Homes in ZIP Code 40391

• 

  

  

  /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
• 

  

  

  /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 $261,391

  Last Listing Agent Tracey Goebel Tom Goebel & Company

  86 Bon-Haven Ave, Winchester, KY 40391
• 

  

  

  /47

  Est $364,117

  Not Listed For Sale

  150 Privacy Ln, Winchester, KY 40391

  • 3 Beds
  • 3 Baths
  • 2,784 Sq Ft
  • Built 1987

  150 Privacy Ln, Winchester, KY 40391

  Last Sold Summary

  • 103 Days On Market

  Last Listing Agent Jason Joseph Keller Williams Commonwealth
• 

  

  

  /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
• 

  

  

  /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 $603,664

  Last Listing Agent Niki Wiley Bluegrass Sotheby's International Realty

  905 Pretty Run Rd, Winchester, KY 40391
• 

  

  /79

  Est $971,133

  Not Listed For Sale

  3714 Wades Mill Rd, Winchester, KY 40391

  • 5 Beds
  • 3.5 Baths
  • 3,818 Sq Ft
  • Built 2001

  3714 Wades Mill Rd, Winchester, KY 40391

  Last Sold Summary

  • 55 Days On Market

  Last Listing Agent Nora Williams Keller Williams Commonwealth
• 

  

  /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
• 

  

  /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 $494,103

  Last Listing Agent Kathryn Cheuvront Coldwell Banker McMahan

  182 Chardonnay Ct, Winchester, KY 40391
• 

  

  /36

  Est $422,056

  Not Listed For Sale

  610 Old Ruckerville Rd, Winchester, KY 40391

  • 2 Beds
  • 2.5 Baths
  • 1,800 Sq Ft
  • Built 1997

  610 Old Ruckerville Rd, Winchester, KY 40391

  Last Sold Summary

  • 37 Days On Market

  Last Listing Agent Garnett Davis Tom Goebel & Company
• 

  /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
• 

  

  /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 $284,983

  Last Listing Agent KB Realty Group -Kevin Bradley KB Realty Group

  146 W Lexington Ave, Winchester, KY 40391
• 

  

  /35

  Est $277,268

  Not Listed For Sale

  3230 Irvine Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,510 Sq Ft
  • Built 1978

  3230 Irvine Rd, Winchester, KY 40391

  Last Sold Summary

  • 47 Days On Market

  Last Listing Agent Cindy Hellinger United Real Estate Bluegrass
• 

  /2

  $110,000

  • Land
  • 20,473 Sq Ft
  • $234,043 per Acre

  139 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

  139 Jacob Ct, 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
• 

  

  /16

  Est $189,432

  Not Listed For Sale

  2584 Irvine Rd, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 990 Sq Ft
  • Built 1950

  2584 Irvine Rd, Winchester, KY 40391

  Last Sold Summary

  • 29 Days On Market

  Last Listing Agent Veronica Norwood All Star Real Estate, Inc.
• 

  

  /43

  $319,900

  • 4 Beds
  • 2 Baths
  • 1,953 Sq Ft

  6 French Ave, Winchester, KY 40391

  SPACE, CHARACTER & LOCATION—THIS HOME HAS IT ALL! Step inside and discover a home filled with charm, character, and plenty of room to make your own. Featuring 4 generously sized bedrooms and 2 bathrooms, this home offers space for everyone to spread out. Beautiful original wood floors throughout the home add warmth and timeless character you just can't recreate. Enjoy the charm of the beautiful

  A. Rebecca Woods Woods Realty Group

  6 French Ave, 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 $429,862

  Last Listing Agent Trina Penn RE/MAX Creative Realty

  188 Big Stoner Rd, Winchester, KY 40391
• 

  

  /32

  Est $337,681

  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
• 

  /2

  $150,000

  • Land
  • 2.11 Acres
  • $71,090 per Acre

  125 Knox 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 Knox Ct, 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 $339,757

  Last Listing Agent Josh Wood Freedom Realty & Property Management

  407 Fairholme Way, Winchester, KY 40391
• 

  

  /29

  Est $232,948

  Not Listed For Sale

  301 Cabin Creek Heights, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,220 Sq Ft
  • Built 1970

  301 Cabin Creek Heights, Winchester, KY 40391

  Last Sold Summary

  • 0 Days On Market

  Last Listing Agent Jason Townsend Kentucky Residential Real Estate, LLC
• 

  

  /40

  $410,000

  • 4 Beds
  • 2 Baths
  • 2,435 Sq Ft

  406 Lynnway Dr, Winchester, KY 40391

  *Seller has accepted a contingent offer with a 24 hour kickout.* Welcome to this inviting brick ranch in the desirable Stoney Brook neighborhood! Step inside through the foyer, where you'll find a formal dining room and a beautifully updated formal living room featuring fresh paint and wainscoting. The kitchen opens to the cozy living room/den with a masonry fireplace, making it a great space to

  Michelle Blackburn RE/MAX Creative, Winchester

  406 Lynnway Dr, Winchester, KY 40391
• 

  

  /55

  $539,000

  Sold Sep 18, 2026

  108 Bella Shae Way, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 2,280 Sq Ft
  • Built 2022

  Last Sold Summary

  • 5% Below List Price
  • $236/SF
  • 69 Days On Market

  Current Estimated Value $547,668

  Last Listing Agent Vickie Skeens RE/MAX Elite Lexington

  108 Bella Shae Way, Winchester, KY 40391
• 

  

  /45

  Est $476,940

  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
• 

  

  /32

  $275,000

  Pending

  • 3 Beds
  • 2 Baths
  • 1,444 Sq Ft

  204 Lindsey Ct, Winchester, KY 40391

  Immaculately maintained and move-in ready! This 3-bedroom, 2-bath home is tucked along a cul-de-sac street and offers a spacious living room with vaulted ceiling, light-filled sunroom, well-kept kitchen with stainless appliances, and both bathrooms updated within the last four years. Enjoy even more living space outdoors on the covered, screened back deck overlooking the backyard. Conveniently

  Michelle Blackburn RE/MAX Creative, Winchester

  204 Lindsey Ct, Winchester, KY 40391
• 

  

  /13

  $4,880,000

  Sold Dec 15, 2025

  2090 Pretty Run Rd, Ford, KY 40391

  Last Sold Summary

  • 16% Below List Price
  • 622 Days On Market

  Last Listing Agent Harvey Mitchell Kentucky Prime Realty, LLC

  2090 Pretty Run Rd, Ford, KY 40391
• 

  

  /10

  Est $341,458

  Not Listed For Sale

  210 Cabin Creek Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,584 Sq Ft
  • Built 1999

  210 Cabin Creek Rd, Winchester, KY 40391

  Last Sold Summary

  Last Listing Agent Janine Shackelford LPT Realty
• 

  

  /16

  $124,500

  $5K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 876 Sq Ft

  122 Calloway St, Winchester, KY 40391

  Investment Opportunity or Perfect Starter Home This charming 2-bedroom, 1-bath property is full of potential! With a strong rental history and an excellent lease track record, it's ideal for investors or first-time buyers. The home requires only light maintenance, and the seller is even willing to fund minor repairs. Don't miss your chance to own a property with great value and endless

  Darrell Tackett Dream Maker Realty, LLC

  122 Calloway St, 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 $392,770

  Last Listing Agent Nancy Smith Rector Hayden Realtors

  4611 Colby Rd, Winchester, KY 40391
• 

  

  /44

  Est $524,847

  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
• 

  

  /10

  $550,000

  New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,200 Sq Ft

  107 Bella Shae Way, Winchester, KY 40391

  Welcome Home to the Winchester Floor Plan by CP Builders. This elegant ranch home features all-brick construction, a welcoming front porch, and a two-car garage. Step inside and be greeted by soaring 9-foot ceilings and a spacious open floor plan. The split bedroom design offers privacy and comfort, with a luxurious primary suite boasting an ensuite bathroom and a walk-in closet. Enjoy easy

  Shane Underwood Keller Williams Commonwealth

  107 Bella Shae Way, 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 $350,026

  Last Listing Agent Meggan Batey Keller Williams Legacy Group

  1270 Sewell Shop Rd, Winchester, KY 40391
• 

  

  /41

  Est $663,522

  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
• 

  

  /8

  $1,500,000

  1015 Old Stone Church Rd, Winchester, KY 40391

  Right off of Boonesboro Road lies 60.65± acres of Kentucky history waiting for its next chapter! This remarkable property sits along historic Howard's Creek and is located on the site of the original Bush Settlement—one of the earliest settlements in Kentucky. Formerly a working tobacco farm, this versatile acreage offers opportunities for cattle, hay, or crops, with timber and mineral rights

  Walker Mack Bluegrass Property Exchange

  1015 Old Stone Church Rd, 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 $377,059

  Last Listing Agent Josh Wood Freedom Realty & Property Management

  1138 Lafayette Blvd, Winchester, KY 40391
• 

  

  /61

  Est $599,297

  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
• 

  

  /87

  $2,999,000

  $101K PRICE DROP

  • 6 Beds
  • 5 Baths
  • 3,693 Sq Ft

  3049 Ironworks Rd, Winchester, KY 40391

  Some properties are special simply because of the story behind them. This 150-acre farm with 3,168 ft of road frontage in Winchester has been cared for by the same family since 1803, and it's now being offered for sale for the very first time. The land is classic Kentucky countryside, rolling pastures, peaceful water, and wide open views in every direction. Four ponds and a gently flowing creek

  Zova Rothchild Keller Williams Legacy Group

  3049 Ironworks Rd, Winchester, KY 40391
• 

  

  /50

  $220,000

  Sold Jun 18, 2026

  314 Snowden Dr, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,196 Sq Ft
  • Built 1960

  Last Sold Summary

  • 2% Below List Price
  • $184/SF
  • 1 Day On Market

  Current Estimated Value $219,694

  Last Listing Agent Josh Wood Freedom Realty & Property Management

  314 Snowden Dr, Winchester, KY 40391
• 

  

  /3

  Est $347,142

  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
• 

  

  /64

  $524,900

  • 3 Beds
  • 2.5 Baths
  • 2,514 Sq Ft

  275 Runnymeade Dr, Winchester, KY 40391

  OK! WOW!!! Location is yes, yes, yes! This house is located in a quiet residential neighborhood and in minutes you can be at the I-64 or I-75 interstate corridors. OK enough about location. This house is pristine! The owners have improved the property with new dimensional style roof shingles in 2025 along with new gutters. They have freshly painted the interior. They have added a new

  Craig Bridgewater Bridgewater Real Estate

  275 Runnymeade Dr, Winchester, KY 40391

Showing Results 161 - 200, Page 5 of 18