Recently Sold Winchester, KY Homes

• 

  

  

  /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
• 

  

  

  /10

  $325,000

  Sold Aug 29, 2025

  210 Cabin Creek Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,584 Sq Ft
  • Built 1999

  Last Sold Summary

  • $205/SF

  Current Estimated Value $342,449

  Last Listing Agent Janine Shackelford LPT Realty

  210 Cabin Creek Rd, Winchester, KY 40391
• 

  

  

  /36

  $261,000

  Sold Feb 04, 2026

  433 Wellington Way, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,234 Sq Ft
  • Built 2010

  Last Sold Summary

  • 2% Below List Price
  • $212/SF
  • 60 Days On Market

  Current Estimated Value $262,444

  Last Listing Agent Nick Ratliff Realty Team - Nicholas Ratliff Real Broker, LLC - Lexington

  433 Wellington Way, 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
• 

  

  /65

  $275,000

  Sold Aug 15, 2025

  151 Hilltop Dr, Winchester, KY 40391

  • 4 Beds
  • 1.5 Baths
  • 1,873 Sq Ft
  • Built 1960

  Last Sold Summary

  • 1% Below List Price
  • $147/SF
  • 130 Days On Market

  Current Estimated Value $278,703

  Last Listing Agent Jason Townsend Kentucky Residential Real Estate, LLC

  151 Hilltop Dr, Winchester, KY 40391
• 

  

  /63

  $445,000

  Sold May 22, 2026

  1911 Trapp-Goffs Corner Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,288 Sq Ft
  • Built 2000

  Last Sold Summary

  • 3% Below List Price
  • $345/SF
  • 51 Days On Market

  Last Listing Agent Cheri Shaffer Lifstyl Real Estate

  1911 Trapp-Goffs Corner Rd, Winchester, KY 40391
• 

  /2

  $610,000

  Sold Aug 29, 2025

  4560 Pine Ridge Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,848 Sq Ft
  • Built 1905

  Last Sold Summary

  • $330/SF
  • 1 Day On Market

  Current Estimated Value $602,378

  Last Listing Agent Natalie Avant Berkshire Hathaway HomeServices Foster Realtors

  4560 Pine Ridge Rd, 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
• 

  

  /35

  $325,000

  Sold Nov 21, 2025

  130 Hibiscus Ln, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 1,900 Sq Ft
  • Built 2000

  Last Sold Summary

  • 7% Below List Price
  • $171/SF
  • 19 Days On Market

  Current Estimated Value $343,201

  Last Listing Agent Ashley Barreto Indigo & Co

  130 Hibiscus Ln, Winchester, KY 40391
• 

  

  /31

  $292,500

  Sold May 22, 2026

  306 Trapp-Goffs Corner Rd, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 1,840 Sq Ft
  • Built 1974

  Last Sold Summary

  • 2% Below List Price
  • $159/SF
  • 1 Day On Market

  Current Estimated Value $293,151

  Last Listing Agent Patrick Arvin Keller Williams Commonwealth

  306 Trapp-Goffs Corner Rd, 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
• 

  

  /22

  $255,000

  Sold May 26, 2026

  35 Cherokee Ct, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 2,332 Sq Ft
  • Built 1968

  Last Sold Summary

  • 6% Below List Price
  • $109/SF
  • 123 Days On Market

  Current Estimated Value $259,130

  Last Listing Agent Brenda Rue Keller Williams Bluegrass Realty

  35 Cherokee Ct, 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
• 

  /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
• 

  /2

  $4,900,000

  Sold Dec 23, 2025

  175 Chatham Place, Winchester, KY 40391

  • 2 Beds
  • 3 Baths
  • 37,192 Sq Ft
  • Built 2007

  Last Sold Summary

  • 13% Below List Price
  • $132/SF
  • 111 Days On Market

  Current Estimated Value $5,168,026

  Last Listing Agent Garry Milton Milton and Associates Real Estate

  175 Chatham Place, Winchester, KY 40391
• 

  

  /51

  $340,000

  Sold Oct 30, 2025

  356 Boone Ave, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 3,200 Sq Ft
  • Built 1940

  Last Sold Summary

  • 5% Below List Price
  • $106/SF
  • 30 Days On Market

  Current Estimated Value $359,737

  Last Listing Agent Elizabeth Hodge Lifstyl Real Estate

  356 Boone Ave, Winchester, KY 40391
• 

  

  /15

  $280,000

  Sold Jul 17, 2026

  327 Newcastle Ln, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 1,693 Sq Ft
  • Built 2005

  Last Sold Summary

  • 6% Below List Price
  • $165/SF
  • 87 Days On Market

  Current Estimated Value $288,703

  Last Listing Agent Huong Dunn Bluegrass Property Exchange

  327 Newcastle Ln, 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
• 

  

  /33

  $340,000

  Sold Jul 10, 2026

  740 Pilot Ridge Ln, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,608 Sq Ft
  • Built 2017

  Last Sold Summary

  • $211/SF
  • 6 Days On Market

  Current Estimated Value $333,363

  Last Listing Agent Holly Goeing The Agency

  740 Pilot Ridge Ln, 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
• 

  

  /38

  $375,750

  Sold Apr 01, 2026

  6239 Old Boonesboro Rd, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 2,659 Sq Ft
  • Built 1960

  Last Sold Summary

  • 6% Below List Price
  • $141/SF
  • 121 Days On Market

  Current Estimated Value $378,745

  Last Listing Agent Kenya Woods United Real Estate Bluegrass

  6239 Old Boonesboro Rd, Winchester, KY 40391
• 

  

  /3

  $94,000

  Sold Aug 22, 2025

  2010 Athens Boonesboro Rd, Winchester, KY 40391

  • Land
  • 4.02 Acres
  • $23,383 per Acre

  Last Sold Summary

  • 14% Below List Price
  • 140 Days On Market

  Current Estimated Value $200,671

  Last Listing Agent Megan McCoy Keller Williams Legacy Group

  2010 Athens Boonesboro Rd, Winchester, KY 40391
• 

  

  /26

  $178,000

  Sold Apr 30, 2026

  356 Colby Ridge Blvd, Winchester, KY 40391

  • 2 Beds
  • 1.5 Baths
  • 1,102 Sq Ft
  • Built 2003

  Last Sold Summary

  • 3% Below List Price
  • $162/SF
  • 51 Days On Market

  Current Estimated Value $179,250

  Last Listing Agent Nena Honaker Tom Goebel & Company

  356 Colby Ridge Blvd, Winchester, KY 40391
• 

  

  /43

  $253,000

  Sold Jun 22, 2026

  564 Trapp-Goffs Corner Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,960 Sq Ft
  • Built 2000

  Last Sold Summary

  • 6% Below List Price
  • $129/SF
  • 54 Days On Market

  Current Estimated Value $257,093

  Last Listing Agent Felicia Mayes The Real Estate Co.

  564 Trapp-Goffs Corner Rd, Winchester, KY 40391
• 

  /2

  $85,000

  Sold Apr 15, 2026

  2465 Flanagan Station Rd, Winchester, KY 40391

  • Land
  • 3.68 Acres
  • $23,098 per Acre

  Last Sold Summary

  • 9 Days On Market

  Current Estimated Value $87,283

  Last Listing Agent Shari Frasure Keller Williams Commonwealth

  2465 Flanagan Station Rd, Winchester, KY 40391
• 

  

  /46

  $282,900

  Sold Jan 02, 2026

  165 Hilltop Dr, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,454 Sq Ft
  • Built 2020

  Last Sold Summary

  • 1% Below List Price
  • $195/SF
  • 6 Days On Market

  Current Estimated Value $285,638

  Last Listing Agent Tyson Walters Kassie & Associates

  165 Hilltop Dr, Winchester, KY 40391
• 

  

  /25

  $262,500

  Sold May 22, 2026

  398 Pine Ridge Rd, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 1,170 Sq Ft
  • Built 1977

  Last Sold Summary

  • 15% Below List Price
  • $224/SF
  • 97 Days On Market

  Current Estimated Value $267,937

  Last Listing Agent Amie Hieneman ERA Select Real Estate

  398 Pine Ridge Rd, Winchester, KY 40391
• 

  

  /52

  $320,000

  Sold Jul 29, 2026

  228 Holiday Rd, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 1,843 Sq Ft
  • Built 1979

  Last Sold Summary

  • 6% Below List Price
  • $174/SF
  • 11 Days On Market

  Current Estimated Value $331,598

  Last Listing Agent Caroline Mucci CENTURY 21 Commonwealth R E

  228 Holiday Rd, Winchester, KY 40391
• 

  

  /26

  $250,000

  Sold Feb 20, 2026

  21 Virginia Ave, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,749 Sq Ft
  • Built 1962

  Last Sold Summary

  • 4% Below List Price
  • $143/SF
  • 40 Days On Market

  Current Estimated Value $247,231

  Last Listing Agent Emily Crump eXp Realty, LLC

  21 Virginia Ave, Winchester, KY 40391
• 

  

  /19

  $199,900

  Sold Feb 12, 2026

  117 Buffalo Trace, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,072 Sq Ft
  • Built 1998

  Last Sold Summary

  • $186/SF
  • 49 Days On Market

  Current Estimated Value $201,521

  Last Listing Agent Nena Honaker Tom Goebel & Company

  117 Buffalo Trace, Winchester, KY 40391
• 

  

  /65

  $609,000

  Sold Jul 17, 2026

  6595 Mount Sterling Rd, Winchester, KY 40391

  • 5 Beds
  • 4 Baths
  • 4,515 Sq Ft
  • Built 2010

  Last Sold Summary

  • $135/SF
  • 21 Days On Market

  Current Estimated Value $606,153

  Last Listing Agent Brooke Otis Mullins RO&CO Real Estate

  6595 Mount Sterling Rd, Winchester, KY 40391
• 

  

  /31

  $205,000

  Sold Jun 12, 2026

  34 Hays St, Winchester, KY 40391

  • 4 Beds
  • 1.5 Baths
  • 2,450 Sq Ft
  • Built 1950

  Last Sold Summary

  • 8% Below List Price
  • $84/SF
  • 18 Days On Market

  Current Estimated Value $209,426

  Last Listing Agent Vickie Skeens RE/MAX Elite Lexington

  34 Hays St, Winchester, KY 40391
• 

  

  /51

  $428,000

  Sold Sep 04, 2025

  17 Hampton Ave, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 3,181 Sq Ft
  • Built 1960

  Last Sold Summary

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

  Current Estimated Value $447,011

  Last Listing Agent Craig Bridgewater Bridgewater Real Estate

  17 Hampton Ave, Winchester, KY 40391
• 

  

  /33

  $275,000

  Sold May 18, 2026

  402 Harney Dr, Winchester, KY 40391

  • 3 Beds
  • 1.5 Baths
  • 1,634 Sq Ft
  • Built 1979

  Last Sold Summary

  • $168/SF
  • 5 Days On Market

  Current Estimated Value $273,338

  Last Listing Agent Michelle Blackburn RE/MAX Creative, Winchester

  402 Harney Dr, Winchester, KY 40391
• 

  

  /34

  $380,000

  Sold Nov 21, 2025

  110 Hampton Avenue Exd, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 2,516 Sq Ft

  Last Sold Summary

  • 1% Above List Price
  • $151/SF
  • 5 Days On Market

  Current Estimated Value $362,707

  Last Listing Agent Erin Lewis Christies International Real Estate Bluegrass

  110 Hampton Avenue Exd, Winchester, KY 40391
• 

  

  /30

  $289,100

  Sold Nov 03, 2025

  223 Bartram Ct, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,606 Sq Ft
  • Built 2004

  Last Sold Summary

  • $180/SF
  • 46 Days On Market

  Current Estimated Value $292,001

  Last Listing Agent Jennifer Parsons RE/MAX Elite Lexington

  223 Bartram Ct, Winchester, KY 40391
• 

  

  /42

  $400,000

  Sold Dec 05, 2025

  210 College St, Winchester, KY 40391

  • 4 Beds
  • 3.5 Baths
  • 2,718 Sq Ft
  • Built 1895

  Last Sold Summary

  • 5% Below List Price
  • $147/SF
  • 59 Days On Market

  Current Estimated Value $398,794

  Last Listing Agent Erin Lewis Christies International Real Estate Bluegrass

  210 College St, Winchester, KY 40391
• 

  

  /34

  $444,000

  Sold Jun 24, 2026

  1478 Donaldson Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 2,442 Sq Ft
  • Built 2004

  Last Sold Summary

  • $182/SF
  • 2 Days On Market

  Current Estimated Value $446,514

  Last Listing Agent Jim Woodrum RE/MAX Creative, Winchester

  1478 Donaldson Rd, Winchester, KY 40391
• 

  

  /15

  $286,000

  Sold Jun 12, 2026

  110 Buckingham Ln, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,240 Sq Ft
  • Built 2001

  Last Sold Summary

  • 4% Above List Price
  • $231/SF
  • 3 Days On Market

  Current Estimated Value $289,894

  Last Listing Agent Oliver Winn ERA Select Real Estate

  110 Buckingham Ln, Winchester, KY 40391

Showing Results 81 - 120, Page 3 of 12