Winchester, KY Homes

• 

  

  

  /57

  Est $468,109

  Not Listed For Sale

  402 S Maple St, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 3,864 Sq Ft
  • Built 1896

  402 S Maple St, Winchester, KY 40391

  Last Sold Summary

  • 24 Days On Market
• 

  

  

  /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
• 

  

  

  /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 $307,988

  Last Listing Agent Shane Underwood Keller Williams Commonwealth

  144 Holly Ave, Winchester, KY 40391
• 

  

  

  /60

  Est $425,286

  Not Listed For Sale

  405 Boone Ave, Winchester, KY 40391

  • 3 Beds
  • 4 Baths
  • 2,718 Sq Ft
  • Built 1945

  405 Boone Ave, Winchester, KY 40391

  Last Sold Summary

  • 16 Days On Market
• 

  

  

  /92

  $795,000

  • 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
• 

  

  /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 $247,551

  Last Listing Agent Brooke Martin RO&CO Real Estate

  204 Moss Ct, Winchester, KY 40391
• 

  

  /57

  Est $303,550

  Not Listed For Sale

  10 Northern Ave, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 2,270 Sq Ft
  • Built 1957

  10 Northern Ave, Winchester, KY 40391

  Last Sold Summary

  • 0 Days On Market
• 

  

  /118

  $635,000

  $40K PRICE DROP Pending

  • 3 Beds
  • 3 Baths
  • 2,765 Sq Ft

  5865 Van Meter Rd, Winchester, KY 40391

  Experience the perfect balance of peaceful country living and modern comfort at 5865 Van Meter Road. Situated on 5.05 scenic acres with breathtaking farmland views, this spacious ranch-style home offers more than 2,700 square feet of thoughtfully designed living space with privacy, versatility, and charm throughout. A brand-new roof installed in May 2026 adds even more value and peace of mind.

  Laura Hayes Carpenter Keller Williams Commonwealth

  5865 Van Meter Rd, Winchester, KY 40391
• 

  

  /58

  $232,500

  Sold Jul 12, 2025

  114 Holiday Rd, Winchester, KY 40391

  • 3 Beds
  • 1.5 Baths
  • 1,161 Sq Ft
  • Built 1980

  Last Sold Summary

  • 7% Below List Price
  • $200/SF
  • 235 Days On Market

  Current Estimated Value $243,287

  Last Listing Agent Karen Smith Emmerich Muzic Realty

  114 Holiday Rd, Winchester, KY 40391
• 

  

  /28

  Est $389,108

  Not Listed For Sale

  29 Manor Dr, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 2,148 Sq Ft
  • Built 1962

  29 Manor Dr, Winchester, KY 40391

  Last Sold Summary

  • 247 Days On Market
• 

  

  /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
• 

  

  /28

  $234,500

  Sold Jul 29, 2025

  108 Sturbridge Ln, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • Built 2004

  Last Sold Summary

  • 4% Below List Price
  • $195/SF
  • 45 Days On Market

  Current Estimated Value $243,488

  Last Listing Agent Jason Szaks EXIT Town & Country Realtors

  108 Sturbridge Ln, Winchester, KY 40391
• 

  

  /35

  Est $357,495

  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
• 

  

  /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
• 

  

  /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 $445,758

  Last Listing Agent Mila Ensor Ensor Real Estate, LLC

  222 Ashton Oak Way, Winchester, KY 40391
• 

  

  /50

  Est $449,427

  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
• 

  

  /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
• 

  

  /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 $228,566

  Last Listing Agent Josh Wood Freedom Realty & Property Management

  19 Cherokee Ct, Winchester, KY 40391
• 

  

  /27

  Est $242,211

  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
• 

  

  /35

  $180,000

  Pending

  • 3 Beds
  • 1 Bath
  • 1,198 Sq Ft

  371 E Washington St, Winchester, KY 40391

  Super cute, move in ready 1.5 story Cape Cod featuring 2 Bedrooms, 1 Bath, small eat in kitchen on 1st floor, Lg Primary bedroom on 2nd floor. Unfinished basement with lots of storage, Bonus Rm, & 3-year-old Sump pump. Updates: New Roof June '26, New front gutter. First & second floors: Fresh neutral painted rooms/trim, New carpets first floor & stairway. Carpet upstairs professionally cleaned,

  Robin Murray The Agency

  371 E Washington St, Winchester, KY 40391
• 

  

  /22

  $334,327

  Sold Jul 01, 2025

  136 Gibson Way, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 1,997 Sq Ft
  • Built 2024

  Last Sold Summary

  • $167/SF
  • 219 Days On Market

  Current Estimated Value $348,029

  Last Listing Agent Neshia Gaines Christies International Real Estate Bluegrass

  136 Gibson Way, Winchester, KY 40391
• 

  

  /46

  Est $361,518

  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
• 

  /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
• 

  

  /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 $309,443

  Last Listing Agent Chase Pennington Team Pannell Real Estate

  279 Ascot Ave, Winchester, KY 40391
• 

  

  /18

  Est $199,966

  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
• 

  

  /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
• 

  

  /24

  $198,000

  Sold Jul 18, 2025

  113 Colonial Park Dr, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,075 Sq Ft
  • Built 1983

  Last Sold Summary

  • 2% Above List Price
  • $184/SF
  • 0 Days On Market

  Current Estimated Value $211,086

  Last Listing Agent Janet Baldwin Kentucky Land and Home

  113 Colonial Park Dr, Winchester, KY 40391
• 

  

  /37

  Est $286,865

  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
• 

  

  /22

  $229,500

  • 2 Beds
  • 1 Bath
  • 1,454 Sq Ft

  2 Western Ave, Winchester, KY 40391

  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 room to add another

  A. Rebecca Woods Woods Realty Group

  2 Western Ave, 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 $94,197

  Last Listing Agent Shane Underwood Keller Williams Commonwealth

  701 Williamsburg Dr, Winchester, KY 40391
• 

  

  /32

  Est $257,253

  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
• 

  

  /90

  $249,990

  $30K PRICE DROP Pending

  • 4 Beds
  • 3 Baths
  • 2,112 Sq Ft

  115 Watercrest Cir, Winchester, KY 40391

  Stunning Home in One of the Area's Most Coveted Neighborhoods!Experience spacious living with 3 generous bedrooms and 2 full baths on the main level, designed for comfort and everyday convenience. The walkout basement offers even more space with a large bedroom and an additional full bath, ideal for guests, extended family, or a private retreat. What truly sets this home apart? This standout

  Darrell Tackett Dream Maker Realty, LLC

  115 Watercrest Cir, 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 $332,671

  Last Listing Agent Jason Szaks EXIT Town & Country Realtors

  2198 Goshen Rd, Winchester, KY 40391
• 

  

  /45

  Est $451,708

  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
• 

  

  /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 Zips Car Wash 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
• 

  

  /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 $413,330

  Last Listing Agent Tracey Goebel Tom Goebel & Company

  220 Spring Valley Dr, Winchester, KY 40391
• 

  

  /32

  Est $216,239

  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
• 

  

  /36

  $225,000

  Pending

  • 3 Beds
  • 2 Baths
  • 1,134 Sq Ft

  516 Hidden Hills Way, Winchester, KY 40391

  Charming 3 bedroom, 2 full bath home featuring a vaulted great room with an open, spacious feel. This move in ready property offers all new appliances, brand new flooring, and modern updates that make everyday living both stylish and comfortable. Step outside to enjoy the private backyard complete with a wood privacy fence and a deck perfect for grilling, entertaining, or relaxing. A wonderful

  Craig Bridgewater Bridgewater Real Estate

  516 Hidden Hills Way, 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 $185,117

  Last Listing Agent Ashley Barreto Indigo & Co

  217 Blair Ave, Winchester, KY 40391
• 

  

  /82

  Est $301,178

  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

Showing Results 641 - 680, Page 17 of 18