeServices Foster Realtors

  265 Cunningham Ln, Winchester, KY 40391
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  /21

  $225,200

  Sold Apr 28, 2026

  514 Hidden Hills Way, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,120 Sq Ft
  • Built 2001

  Last Sold Summary

  • 2% Below List Price
  • $201/SF
  • 7 Days On Market

  Current Estimated Value $224,668

  Last Listing Agent Mary Layton FC Tucker Bluegrass

  514 Hidden Hills Way, Winchester, KY 40391
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  /36

  $315,000

  Sold Mar 04, 2026

  208 Citation Ct, Winchester, KY 40391

  • 2 Beds
  • 2 Baths
  • 1,568 Sq Ft
  • Built 2020

  Last Sold Summary

  • 12% Below List Price
  • $201/SF
  • 152 Days On Market

  Current Estimated Value $317,881

  Last Listing Agent Garnett Davis Tom Goebel & Company

  208 Citation Ct, Winchester, KY 40391
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  /4

  $110,000

  Sold Jan 23, 2026

  205 E Washington St, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,131 Sq Ft
  • Built 1940

  Last Sold Summary

  • 15% Below List Price
  • $52/SF
  • 53 Days On Market

  Current Estimated Value $157,462

  Last Listing Agent Patrick Arvin Keller Williams Commonwealth

  205 E Washington St, Winchester, KY 40391
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  /33

  $275,000

  Sold Jun 03, 2026

  211 Lindsey Ct, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,790 Sq Ft
  • Built 1997

  Last Sold Summary

  • 15% Below List Price
  • $154/SF
  • 62 Days On Market

  Current Estimated Value $278,755

  Last Listing Agent Lesley Ward Biederman Real Estate

  211 Lindsey Ct, Winchester, KY 40391
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  /32

  $252,000

  Sold Feb 27, 2026

  4074 Ironworks Rd, Winchester, KY 40391

  • 3 Beds
  • 1.5 Baths
  • 1,356 Sq Ft
  • Built 1973

  Last Sold Summary

  • 18% Below List Price
  • $186/SF
  • 28 Days On Market

  Current Estimated Value $259,370

  Last Listing Agent Ashley Spencer Keller Williams Commonwealth

  4074 Ironworks Rd, Winchester, KY 40391
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  /45

  $334,000

  Sold Apr 08, 2026

  120 Pilot View Rd, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,900 Sq Ft
  • Built 1930

  Last Sold Summary

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

  Current Estimated Value $325,766

  Last Listing Agent Jennifer Parsons RE/MAX Elite Lexington

  120 Pilot View Rd, Winchester, KY 40391
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  /2

  $75,000

  Sold Jan 16, 2026

  1431 Sewell Shop Rd, Winchester, KY 40391

  • Land
  • 6.43 Acres
  • $11,664 per Acre

  Last Sold Summary

  • 0 Days On Market

  Last Listing Agent Zella Rosenthal Tom Goebel & Company

  1431 Sewell Shop Rd, Winchester, KY 40391
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  /45

  $269,000

  Sold Aug 22, 2025

  402 Mcdowell Dr, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,136 Sq Ft
  • Built 1986

  Last Sold Summary

  • 22% Below List Price
  • $126/SF
  • 2 Days On Market

  Current Estimated Value $292,960

  Last Listing Agent Christine McDonald FC Tucker Bluegrass

  402 Mcdowell Dr, Winchester, KY 40391
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  /38

  $290,000

  Sold Jul 27, 2026

  147 Sunset Heights, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 2,128 Sq Ft
  • Built 1952

  Last Sold Summary

  • 3% Below List Price
  • $136/SF
  • 43 Days On Market

  Current Estimated Value $293,535

  Last Listing Agent Lyndsey Martin Kentucky Land and Home

  147 Sunset Heights, Winchester, KY 40391
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  /19

  $219,000

  Sold Sep 17, 2025

  521 Hidden Hills Way, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,335 Sq Ft
  • Built 2003

  Last Sold Summary

  • $164/SF
  • 4 Days On Market

  Current Estimated Value $225,541

  Last Listing Agent Cathy Cornett-Wilson Rector Hayden Realtors

  521 Hidden Hills Way, Winchester, KY 40391
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  /65

  $660,000

  Sold Apr 24, 2026

  20 Stoney Brook Dr, Winchester, KY 40391

  • 5 Beds
  • 4.5 Baths
  • 4,712 Sq Ft
  • Built 1998

  Last Sold Summary

  • 1% Below List Price
  • $140/SF
  • 2 Days On Market

  Current Estimated Value $657,395

  Last Listing Agent Lucy Martin Jenkins United Real Estate Bluegrass

  20 Stoney Brook Dr, Winchester, KY 40391
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  /43

  $550,000

  Sold May 22, 2026

  556 Earlymeade Dr, Winchester, KY 40391

  • 4 Beds
  • 4.5 Baths
  • 4,185 Sq Ft
  • Built 2015

  Last Sold Summary

  • 2% Below List Price
  • $131/SF
  • 7 Days On Market

  Current Estimated Value $547,330

  Last Listing Agent Craig Bridgewater Bridgewater Real Estate

  556 Earlymeade Dr, Winchester, KY 40391
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  /21

  $245,000

  Sold Jul 10, 2026

  12 Pocahontas Trail, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,064 Sq Ft
  • Built 2026

  Last Sold Summary

  • 2% Below List Price
  • $230/SF
  • 16 Days On Market

  Current Estimated Value $227,902

  Last Listing Agent Brian England Keller Williams Bluegrass Realty

  12 Pocahontas Trail, Winchester, KY 40391
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  /55

  $389,000

  Sold Feb 24, 2026

  4530 Ironworks Rd, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 2,518 Sq Ft
  • Built 1994

  Last Sold Summary

  • 3% Below List Price
  • $154/SF
  • 8 Days On Market

  Current Estimated Value $388,077

  Last Listing Agent Montlee Wickline Stone Ridge Realty LLC

  4530 Ironworks Rd, Winchester, KY 40391
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  /8

  $195,000

  Sold Dec 08, 2025

  222 Holiday Rd, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,100 Sq Ft
  • Built 1985

  Last Sold Summary

  • 7% Below List Price
  • $177/SF
  • 349 Days On Market

  Current Estimated Value $210,139

  Last Listing Agent Sophia Herald Herald Real Estate

  222 Holiday Rd, Winchester, KY 40391
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  /34

  $265,000

  Sold May 11, 2026

  404 Wellington Way, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,682 Sq Ft
  • Built 2005

  Last Sold Summary

  • 5% Below List Price
  • $158/SF
  • 158 Days On Market

  Current Estimated Value $267,028

  Last Listing Agent Craig Bridgewater Bridgewater Real Estate

  404 Wellington Way, Winchester, KY 40391
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  /41

  $270,000

  Sold Oct 14, 2025

  321 S Maple St, Winchester, KY 40391

  • 6 Beds
  • 4 Baths
  • 4,490 Sq Ft
  • Built 1900

  Last Sold Summary

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

  Current Estimated Value $291,532

  Last Listing Agent Josh Wood Freedom Realty & Property Management

  321 S Maple St, Winchester, KY 40391
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  /7

  $650,000

  Sold Jul 31, 2026

  1108 W Lexington Ave, Winchester, KY 40391

  • Land
  • 4.87 Acres
  • $133,470 per Acre

  Last Sold Summary

  • 19% Below List Price
  • 6 Days On Market

  Current Estimated Value $782,039

  Last Listing Agent Jason Townsend Kentucky Residential Real Estate, LLC

  1108 W Lexington Ave, Winchester, KY 40391
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  /16

  $201,000

  Sold Sep 05, 2025

  128 Alabama St, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,526 Sq Ft
  • Built 1930

  Last Sold Summary

  • 7% Below List Price
  • $132/SF
  • 66 Days On Market

  Current Estimated Value $211,442

  Last Listing Agent Paul Eads Freedom Realty & Property Management

  128 Alabama St, Winchester, KY 40391
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  /33

  $180,000

  Sold Sep 02, 2025

  307 Blair Ave, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,000 Sq Ft
  • Built 1977

  Last Sold Summary

  • $180/SF
  • 22 Days On Market

  Current Estimated Value $174,198

  Last Listing Agent Brooke Otis Mullins RO&CO Real Estate

  307 Blair Ave, Winchester, KY 40391
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  /38

  $285,000

  Sold Jul 31, 2026

  618 Westmeade Dr, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 2,116 Sq Ft
  • Built 1983

  Last Sold Summary

  • 4% Below List Price
  • $135/SF
  • 58 Days On Market

  Current Estimated Value $291,081

  Last Listing Agent Kristi Donaldson United Real Estate Bluegrass

  618 Westmeade Dr, Winchester, KY 40391
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  /47

  $347,000

  Sold Jan 05, 2026

  23 1/2 Wheeler Ave, Winchester, KY 40391

  • 8 Beds
  • 4 Baths
  • 3,706 Sq Ft
  • Built 1942

  Last Sold Summary

  • 12% Below List Price
  • $94/SF
  • 70 Days On Market

  Current Estimated Value $364,549

  Last Listing Agent Michelle Blackburn RE/MAX Creative, Winchester

  23 1/2 Wheeler Ave, Winchester, KY 40391
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  /37

  $392,500

  Sold Sep 08, 2025

  576 Marseille Blvd, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 2,991 Sq Ft
  • Built 1991

  Last Sold Summary

  • 2% Below List Price
  • $131/SF
  • 24 Days On Market

  Current Estimated Value $397,767

  Last Listing Agent James Turek Bluegrass Sotheby's International Realty

  576 Marseille Blvd, Winchester, KY 40391
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  /27

  $190,000

  Sold Apr 30, 2026

  29 Euclid Ave, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,498 Sq Ft
  • Built 1943

  Last Sold Summary

  • $127/SF
  • 6 Days On Market

  Current Estimated Value $188,562

  Last Listing Agent Autumn Johannes National Real Estate

  29 Euclid Ave, Winchester, KY 40391
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  /34

  $215,000

  Sold Mar 18, 2026

  37 7th St, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,680 Sq Ft
  • Built 1970

  Last Sold Summary

  • 9% Below List Price
  • $128/SF
  • 25 Days On Market

  Current Estimated Value $219,636

  Last Listing Agent Andrew Fugitt KY Property Hunters

  37 7th St, Winchester, KY 40391
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  /41

  $60,000

  Sold Oct 24, 2025

  145 Riverbend Ln, Winchester, KY 40391

  • 1 Bed
  • 1 Bath
  • 740 Sq Ft
  • Built 1984

  Last Sold Summary

  • 20% Below List Price
  • $81/SF
  • 6 Days On Market

  Current Estimated Value $67,461

  Last Listing Agent Darrell Tackett Dream Maker Realty, LLC

  145 Riverbend Ln, Winchester, KY 40391
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  /47

  $475,000

  Sold May 29, 2026

  595 Earlymeade Dr, Winchester, KY 40391

  • 5 Beds
  • 3.5 Baths
  • 3,823 Sq Ft
  • Built 2005

  Last Sold Summary

  • 5% Below List Price
  • $124/SF
  • 155 Days On Market

  Current Estimated Value $491,856

  Last Listing Agent Craig Bridgewater Bridgewater Real Estate

  595 Earlymeade Dr, Winchester, KY 40391
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  /54

  $269,900

  Sold Aug 12, 2025

  137 Sturbridge Ln, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,536 Sq Ft
  • Built 2006

  Last Sold Summary

  • 2% Below List Price
  • $176/SF
  • 11 Days On Market

  Current Estimated Value $275,361

  Last Listing Agent Josh Wood Freedom Realty & Property Management

  137 Sturbridge Ln, Winchester, KY 40391
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  /40

  $268,000

  Sold Oct 03, 2025

  58 Fitch Ave, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 1,736 Sq Ft
  • Built 1940

  Last Sold Summary

  • 3% Below List Price
  • $154/SF
  • 18 Days On Market

  Current Estimated Value $268,188

  Last Listing Agent Andrea Coughtry Lifstyl Real Estate

  58 Fitch Ave, Winchester, KY 40391
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  /15

  $580,000

  Sold May 29, 2026

  101 S Burns Ave Unit 1,2,3,4, Winchester, KY 40391

  • 8 Beds
  • 4 Baths
  • 5,046 Sq Ft
  • Built 1912

  Last Sold Summary

  • 14% Below List Price
  • $115/SF
  • 165 Days On Market

  Current Estimated Value $570,924

  Last Listing Agent Priya Patel-Rossetti Big Blue Realty

  101 S Burns Ave Unit 1,2,3,4, Winchester, KY 40391
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  /64

  $359,000

  Sold Sep 22, 2025

  616 Colby Ridge Blvd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,612 Sq Ft
  • Built 2025

  Last Sold Summary

  • 2% Below List Price
  • $223/SF
  • 26 Days On Market

  Current Estimated Value $363,563

  Last Listing Agent Josh Wood Freedom Realty & Property Management

  616 Colby Ridge Blvd, Winchester, KY 40391
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  /32

  $344,000

  Sold May 14, 2026

  538 S Maple St, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,628 Sq Ft
  • Built 2025

  Last Sold Summary

  • 4% Below List Price
  • $211/SF
  • 84 Days On Market

  Current Estimated Value $331,757

  Last Listing Agent Heather Kuykendoll Bluegrass Properties Group

  538 S Maple St, Winchester, KY 40391
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  /62

  $399,900

  Sold Apr 15, 2026

  601 Gilbert Ct, Winchester, KY 40391

  • 3 Beds
  • 3 Baths
  • 2,475 Sq Ft
  • Built 1992

  Last Sold Summary

  • $162/SF
  • 2 Days On Market

  Current Estimated Value $399,636

  Last Listing Agent Brooke Otis Mullins RO&CO Real Estate

  601 Gilbert Ct, Winchester, KY 40391
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  /103

  $345,000

  Sold Dec 22, 2025

  145 Shanahan Ln, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 2,520 Sq Ft
  • Built 1996

  Last Sold Summary

  • 1% Below List Price
  • $137/SF
  • 9 Days On Market

  Current Estimated Value $354,340

  Last Listing Agent Josh Wood Freedom Realty & Property Management

  145 Shanahan Ln, Winchester, KY 40391

Showing Results 241 - 280, Page 7 of 12