Winchester, KY Homes

• 

  

  

  /32

  Est $311,837

  Not Listed For Sale

  2615 Ironworks Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,694 Sq Ft
  • Built 1965

  2615 Ironworks Rd, Winchester, KY 40391

  Last Sold Summary

  • 1 Day On Market

  Last Listing Agent Jim Woodrum RE/MAX Creative, Winchester
• 

  

  

  /62

  $484,900

  Pending

  • 3 Beds
  • 2 Baths
  • 2,844 Sq Ft

  919 Elkin Station Rd, Winchester, KY 40391

  Enjoy country living on approximately seven acres at 919 Elkin Station Road! A welcoming wraparound front porch sets the tone for this spacious three-bedroom, two-bath home featuring beautiful hardwood floors throughout. The kitchen is enhanced by granite countertops, while a charming sunroom offers a cozy place to relax and enjoy the surrounding views. A versatile bonus room is perfect for a

  Lori Tolson Lifstyl Real Estate

  919 Elkin Station Rd, Winchester, KY 40391
• 

  

  

  /48

  $550,000

  Sold Sep 04, 2025

  594 Earlymeade Dr, Winchester, KY 40391

  • 5 Beds
  • 3 Baths
  • 3,489 Sq Ft
  • Built 2007

  Last Sold Summary

  • 4% Below List Price
  • $158/SF
  • 43 Days On Market

  Current Estimated Value $565,206

  Last Listing Agent Alyssa M Boley Coldwell Banker McMahan

  594 Earlymeade Dr, Winchester, KY 40391
• 

  

  

  /45

  Est $489,007

  Not Listed For Sale

  1159 Cabin Creek Rd, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 2,244 Sq Ft
  • Built 2007

  1159 Cabin Creek Rd, Winchester, KY 40391

  Last Sold Summary

  • 14 Days On Market

  Last Listing Agent Kimberly Fields Coldwell Banker McMahan
• 

  

  /2

  $1,200,000

  $596K PRICE INCREASE

  • Land
  • 24.15 Acres
  • $49,689 per Acre

  1395 Two Mile Rd, Winchester, KY 40391

  PLANNED DEVELOPMENT INVESTMENT INVESTMENT OPPORTUNITY! Already zoned Planned Development! There is an approximately 24 acre tract zoned for all forms of Residential use. (In addition there is an approximately 21 acre Residential tract that adjoins the Winchester Country Club. The two Residential tracts have access to gravity flow sewer. Sewer maps available. The remaining

  Garnett Davis Tom Goebel & Company

  1395 Two Mile Rd, 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
• 

  

  /15

  Est $325,146

  Not Listed For Sale

  158 Cabin Creek Heights, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,580 Sq Ft
  • Built 2005

  158 Cabin Creek Heights, Winchester, KY 40391

  Last Sold Summary

  • 5 Days On Market

  Last Listing Agent Sondra Clark Taylor Real Estate, LLC
• 

  

  /59

  $499,900

  • 4 Beds
  • 3 Baths
  • 5,646 Sq Ft

  16 Manor Dr, Winchester, KY 40391

  One Time Homeowner! Beautiful fieldstone ranch on full finished basement. 4 Bedrooms, 3 full bathrooms. This home has a very large great room, perfect for entertaining! Home has a new roof and siding as of 2024, new windows as of 2025. Home has tons of storage and tons of character. Come see this wonderful house and make it your forever home!

  Zella Rosenthal Tom Goebel & Company

  16 Manor Dr, Winchester, KY 40391
• 

  

  /75

  $600,000

  Sold May 29, 2026

  905 Pretty Run Rd, Winchester, KY 40391

  • 3 Beds
  • 3.5 Baths
  • 3,391 Sq Ft
  • Built 1997

  Last Sold Summary

  • $177/SF
  • 3 Days On Market

  Current Estimated Value $595,025

  Last Listing Agent Niki Wiley Bluegrass Sotheby's International Realty

  905 Pretty Run Rd, Winchester, KY 40391
• 

  

  /43

  Est $528,872

  Not Listed For Sale

  2100 Ecton Rd, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 2,060 Sq Ft
  • Built 1978

  2100 Ecton Rd, Winchester, KY 40391

  Last Sold Summary

  • 35 Days On Market

  Last Listing Agent Patrick Arvin Keller Williams Commonwealth
• 

  /2

  $110,000

  • Land
  • 16,552 Sq Ft
  • $289,474 per Acre

  200 Duclair Dr, Winchester, KY 40391

  Looking for a place to build a Upscale homein Central Kentucky? The Reserve is what Winchester has been waiting for! The development has 38 large lots that overlook central KY bluegrass. This Luxury subdivision is going to be the place to built your Dream home.

  John Wilson Bluegrass Properties Group

  200 Duclair Dr, Winchester, KY 40391
• 

  

  /64

  $490,000

  Sold Aug 05, 2026

  182 Chardonnay Ct, Winchester, KY 40391

  • 5 Beds
  • 2.5 Baths
  • 3,097 Sq Ft
  • Built 1994

  Last Sold Summary

  • 2% Below List Price
  • $158/SF
  • 10 Days On Market

  Current Estimated Value $497,650

  Last Listing Agent Kathryn Cheuvront Coldwell Banker McMahan

  182 Chardonnay Ct, Winchester, KY 40391
• 

  

  /44

  Est $527,646

  Not Listed For Sale

  601 Wades Mill Rd, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 2,070 Sq Ft
  • Built 2000

  601 Wades Mill Rd, Winchester, KY 40391

  Last Sold Summary

  • 7 Days On Market

  Last Listing Agent Kelly Nisbet Coldwell Banker McMahan
• 

  

  /34

  $274,900

  Pending

  • 4 Beds
  • 2.5 Baths
  • 1,377 Sq Ft

  304 Sandra Dr, Winchester, KY 40391

  Welcome to 304 Sandra Drive. This 4 bedroom, 2 bath ranch is quietly nestled within the desirable Westmeade subdivision. While location is obvious, this property features many updates that can be seen throughout. Multiple primary bedroom with on-suites, large backyard, new HVAC and water heater, including duct work, and so much more. Schedule your showing today!

  Michael Hilario The Agency

  304 Sandra Dr, 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
• 

  

  /41

  Est $667,526

  Not Listed For Sale

  357 Wades Mill Rd, Winchester, KY 40391

  • 4 Beds
  • 3.5 Baths
  • 3,007 Sq Ft
  • Built 2002

  357 Wades Mill Rd, Winchester, KY 40391

  Last Sold Summary

  • 15 Days On Market

  Last Listing Agent Emily Belcher Rector Hayden Realtors
• 

  

  /34

  $229,000

  • 3 Beds
  • 2 Baths
  • 1,297 Sq Ft

  13 Long Ave, Winchester, KY 40391

  Charming 3 bedroom, 2 bath home situated on a large, level lot! Relax and enjoy the inviting covered front porch, perfect for morning coffee or evening unwinding. Inside, you'll find a spacious living room and dining room featuring beautiful hardwood floors that add warmth and character. The generous yard offers plenty of space for outdoor entertaining, gardening, play or future possibilities.

  Kathryn Cheuvront Coldwell Banker McMahan

  13 Long 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
• 

  

  /61

  Est $578,288

  Not Listed For Sale

  1063 Wades Mill Rd, Winchester, KY 40391

  • 4 Beds
  • 3.5 Baths
  • 3,958 Sq Ft
  • Built 2000

  1063 Wades Mill Rd, Winchester, KY 40391

  Last Sold Summary

  • 180 Days On Market

  Last Listing Agent Joseph Smallwood Christies International Real Estate Bluegrass
• 

  

  /38

  $484,900

  New Construction Pending

  • 4 Beds
  • 3 Baths
  • 2,418 Sq Ft

  414 Fairholme Way, Winchester, KY 40391

  Step into a lifestyle where modern luxury and brand-new construction come together seamlessly. This home is perfectly positioned with golf course views and unforgettable sunset skies, this newly built home offers the kind of setting that turns ordinary evenings into your favorite part of the day—without sacrificing style, comfort, or convenience. Inside, soaring vaulted ceilings and a warm

  Morgan Withrow The Brokerage

  414 Fairholme Way, Winchester, KY 40391
• 

  

  /71

  $410,000

  Sold Nov 07, 2025

  188 Big Stoner Rd, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,388 Sq Ft
  • Built 2001

  Last Sold Summary

  • 2% Below List Price
  • $172/SF
  • 9 Days On Market

  Current Estimated Value $430,473

  Last Listing Agent Trina Penn RE/MAX Creative Realty

  188 Big Stoner Rd, Winchester, KY 40391
• 

  

  /3

  Est $365,873

  Not Listed For Sale

  1591 Gay Evans Rd, Winchester, KY 40391

  • 3 Beds
  • 1,260 Sq Ft
  • Built 1940

  1591 Gay Evans Rd, Winchester, KY 40391

  Last Sold Summary

  • 17 Days On Market

  Last Listing Agent Holly Goeing The Agency
• 

  

  /3

  $399,000

  • Land
  • 11.3 Acres
  • $35,310 per Acre

  0 Fairholme Way, Winchester, KY 40391

  11 acres of golf course adjacent land with development plan. Owner/Broker. Road and utility estimates available upon request. A list of individuals interested in lots available upon contract.

  Steve Adams Steven D Adams Real Estate Services, LLC

  0 Fairholme Way, Winchester, KY 40391
• 

  

  /73

  $325,000

  Sold Sep 23, 2025

  407 Fairholme Way, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,805 Sq Ft
  • Built 2021

  Last Sold Summary

  • 4% Below List Price
  • $180/SF
  • 123 Days On Market

  Current Estimated Value $339,136

  Last Listing Agent Josh Wood Freedom Realty & Property Management

  407 Fairholme Way, Winchester, KY 40391
• 

  

  /96

  Est $795,414

  Not Listed For Sale

  1995 Gay Evans Rd, Winchester, KY 40391

  • 4 Beds
  • 3.5 Baths
  • 3,272 Sq Ft
  • Built 1998

  1995 Gay Evans Rd, Winchester, KY 40391

  Last Sold Summary

  • 82 Days On Market

  Last Listing Agent Andrea Coughtry Lifstyl Real Estate
• 

  

  /26

  $274,900

  $5K PRICE DROP Pending

  • 3 Beds
  • 2.5 Baths
  • 1,604 Sq Ft

  136 Sturbridge Ln, Winchester, KY 40391

  Good things absolutely do come in affordable packages! This well maintained 3 bed 2.5 bath home on the Lexington side of Winchester has a beautiful back yard with a deck and built-in porch swing. It is privacy fenced and ready for you to enjoy, but not at the expense of access to town! With shopping right around the corner, and access to the highway not far off, this home would be great for

  Sarah MacHarg Kentucky Land and Home

  136 Sturbridge Ln, Winchester, KY 40391
• 

  

  /40

  $210,000

  Sold Sep 11, 2025

  635 Lisletown Ln, Winchester, KY 40391

  • 2 Beds
  • 2 Baths
  • 1,628 Sq Ft
  • Built 1981

  Last Sold Summary

  • 12% Below List Price
  • $129/SF
  • 31 Days On Market

  Current Estimated Value $222,356

  Last Listing Agent Robin Jones Keller Williams Legacy Group

  635 Lisletown Ln, Winchester, KY 40391
• 

  

  /60

  Est $162,687

  Not Listed For Sale

  1333 Jackson Ferry Rd, Winchester, KY 40391

  • 2 Beds
  • 2 Baths
  • 1,492 Sq Ft
  • Built 1964

  1333 Jackson Ferry Rd, Winchester, KY 40391

  Last Sold Summary

  • 60 Days On Market

  Last Listing Agent Teresa Richmond Freedom Realty & Property Management
• 

  

  /15

  $128,800

  • Land
  • 2.3 Acres
  • $56,000 per Acre

  110 Knox Ct, Winchester, KY 40391

  This exceptional 2.3 acre homesite offers the perfect canvas to bring your vision to life. With ample space, a prime cul-de-sac setting, and stunning surroundings, it's an ideal opportunity to create the custom home you've always wanted. Located in The Reserve, one of Winchester's premier subdivisions, this property boasts scenic daytime views and unforgettable sunsets each evening. Enjoy the

  Jarran Thomas The Agency

  110 Knox Ct, Winchester, KY 40391
• 

  

  /74

  $350,000

  Sold Mar 06, 2026

  4611 Colby Rd, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 3,712 Sq Ft
  • Built 1980

  Last Sold Summary

  • $94/SF
  • 2 Days On Market

  Current Estimated Value $359,577

  Last Listing Agent Nancy Smith Rector Hayden Realtors

  4611 Colby Rd, Winchester, KY 40391
• 

  

  /91

  Est $383,013

  Not Listed For Sale

  2184 Cole Rd, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,514 Sq Ft
  • Built 1970

  2184 Cole Rd, Winchester, KY 40391

  Last Sold Summary

  • 11 Days On Market

  Last Listing Agent Greg Wood Freedom Realty & Property Management
• 

  

  /57

  $340,000

  $10K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 3,261 Sq Ft

  443 S Maple St, Winchester, KY 40391

  Full of history and charm, this 1905 home sits on one of Winchester's most beloved and cherished streets, a place where homes like this are held onto for generations. It offers a rare opportunity to own a piece of the past while creating something truly your own. The inviting, oversized front porch sets the tone, perfect for quiet mornings, evening conversations, and the simple moments that make

  Terra Long Keller Williams Commonwealth

  443 S Maple St, Winchester, KY 40391
• 

  

  /33

  $340,000

  Sold May 12, 2026

  1270 Sewell Shop Rd, Winchester, KY 40391

  • 5 Beds
  • 2 Baths
  • 1,952 Sq Ft
  • Built 2020

  Last Sold Summary

  • 7% Below List Price
  • $174/SF
  • 73 Days On Market

  Current Estimated Value $342,910

  Last Listing Agent Meggan Batey Keller Williams Legacy Group

  1270 Sewell Shop Rd, Winchester, KY 40391
• 

  

  /47

  Est $410,904

  Not Listed For Sale

  520 Bailey Ln, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 2,400 Sq Ft
  • Built 1980

  520 Bailey Ln, Winchester, KY 40391

  Last Sold Summary

  • 51 Days On Market

  Last Listing Agent Paul Waddelow Hand in Hand Realty Central KY
• 

  

  /92

  $795,000

  Pending

  • 3 Beds
  • 3 Baths
  • 3,336 Sq Ft

  6356 Van Meter Rd, Winchester, KY 40391

  **Click on the Virtual Tour section to see the video walk through!** Nestled in the peaceful countryside of Winchester, this charming property on Van Meter Road offers the perfect blend of privacy, comfort, access and room to roam. Set on 13.74 beautiful, fenced acres and located within minutes of I-64, I-75 and the Mountain Parkway, this unique property offers easy access to Lexington,

  Josh Wood Freedom Realty & Property Management

  6356 Van Meter Rd, 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
• 

  

  /23

  Est $262,493

  Not Listed For Sale

  421 Jameson Way, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,487 Sq Ft
  • Built 2003

  421 Jameson Way, Winchester, KY 40391

  Last Sold Summary

  • 9 Days On Market

  Last Listing Agent Cathleen Gedeon CENTURY 21 Advantage Realty
• 

  /2

  $10,000

  Pending

  • Land
  • 2,613 Sq Ft
  • $166,667 per Acre

  75 4th St, Winchester, KY 40391

  Explore the opportunity to build your next home or investment property on this 0.06-acre residential lot located at 75 4th Street. Nestled in an established neighborhood, this lot offers convenient access to local amenities, schools, and nearby roadways. With public utilities available in the area, it's a great option for new construction or future development. Whether you're a builder, investor,

  Bob Sophiea eXp Realty, LLC

  75 4th St, Winchester, KY 40391
• 

  

  /82

  $385,000

  Sold Nov 07, 2025

  1138 Lafayette Blvd, Winchester, KY 40391

  • 3 Beds
  • 3 Baths
  • 2,300 Sq Ft
  • Built 1995

  Last Sold Summary

  • 4% Above List Price
  • $167/SF
  • 1 Day On Market

  Current Estimated Value $371,391

  Last Listing Agent Josh Wood Freedom Realty & Property Management

  1138 Lafayette Blvd, Winchester, KY 40391
• 

  

  /54

  Est $276,910

  Not Listed For Sale

  427 Jameson Way, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,776 Sq Ft
  • Built 2002

  427 Jameson Way, Winchester, KY 40391

  Last Sold Summary

  • 121 Days On Market

  Last Listing Agent Christa Joynt Keller Williams Commonwealth

Showing Results 161 - 200, Page 5 of 18