Winchester, KY Homes

• 

  

  

  /17

  Est $310,096

  Not Listed For Sale

  129 S Highland St, Winchester, KY 40391

  • 6 Beds
  • 4 Baths
  • 3,608 Sq Ft
  • Built 1940

  129 S Highland St, Winchester, KY 40391

  Last Sold Summary

  • 86 Days On Market

  Last Listing Agent Joshua Lynch The Brokerage
• 

  

  /2

  $110,000

  • Land
  • 11,761 Sq Ft
  • $407,407 per Acre

  125 Jacob Ct, 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

  125 Jacob Ct, Winchester, KY 40391
• 

  

  

  /34

  $349,000

  Sold Jul 16, 2026

  405 Tremont Ln, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,274 Sq Ft
  • Built 2005

  Last Sold Summary

  • $153/SF
  • 6 Days On Market

  Current Estimated Value $351,826

  Last Listing Agent Darryl Bond Guide Realty, Inc.

  405 Tremont Ln, Winchester, KY 40391
• 

  

  

  /17

  Est $165,033

  Not Listed For Sale

  21 Franklin Ave, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,006 Sq Ft
  • Built 1940

  21 Franklin Ave, Winchester, KY 40391

  Last Sold Summary

  • 1 Day On Market

  Last Listing Agent Austin Polley The Polley Group
• 

  

  

  /8

  $175,000

  $20K PRICE DROP

  • Land
  • 6.59 Acres
  • $26,555 per Acre

  990 Craig Crossing Rd, Winchester, KY 40391

  Lot # 13 contains 6.588 acres of gently rolling land perfect for your new home. This is a rare opportunity to own a piece of western Clark County real estate in the sought-after McClure Road area. Thoroughbred Estates is Winchester's newest upscale development containing 33 lots from 2 acres to nearly 7 acres. Lots are located just minutes from Winchester and Lexington.

  Keith Wilson Coldwell Banker McMahan

  990 Craig Crossing Rd, Winchester, KY 40391
• 

  

  /36

  $420,000

  Sold Feb 25, 2026

  134 Fontaine Blvd, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,747 Sq Ft
  • Built 1994

  Last Sold Summary

  • 7% Below List Price
  • $153/SF
  • 126 Days On Market

  Current Estimated Value $420,852

  Last Listing Agent Craig Bridgewater Bridgewater Real Estate

  134 Fontaine Blvd, Winchester, KY 40391
• 

  

  /23

  Est $196,430

  Not Listed For Sale

  353 E Broadway St, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 1,905 Sq Ft
  • Built 1940

  353 E Broadway St, Winchester, KY 40391

  Last Sold Summary

  • 1 Day On Market

  Last Listing Agent Keith Wilson Coldwell Banker McMahan
• 

  

  /21

  $225,000

  • 3 Beds
  • 3.5 Baths
  • 1,892 Sq Ft

  128 Abbeywood Ct, Winchester, KY 40391

  This beautifully maintained 3 bedroom, 3.5 bath townhouse offers the perfect blend of comfort, convenience, and low-maintenance living. Ideally situated in a desirable location, this spacious home features a functional floor plan with generous living areas, well appointed bedrooms, and a bathroom for each bedroom, providing comfort and privacy for family and guests alike. Enjoy the benefits of

  Judd Hisel ERA Select Real Estate

  128 Abbeywood Ct, Winchester, KY 40391
• 

  

  /59

  $277,500

  Sold Jun 30, 2026

  403 Pueblo Ct, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,311 Sq Ft
  • Built 2020

  Last Sold Summary

  • 1% Above List Price
  • $212/SF
  • 8 Days On Market

  Current Estimated Value $273,917

  Last Listing Agent Josh Wood Freedom Realty & Property Management

  403 Pueblo Ct, Winchester, KY 40391
• 

  

  /53

  Est $140,715

  Not Listed For Sale

  307 Jackson St, Winchester, KY 40391

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

  307 Jackson St, Winchester, KY 40391

  Last Sold Summary

  • 67 Days On Market

  Last Listing Agent Josh Wood Freedom Realty & Property Management
• 

  

  /22

  $138,000

  $2K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 986 Sq Ft

  174 Cook Ave, Winchester, KY 40391

  Charming Fixer-Upper with Endless Potential - Priced to Sell!! This older gem is full of character and opportunity! Featuring solid bones and classic charm, this property is perfect for buyers with a vision who are not afraid to add a little TLC! Whether you're an investor, DIY entusiast, or someone dreaming of restoring a home to its former glory, this is your chance to build equity and create

  A. Rebecca Woods Woods Realty Group

  174 Cook Ave, Winchester, KY 40391
• 

  

  /41

  $310,000

  Sold Dec 29, 2025

  1996 White Conkwright Rd, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 1,055 Sq Ft
  • Built 1966

  Last Sold Summary

  • 9% Below List Price
  • $294/SF
  • 45 Days On Market

  Current Estimated Value $338,478

  Last Listing Agent Lucy Martin Jenkins United Real Estate Bluegrass

  1996 White Conkwright Rd, Winchester, KY 40391
• 

  

  /32

  Est $200,207

  Not Listed For Sale

  230 Winn Ave, Winchester, KY 40391

  • 4 Beds
  • 1.5 Baths
  • 1,400 Sq Ft
  • Built 1940

  230 Winn Ave, Winchester, KY 40391

  Last Sold Summary

  • 73 Days On Market

  Last Listing Agent Cindy Walker Sandy Stuart Realty
• 

  

  /4

  $164,000

  $15K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 1,472 Sq Ft

  13 Maryland Ave, Winchester, KY 40391

  Welcome Home! Located across the street from a park with walking trails and 2 dog runs, this home is ready for a new owner. Featuring 2 bedrooms on the first floor and an optional 3rd bedroom or bonus room in the partially finished attic space. The original hardwood floors are located throughout the home. VA assumable loan with a 2.99% interest rate - you can't beat that in today's market! Home

  Clay David Sutherland ERA Select Real Estate

  13 Maryland Ave, Winchester, KY 40391
• 

  

  /43

  $299,900

  Sold Jul 14, 2026

  3622 Stamper Dr, Winchester, KY 40391

  • 3 Beds
  • 3 Baths
  • 2,821 Sq Ft
  • Built 1983

  Last Sold Summary

  • $106/SF
  • 12 Days On Market

  Current Estimated Value $305,088

  Last Listing Agent Josh Wood Freedom Realty & Property Management

  3622 Stamper Dr, Winchester, KY 40391
• 

  

  /17

  Est $162,661

  Not Listed For Sale

  30 Rowland Ave, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 956 Sq Ft
  • Built 1952

  30 Rowland Ave, Winchester, KY 40391

  Last Sold Summary

  • 0 Days On Market

  Last Listing Agent Lyndsey Ryles Kentucky Elite Real Estate
• 

  

  /27

  $149,900

  Pending

  • 3 Beds
  • 1 Bath
  • 1,775 Sq Ft

  60 Fitch Ave, Winchester, KY 40391

  This one is on the market for someone who loves to make this nice frame home new again, lots of hardwood floors, nice size rooms, as per seller upstairs has some plumbing for a 2nd bathroom, metal roof, house will need new HVAC, newer nice windows, deck overlooking back yard, The Upstairs is not finished, please be careful walking on the upstairs floor, would be a nice second bedroom and/or den

  Mila Ensor Ensor Real Estate, LLC

  60 Fitch Ave, Winchester, KY 40391
• 

  

  /38

  $599,500

  Sold Sep 08, 2025

  102 Bella Shae Way, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 2,204 Sq Ft
  • Built 2025

  Last Sold Summary

  • $272/SF
  • 72 Days On Market

  Current Estimated Value $599,255

  Last Listing Agent Shane Underwood Keller Williams Commonwealth

  102 Bella Shae Way, Winchester, KY 40391
• 

  

  /20

  Est $197,775

  Not Listed For Sale

  314 E Broadway St, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,188 Sq Ft
  • Built 1950

  314 E Broadway St, Winchester, KY 40391

  Last Sold Summary

  • 22 Days On Market

  Last Listing Agent Amanda Stewart Stewart & Co Realty LLC
• 

  

  /26

  $179,900

  $5K PRICE DROP Pending

  • 3 Beds
  • 2 Baths
  • 1,176 Sq Ft

  76 Clay St, Winchester, KY 40391

  Welcome to 76 Clay Street in Winchester—a beautifully remodeled 3-bedroom, 2-bath home that combines modern style with everyday comfort. Completely renovated and move-in ready, this home offers quality updates throughout. Inside, you'll find durable luxury vinyl plank flooring, abundant natural light from all-new windows, and a beautifully updated kitchen featuring butcher block countertops, a

  Alyssa Weir ERA Select Real Estate

  76 Clay St, Winchester, KY 40391
• 

  

  /37

  $220,000

  Sold Sep 23, 2025

  213 Blair Ave, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,025 Sq Ft
  • Built 1979

  Last Sold Summary

  • 2% Below List Price
  • $215/SF
  • 4 Days On Market

  Current Estimated Value $217,503

  Last Listing Agent Elizabeth Hodge Lifstyl Real Estate

  213 Blair Ave, Winchester, KY 40391
• 

  

  /27

  Est $188,199

  Not Listed For Sale

  37 Jackson St, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,400 Sq Ft
  • Built 1940

  37 Jackson St, Winchester, KY 40391

  Last Sold Summary

  • 30 Days On Market

  Last Listing Agent O. Debbie Pennington CENTURY 21 Advantage Realty
• 

  

  /40

  $306,000

  • 4 Beds
  • 2.5 Baths
  • 1,970 Sq Ft

  428 Waycross Dr, Winchester, KY 40391

  Wow! Pack your belongings and get ready to move! Your dream house just hit the market and It is going to go quick. Imagine sitting on the back deck , sipping your favorite beverage while your children and pets play safely in this large fenced in back yard. Or set up your home theatre in the spacious finished basement. This home has so much to offer, very spacious with the primary bed room and

  Wayne Elkins RE/MAX Creative Realty

  428 Waycross Dr, Winchester, KY 40391
• 

  

  /54

  $649,900

  Sold Aug 06, 2026

  1480 Irvine Rd, Winchester, KY 40391

  • 3 Beds
  • 3.5 Baths
  • 3,388 Sq Ft
  • Built 1920

  Last Sold Summary

  • 13% Below List Price
  • $192/SF
  • 87 Days On Market

  Current Estimated Value $642,559

  Last Listing Agent Ivanna Barko National Real Estate

  1480 Irvine Rd, Winchester, KY 40391
• 

  

  /23

  Est $214,213

  Not Listed For Sale

  42 Park Ave, Winchester, KY 40391

  • 3 Beds
  • 1.5 Baths
  • 1,129 Sq Ft
  • Built 1940

  42 Park Ave, Winchester, KY 40391

  Last Sold Summary

  • 54 Days On Market

  Last Listing Agent Jonathan McMahan Coldwell Banker McMahan
• 

  

  /6

  $49,500

  • Land
  • 42,688 Sq Ft
  • $50,510 per Acre

  204 Wigeon Ct, Winchester, KY 40391

  Choose your preferred builder to construct your dream home in Mallard Place. Located in a quiet cul-de-sac at the rear of the subdivision. Only a 20 minute drive to Hamburg/Lexington and only a 5 minute drive to the Winchester Bypass. Enjoy the serenity of living in a private setting AND the convenience of being close to schools, shopping and I-64 and I-75.

  Jim Woodrum RE/MAX Creative, Winchester

  204 Wigeon Ct, Winchester, KY 40391
• 

  

  /20

  $339,000

  Sold Aug 04, 2026

  107 Gibson Way, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 2,266 Sq Ft
  • Built 2020

  Last Sold Summary

  • 8% Below List Price
  • $150/SF
  • 26 Days On Market

  Current Estimated Value $356,467

  Last Listing Agent Vanessa Highland Stewart & Co Realty LLC

  107 Gibson Way, Winchester, KY 40391
• 

  

  /43

  Est $152,615

  Not Listed For Sale

  116 Park Ave, Winchester, KY 40391

  • 1 Bed
  • 1 Bath
  • 1,576 Sq Ft
  • Built 1940

  116 Park Ave, Winchester, KY 40391

  Last Sold Summary

  • 23 Days On Market

  Last Listing Agent Christa Joynt Keller Williams Commonwealth
• 

  

  /3

  $395,000

  New Construction Pending

  • 3 Beds
  • 2 Baths
  • 1,855 Sq Ft

  205 Evergreen Dr, Winchester, KY 40391

  Introducing The Mulberry floor plan - a beautifully designed proposed construction home in the scenic Locust Hill Acres community. This open-concept floor plan offers the perfect blend of comfort and functionality with 3 bedrooms, 2 full bathrooms, and thoughtful living spaces throughout.The spacious primary suite features a large walk-in closet and a private ensuite bath, providing a

  Rex Hall United Real Estate Bluegrass

  205 Evergreen Dr, Winchester, KY 40391
• 

  

  /33

  $208,000

  Sold May 15, 2026

  59 Holiday Rd, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,050 Sq Ft
  • Built 1985

  Last Sold Summary

  • 1% Below List Price
  • $198/SF
  • 6 Days On Market

  Current Estimated Value $207,702

  Last Listing Agent Kathy Burton Coldwell Banker McMahan

  59 Holiday Rd, Winchester, KY 40391
• 

  

  /25

  Est $213,743

  Not Listed For Sale

  21 Vine St, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,080 Sq Ft
  • Built 1960

  21 Vine St, Winchester, KY 40391

  Last Sold Summary

  • 0 Days On Market

  Last Listing Agent Kymberly McCreary eXp Realty, LLC
• 

  /2

  $600,000

  • Land
  • 6.13 Acres
  • $97,879 per Acre

  722 Colby Rd Unit 2, Winchester, KY 40391

  Discover an exceptional opportunity for retail investment in the thriving Winchester area. Zoned B-4, this versatile property offers a wide array of possibilities for retail development, providing a strategic location for businesses seeking to establish a prominent presence. With its prime zoning and desirable position within the Winchester area, this property presents a compelling prospect for

  Cheryl Johnston CMI Properties

  722 Colby Rd Unit 2, Winchester, KY 40391
• 

  

  /14

  $200,000

  Sold Sep 19, 2025

  9711 Ironworks Rd, Winchester, KY 40391

  Last Sold Summary

  • 11% Below List Price
  • 19 Days On Market

  Last Listing Agent Jessica Maloney Denniston Realty

  9711 Ironworks Rd, Winchester, KY 40391
• 

  

  /39

  Est $269,304

  Not Listed For Sale

  217 E Washington St, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 2,183 Sq Ft
  • Built 1940

  217 E Washington St, Winchester, KY 40391

  Last Sold Summary

  • 21 Days On Market

  Last Listing Agent Joshua Lynch The Brokerage
• 

  

  /9

  $139,900

  $20K PRICE DROP Pending

  • 3 Beds
  • 1 Bath
  • 1,097 Sq Ft

  220 E Washington St, Winchester, KY 40391

  Charming 3-Bedroom Home with Great Investment Potential....Welcome to this charming 3-bedroom, 1-bath home offering comfortable living space and plenty of opportunity for homeowners or investors alike. Featuring an easy layout with generously sized bedrooms, a large eat-in kitchen, and a bright living area, Outside, you'll find a covered front porch perfect for relaxing, along with a private

  Whitney Ensor Ensor Real Estate, LLC

  220 E Washington St, Winchester, KY 40391
• 

  

  /75

  $490,000

  Sold Sep 26, 2025

  497 Goose Creek Rd, Winchester, KY 40391

  • 4 Beds
  • 3.5 Baths
  • 2,972 Sq Ft
  • Built 1993

  Last Sold Summary

  • 1% Below List Price
  • $165/SF
  • 2 Days On Market

  Current Estimated Value $478,133

  Last Listing Agent O Eve Stern Threshold Real Estate Services

  497 Goose Creek Rd, Winchester, KY 40391
• 

  

  /29

  Est $241,244

  Not Listed For Sale

  167 E Washington St, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,763 Sq Ft
  • Built 1940

  167 E Washington St, Winchester, KY 40391

  Last Sold Summary

  • 5 Days On Market

  Last Listing Agent Kymberly McCreary eXp Realty, LLC
• 

  

  /32

  $209,000

  • 3 Beds
  • 1 Bath
  • 1,152 Sq Ft

  32 Jackson St, Winchester, KY 40391

  This beautiful home is located just minutes from historic downtown Winchester. It has 3 spacious bedrooms and 1 full bath. The home has a new roof. When you walk out back you will find an oversized garage. The huge backyard is all fenced in. Make an appointment to tour this one before it's gone.

  Dale Hatton Dream Maker Realty, LLC

  32 Jackson St, Winchester, KY 40391
• 

  

  /25

  $287,000

  Sold Aug 20, 2025

  220 Mcdowell Dr, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,402 Sq Ft
  • Built 1987

  Last Sold Summary

  • 12% Below List Price
  • $205/SF
  • 36 Days On Market

  Current Estimated Value $296,368

  Last Listing Agent Alyssa M Boley Coldwell Banker McMahan

  220 Mcdowell Dr, Winchester, KY 40391
• 

  

  /26

  Est $191,473

  Not Listed For Sale

  150 W Broadway St, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,696 Sq Ft
  • Built 1940

  150 W Broadway St, Winchester, KY 40391

  Last Sold Summary

  • 39 Days On Market

  Last Listing Agent Michelle Blackburn RE/MAX Creative, Winchester

Showing Results 521 - 560, Page 14 of 18