Homes in ZIP Code 40391

• 

  

  

  /46

  Est $206,673

  Not Listed For Sale

  115 Georgia St, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,167 Sq Ft
  • Built 1940

  115 Georgia St, Winchester, KY 40391

  Last Sold Summary

  • 66 Days On Market

  Last Listing Agent Darrell Tackett Dream Maker Realty, LLC
• 

  

  

  /14

  $165,000

  $15K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 3,462 Sq Ft

  229 S Highland St, Winchester, KY 40391

  Investor special with historic charm on corner lot! Opportunity awaits with this spacious 5 bedroom, 3 full bath home offering 3,462 sq ft of potential. Situated on a corner lot and walkable to downtown, this classic 2 story property is rich in character, featuring original hardwood floors, detailed woodwork, a welcoming front porch with columns, and a striking staircase with stained glass

  Michelle Blackburn RE/MAX Creative, Winchester

  229 S Highland St, Winchester, KY 40391
• 

  

  

  /22

  $220,000

  Sold Mar 31, 2026

  443 Jameson Way, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 1,400 Sq Ft
  • Built 2002

  Last Sold Summary

  • 1% Below List Price
  • $157/SF
  • 64 Days On Market

  Current Estimated Value $227,192

  Last Listing Agent Tyler I Back The Brokerage

  443 Jameson Way, Winchester, KY 40391
• 

  

  

  /17

  Est $231,123

  Not Listed For Sale

  102 Kentucky St, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,734 Sq Ft
  • Built 1940

  102 Kentucky St, Winchester, KY 40391

  Last Sold Summary

  • 41 Days On Market

  Last Listing Agent Holly Spradlin KY Realty Co
• 

  

  

  /55

  $515,000

  $10K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,563 Sq Ft

  935 Stoner-Ephesus Rd, Winchester, KY 40391

  Picture this: over five acres of Kentucky countryside, a handsome ranch-style home, and enough elbow room to finally breathe. This stunning 2,563 square foot retreat delivers the rare combination of refined interior finishes and genuine rural charm, all without sacrificing modern convenience. Inside, discover a generous family room anchored by a striking stone fireplace — the kind of space that

  Timothy Saylor Threshold Real Estate Services

  935 Stoner-Ephesus Rd, Winchester, KY 40391
• 

  

  /5

  $175,000

  Sold Jun 11, 2026

  5105 Combs Ferry Rd, Ford, KY 40391

  • Land
  • 6.1 Acres
  • $28,693 per Acre

  Last Sold Summary

  • 61% Below List Price
  • 88 Days On Market

  Last Listing Agent John Martin EXIT Realty Crutcher Frankfort

  5105 Combs Ferry Rd, Ford, KY 40391
• 

  

  /31

  Est $181,310

  Not Listed For Sale

  134 Central Ave, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,946 Sq Ft
  • Built 1930

  134 Central Ave, Winchester, KY 40391

  Last Sold Summary

  • 1 Day On Market

  Last Listing Agent Mila Ensor Ensor Real Estate, LLC
• 

  

  /48

  $1,500,000

  • 3 Beds
  • 2 Baths
  • 1,860 Sq Ft

  4578 Combs Ferry Rd, Ford, KY 40391

  Welcome to your own slice of Kentucky countryside! Situated on 59.104 picturesque acres, this beautifully maintained 3 bedroom, 2 bath home offers the perfect blend of modern comfort and functional farm living. Built in 2015 with 1,860 sq ft of open-concept living space, the home features soaring ceilings, abundant natural light, a spacious kitchen with oversized island, and a warm, inviting

  Joshua Davis The Agency

  4578 Combs Ferry Rd, Ford, KY 40391
• 

  

  /28

  $290,000

  Sold Apr 17, 2026

  24 N Burns Ave, Winchester, KY 40391

  • 3 Beds
  • 3.5 Baths
  • 2,526 Sq Ft
  • Built 1920

  Last Sold Summary

  • 6% Below List Price
  • $115/SF
  • 92 Days On Market

  Current Estimated Value $289,526

  Last Listing Agent Sarah Hess Keller Williams Commonwealth

  24 N Burns Ave, Winchester, KY 40391
• 

  

  /19

  Est $206,484

  Not Listed For Sale

  130 Central Ave, Winchester, KY 40391

  • 3 Beds
  • 1.5 Baths
  • 1,322 Sq Ft
  • Built 1930

  130 Central Ave, Winchester, KY 40391

  Last Sold Summary

  • 1 Day On Market

  Last Listing Agent Lukas Owens The Brokerage
• 

  

  /14

  $269,900

  Pending

  • 3 Beds
  • 1 Bath
  • 1,644 Sq Ft

  205 Providence Ln, Winchester, KY 40391

  You Wont Find A More Beautiful And Private Setting!!! This Home Features 3 Bedrooms And 1 Bath And Sits On 5.05 Acres; Two Front Porches; Large Rear Porch; A Separate Room Downstairs That Would Make A Great Master Bedroom/Suite Potentially; Huge Mudroom/Flex Space! Possibilities Are Endless With This Property. This Home Has Replacement Vinyl Clad Windows, Roof And HVAC All Replaced In Last 10

  Patrick Arvin Keller Williams Commonwealth

  205 Providence Ln, Winchester, KY 40391
• 

  

  /101

  $1,050,000

  Sold Jun 01, 2026

  3760 Old Boonesboro Rd, Winchester, KY 40391

  • 5 Beds
  • 5 Baths
  • 5,666 Sq Ft
  • Built 1985

  Last Sold Summary

  • 19% Below List Price
  • $185/SF
  • 15 Days On Market

  Current Estimated Value $1,052,416

  Last Listing Agent Josh Wood Freedom Realty & Property Management

  3760 Old Boonesboro Rd, Winchester, KY 40391
• 

  

  /19

  Est $223,280

  Not Listed For Sale

  112 Central Ave, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • Built 2025

  112 Central Ave, Winchester, KY 40391

  Last Sold Summary

  • 1 Day On Market

  Last Listing Agent Nena Honaker Tom Goebel & Company
• 

  

  /5

  $575,000

  • Land
  • 1.71 Acres
  • $336,257 per Acre

  1025 Colby Rd, Winchester, KY 40391

  This 1.7+/- acre parcel represents an excellent opportunity for almost any commercial application. The property has 397 feet of frontage along busy Colby Road (9,170 AADT, 2015) near its intersection with the Winchester Bypass (23,200 AADT, 2011). Located in the main shopping corridor of Clark County, this property receives tons of exposure and traffic from the adjacent Walmart Super-center,

  Jo Gawthrop Keller Williams Bluegrass Realty

  1025 Colby Rd, Winchester, KY 40391
• 

  

  /42

  $339,500

  Sold Jul 15, 2026

  221 W Hickman St, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 2,800 Sq Ft
  • Built 1940

  Last Sold Summary

  • 3% Below List Price
  • $121/SF
  • 4 Days On Market

  Current Estimated Value $337,406

  Last Listing Agent Brandon Hedinger Keller Williams Bluegrass Realty

  221 W Hickman St, Winchester, KY 40391
• 

  

  /23

  Est $198,125

  Not Listed For Sale

  112 Georgia St, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,738 Sq Ft
  • Built 1930

  112 Georgia St, Winchester, KY 40391

  Last Sold Summary

  • 8 Days On Market

  Last Listing Agent Wayne Elkins RE/MAX Creative Realty
• 

  

  /15

  $925,000

  • Land
  • 3.77 Acres
  • $245,358 per Acre

  300 Rolling Hills Ln, Winchester, KY 40391

  Great location just off exit 96 on I-64 and easy access to the Mountain Parkway. Only 15 minutes from I-75. Located near the entrance to the Winchester Kentucky Industrial Park. 3.774 flat acres to build your next business location.

  Josh Wood Freedom Realty & Property Management

  300 Rolling Hills Ln, Winchester, KY 40391
• 

  /2

  $85,000

  Sold Dec 12, 2025

  1385 Sewell Shop Rd, Winchester, KY 40391

  • Land
  • 6.43 Acres
  • $13,219 per Acre

  Last Sold Summary

  • 6% Below List Price
  • 6 Days On Market

  Last Listing Agent Zella Rosenthal Tom Goebel & Company

  1385 Sewell Shop Rd, Winchester, KY 40391
• 

  

  /48

  Est $264,352

  Not Listed For Sale

  104 Georgia St, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,758 Sq Ft
  • Built 1930

  104 Georgia St, Winchester, KY 40391

  Last Sold Summary

  • 9 Days On Market

  Last Listing Agent Libby VanMeter Marshall Lane Real Estate - Lexington
• 

  

  /50

  $545,000

  Pending

  665 Lillies Ferry Rd, Winchester, KY 40391

  You do not want to sleep on this one, it is a beautiful working farm with multiple building sites and amazing views and tranquility. Two farms are selling together for a total of 91.28 acres that is already a very productive cattle farm. The fencing, gates, waterers and infrastructure is already in place to move right in and produce income. There are multiple possible building sites with amazing

  Carrie Taylor Taylor Real Estate, LLC

  665 Lillies Ferry Rd, Winchester, KY 40391
• 

  

  /20

  $228,500

  Sold Aug 13, 2026

  122 Spruce Ct, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,210 Sq Ft
  • Built 1970

  Last Sold Summary

  • 3% Below List Price
  • $189/SF
  • 24 Days On Market

  Current Estimated Value $227,703

  Last Listing Agent Peggy Baldridge HomeFirst Real Estate

  122 Spruce Ct, Winchester, KY 40391
• 

  

  /16

  Est $213,074

  Not Listed For Sale

  128 Alabama St, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,526 Sq Ft
  • Built 1930

  128 Alabama St, Winchester, KY 40391

  Last Sold Summary

  • 66 Days On Market

  Last Listing Agent Paul Eads Freedom Realty & Property Management
• 

  /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 $352,114

  Last Listing Agent Darryl Bond Guide Realty, Inc.

  405 Tremont Ln, Winchester, KY 40391
• 

  

  /44

  Est $183,746

  Not Listed For Sale

  118 Alabama St, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,408 Sq Ft
  • Built 1940

  118 Alabama St, Winchester, KY 40391

  Last Sold Summary

  • 1 Day On Market

  Last Listing Agent Susan Moore Keller Williams Legacy Group
• 

  

  /7

  $365,900

  New Construction

  • 3 Beds
  • 2 Baths
  • 1,558 Sq Ft

  204 Jett Dr, Winchester, KY 40391

  New Construction, don't wait this one will not last, 3 bed/2 bath ranch, great floor plan, close to I-64 and I-75, lexington, richmond, call today! All colors, fixtures, granite, siding, outside landscaping, stone/brick, deck size, flooring have been ordered, New photos will be posted as house construction continues

  Mila Ensor Ensor Real Estate, LLC

  204 Jett Dr, 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 $426,530

  Last Listing Agent Craig Bridgewater Bridgewater Real Estate

  134 Fontaine Blvd, Winchester, KY 40391
• 

  

  /28

  Est $240,326

  Not Listed For Sale

  116 Alabama St, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 1,626 Sq Ft
  • Built 1940

  116 Alabama St, Winchester, KY 40391

  Last Sold Summary

  • 95 Days On Market

  Last Listing Agent Cheri Shaffer Keller Williams Commonwealth
• 

  

  /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
• 

  

  /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 $277,785

  Last Listing Agent Josh Wood Freedom Realty & Property Management

  403 Pueblo Ct, Winchester, KY 40391
• 

  

  /33

  Est $278,623

  Not Listed For Sale

  14 Calloway St, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,500 Sq Ft
  • Built 1940

  14 Calloway St, Winchester, KY 40391

  Last Sold Summary

  • 75 Days On Market

  Last Listing Agent Libby VanMeter Marshall Lane Real Estate - Lexington
• 

  

  /19

  $350,000

  • 3 Beds
  • 3 Baths
  • 2,592 Sq Ft

  135 E Broadway St, Winchester, KY 40391

  Attention Investors! This 3 plex in the heart of Winchester is a great investment. There are 3 apartments that are all currently rented out. The bottom floor has a huge living room, bathroom, and kitchen. The other two upstairs also have a living room, kitchen, bathroom, and bedroom. There is also a huge deck on the back for entertaining. Schedule an appointment to take a look before this one is

  Dale Hatton Dream Maker Realty, LLC

  135 E Broadway St, 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 $330,391

  Last Listing Agent Lucy Martin Jenkins United Real Estate Bluegrass

  1996 White Conkwright Rd, Winchester, KY 40391
• 

  

  /27

  Est $262,937

  Not Listed For Sale

  335 S Main St, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 1,968 Sq Ft
  • Built 1920

  335 S Main St, Winchester, KY 40391

  Last Sold Summary

  • 41 Days On Market

  Last Listing Agent Shari Frasure Keller Williams Commonwealth
• 

  

  /24

  $199,900

  • 2 Beds
  • 1 Bath
  • 1,149 Sq Ft

  287 Ecton Rd, Winchester, KY 40391

  Country living with city convenience! Move in ready two bedroom home, large kitchen with lots of cabinets, expansive living room and bonus room--currently used as office/den and laundry area! Lots of natural light throughout! Step out back to the deck to sit and enjoy the outdoors! Christmas Tree Farm and Wild Flower field next door. Nice fenced yard! Full house cellar with outdoor entrance,

  Vicky Kamousi Metro Realty

  287 Ecton Rd, 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 $304,322

  Last Listing Agent Josh Wood Freedom Realty & Property Management

  3622 Stamper Dr, Winchester, KY 40391
• 

  

  /35

  Est $231,619

  Not Listed For Sale

  24 Hughes Ave, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,200 Sq Ft
  • Built 2024

  24 Hughes Ave, Winchester, KY 40391

  Last Sold Summary

  • 24 Days On Market

  Last Listing Agent Nena Honaker Tom Goebel & Company
• 

  

  /22

  $134,900

  $5K 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 enthusiast, 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
• 

  

  /4

  $35,000

  Sold Jul 29, 2026

  2828 Athens Boonesboro Rd, Winchester, KY 40391

  • Land
  • 1 Acre
  • $35,000 per Acre

  Last Sold Summary

  • 14 Days On Market

  Current Estimated Value $35,281

  Last Listing Agent Kristian Kiskaden Keller Williams Commonwealth

  2828 Athens Boonesboro Rd, Winchester, KY 40391
• 

  

  /31

  Est $502,880

  Not Listed For Sale

  10 French Ave, Winchester, KY 40391

  • 5 Beds
  • 3 Baths
  • 3,262 Sq Ft
  • Built 1906

  10 French Ave, Winchester, KY 40391

  Last Sold Summary

  • 11 Days On Market

  Last Listing Agent Brian England Keller Williams Bluegrass Realty

Showing Results 481 - 520, Page 13 of 18