Recently Sold Winchester, KY Homes

• 

  

  

  /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 $426,622

  Last Listing Agent Craig Bridgewater Bridgewater Real Estate

  17 Hampton Ave, Winchester, KY 40391
• 

  

  

  /19

  $175,000 Sold Apr 18, 2025

  11 Shelley Dr, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,188 Sq Ft
  • Built 1970

  Last Sold Summary

  • 3% Below List Price
  • $147/SF
  • 5 Days On Market

  Current Estimated Value $190,097

  Last Listing Agent Tonya Morrow KY Local

  11 Shelley Dr, Winchester, KY 40391
• 

  

  

  /26

  $239,500 Sold Jul 15, 2025

  129 Bay Hill Dr, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 2,017 Sq Ft
  • Built 1998

  Last Sold Summary

  • 2% Below List Price
  • $119/SF
  • 26 Days On Market

  Current Estimated Value $238,730

  Last Listing Agent Vickie Skeens RE/MAX Elite Lexington

  129 Bay Hill 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 $373,324

  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 $287,106

  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 $395,211

  Last Listing Agent Erin Lewis Christies International Real Estate Bluegrass

  210 College St, Winchester, KY 40391
• 

  

  /64

  $360,000 Sold Oct 17, 2025

  309 Gallahadion Ct, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,920 Sq Ft
  • Built 2024

  Last Sold Summary

  • 3% Below List Price
  • $188/SF
  • 60 Days On Market

  Current Estimated Value $362,790

  Last Listing Agent Josh Wood Freedom Realty & Property Management

  309 Gallahadion Ct, Winchester, KY 40391
• 

  

  /23

  $130,000 Sold Apr 24, 2025

  103 Gary Ct, Winchester, KY 40391

  • 2 Beds
  • 1.5 Baths
  • 1,008 Sq Ft

  Last Sold Summary

  • 7% Below List Price
  • $129/SF
  • 13 Days On Market

  Current Estimated Value $144,500

  Last Listing Agent Dawn Wheeler United Real Estate Bluegrass

  103 Gary Ct, Winchester, KY 40391
• 

  

  /64

  $415,000 Sold Feb 25, 2026

  1857 Ironworks Rd, Winchester, KY 40391

  • 5 Beds
  • 2.5 Baths
  • 2,924 Sq Ft
  • Built 1865

  Last Sold Summary

  • 3% Below List Price
  • $142/SF
  • 70 Days On Market

  Current Estimated Value $413,670

  Last Listing Agent Meredith Walker Bluegrass Sotheby's International Realty

  1857 Ironworks Rd, Winchester, KY 40391
• 

  

  /23

  $225,000 Sold Aug 21, 2025

  26 Stefanie Ct, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,080 Sq Ft
  • Built 1972

  Last Sold Summary

  • $208/SF
  • 12 Days On Market

  Current Estimated Value $225,350

  Last Listing Agent Alyssa M Boley Coldwell Banker McMahan

  26 Stefanie Ct, Winchester, KY 40391
• 

  

  /50

  $465,000 Sold Aug 11, 2025

  701 Lisletown Ln, Winchester, KY 40391

  • 2 Beds
  • 2.5 Baths
  • 2,784 Sq Ft
  • Built 2008

  Last Sold Summary

  • $167/SF
  • 2 Days On Market

  Current Estimated Value $469,794

  Last Listing Agent Robin Jones Keller Williams Legacy Group

  701 Lisletown Ln, Winchester, KY 40391
• 

  /2

  $75,000 Sold Jan 05, 2026

  1341 Sewell Shop Rd, Winchester, KY 40391

  • Land
  • 5.75 Acres
  • $13,043 per Acre

  Last Sold Summary

  • 6% Below List Price
  • 10 Days On Market

  Last Listing Agent Zella Rosenthal Tom Goebel & Company

  1341 Sewell Shop Rd, Winchester, KY 40391
• 

  /2

  $555,000 Sold Jan 16, 2026

  184 Casa Landa Way, Winchester, KY 40391

  • 4 Beds
  • 3.5 Baths
  • 3,585 Sq Ft
  • Built 1998

  Last Sold Summary

  • 6% Below List Price
  • $155/SF

  Current Estimated Value $577,412

  Last Listing Agent Jim Woodrum RE/MAX Creative, Winchester

  184 Casa Landa Way, Winchester, KY 40391
• 

  

  /29

  $408,000 Sold Sep 12, 2025

  4732 Old Boonesboro Rd, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 2,361 Sq Ft
  • Built 1945

  Last Sold Summary

  • 18% Below List Price
  • $173/SF
  • 285 Days On Market

  Current Estimated Value $409,663

  Last Listing Agent Patrick Arvin Keller Williams Commonwealth

  4732 Old Boonesboro Rd, Winchester, KY 40391
• 

  

  /43

  $165,000 Sold May 20, 2025

  12005 Irvine Rd, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 1,130 Sq Ft
  • Built 1980

  Last Sold Summary

  • 13% Below List Price
  • $146/SF
  • 96 Days On Market

  Current Estimated Value $174,267

  Last Listing Agent Patrick Arvin Keller Williams Commonwealth

  12005 Irvine Rd, Winchester, KY 40391
• 

  

  /22

  $88,000 Sold May 08, 2025

  423 E Broadway St, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 2,363 Sq Ft
  • Built 1878

  Last Sold Summary

  • 76% Above List Price
  • $37/SF
  • 23 Days On Market

  Current Estimated Value $189,306

  Last Listing Agent Tanya McKee Bluegrass Auction, Appraisal & Realty, LLC

  423 E Broadway St, Winchester, KY 40391
• 

  

  /44

  $315,000 Sold Jun 27, 2025

  43 Skylark Dr, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 2,459 Sq Ft
  • Built 1981

  Last Sold Summary

  • 6% Below List Price
  • $128/SF
  • 70 Days On Market

  Current Estimated Value $334,670

  Last Listing Agent Chad Bowman The Brokerage

  43 Skylark Dr, Winchester, KY 40391
• 

  

  /28

  $265,000 Sold Jul 02, 2025

  609 Clintonville Rd, Winchester, KY 40391

  • 3 Beds
  • 1.5 Baths
  • 1,305 Sq Ft
  • Built 1980

  Last Sold Summary

  • 2% Above List Price
  • $203/SF
  • 2 Days On Market

  Current Estimated Value $264,172

  Last Listing Agent Craig Bridgewater Bridgewater Real Estate

  609 Clintonville Rd, Winchester, KY 40391
• 

  /2

  $350,000 Sold Aug 14, 2025

  Unlisted Address

  • 4 Beds
  • 2.5 Baths
  • 3,672 Sq Ft
  • Built 1960

  Last Sold Summary

  • $95/SF

  Current Estimated Value $339,409

  Last Listing Agent Null Non-Member Non-Member Office

  Unlisted Address
• 

  

  /12

  $9,000 Sold Sep 18, 2025

  406 W Washington St, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 1,428 Sq Ft
  • Built 1945

  Last Sold Summary

  • 10% Below List Price
  • $6/SF
  • 19 Days On Market

  Current Estimated Value $129,892

  Last Listing Agent Jack Rookard Rookard Real Estate Consultants

  406 W Washington St, Winchester, KY 40391
• 

  

  /79

  $425,000 Sold Feb 23, 2026

  1410 Dry Fork Creek Rd, Winchester, KY 40391

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

  Last Sold Summary

  • 15% Below List Price
  • $399/SF
  • 78 Days On Market

  Last Listing Agent Skyler Lewis Dream Maker Realty, LLC

  1410 Dry Fork Creek Rd, Winchester, KY 40391
• 

  

  /55

  $520,000 Sold May 15, 2025

  427 Calmes Blvd, Winchester, KY 40391

  • 4 Beds
  • 3.5 Baths
  • 4,659 Sq Ft
  • Built 1995

  Last Sold Summary

  • 4% Below List Price
  • $112/SF
  • 61 Days On Market

  Current Estimated Value $492,319

  Last Listing Agent Kymberly McCreary EXP Realty, LLC

  427 Calmes Blvd, Winchester, KY 40391
• 

  

  /24

  $188,000 Sold Jan 29, 2026

  27 Ashland Ave, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,653 Sq Ft
  • Built 1950

  Last Sold Summary

  • 6% Below List Price
  • $114/SF
  • 112 Days On Market

  Current Estimated Value $186,929

  Last Listing Agent Robin Mobley-Mosher Marshall Lane Real Estate - Lexington

  27 Ashland Ave, Winchester, KY 40391
• 

  

  /25

  $375,000 Sold Aug 29, 2025

  317 Hanover Dr, Winchester, KY 40391

  • 5 Beds
  • 3.5 Baths
  • 3,111 Sq Ft
  • Built 2001

  Last Sold Summary

  • 1% Below List Price
  • $121/SF
  • 8 Days On Market

  Current Estimated Value $377,496

  Last Listing Agent Mike Wheatley Bluegrass Properties Group

  317 Hanover Dr, Winchester, KY 40391
• 

  

  /60

  $545,000 Sold Oct 31, 2025

  445 Lynnway Dr, Winchester, KY 40391

  • 4 Beds
  • 3.5 Baths
  • 3,649 Sq Ft
  • Built 1993

  Last Sold Summary

  • $149/SF
  • 4 Days On Market

  Current Estimated Value $546,710

  Last Listing Agent Janna Chalfant Smith United Real Estate Bluegrass

  445 Lynnway Dr, Winchester, KY 40391
• 

  

  /27

  $380,000 Sold Nov 10, 2025

  5705 Mount Sterling Rd, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,980 Sq Ft
  • Built 1971

  Last Sold Summary

  • 5% Below List Price
  • $128/SF
  • 50 Days On Market

  Current Estimated Value $378,028

  Last Listing Agent Dale Hatton Dream Maker Realty, LLC

  5705 Mount Sterling Rd, Winchester, KY 40391
• 

  

  /102

  $525,000 Sold Dec 22, 2025

  1953 Cabin Creek Rd, Winchester, KY 40391

  • 6 Beds
  • 4.5 Baths
  • 3,846 Sq Ft
  • Built 1980

  Last Sold Summary

  • 4% Below List Price
  • $137/SF
  • 9 Days On Market

  Current Estimated Value $528,414

  Last Listing Agent Josh Wood Freedom Realty & Property Management

  1953 Cabin Creek Rd, Winchester, KY 40391
• 

  

  /28

  $345,000 Sold Jun 19, 2025

  512 Boone Ave, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 3,149 Sq Ft
  • Built 1950

  Last Sold Summary

  • 14% Below List Price
  • $110/SF
  • 58 Days On Market

  Current Estimated Value $377,734

  Last Listing Agent Jordan James Lifstyl Real Estate

  512 Boone Ave, Winchester, KY 40391
• 

  

  /65

  $380,000 Sold Jun 19, 2025

  399 Stonecrest Rd, Winchester, KY 40391

  • 3 Beds
  • 4 Baths
  • 4,572 Sq Ft
  • Built 1976

  Last Sold Summary

  • 4% Below List Price
  • $83/SF
  • 3 Days On Market

  Current Estimated Value $394,855

  Last Listing Agent ROBIN TRIMBLE HomeFirst Real Estate

  399 Stonecrest Rd, Winchester, KY 40391
• 

  

  /114

  $635,000 Sold Sep 30, 2025

  315 The Woods Ln, Winchester, KY 40391

  • 5 Beds
  • 4.5 Baths
  • 5,524 Sq Ft
  • Built 1995

  Last Sold Summary

  • 2% Below List Price
  • $115/SF
  • 63 Days On Market

  Current Estimated Value $622,074

  Last Listing Agent Terri McGraw FC Tucker Bluegrass

  315 The Woods Ln, Winchester, KY 40391
• 

  

  /30

  $189,900 Sold Mar 16, 2026

  357 E Washington St, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,328 Sq Ft
  • Built 1940

  Last Sold Summary

  • 5% Below List Price
  • $143/SF
  • 26 Days On Market

  Current Estimated Value $196,139

  Last Listing Agent Dylan Justice GSP Homes

  357 E Washington St, Winchester, KY 40391
• 

  

  /33

  $159,200 Sold Oct 09, 2025

  646 Laura Dr, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 1,534 Sq Ft
  • Built 1980

  Last Sold Summary

  • 6% Below List Price
  • $104/SF
  • 16 Days On Market

  Current Estimated Value $239,919

  Last Listing Agent Kimberly Brunson Hunter Real Estate

  646 Laura Dr, Winchester, KY 40391
• 

  

  /32

  $183,000 Sold Jul 30, 2025

  517 Hidden Hills Way, Winchester, KY 40391

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

  Last Sold Summary

  • $163/SF
  • 78 Days On Market

  Current Estimated Value $188,332

  Last Listing Agent Brenda Sipes Bridgewater Real Estate

  517 Hidden Hills Way, Winchester, KY 40391
• 

  

  /17

  $175,000 Sold May 07, 2025

  220 Jackson St, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 1,228 Sq Ft
  • Built 1940

  Last Sold Summary

  • $143/SF
  • 1 Day On Market

  Current Estimated Value $176,118

  Last Listing Agent Joanna Howell Bluegrass Properties Group

  220 Jackson St, Winchester, KY 40391
• 

  

  /61

  $220,000 Sold Nov 10, 2025

  313 Snowden Dr, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,232 Sq Ft
  • Built 1960

  Last Sold Summary

  • 12% Below List Price
  • $179/SF
  • 51 Days On Market

  Current Estimated Value $225,405

  Last Listing Agent Josh Wood Freedom Realty & Property Management

  313 Snowden Dr, Winchester, KY 40391
• 

  

  /53

  $80,000 Sold Apr 30, 2025

  307 Jackson St, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 1,629 Sq Ft
  • Built 1950

  Last Sold Summary

  • 33% Below List Price
  • $49/SF
  • 67 Days On Market

  Current Estimated Value $89,829

  Last Listing Agent Josh Wood Freedom Realty & Property Management

  307 Jackson St, Winchester, KY 40391
• 

  

  /32

  $285,000 Sold Jul 03, 2025

  602 Laura Dr, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,690 Sq Ft
  • Built 1976

  Last Sold Summary

  • 11% Below List Price
  • $169/SF
  • 168 Days On Market

  Current Estimated Value $287,760

  Last Listing Agent Ryan O'Gara Real Broker, LLC

  602 Laura Dr, Winchester, KY 40391
• 

  /2

  $401,500 Sold May 15, 2025

  Unlisted Address

  • 3 Beds
  • 2 Baths
  • 2,000 Sq Ft
  • Built 1998

  Last Sold Summary

  • $201/SF

  Current Estimated Value $409,226

  Last Listing Agent Null Non-Member Non-Member Office

  Unlisted Address
• 

  

  /17

  $595,000 Sold Nov 17, 2025

  304 Winterberry Dr, Winchester, KY 40391

  • 7 Beds
  • 4 Baths
  • 4,386 Sq Ft
  • Built 1999

  Last Sold Summary

  • 1% Below List Price
  • $136/SF
  • 10 Days On Market

  Current Estimated Value $592,964

  Last Listing Agent Beckie Moore Bluegrass Properties Group

  304 Winterberry Dr, Winchester, KY 40391
• 

  

  /18

  $246,500 Sold May 16, 2025

  6278 Irvine Rd, Winchester, KY 40391

  • 3 Beds
  • 1.5 Baths
  • 1,176 Sq Ft
  • Built 1978

  Last Sold Summary

  • 7% Below List Price
  • $210/SF
  • 35 Days On Market

  Current Estimated Value $268,492

  Last Listing Agent Angela Yonts EXP Realty, LLC

  6278 Irvine Rd, Winchester, KY 40391

Showing Results 121 - 160, Page 4 of 12