Winchester, KY Homes

• 

  

  

  /35

  Est $370,059

  Not Listed For Sale

  121 Hampton Ave, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 2,248 Sq Ft
  • Built 1958

  121 Hampton Ave, Winchester, KY 40391

  Last Sold Summary

  • 60 Days On Market

  Last Listing Agent Patrick Arvin Keller Williams Commonwealth
• 

  

  

  /16

  $168,500

  Open Sat 11AM - 1PM $21K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 950 Sq Ft

  41 Hiawatha Trail, Winchester, KY 40391

  Great Opportunity for First-Time Homebuyers! This charming 3-bedroom, 1-bath home features beautiful hardwood floors, an updated kitchen, and a fenced backyard perfect for relaxing, entertaining, or pets. Move-in ready and full of value, this is a wonderful opportunity to own a home with both character and convenience. Schedule your showing today!

  Hannah Toole Coldwell Banker McMahan

  41 Hiawatha Trail, Winchester, KY 40391
• 

  

  

  /62

  $260,000

  Sold Jun 09, 2026

  144 Holly Ave, Winchester, KY 40391

  • 8 Beds
  • 5 Baths
  • 3,637 Sq Ft
  • Built 2001

  Last Sold Summary

  • 19% Below List Price
  • $71/SF
  • 69 Days On Market

  Current Estimated Value $270,427

  Last Listing Agent Shane Underwood Keller Williams Commonwealth

  144 Holly Ave, Winchester, KY 40391
• 

  

  

  /50

  Est $428,159

  Not Listed For Sale

  33 Hampton Ave, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 3,580 Sq Ft
  • Built 1958

  33 Hampton Ave, Winchester, KY 40391

  Last Sold Summary

  • 16 Days On Market

  Last Listing Agent Robert Coburn Kentucky Realty Group, LLC
• 

  

  

  /26

  $215,000

  Pending

  • 2 Beds
  • 1.5 Baths
  • 1,120 Sq Ft

  271 April Way, Winchester, KY 40391

  This charming 2 - story townhouse is in a prime location.. Welcome to this beautifully maintained 2 bedroom, 1.5 bath townhouse offering the perfect blend of comfort, style and convenience. Spread over two spacious levels, this home features an inviting living area, a modern kitchen with ample cabinetry and a cozy dining space-perfect for every day living or entertaining guests. Upstairs,

  Kimberly Fugate Keller Williams Commonwealth

  271 April Way, Winchester, KY 40391
• 

  

  /28

  $246,000

  Sold Nov 06, 2025

  204 Moss Ct, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,430 Sq Ft
  • Built 1998

  Last Sold Summary

  • 3% Above List Price
  • $172/SF
  • 1 Day On Market

  Current Estimated Value $251,127

  Last Listing Agent Brooke Martin RO&CO Real Estate

  204 Moss Ct, Winchester, KY 40391
• 

  

  /27

  Est $242,757

  Not Listed For Sale

  118 Southern Ct, Winchester, KY 40391

  • 4 Beds
  • 1.5 Baths
  • 1,598 Sq Ft
  • Built 1943

  118 Southern Ct, Winchester, KY 40391

  Last Sold Summary

  • 31 Days On Market

  Last Listing Agent Susan Baldwin Threshold Real Estate Services
• 

  

  /21

  $326,000

  $1K PRICE INCREASE Pending

  • Land
  • 48.54 Acres
  • $6,716 per Acre

  380 Howard Creek Rd Unit 380, Winchester, KY 40391

  Escape to the peace and privacy of this beautiful 48.54-acre unimproved property in a remote rural setting. Featuring a mix of rolling pasture and wooded acreage with gentle slopes, this versatile tract is ideal for farming, cattle, horses, recreation, hunting, or building your dream country retreat. Whether you're looking for productive agricultural land or a private getaway, this property

  Kathy Burton Coldwell Banker McMahan

  380 Howard Creek Rd Unit 380, Winchester, KY 40391
• 

  

  /26

  $390,000

  Sold Jul 22, 2026

  178 Hawthorne Dr, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 2,156 Sq Ft
  • Built 2018

  Last Sold Summary

  • $181/SF
  • 6 Days On Market

  Current Estimated Value $392,941

  Last Listing Agent Tiffani Casey Waizenhofer Real Estate

  178 Hawthorne Dr, Winchester, KY 40391
• 

  

  /46

  Est $333,144

  Not Listed For Sale

  14 Western Ave, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,676 Sq Ft
  • Built 2023

  14 Western Ave, Winchester, KY 40391

  Last Sold Summary

  • 79 Days On Market

  Last Listing Agent Dale Hatton Dream Maker Realty, LLC
• 

  

  /4

  $10,000

  $15K PRICE DROP Pending

  • Land
  • 7,274 Sq Ft
  • $59,880 per Acre

  117 4th St, Winchester, KY 40391

  Discover the potential of this spacious 0.17-acre residential property nestled in a neighborhood community on clear and level vacant lot located in a Cul-de-sac of Lincoln Park Subdivision. This could be an investment opportunity as well, for ideal savvy investors looking to diversify your portfolio this property would be perfect for building a custom home, holding for future value, or develop

  Anita McDermott Keller Williams Bluegrass Realty

  117 4th St, Winchester, KY 40391
• 

  

  /43

  $450,000

  Sold May 26, 2026

  222 Ashton Oak Way, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 3,444 Sq Ft
  • Built 2006

  Last Sold Summary

  • $131/SF
  • 4 Days On Market

  Current Estimated Value $439,079

  Last Listing Agent Mila Ensor Ensor Real Estate, LLC

  222 Ashton Oak Way, Winchester, KY 40391
• 

  

  /18

  Est $200,529

  Not Listed For Sale

  6 Western Ave, Winchester, KY 40391

  • 2 Beds
  • 2 Baths
  • 2,109 Sq Ft
  • Built 1950

  6 Western Ave, Winchester, KY 40391

  Last Sold Summary

  • 46 Days On Market

  Last Listing Agent Steven G King CENTURY 21 Advantage Realty
• 

  

  /7

  $150,000

  $30K PRICE DROP

  • Land
  • 4.21 Acres
  • $35,629 per Acre

  1030 Craig Crossing Rd, Winchester, KY 40391

  Lot # 14 contains 4.21 acres of gently rolling land with small stream 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

  1030 Craig Crossing Rd, Winchester, KY 40391
• 

  

  /52

  $230,000

  Sold Jan 20, 2026

  19 Cherokee Ct, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,134 Sq Ft
  • Built 1968

  Last Sold Summary

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

  Current Estimated Value $229,579

  Last Listing Agent Josh Wood Freedom Realty & Property Management

  19 Cherokee Ct, Winchester, KY 40391
• 

  

  /37

  Est $284,018

  Not Listed For Sale

  120 Milwood Dr, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,853 Sq Ft
  • Built 1965

  120 Milwood Dr, Winchester, KY 40391

  Last Sold Summary

  • 80 Days On Market

  Last Listing Agent Michelle Blackburn RE/MAX Creative, Winchester
• 

  

  /27

  $234,900

  • 3 Beds
  • 2 Baths
  • 1,108 Sq Ft

  227 Leslie Dr, Winchester, KY 40391

  This 3 Bedroom, 2 bath home is quietly nestled within the Saddle Brook subdivision. Conveniently located just outside of Winchester New Bypass, this property also qualifies for zero down rural housing financing. Updates can be seen throughout along with spacious master bedroom with on-suite, large back yard and open concept living. Schedule your showing today!

  Michael Hilario The Agency

  227 Leslie Dr, Winchester, KY 40391
• 

  

  /36

  $202,000

  Sold Mar 18, 2026

  58 Hughes Ave, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,456 Sq Ft

  Last Sold Summary

  • 6% Below List Price
  • $139/SF
  • 15 Days On Market

  Current Estimated Value $193,219

  Last Listing Agent E Anthony Phillips RE/MAX Creative Realty

  58 Hughes Ave, Winchester, KY 40391
• 

  

  /26

  Est $266,176

  Not Listed For Sale

  134 Boone Ave, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,878 Sq Ft
  • Built 1920

  134 Boone Ave, Winchester, KY 40391

  Last Sold Summary

  • 74 Days On Market

  Last Listing Agent Steve Lindsey CENTURY 21 Commonwealth Real Estate
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  /38

  $285,000

  $5K PRICE INCREASE Pending

  • 3 Beds
  • 2 Baths
  • 1,955 Sq Ft

  108 Milwood Dr, Winchester, KY 40391

  Welcome to 108 Milwood Drive\! Nestled in one of Winchester's most desirable neighborhoods, this well\-maintained 3\-bedroom, 2\-bath ranch offers a functional floor plan and peaceful backyard setting\. The spacious living room features a gas log fireplace, while the primary suite includes a private en suite bath\. A cozy den opens to a wooden deck overlooking the fenced backyard and wooded

  Laura Disney Disney & Company

  108 Milwood Dr, Winchester, KY 40391
• 

  

  /39

  $395,000

  Sold Jun 18, 2026

  18 Casa Landa Way, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,883 Sq Ft
  • Built 1975

  Last Sold Summary

  • $210/SF
  • 0 Days On Market

  Current Estimated Value $395,130

  Last Listing Agent Steve Charles Freedom Realty & Property Management

  18 Casa Landa Way, Winchester, KY 40391
• 

  

  /32

  Est $257,417

  Not Listed For Sale

  13 Euclid Ave, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,893 Sq Ft
  • Built 1917

  13 Euclid Ave, Winchester, KY 40391

  Last Sold Summary

  • 75 Days On Market

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

  

  /14

  $152,500

  $7K PRICE DROP Pending

  • Land
  • 2.66 Acres
  • $57,374 per Acre

  590 Craig Crossing, Winchester, KY 40391

  Don't let this opportunity pass you by again. This prime lot in Thoroughbred Estates is back on the market due to Current owners change of plans. This lot is ready for your new home with a beautiful setting and located close to Winchester and Lexington in a new Luxury Subdivision. Watch the sun set each night from your rear deck or pool. Call today!!!

  Keith Wilson Coldwell Banker McMahan

  590 Craig Crossing, Winchester, KY 40391
• 

  

  /37

  $275,000

  Sold Sep 10, 2025

  279 Ascot Ave, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,247 Sq Ft
  • Built 2000

  Last Sold Summary

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

  Current Estimated Value $312,438

  Last Listing Agent Chase Pennington Team Pannell Real Estate

  279 Ascot Ave, Winchester, KY 40391
• 

  

  /45

  Est $433,271

  Not Listed For Sale

  142 College St, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 3,012 Sq Ft
  • Built 1940

  142 College St, Winchester, KY 40391

  Last Sold Summary

  • 87 Days On Market

  Last Listing Agent Patrick Arvin Keller Williams Commonwealth
• 

  /2

  $150,000

  • Land
  • 2.77 Acres
  • $54,074 per Acre

  3385 Colby Rd, Winchester, KY 40391

  Parcel 4 in the photos. This 2.774 acre lot is available on Colby Road just 1.5 miles from the Winchester Bypass. No building restrictions other than no manufactured housing and a paved driveway must be completed within a year of finishing a residence.

  Steve Adams Steven D Adams Real Estate Services, LLC

  3385 Colby Rd, Winchester, KY 40391
• 

  

  /24

  $90,000

  Sold Mar 23, 2026

  701 Williamsburg Dr, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 996 Sq Ft
  • Built 1971

  Last Sold Summary

  • 7% Below List Price
  • $90/SF
  • 2 Days On Market

  Current Estimated Value $94,208

  Last Listing Agent Shane Underwood Keller Williams Commonwealth

  701 Williamsburg Dr, Winchester, KY 40391
• 

  

  /32

  Est $212,773

  Not Listed For Sale

  8 Nunnelly Ct, Winchester, KY 40391

  • 2 Beds
  • 1.5 Baths
  • 1,255 Sq Ft
  • Built 1940

  8 Nunnelly Ct, Winchester, KY 40391

  Last Sold Summary

  • 33 Days On Market

  Last Listing Agent Timothy Saylor Threshold Real Estate Services
• 

  

  /3

  $700,000

  New Construction

  • 3 Beds
  • 2 Baths
  • 2,400 Sq Ft

  415 Alexis Way, Winchester, KY 40391

  Introducing the Merango, a classic all-brick ranch home designed for both comfort and style. With stunning double front doors and a 2-car attached garage, this home offers incredible curb appeal and modern living. The spacious 3-bedroom, 2-bath layout features a split-bedroom design for added privacy, along with a dedicated study perfect for a home office. The open-concept kitchen is ideal for

  Shane Underwood Keller Williams Commonwealth

  415 Alexis Way, Winchester, KY 40391
• 

  

  /28

  $370,000

  Sold Sep 03, 2025

  220 Spring Valley Dr, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 3,078 Sq Ft
  • Built 1975

  Last Sold Summary

  • 7% Below List Price
  • $120/SF
  • 3 Days On Market

  Current Estimated Value $409,740

  Last Listing Agent Tracey Goebel Tom Goebel & Company

  220 Spring Valley Dr, Winchester, KY 40391
• 

  

  /82

  Est $297,157

  Not Listed For Sale

  111 S Burns Ave, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 2,994 Sq Ft
  • Built 1920

  111 S Burns Ave, Winchester, KY 40391

  Last Sold Summary

  • 202 Days On Market

  Last Listing Agent Melodie Lincavage Berkshire Hathaway HomeServices Foster Realtors
• 

  

  /25

  $221,500

  $8K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 1,454 Sq Ft

  2 Western Ave, Winchester, KY 40391

  MOTIVATED SELLER!! Don't miss this wonderful home offering convenience, comfort, and value!! Ideally situated near shopping, dining, schools, churches and everyday amenities. This property is perfect for first-time buyers or downsizers. The backyard provides ample space for entertaining is completely fenced in for children and pets. Home also provides room to grow. The attic space has plenty of

  A. Rebecca Woods Woods Realty Group

  2 Western Ave, Winchester, KY 40391
• 

  

  /27

  $335,000

  Sold Dec 18, 2025

  2198 Goshen Rd, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,730 Sq Ft
  • Built 1997

  Last Sold Summary

  • 5% Above List Price
  • $194/SF
  • 31 Days On Market

  Current Estimated Value $334,859

  Last Listing Agent Jason Szaks EXIT Town & Country Realtors

  2198 Goshen Rd, Winchester, KY 40391
• 

  

  /47

  Est $364,785

  Not Listed For Sale

  113 S Burns Ave, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 3,299 Sq Ft
  • Built 1895

  113 S Burns Ave, Winchester, KY 40391

  Last Sold Summary

  • 1 Day On Market

  Last Listing Agent Ginger Mccoy Kentucky Residential Real Estate, LLC
• 

  

  /13

  $400,000

  • Land
  • 2.19 Acres
  • $182,648 per Acre

  145 Codella Dr, Winchester, KY 40391

  Great opportunity to buy and build just off the Winchester Bypass. This property is nicely located in the midst of a great deal of new development including a brand new, state-of-the-art CHI Saint Joseph Health Center. Other new development in the immediate area includes Clean Sweeps and Domino's Pizza. Additionally, Walmart and Kroger are located directly across the Bypass from this site. See

  Greg Leveridge Block + Lot Homes

  145 Codella Dr, Winchester, KY 40391
• 

  

  /29

  $180,000

  Sold Aug 11, 2025

  217 Blair Ave, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,025 Sq Ft
  • Built 1970

  Last Sold Summary

  • 3% Above List Price
  • $176/SF
  • 0 Days On Market

  Current Estimated Value $184,013

  Last Listing Agent Ashley Barreto Indigo & Co

  217 Blair Ave, Winchester, KY 40391
• 

  

  /27

  Est $202,223

  Not Listed For Sale

  139 W Hickman St, Winchester, KY 40391

  • 3 Beds
  • 1.5 Baths
  • 1,348 Sq Ft
  • Built 1940

  139 W Hickman St, Winchester, KY 40391

  Last Sold Summary

  • 18 Days On Market

  Last Listing Agent Clay David Sutherland ERA Select Real Estate
• 

  

  /52

  $539,000

  • 3 Beds
  • 2.5 Baths
  • 2,732 Sq Ft

  267 Runnymeade Dr, Winchester, KY 40391

  Welcome to this beautifully designed 3-bedroom, 2.5-bath ranch in the highly sought-after Earlymeade subdivision, where comfort, style, and exceptional efficiency come together. This spacious one-story home offers an open, inviting floor plan highlighted by a stunning floor-to-ceiling stone fireplace that anchors the expansive great room. The well-appointed kitchen features granite countertops,

  Jason Caudill RE/MAX Creative Realty

  267 Runnymeade Dr, Winchester, KY 40391
• 

  /2

  $224,900

  Sold May 08, 2026

  11 Shelley Dr, Winchester, KY 40391

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

  Last Sold Summary

  • $189/SF

  Current Estimated Value $225,046

  Last Listing Agent Mark Wallace Transactionbroker.com

  11 Shelley Dr, Winchester, KY 40391
• 

  

  /35

  Est $332,462

  Not Listed For Sale

  123 W Hickman St, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 2,498 Sq Ft
  • Built 1940

  123 W Hickman St, Winchester, KY 40391

  Last Sold Summary

  • 1 Day On Market

  Last Listing Agent Lukas Owens The Brokerage

Showing Results 641 - 680, Page 17 of 18