Homes in ZIP Code 40391

• 

  

  

  /34

  Est $287,328

  Not Listed For Sale

  312 S Main St, Winchester, KY 40391

  • 3 Beds
  • 1.5 Baths
  • 2,355 Sq Ft
  • Built 1920

  312 S Main St, Winchester, KY 40391

  Last Sold Summary

  • 1 Day On Market
• 

  

  

  /36

  $280,000

  $10K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,650 Sq Ft

  20 Jackson St, Winchester, KY 40391

  Beautifully updated and move-in ready, this 3-bedroom, 2-bath home offers comfort, style, and versatility throughout. Inside, you'll find a spacious living room, an updated kitchen with ample cabinetry, tile showers, original hardwood, modern LVP, and thoughtful finishes throughout. A large utility room offers flexible space for a home office, playroom, or extra storage. The unfinished basement,

  Zova Rothchild Keller Williams Legacy Group

  20 Jackson St, 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
• 

  

  

  /52

  Est $286,111

  Not Listed For Sale

  14 Lisle Ln, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,673 Sq Ft
  • Built 1955

  14 Lisle Ln, Winchester, KY 40391

  Last Sold Summary

  • 1 Day On Market
• 

  

  

  /52

  $785,000

  • 4 Beds
  • 3 Baths
  • 3,311 Sq Ft

  7300 Old Boonesboro Rd, Winchester, KY 40391

  This beautiful home sits on over 7 acres of peaceful countryside. Bring your horse! The back portion of the land is completely fenced. The private outdoor space includes a huge deck with a lovely view and an inviting covered front porch. The backyard would make the perfect space for your own dream swimming pool. Since the property has a 3-car detached garage; a 2-car attached garage plus a 1275

  Vickie Skeens RE/MAX Elite Lexington

  7300 Old Boonesboro 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
• 

  

  /20

  Est $225,444

  Not Listed For Sale

  18 Lisle Ln, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,082 Sq Ft
  • Built 1950

  18 Lisle Ln, Winchester, KY 40391

  Last Sold Summary

  • 0 Days On Market
• 

  

  /4

  $635,000

  New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,537 Sq Ft

  422 Alexis Way, Winchester, KY 40391

  Introducing the Denver, a gorgeous all-brick ranch home offering 4 bedrooms and 2.5 baths, designed for both luxury and practicality. With its stunning curb appeal, front porch, and beam accents, this home makes a lasting first impression. Inside, the split-bedroom layout offers privacy and space for everyone, with a large primary suite featuring a walk-in closet, soaking tub, separate shower,

  Shane Underwood Keller Williams Commonwealth

  422 Alexis Way, 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
• 

  

  /54

  Est $339,619

  Not Listed For Sale

  35 Lisle Ln, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 1,816 Sq Ft
  • Built 1953

  35 Lisle Ln, Winchester, KY 40391

  Last Sold Summary

  • 27 Days On Market
• 

  /2

  $110,000

  • Land
  • 21,780 Sq Ft
  • $220,000 per Acre

  260 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

  260 Duclair Dr, 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
• 

  

  /32

  Est $247,732

  Not Listed For Sale

  540 S Maple St, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 1,740 Sq Ft
  • Built 1940

  540 S Maple St, Winchester, KY 40391

  Last Sold Summary

  • 86 Days On Market
• 

  

  /12

  $264,900

  $40K PRICE DROP

  • 5 Beds
  • 2 Baths
  • 2,214 Sq Ft

  55 Hillcrest Dr, Winchester, KY 40391

  **Don't miss this exciting opportunity to pick out the new flooring for the basement and kitchen with a full price offer.****New roof (8 months old), one year old AC and heating unit, new large storage shed, and one year old wooden fence All of the expensive upgrades have been done. Come make this home your own. All-brick ranch with a full walk-out basement! This charming home offers excellent

  Nina Vanetten RE/MAX Elite Lexington

  55 Hillcrest Dr, 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
• 

  

  /37

  Est $281,725

  Not Listed For Sale

  17 Short St, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,783 Sq Ft
  • Built 1942

  17 Short St, Winchester, KY 40391

  Last Sold Summary

  • 27 Days On Market
• 

  

  /16

  $188,500

  $1K 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! Home being sold AS-IS

  Hannah Toole Coldwell Banker McMahan

  41 Hiawatha Trail, 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
• 

  

  /34

  Est $372,477

  Not Listed For Sale

  214 Boone Ave, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 2,928 Sq Ft
  • Built 1930

  214 Boone Ave, Winchester, KY 40391

  Last Sold Summary

  • 107 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
• 

  

  /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
• 

  

  /65

  Est $383,056

  Not Listed For Sale

  408 S Maple St, Winchester, KY 40391

  • 5 Beds
  • 3 Baths
  • 3,372 Sq Ft
  • Built 1910

  408 S Maple St, Winchester, KY 40391

  Last Sold Summary

  • 62 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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  /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 $227,114

  Last Listing Agent Mark Wallace Transactionbroker.com

  11 Shelley Dr, 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

Showing Results 641 - 680, Page 17 of 18