Recently Sold Winchester, KY Homes

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  /46

  $550,000

  Sold Jul 09, 2026

  7919 Mount Sterling Rd, Winchester, KY 40391

  • 4 Beds
  • 3.5 Baths
  • 3,431 Sq Ft
  • Built 1975

  Last Sold Summary

  • 8% Below List Price
  • $160/SF
  • 11 Days On Market

  Current Estimated Value $529,482

  Last Listing Agent Hannah Toole Coldwell Banker McMahan

  7919 Mount Sterling Rd, Winchester, KY 40391
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  /65

  $629,000

  Sold Nov 07, 2025

  418 David Ln, Winchester, KY 40391

  • 6 Beds
  • 4.5 Baths
  • 5,302 Sq Ft
  • Built 1993

  Last Sold Summary

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

  Current Estimated Value $662,037

  Last Listing Agent Craig Bridgewater Bridgewater Real Estate

  418 David Ln, Winchester, KY 40391
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  /12

  $179,000

  Sold Aug 05, 2026

  605 College St, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 1,484 Sq Ft
  • Built 1960

  Last Sold Summary

  • 22% Below List Price
  • $121/SF
  • 83 Days On Market

  Current Estimated Value $196,335

  Last Listing Agent Steve Adams Steven D Adams Real Estate Services, LLC

  605 College St, Winchester, KY 40391
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  /32

  $245,000

  Sold May 08, 2026

  17 Euclid Ave, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,656 Sq Ft
  • Built 1914

  Last Sold Summary

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

  Current Estimated Value $241,683

  Last Listing Agent Donna Thwaites Thwaites Realtors LLC

  17 Euclid Ave, Winchester, KY 40391
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  /2

  $74,000

  Sold Dec 16, 2025

  7290 Ecton Rd, Winchester, KY 40391

  • Land
  • 3.55 Acres
  • $20,845 per Acre

  Last Sold Summary

  • 1% Below List Price
  • 3 Days On Market

  Last Listing Agent Zella Rosenthal Tom Goebel & Company

  7290 Ecton Rd, Winchester, KY 40391
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  /9

  $378,000

  Sold Mar 09, 2026

  140 Gibson Way, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,269 Sq Ft
  • Built 2025

  Last Sold Summary

  • $167/SF
  • 0 Days On Market

  Current Estimated Value $376,898

  Last Listing Agent Amanda Stewart Stewart & Co Realty LLC

  140 Gibson Way, Winchester, KY 40391
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  /31

  $335,000

  Sold Nov 10, 2025

  536 S Maple St, Winchester, KY 40391

  • 3 Beds
  • 3 Baths
  • 1,832 Sq Ft
  • Built 1900

  Last Sold Summary

  • 8% Below List Price
  • $183/SF
  • 17 Days On Market

  Current Estimated Value $302,708

  Last Listing Agent Whitney Ensor Ensor Real Estate, LLC

  536 S Maple St, Winchester, KY 40391
• 

  

  /25

  $250,000

  Sold Sep 23, 2025

  816 Stratton Ln, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 3,024 Sq Ft
  • Built 1986

  Last Sold Summary

  • 23% Below List Price
  • $83/SF
  • 7 Days On Market

  Current Estimated Value $283,463

  Last Listing Agent Haley Rollins Dream Maker Realty, LLC

  816 Stratton Ln, Winchester, KY 40391
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  /31

  $305,000

  Sold Jul 09, 2026

  28 Churchill Dr, Winchester, KY 40391

  • 5 Beds
  • 3 Baths
  • 2,624 Sq Ft
  • Built 1981

  Last Sold Summary

  • 8% Below List Price
  • $116/SF
  • 32 Days On Market

  Current Estimated Value $310,021

  Last Listing Agent Libby VanMeter Marshall Lane Real Estate - Lexington

  28 Churchill Dr, Winchester, KY 40391
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  /2

  $363,000

  Sold Oct 30, 2025

  614 S Maple St Unit B3, Winchester, KY 40391

  • 2 Beds
  • 2.5 Baths
  • 1,734 Sq Ft
  • Built 1985

  Last Sold Summary

  • $209/SF
  • 0 Days On Market

  Current Estimated Value $352,406

  Last Listing Agent Holly Goeing The Agency

  614 S Maple St Unit B3, Winchester, KY 40391
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  /34

  $305,000

  Sold Nov 04, 2025

  123 Strawberry Ln, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,792 Sq Ft
  • Built 2024

  Last Sold Summary

  • 2% Below List Price
  • $170/SF
  • 1 Day On Market

  Current Estimated Value $316,392

  Last Listing Agent Joseph Smallwood Christies International Real Estate Bluegrass

  123 Strawberry Ln, Winchester, KY 40391
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  /31

  $222,500

  Sold Dec 19, 2025

  359 Silverton Way, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,502 Sq Ft
  • Built 1999

  Last Sold Summary

  • 1% Below List Price
  • $148/SF
  • 18 Days On Market

  Current Estimated Value $225,828

  Last Listing Agent Christal Browning Four Seasons Realty

  359 Silverton Way, Winchester, KY 40391
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  /50

  $359,000

  Sold Mar 27, 2026

  175 Overlooking Dr, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 2,080 Sq Ft
  • Built 1970

  Last Sold Summary

  • $173/SF
  • 0 Days On Market

  Current Estimated Value $357,784

  Last Listing Agent Keith Wilson Coldwell Banker McMahan

  175 Overlooking Dr, Winchester, KY 40391
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  /36

  $205,000

  Sold Jun 03, 2026

  415 L East Junction Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,152 Sq Ft
  • Built 2016

  Last Sold Summary

  • 9% Below List Price
  • $178/SF
  • 21 Days On Market

  Current Estimated Value $210,937

  Last Listing Agent Rachel Rainey Kentucky Land and Home

  415 L East Junction Rd, Winchester, KY 40391
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  /28

  $244,000

  Sold Sep 12, 2025

  252 S Highland St, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,944 Sq Ft
  • Built 1935

  Last Sold Summary

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

  Current Estimated Value $245,758

  Last Listing Agent Austina Bruton Re/Max Elite Realty - Hamburg

  252 S Highland St, Winchester, KY 40391
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  /36

  $100,000

  Sold Aug 07, 2026

  25 Oliver St, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 900 Sq Ft
  • Built 1940

  Last Sold Summary

  • 20% Below List Price
  • $111/SF
  • 37 Days On Market

  Current Estimated Value $127,782

  Last Listing Agent Jacob Jones Keller Williams Bluegrass Realty

  25 Oliver St, Winchester, KY 40391
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  /52

  $165,000

  Sold Jun 12, 2026

  334 S Burns Ave, Winchester, KY 40391

  • 3 Beds
  • 1.5 Baths
  • 1,636 Sq Ft
  • Built 1940

  Last Sold Summary

  • 28% Below List Price
  • $101/SF
  • 79 Days On Market

  Current Estimated Value $174,855

  Last Listing Agent Jeanne Beaven Rector Hayden Realtors

  334 S Burns Ave, Winchester, KY 40391
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  /97

  $290,000

  Sold Jul 24, 2026

  322 S Burns Ave, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,794 Sq Ft
  • Built 1940

  Last Sold Summary

  • 15% Below List Price
  • $162/SF
  • 87 Days On Market

  Current Estimated Value $293,241

  Last Listing Agent Nancy Hibbitts CENTURY 21 Advantage Realty

  322 S Burns Ave, Winchester, KY 40391
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  /37

  $379,000

  Sold Dec 22, 2025

  122 Le Ann Ln, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,587 Sq Ft
  • Built 1978

  Last Sold Summary

  • $147/SF
  • 7 Days On Market

  Current Estimated Value $383,627

  Last Listing Agent Tracey Goebel Tom Goebel & Company

  122 Le Ann Ln, Winchester, KY 40391
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  /56

  $375,000

  Sold Jul 01, 2026

  1503 Schollsville Rd, Winchester, KY 40391

  • 5 Beds
  • 3 Baths
  • 3,718 Sq Ft
  • Built 1948

  Last Sold Summary

  • 25% Below List Price
  • $101/SF
  • 149 Days On Market

  Current Estimated Value $410,000

  Last Listing Agent Keith Wilson Coldwell Banker McMahan

  1503 Schollsville Rd, Winchester, KY 40391
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  /21

  $173,000

  Sold Aug 15, 2025

  222 Buffalo Trace, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 964 Sq Ft
  • Built 1998

  Last Sold Summary

  • $179/SF
  • 2 Days On Market

  Current Estimated Value $180,317

  Last Listing Agent Elizabeth Herrington Bluegrass Sotheby's International Realty

  222 Buffalo Trace, Winchester, KY 40391
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  /23

  $197,377

  Sold May 15, 2026

  313 S Burns Ave, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,518 Sq Ft
  • Built 1903

  Last Sold Summary

  • 21% Below List Price
  • $130/SF
  • 106 Days On Market

  Current Estimated Value $214,482

  Last Listing Agent Michelle Blackburn RE/MAX Creative, Winchester

  313 S Burns Ave, Winchester, KY 40391
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  /26

  $195,000

  Sold Nov 06, 2025

  388 Colby Ridge Blvd, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,224 Sq Ft
  • Built 2000

  Last Sold Summary

  • 9% Below List Price
  • $159/SF
  • 31 Days On Market

  Current Estimated Value $206,496

  Last Listing Agent Joyce Ratliff Tom Goebel & Company

  388 Colby Ridge Blvd, Winchester, KY 40391
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  /46

  $365,000

  Sold Oct 27, 2025

  7875 Bybee Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,616 Sq Ft
  • Built 2021

  Last Sold Summary

  • 9% Below List Price
  • $226/SF
  • 79 Days On Market

  Current Estimated Value $341,614

  Last Listing Agent Joyce Ratliff Tom Goebel & Company

  7875 Bybee Rd, Winchester, KY 40391
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  /33

  $285,000

  Sold Jul 28, 2026

  414 Pueblo Ct, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 2,648 Sq Ft
  • Built 2021

  Last Sold Summary

  • 14% Below List Price
  • $108/SF
  • 48 Days On Market

  Current Estimated Value $295,762

  Last Listing Agent Walker Sabourin The Local Agents

  414 Pueblo Ct, Winchester, KY 40391
• 

  

  /25

  $263,000

  Sold Jun 16, 2026

  164 Buckingham Ln, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,190 Sq Ft
  • Built 2000

  Last Sold Summary

  • 3% Below List Price
  • $221/SF
  • 14 Days On Market

  Current Estimated Value $267,962

  Last Listing Agent Heather Baber Rector Hayden Realtors

  164 Buckingham Ln, Winchester, KY 40391
• 

  /2

  $470,000

  Sold Dec 02, 2025

  415 David Ln, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 3,989 Sq Ft
  • Built 1999

  Last Sold Summary

  • 19% Below List Price
  • $118/SF
  • 58 Days On Market

  Current Estimated Value $501,547

  Last Listing Agent Craig Bridgewater Bridgewater Real Estate

  415 David Ln, Winchester, KY 40391
• 

  

  /11

  $205,000

  Sold Oct 10, 2025

  322 Buffalo Trace, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,110 Sq Ft
  • Built 2001

  Last Sold Summary

  • 5% Above List Price
  • $185/SF
  • 1 Day On Market

  Current Estimated Value $209,338

  Last Listing Agent Sondra Clark Taylor Real Estate, LLC

  322 Buffalo Trace, Winchester, KY 40391
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  /33

  $333,500

  Sold Aug 20, 2025

  543 S Maple St, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,527 Sq Ft
  • Built 1946

  Last Sold Summary

  • 5% Below List Price
  • $218/SF
  • 38 Days On Market

  Current Estimated Value $336,879

  Last Listing Agent Lucy Martin Jenkins United Real Estate Bluegrass

  543 S Maple St, Winchester, KY 40391
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  /82

  $475,000

  Sold Oct 23, 2025

  102 Camelot Dr, Winchester, KY 40391

  • 5 Beds
  • 3.5 Baths
  • 3,679 Sq Ft
  • Built 1987

  Last Sold Summary

  • 12% Above List Price
  • $129/SF
  • 3 Days On Market

  Current Estimated Value $495,183

  Last Listing Agent Scott Fryar Keller Williams Bluegrass Realty

  102 Camelot Dr, Winchester, KY 40391
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  /68

  $460,000

  Sold Oct 10, 2025

  946 Pine Ridge Rd, Winchester, KY 40391

  • 4 Beds
  • 4 Baths
  • 3,523 Sq Ft
  • Built 2003

  Last Sold Summary

  • 8% Below List Price
  • $131/SF
  • 8 Days On Market

  Current Estimated Value $469,909

  Last Listing Agent Jason Townsend Kentucky Residential Real Estate, LLC

  946 Pine Ridge Rd, Winchester, KY 40391
• 

  

  /25

  $247,500

  Sold May 15, 2026

  201 Prescott Ln, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,304 Sq Ft
  • Built 2005

  Last Sold Summary

  • 7% Below List Price
  • $190/SF
  • 19 Days On Market

  Current Estimated Value $248,091

  Last Listing Agent Patrick Arvin Keller Williams Commonwealth

  201 Prescott Ln, Winchester, KY 40391
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  /32

  $255,000

  Sold May 14, 2026

  504 Harvard Dr, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 1,739 Sq Ft
  • Built 1978

  Last Sold Summary

  • 4% Below List Price
  • $147/SF
  • 11 Days On Market

  Current Estimated Value $255,085

  Last Listing Agent Justin Lee JL Realty Group, LLC

  504 Harvard Dr, Winchester, KY 40391
• 

  

  /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

  Current Estimated Value $666,005

  Last Listing Agent Josh Wood Freedom Realty & Property Management

  1203 Irvine Rd, Winchester, KY 40391
• 

  

  /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 $233,314

  Last Listing Agent Tracey Goebel Tom Goebel & Company

  394 S Main St, Winchester, KY 40391
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  /32

  $253,000

  Sold Jun 12, 2026

  363 S Main St, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 2,142 Sq Ft
  • Built 1940

  Last Sold Summary

  • 1% Above List Price
  • $118/SF
  • 2 Days On Market

  Current Estimated Value $252,203

  Last Listing Agent Zachary Otis HomeLand Real Estate Inc

  363 S Main St, Winchester, KY 40391
• 

  

  /33

  $420,000

  Sold May 21, 2026

  107 Woodduck Ct, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 2,652 Sq Ft
  • Built 2000

  Last Sold Summary

  • 7% Below List Price
  • $158/SF
  • 66 Days On Market

  Current Estimated Value $420,153

  Last Listing Agent Laura Eaves Berkshire Hathaway de Movellan Properties

  107 Woodduck Ct, Winchester, KY 40391
• 

  /2

  $125,000

  Sold May 15, 2026

  39 Casa Landa Way, Winchester, KY 40391

  • Land
  • 17,859 Sq Ft
  • $304,878 per Acre

  Last Sold Summary

  • 2 Days On Market

  Current Estimated Value $136,053

  Last Listing Agent Tracey Goebel Tom Goebel & Company

  39 Casa Landa Way, Winchester, KY 40391
• 

  /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
• 

  

  /16

  $155,000

  Sold Jul 20, 2026

  697 Goose Creek Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,848 Sq Ft
  • Built 1991

  Last Sold Summary

  • 14% Below List Price
  • $84/SF
  • 62 Days On Market

  Current Estimated Value $155,433

  Last Listing Agent R Michelle Rowland Dream Maker Realty, LLC

  697 Goose Creek Rd, Winchester, KY 40391

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