Recently Sold Winchester, KY Homes

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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 $313,300

  Last Listing Agent Joseph Smallwood Christies International Real Estate Bluegrass

  123 Strawberry Ln, Winchester, KY 40391
• 

  

  

  /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 $225,940

  Last Listing Agent Christal Browning Four Seasons Realty

  359 Silverton Way, Winchester, KY 40391
• 

  

  

  /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 $362,143

  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 $208,587

  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 $246,497

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

  252 S Highland St, Winchester, KY 40391
• 

  

  /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 $183,541

  Last Listing Agent Jeanne Beaven Rector Hayden Realtors

  334 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 $382,879

  Last Listing Agent Tracey Goebel Tom Goebel & Company

  122 Le Ann Ln, Winchester, KY 40391
• 

  

  /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 $179,925

  Last Listing Agent Elizabeth Herrington Bluegrass Sotheby's International Realty

  222 Buffalo Trace, Winchester, KY 40391
• 

  /2

  $247,000

  Sold Jul 31, 2025

  724 Terry Dr, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 2,250 Sq Ft
  • Built 1980

  Last Sold Summary

  • 3% Below List Price
  • $110/SF
  • 6 Days On Market

  Current Estimated Value $269,814

  Last Listing Agent Samantha Gray National Real Estate

  724 Terry Dr, Winchester, KY 40391
• 

  

  /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 $213,961

  Last Listing Agent Michelle Blackburn RE/MAX Creative, Winchester

  313 S Burns Ave, Winchester, KY 40391
• 

  

  /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 $204,530

  Last Listing Agent Joyce Ratliff Tom Goebel & Company

  388 Colby Ridge Blvd, Winchester, KY 40391
• 

  

  /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 $355,034

  Last Listing Agent Joyce Ratliff Tom Goebel & Company

  7875 Bybee Rd, Winchester, KY 40391
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  /34

  $205,000

  Sold Jun 30, 2025

  42 Wheeler Ave, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 1,013 Sq Ft
  • Built 1950

  Last Sold Summary

  • 16% Below List Price
  • $202/SF
  • 13 Days On Market

  Current Estimated Value $213,089

  Last Listing Agent Jason Townsend Kentucky Residential Real Estate, LLC

  42 Wheeler Ave, 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 $266,905

  Last Listing Agent Heather Baber Rector Hayden Realtors

  164 Buckingham Ln, Winchester, KY 40391
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  /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 $505,119

  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 $203,476

  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 $337,986

  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 $495,767

  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 $472,300

  Last Listing Agent Jason Townsend Kentucky Residential Real Estate, LLC

  946 Pine Ridge Rd, Winchester, KY 40391
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  /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 $260,213

  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 $252,548

  Last Listing Agent Justin Lee JL Realty Group, LLC

  504 Harvard Dr, Winchester, KY 40391
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  /34

  $252,000

  Sold Jul 30, 2025

  216 Connie Ln, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,248 Sq Ft
  • Built 2017

  Last Sold Summary

  • $202/SF
  • 2 Days On Market

  Current Estimated Value $255,483

  Last Listing Agent Elizabeth Hodge Lifstyl Real Estate

  216 Connie Ln, Winchester, KY 40391
• 

  

  /21

  $259,900

  Sold Jul 10, 2025

  302 April Way, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,321 Sq Ft
  • Built 2002

  Last Sold Summary

  • $197/SF
  • 12 Days On Market

  Current Estimated Value $266,482

  Last Listing Agent Michael Hilario The Agency

  302 April Way, 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 $647,237

  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 $232,088

  Last Listing Agent Tracey Goebel Tom Goebel & Company

  394 S Main St, Winchester, KY 40391
• 

  

  /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 $245,252

  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 $430,385

  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 $136,256

  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
• 

  

  /83

  $850,000

  Sold Mar 25, 2026

  4755 Combs Ferry Rd, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 2,768 Sq Ft
  • Built 1993

  Last Sold Summary

  • $307/SF
  • 13 Days On Market

  Current Estimated Value $844,476

  Last Listing Agent Craig Bridgewater Bridgewater Real Estate

  4755 Combs Ferry Rd, Winchester, KY 40391
• 

  

  /27

  $199,900

  Sold May 15, 2026

  215 Short St, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,036 Sq Ft
  • Built 1955

  Last Sold Summary

  • $193/SF
  • 1 Day On Market

  Current Estimated Value $199,007

  Last Listing Agent Amanda Marcum Berkshire Hathaway HomeServices Foster Realtors

  215 Short St, Winchester, KY 40391
• 

  

  /67

  $307,900

  Sold May 29, 2026

  118 Windridge Dr, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,617 Sq Ft
  • Built 1978

  Last Sold Summary

  • 2% Below List Price
  • $190/SF
  • 3 Days On Market

  Current Estimated Value $307,352

  Last Listing Agent Amber Hunt Whalen & Company

  118 Windridge Dr, Winchester, KY 40391
• 

  

  /42

  $249,000

  Sold Oct 22, 2025

  9 Apache Trail, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 1,750 Sq Ft
  • Built 1960

  Last Sold Summary

  • 6% Below List Price
  • $142/SF
  • 117 Days On Market

  Current Estimated Value $261,586

  Last Listing Agent Joyce Ratliff Tom Goebel & Company

  9 Apache Trail, Winchester, KY 40391
• 

  

  /34

  $405,000

  Sold May 26, 2026

  505 Lasalle Ct, Winchester, KY 40391

  • 5 Beds
  • 3 Baths
  • 2,944 Sq Ft
  • Built 1995

  Last Sold Summary

  • $138/SF
  • 1 Day On Market

  Current Estimated Value $399,048

  Last Listing Agent Amanda Thomas The Agency

  505 Lasalle Ct, Winchester, KY 40391
• 

  

  /92

  $364,900

  Sold Jul 31, 2025

  31 Mockingbird Valley Rd, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 2,520 Sq Ft
  • Built 1962

  Last Sold Summary

  • 6% Below List Price
  • $145/SF
  • 209 Days On Market

  Current Estimated Value $385,088

  Last Listing Agent Josh Wood Freedom Realty & Property Management

  31 Mockingbird Valley Rd, Winchester, KY 40391
• 

  

  /23

  $335,000

  Sold Aug 27, 2025

  413 Lyon Dr, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 2,936 Sq Ft
  • Built 1986

  Last Sold Summary

  • 4% Below List Price
  • $114/SF
  • 8 Days On Market

  Current Estimated Value $327,243

  Last Listing Agent Ray Rush Rush Real Estate

  413 Lyon Dr, Winchester, KY 40391
• 

  

  /17

  $86,008

  Sold Jul 30, 2025

  977 Muddy Creek Rd, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,030 Sq Ft
  • Built 1940

  Last Sold Summary

  • 28% Below List Price
  • $84/SF
  • 37 Days On Market

  Current Estimated Value $95,452

  Last Listing Agent Jason Szaks EXIT Town & Country Realtors

  977 Muddy Creek Rd, Winchester, KY 40391
• 

  

  /27

  $199,900

  Sold Jul 15, 2025

  139 W Hickman St, Winchester, KY 40391

  • 3 Beds
  • 1.5 Baths
  • 1,348 Sq Ft
  • Built 1940

  Last Sold Summary

  • $148/SF
  • 18 Days On Market

  Current Estimated Value $205,511

  Last Listing Agent Clay David Sutherland ERA Select Real Estate

  139 W Hickman St, Winchester, KY 40391
• 

  

  /31

  $295,000

  Sold Feb 24, 2026

  420 Willowbrook Rd, Winchester, KY 40391

  • 3 Beds
  • 3 Baths
  • 1,738 Sq Ft
  • Built 1980

  Last Sold Summary

  • $170/SF
  • 32 Days On Market

  Current Estimated Value $295,019

  Last Listing Agent Michelle Blackburn RE/MAX Creative, Winchester

  420 Willowbrook Rd, Winchester, KY 40391
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  /42

  $247,500

  Sold Jan 16, 2026

  125 Summerhill Way, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,333 Sq Ft
  • Built 2003

  Last Sold Summary

  • 5% Below List Price
  • $186/SF
  • 15 Days On Market

  Current Estimated Value $255,205

  Last Listing Agent Gwen Mathews Bluegrass Sotheby's International Realty

  125 Summerhill Way, Winchester, KY 40391

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