Recently Sold Winchester Homes

• 

  

  

  /8

  $15,000

  Sold Dec 30, 2025

  61 Melbourne St, Winchester, KY 40391

  • Land
  • 4,356 Sq Ft
  • $150,000 per Acre

  Last Sold Summary

  • 40% Below List Price
  • 57 Days On Market

  Current Estimated Value $108,274

  Last Listing Agent Brian Lewis Guide Realty, Inc.

  61 Melbourne St, Winchester, KY 40391
• Explore Winchester

• 

  

  

  /20

  $189,500

  Sold Dec 18, 2025

  13015 Irvine Rd, Winchester, KY 40391

  Last Sold Summary

  • 17% Below List Price
  • 134 Days On Market

  Last Listing Agent Mendel Tipton Natural Bridge Realty

  13015 Irvine Rd, Winchester, KY 40391
• 

  

  

  /41

  $265,000

  Sold Nov 12, 2025

  130 Village Ct, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 1,988 Sq Ft
  • Built 1970

  Last Sold Summary

  • 2% Below List Price
  • $133/SF
  • 4 Days On Market

  Current Estimated Value $276,408

  Last Listing Agent Joyce Ratliff Tom Goebel & Company

  130 Village Ct, Winchester, KY 40391
• 

  

  

  /29

  $285,000

  Sold Jun 12, 2026

  426 E Broadway St, Winchester, KY 40391

  • 5 Beds
  • 2 Baths
  • 1,838 Sq Ft
  • Built 1945

  Last Sold Summary

  • 1% Below List Price
  • $155/SF
  • 12 Days On Market

  Current Estimated Value $280,777

  Last Listing Agent Alyssa M Boley Coldwell Banker McMahan

  426 E Broadway St, Winchester, KY 40391
• 

  

  

  /14

  $125,000

  Sold Apr 01, 2026

  464 Ecton Rd, Winchester, KY 40391

  • Land
  • 1.03 Acres
  • $121,359 per Acre

  Last Sold Summary

  • 16% Below List Price
  • 3 Days On Market

  Current Estimated Value $130,253

  Last Listing Agent Vickie Skeens RE/MAX Elite Lexington

  464 Ecton Rd, Winchester, KY 40391
• 

  

  /8

  $160,000

  Sold Jul 13, 2026

  107 Patio St, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 864 Sq Ft
  • Built 1997

  Last Sold Summary

  • $185/SF
  • 0 Days On Market

  Current Estimated Value $160,815

  Last Listing Agent Sherry Stephens Murphy Realty Group

  107 Patio St, Winchester, KY 40391
• 

  

  /25

  $223,000

  Sold Nov 04, 2025

  204 Crawford Ct, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 1,636 Sq Ft
  • Built 1960

  Last Sold Summary

  • 3% Below List Price
  • $136/SF
  • 1 Day On Market

  Current Estimated Value $230,681

  Last Listing Agent Tisha Monte Bluegrass Properties Group

  204 Crawford Ct, Winchester, KY 40391
• 

  

  /16

  $165,000

  Sold Apr 30, 2026

  47 Buckner St, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,635 Sq Ft
  • Built 1930

  Last Sold Summary

  • 8% Below List Price
  • $101/SF
  • 24 Days On Market

  Current Estimated Value $167,928

  Last Listing Agent Michael Hilario The Agency

  47 Buckner St, Winchester, KY 40391
• 

  

  /20

  $217,500

  Sold May 22, 2026

  7 Hiawatha Trail, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,190 Sq Ft
  • Built 1968

  Last Sold Summary

  • 3% Below List Price
  • $183/SF
  • 10 Days On Market

  Current Estimated Value $215,704

  Last Listing Agent Serena Cassidy Coldwell Banker McMahan

  7 Hiawatha Trail, Winchester, KY 40391
• 

  

  /39

  $340,000

  Sold Oct 10, 2025

  219 Hampton Ave, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,929 Sq Ft
  • Built 1972

  Last Sold Summary

  • 7% Below List Price
  • $116/SF
  • 48 Days On Market

  Current Estimated Value $344,425

  Last Listing Agent Jo Gawthrop Keller Williams Bluegrass Realty

  219 Hampton Ave, Winchester, KY 40391
• 

  

  /28

  $83,000

  Sold May 08, 2026

  32 Hays St, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,540 Sq Ft
  • Built 1950

  Last Sold Summary

  • 8% Below List Price
  • $54/SF
  • 5 Days On Market

  Current Estimated Value $96,246

  Last Listing Agent Christa Joynt Keller Williams Commonwealth

  32 Hays St, Winchester, KY 40391
• 

  

  /30

  $180,000

  Sold Jul 02, 2026

  217 S Highland St, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 2,683 Sq Ft
  • Built 1930

  Last Sold Summary

  • 31% Below List Price
  • $67/SF
  • 151 Days On Market

  Current Estimated Value $206,616

  Last Listing Agent Michael Hilario The Agency

  217 S Highland St, Winchester, KY 40391
• 

  

  /27

  $210,000

  Sold Sep 04, 2025

  305 Geronimo Ct, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,150 Sq Ft
  • Built 1999

  Last Sold Summary

  • 5% Below List Price
  • $183/SF
  • 1 Day On Market

  Current Estimated Value $219,017

  Last Listing Agent Aaron Kendall Lifstyl Real Estate

  305 Geronimo Ct, Winchester, KY 40391
• 

  

  /33

  $219,900

  Sold May 28, 2026

  21 Kentucky St, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,340 Sq Ft
  • Built 1920

  Last Sold Summary

  • $164/SF
  • 2 Days On Market

  Current Estimated Value $213,701

  Last Listing Agent Jenny Mateyoke Keller Williams Legacy Group

  21 Kentucky St, Winchester, KY 40391
• 

  

  /20

  $205,000

  Sold Jul 27, 2026

  301 Snowden Dr, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,386 Sq Ft
  • Built 1960

  Last Sold Summary

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

  Current Estimated Value $211,177

  Last Listing Agent Julia Lark The Brokerage

  301 Snowden Dr, Winchester, KY 40391
• 

  

  /26

  $200,000

  Sold Oct 02, 2025

  34 N Burns Ave, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,500 Sq Ft
  • Built 1945

  Last Sold Summary

  • 11% Below List Price
  • $133/SF
  • 8 Days On Market

  Current Estimated Value $214,473

  Last Listing Agent Ashley Barreto Indigo & Co

  34 N Burns Ave, Winchester, KY 40391
• 

  

  /16

  $214,900

  Sold Dec 05, 2025

  15 Holly Ave, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • Built 2025

  Last Sold Summary

  • 4% Below List Price
  • $179/SF
  • 52 Days On Market

  Current Estimated Value $217,595

  Last Listing Agent Nena Honaker Tom Goebel & Company

  15 Holly Ave, Winchester, KY 40391
• 

  

  /26

  $259,000

  Sold Jun 22, 2026

  86 Bon-Haven Ave, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 2,295 Sq Ft
  • Built 1960

  Last Sold Summary

  • 4% Below List Price
  • $113/SF
  • 1 Day On Market

  Current Estimated Value $263,355

  Last Listing Agent Tracey Goebel Tom Goebel & Company

  86 Bon-Haven Ave, Winchester, KY 40391
• 

  

  /44

  $267,000

  Sold Mar 24, 2026

  146 W Lexington Ave, Winchester, KY 40391

  • 8 Beds
  • 3 Baths
  • 3,393 Sq Ft
  • Built 1940

  Last Sold Summary

  • 1% Below List Price
  • $79/SF
  • 54 Days On Market

  Current Estimated Value $273,739

  Last Listing Agent KB Realty Group -Kevin Bradley KB Realty Group

  146 W Lexington Ave, Winchester, KY 40391
• 

  

  /22

  $156,000

  Sold Jan 16, 2026

  146 Cook Ave, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,274 Sq Ft
  • Built 1940

  Last Sold Summary

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

  Current Estimated Value $164,871

  Last Listing Agent Autumn Johannes National Real Estate

  146 Cook Ave, Winchester, KY 40391
• 

  

  /30

  $310,900

  Sold Sep 12, 2025

  115 Hampton Ave, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 3,042 Sq Ft
  • Built 1960

  Last Sold Summary

  • 4% Below List Price
  • $102/SF
  • 2 Days On Market

  Current Estimated Value $346,790

  Last Listing Agent Lauren Ball Deborah Ball Realty

  115 Hampton Ave, Winchester, KY 40391
• 

  

  /50

  $220,000

  Sold Jun 18, 2026

  314 Snowden Dr, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,196 Sq Ft
  • Built 1960

  Last Sold Summary

  • 2% Below List Price
  • $184/SF
  • 1 Day On Market

  Current Estimated Value $223,189

  Last Listing Agent Josh Wood Freedom Realty & Property Management

  314 Snowden Dr, Winchester, KY 40391
• 

  

  /17

  $190,000

  Sold Sep 10, 2025

  114 Sunset Heights, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,059 Sq Ft
  • Built 1960

  Last Sold Summary

  • 3% Below List Price
  • $179/SF
  • 50 Days On Market

  Current Estimated Value $191,407

  Last Listing Agent Susan Baldwin Threshold Real Estate Services

  114 Sunset Heights, Winchester, KY 40391
• 

  

  /35

  $355,000

  Sold Aug 06, 2026

  411 Skylark Dr, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,591 Sq Ft
  • Built 1989

  Last Sold Summary

  • 1% Above List Price
  • $137/SF
  • 0 Days On Market

  Current Estimated Value $344,192

  Last Listing Agent Jennifer Hickman Keller Williams Commonwealth

  411 Skylark Dr, Winchester, KY 40391
• 

  

  /58

  $239,900

  Sold Jun 08, 2026

  3610 Stamper Dr, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,148 Sq Ft
  • Built 1986

  Last Sold Summary

  • $209/SF
  • 4 Days On Market

  Current Estimated Value $240,558

  Last Listing Agent Pete doCouto Plum Tree Realty

  3610 Stamper Dr, Winchester, KY 40391
• 

  

  /60

  $249,900

  Sold Jul 22, 2026

  17 Holiday Rd, Winchester, KY 40391

  • 3 Beds
  • 1.5 Baths
  • 1,161 Sq Ft
  • Built 1992

  Last Sold Summary

  • $215/SF
  • 8 Days On Market

  Current Estimated Value $250,763

  Last Listing Agent Josh Wood Freedom Realty & Property Management

  17 Holiday Rd, Winchester, KY 40391
• 

  

  /38

  $173,000

  Sold Sep 22, 2025

  44 5th St, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,270 Sq Ft
  • Built 1952

  Last Sold Summary

  • 2% Above List Price
  • $136/SF
  • 2 Days On Market

  Current Estimated Value $181,397

  Last Listing Agent Tirza Howard The Howard Realty Co

  44 5th St, Winchester, KY 40391
• 

  

  /18

  $200,000

  Sold Jan 14, 2026

  245 Ecton Rd, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,074 Sq Ft
  • Built 1940

  Last Sold Summary

  • 9% Below List Price
  • $186/SF
  • 2 Days On Market

  Current Estimated Value $201,682

  Last Listing Agent Anthony Gigilo ListWithFreedom.com

  245 Ecton Rd, Winchester, KY 40391
• 

  

  /28

  $203,900

  Sold Dec 10, 2025

  25 Hiawatha Trail, Winchester, KY 40391

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

  Last Sold Summary

  • 3% Below List Price
  • $220/SF
  • 35 Days On Market

  Current Estimated Value $204,810

  Last Listing Agent Sarah Hess Keller Williams Commonwealth

  25 Hiawatha Trail, Winchester, KY 40391
• 

  

  /41

  $247,000

  Sold Sep 19, 2025

  3588 Stamper Dr, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,530 Sq Ft
  • Built 1987

  Last Sold Summary

  • 1% Below List Price
  • $161/SF
  • 4 Days On Market

  Current Estimated Value $251,494

  Last Listing Agent Zach Johnson The Brokerage

  3588 Stamper Dr, Winchester, KY 40391
• 

  

  /27

  $355,000

  Sold Jul 06, 2026

  17 W Lexington Ave, Winchester, KY 40391

  • 8 Beds
  • 8 Baths
  • 4,000 Sq Ft

  Last Sold Summary

  • 9% Below List Price
  • $89/SF
  • 25 Days On Market

  Current Estimated Value $382,102

  Last Listing Agent Libby VanMeter Marshall Lane Real Estate - Lexington

  17 W Lexington Ave, Winchester, KY 40391
• 

  

  /21

  $240,000

  Sold Jun 09, 2026

  720 Estes Dr, Winchester, KY 40391

  • 3 Beds
  • 1.5 Baths
  • 1,494 Sq Ft
  • Built 1970

  Last Sold Summary

  • 2% Below List Price
  • $161/SF
  • 28 Days On Market

  Current Estimated Value $243,267

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

  720 Estes Dr, Winchester, KY 40391
• 

  

  /7

  $55,000

  Sold Nov 06, 2025

  76 Clay St, Winchester, KY 40391

  • 1,768 Sq Ft
  • Built 1945

  Last Sold Summary

  • $31/SF
  • 2 Days On Market

  Current Estimated Value $61,103

  Last Listing Agent Brian Lewis Guide Realty, Inc.

  76 Clay St, Winchester, KY 40391
• 

  

  /32

  $263,000

  Sold Sep 05, 2025

  2 Chickadee Ln, Winchester, KY 40391

  • 3 Beds
  • 1.5 Baths
  • 1,397 Sq Ft
  • Built 1960

  Last Sold Summary

  • 1% Above List Price
  • $188/SF
  • 2 Days On Market

  Current Estimated Value $264,065

  Last Listing Agent Ashley Spencer Keller Williams Commonwealth

  2 Chickadee Ln, Winchester, KY 40391
• 

  

  /43

  $356,000

  Sold Jul 10, 2026

  274 Greenway Dr, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 2,208 Sq Ft
  • Built 1970

  Last Sold Summary

  • 2% Above List Price
  • $161/SF
  • 1 Day On Market

  Current Estimated Value $350,117

  Last Listing Agent Michelle Blackburn RE/MAX Creative, Winchester

  274 Greenway Dr, Winchester, KY 40391
• 

  

  /51

  $303,000

  Sold Jan 16, 2026

  22 N Bloomfield Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,913 Sq Ft
  • Built 1919

  Last Sold Summary

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

  Current Estimated Value $307,676

  Last Listing Agent Libby VanMeter Marshall Lane Real Estate - Lexington

  22 N Bloomfield Rd, Winchester, KY 40391
• 

  

  /21

  $130,000

  Sold Aug 07, 2026

  9 Linden Ave, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 886 Sq Ft
  • Built 1945

  Last Sold Summary

  • 13% Below List Price
  • $147/SF
  • 69 Days On Market

  Current Estimated Value $138,740

  Last Listing Agent Emily Hacker-Todd CENTURY 21 Advantage Realty

  9 Linden Ave, Winchester, KY 40391
• 

  /2

  $89,000

  Sold Dec 18, 2025

  13067 Irvine Rd, Winchester, KY 40391

  • Land
  • 7.86 Acres
  • $11,323 per Acre

  Last Sold Summary

  • 78 Days On Market

  Last Listing Agent Mendel Tipton Natural Bridge Realty

  13067 Irvine Rd, Winchester, KY 40391
• 

  

  /28

  $131,000

  Sold Mar 12, 2026

  46 Judy Ann Ct, Winchester, KY 40391

  • 2 Beds
  • 1.5 Baths
  • 960 Sq Ft

  Last Sold Summary

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

  Current Estimated Value $134,900

  Last Listing Agent Lukas Owens The Brokerage

  46 Judy Ann Ct, Winchester, KY 40391
• 

  

  /31

  $249,900

  Sold Jul 28, 2026

  312 Buffalo Trace, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,284 Sq Ft
  • Built 2001

  Last Sold Summary

  • $195/SF
  • 10 Days On Market

  Current Estimated Value $249,453

  Last Listing Agent Paula Cole The Agency

  312 Buffalo Trace, Winchester, KY 40391

Showing Results 1 - 40, Page 1 of 5