Homes in ZIP Code 40391

• 

  

  

  /52

  $320,000

  Sold Jul 29, 2026

  228 Holiday Rd, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 1,843 Sq Ft
  • Built 1979

  Last Sold Summary

  • 6% Below List Price
  • $174/SF
  • 11 Days On Market

  Current Estimated Value $329,041

  Last Listing Agent Caroline Mucci CENTURY 21 Commonwealth R E

  228 Holiday Rd, Winchester, KY 40391
• 

  

  

  /30

  Est $171,911

  Not Listed For Sale

  370 E Washington St, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 1,126 Sq Ft
  • Built 1930

  370 E Washington St, Winchester, KY 40391

  Last Sold Summary

  • 3 Days On Market

  Last Listing Agent Meredith Story Story Realty
• 

  

  

  /54

  $155,900

  $14K PRICE DROP

  • 1 Bed
  • 2 Baths
  • 1,056 Sq Ft

  101 Alabama St, Winchester, KY 40391

  Step back in time and discover the possibilities in this classic 1930-built home full of character and opportunity! With solid bones and vintage details, this property is the perfect canvas for investors, renovators, or anyone dreaming of restoring a piece of history. Featuring spacious rooms, original architectrual touches, and a layout just waiting to be reimagined. This home offers incredible

  A. Rebecca Woods Woods Realty Group

  101 Alabama St, Winchester, KY 40391
• 

  

  

  /26

  $250,000

  Sold Feb 20, 2026

  21 Virginia Ave, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,749 Sq Ft
  • Built 1962

  Last Sold Summary

  • 4% Below List Price
  • $143/SF
  • 40 Days On Market

  Current Estimated Value $250,854

  Last Listing Agent Emily Crump eXp Realty, LLC

  21 Virginia Ave, Winchester, KY 40391
• 

  

  

  /32

  Est $206,285

  Not Listed For Sale

  203 Crawford Ct, Winchester, KY 40391

  • 2 Beds
  • 2 Baths
  • 1,900 Sq Ft
  • Built 1960

  203 Crawford Ct, Winchester, KY 40391

  Last Sold Summary

  • 17 Days On Market

  Last Listing Agent Andrew Fugitt KY Property Hunters
• 

  

  /20

  $316,900

  $100K PRICE INCREASE

  • 3 Beds
  • 2.5 Baths
  • 1,858 Sq Ft

  200 Dubuy Dr, Winchester, KY 40391

  Search no more your dream home just hit the market! You will fall in love with this one as soon as you walk through the front door. Beautiful open concept, very modern new home just built in 2022. You're going to love the open kitchen and living room area with the large kitchen island, beautiful stainless steel appliances and granite countertops. Primary bedroom on the first floor with a full

  Wayne Elkins RE/MAX Creative Realty

  200 Dubuy Dr, Winchester, KY 40391
• 

  

  /19

  $199,900

  Sold Feb 12, 2026

  117 Buffalo Trace, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,072 Sq Ft
  • Built 1998

  Last Sold Summary

  • $186/SF
  • 49 Days On Market

  Current Estimated Value $200,722

  Last Listing Agent Nena Honaker Tom Goebel & Company

  117 Buffalo Trace, Winchester, KY 40391
• 

  

  /27

  Est $234,149

  Not Listed For Sale

  13 Fairview Ave, Winchester, KY 40391

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

  13 Fairview Ave, Winchester, KY 40391

  Last Sold Summary

  • 2 Days On Market

  Last Listing Agent Nena Honaker Tom Goebel & Company
• 

  /2

  $100,000

  $10K PRICE INCREASE

  • Land
  • 1.1 Acres
  • $90,909 per Acre

  270 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

  270 Duclair Dr, Winchester, KY 40391
• 

  

  /65

  $609,000

  Sold Jul 17, 2026

  6595 Mount Sterling Rd, Winchester, KY 40391

  • 5 Beds
  • 4 Baths
  • 4,515 Sq Ft
  • Built 2010

  Last Sold Summary

  • $135/SF
  • 21 Days On Market

  Current Estimated Value $606,356

  Last Listing Agent Brooke Otis Mullins RO&CO Real Estate

  6595 Mount Sterling Rd, Winchester, KY 40391
• 

  

  /39

  Est $170,490

  Not Listed For Sale

  10 Sylvania Ave, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 953 Sq Ft
  • Built 1961

  10 Sylvania Ave, Winchester, KY 40391

  Last Sold Summary

  • 207 Days On Market

  Last Listing Agent Christa Joynt Keller Williams Commonwealth
• 

  

  /9

  $500,000

  $100K PRICE DROP

  • Land
  • 1.52 Acres
  • $328,947 per Acre

  1005 Early Dr, Winchester, KY 40391

  Visibility, Access, Utilities on site per seller/per plat-buyer to verify, zoned B-3. 1.52 acres located at I-64 exit 96, Right in front of the Hampton Inn, buyer to verify and satisfy themselves to all aspects and information on property. and inspections sold as is. Buyer to Check with all utilities companies to very water electric and gas availability and locations on all utilities.

  Whitney Ensor Ensor Real Estate, LLC

  1005 Early Dr, Winchester, KY 40391
• 

  

  /31

  $205,000

  Sold Jun 12, 2026

  34 Hays St, Winchester, KY 40391

  • 4 Beds
  • 1.5 Baths
  • 2,450 Sq Ft
  • Built 1950

  Last Sold Summary

  • 8% Below List Price
  • $84/SF
  • 18 Days On Market

  Current Estimated Value $206,950

  Last Listing Agent Vickie Skeens RE/MAX Elite Lexington

  34 Hays St, Winchester, KY 40391
• 

  

  /43

  Est $139,322

  Not Listed For Sale

  44 Watts Rd, Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 858 Sq Ft
  • Built 1959

  44 Watts Rd, Winchester, KY 40391

  Last Sold Summary

  • 3 Days On Market

  Last Listing Agent Josh Wood Freedom Realty & Property Management
• 

  

  /14

  $650,000

  • Land
  • 3 Acres
  • $216,667 per Acre

  205 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

  205 Codella Dr, Winchester, KY 40391
• 

  

  /33

  $275,000

  Sold May 18, 2026

  402 Harney Dr, Winchester, KY 40391

  • 3 Beds
  • 1.5 Baths
  • 1,634 Sq Ft
  • Built 1979

  Last Sold Summary

  • $168/SF
  • 5 Days On Market

  Current Estimated Value $277,895

  Last Listing Agent Michelle Blackburn RE/MAX Creative, Winchester

  402 Harney Dr, Winchester, KY 40391
• 

  

  /25

  Est $124,595

  Not Listed For Sale

  248 Cook Ave, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,465 Sq Ft
  • Built 1940

  248 Cook Ave, Winchester, KY 40391

  Last Sold Summary

  • 27 Days On Market

  Last Listing Agent Chris Johnson Plum Tree Realty
• 

  /2

  $67,500

  • Land
  • 1.89 Acres
  • $35,695 per Acre

  250 Spencer Ln, Winchester, KY 40391

  Unique triangular shaped lot in a wooded rural setting, interesting opportunities for privacy in a beautiful area of Clark County where you can enjoy the outdoors and create memories galore.

  Craig Bridgewater Bridgewater Real Estate

  250 Spencer Ln, Winchester, KY 40391
• 

  

  /55

  $280,000

  Sold Aug 26, 2026

  21 Beckner St, Winchester, KY 40391

  • 6 Beds
  • 4 Baths
  • 3,090 Sq Ft
  • Built 1940

  Last Sold Summary

  • 4% Above List Price
  • $91/SF
  • 4 Days On Market

  Current Estimated Value $266,897

  Last Listing Agent Rex Hall United Real Estate Bluegrass

  21 Beckner St, Winchester, KY 40391
• 

  

  /41

  Est $201,074

  Not Listed For Sale

  31 Watts Rd, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,343 Sq Ft
  • Built 1960

  31 Watts Rd, Winchester, KY 40391

  Last Sold Summary

  • 24 Days On Market

  Last Listing Agent Christa Joynt Keller Williams Commonwealth
• 

  

  /3

  $430,000

  New Construction Pending

  • 3 Beds
  • 2 Baths
  • 1,855 Sq Ft

  250 Evergreen Dr, Winchester, KY 40391

  Introducing The Mulberry floor plan - a beautifully designed proposed construction home in the scenic Locust Hill Acres community. This open-concept floor plan offers the perfect blend of comfort and functionality with 3 bedrooms, 2 full bathrooms, unfinished walkout basement and thoughtful living spaces throughout. The spacious primary suite features a large walk-in closet and a private ensuite

  Rex Hall United Real Estate Bluegrass

  250 Evergreen Dr, Winchester, KY 40391
• 

  

  /34

  $380,000

  Sold Nov 21, 2025

  110 Hampton Avenue Exd, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 2,516 Sq Ft

  Last Sold Summary

  • 1% Above List Price
  • $151/SF
  • 5 Days On Market

  Current Estimated Value $368,516

  Last Listing Agent Erin Lewis Christies International Real Estate Bluegrass

  110 Hampton Avenue Exd, Winchester, KY 40391
• 

  

  /65

  Est $278,289

  Not Listed For Sale

  151 Hilltop Dr, Winchester, KY 40391

  • 4 Beds
  • 1.5 Baths
  • 1,873 Sq Ft
  • Built 1960

  151 Hilltop Dr, Winchester, KY 40391

  Last Sold Summary

  • 130 Days On Market

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

  

  /6

  $110,000

  • Land
  • 2.06 Acres
  • $53,398 per Acre

  1185 Craig Crossing Rd, Winchester, KY 40391

  Lot # 30 contains 2.058 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

  1185 Craig Crossing Rd, Winchester, KY 40391
• 

  

  /30

  $289,100

  Sold Nov 03, 2025

  223 Bartram Ct, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,606 Sq Ft
  • Built 2004

  Last Sold Summary

  • $180/SF
  • 46 Days On Market

  Current Estimated Value $297,423

  Last Listing Agent Jennifer Parsons RE/MAX Elite Lexington

  223 Bartram Ct, Winchester, KY 40391
• 

  

  /23

  Est $258,781

  Not Listed For Sale

  130 Hilltop Dr, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,465 Sq Ft
  • Built 1960

  130 Hilltop Dr, Winchester, KY 40391

  Last Sold Summary

  • 2 Days On Market

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

  

  /31

  $229,500

  $10K PRICE DROP Pending

  • 3 Beds
  • 2 Baths
  • 1,228 Sq Ft

  22 Apache Trail, Winchester, KY 40391

  Enjoy small town living! The seller is offering up to $5000 toward buyer's closing cost with an acceptable offer. This 3-bedroom 2 bath budget friendly home is ready and waiting for new owners. The unique loft space adds additional space to make it your own. Sitting on just under a third of an acre which will provide a lot of outdoor space to enjoy with friends and family. The backyard is fenced

  Vickie Skeens RE/MAX Elite Lexington

  22 Apache Trail, Winchester, KY 40391
• 

  

  /42

  $400,000

  Sold Dec 05, 2025

  210 College St, Winchester, KY 40391

  • 4 Beds
  • 3.5 Baths
  • 2,718 Sq Ft
  • Built 1895

  Last Sold Summary

  • 5% Below List Price
  • $147/SF
  • 59 Days On Market

  Current Estimated Value $407,508

  Last Listing Agent Erin Lewis Christies International Real Estate Bluegrass

  210 College St, Winchester, KY 40391
• 

  

  /54

  Est $422,819

  Not Listed For Sale

  1455 Irvine Rd, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 2,901 Sq Ft
  • Built 1940

  1455 Irvine Rd, Winchester, KY 40391

  Last Sold Summary

  • 35 Days On Market

  Last Listing Agent Shari Frasure Keller Williams Commonwealth
• 

  /2

  $110,000

  $10K PRICE INCREASE

  • Land
  • 15,246 Sq Ft
  • $314,286 per Acre

  150 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

  150 Duclair Dr, Winchester, KY 40391
• 

  

  /34

  $444,000

  Sold Jun 24, 2026

  1478 Donaldson Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 2,442 Sq Ft
  • Built 2004

  Last Sold Summary

  • $182/SF
  • 2 Days On Market

  Current Estimated Value $447,798

  Last Listing Agent Jim Woodrum RE/MAX Creative, Winchester

  1478 Donaldson Rd, Winchester, KY 40391
• 

  

  /70

  Est $278,782

  Not Listed For Sale

  1131 Ironworks Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 2,321 Sq Ft
  • Built 1960

  1131 Ironworks Rd, Winchester, KY 40391

  Last Sold Summary

  • 45 Days On Market

  Last Listing Agent Christa Joynt Keller Williams Commonwealth
• 

  

  /51

  $264,900

  Pending

  • 3 Beds
  • 2 Baths
  • 1,323 Sq Ft

  244 Prescott Ln, Winchester, KY 40391

  Move-in ready with several recent updates, this 3-bedroom, 2-bath, one-story home offers comfortable living in a convenient Winchester location. This home features an open-concept floor plan with a spacious living area that flows into the kitchen, complete with a pantry and newer kitchen appliances. New vinyl plank flooring adds a fresh, updated feel throughout the home, while major improvements

  Josh Wood Freedom Realty & Property Management

  244 Prescott Ln, Winchester, KY 40391
• 

  

  /15

  $286,000

  Sold Jun 12, 2026

  110 Buckingham Ln, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,240 Sq Ft
  • Built 2001

  Last Sold Summary

  • 4% Above List Price
  • $231/SF
  • 3 Days On Market

  Current Estimated Value $291,700

  Last Listing Agent Oliver Winn ERA Select Real Estate

  110 Buckingham Ln, Winchester, KY 40391
• 

  

  /26

  Est $239,978

  Not Listed For Sale

  1124 Ironworks Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,176 Sq Ft
  • Built 2006

  1124 Ironworks Rd, Winchester, KY 40391

  Last Sold Summary

  • 7 Days On Market

  Last Listing Agent Kathryn Cheuvront Coldwell Banker McMahan
• 

  

  /32

  $175,000

  • 3 Beds
  • 1 Bath
  • 1,173 Sq Ft

  24 Spring St, Winchester, KY 40391

  Lovely one story home located minutes from downtown Winchester with large detached garage ans shed! This home as three bedrooms and one bath with covered porch and walled patio outside. The garage is equipped with large ares for parking and storage and also has its own kitchen. Don't let this one pass by. Come see TODAY!!! Note: This is an auction property. Please call agent for more info Buyer

  Jason Szaks EXIT Town & Country Realtors

  24 Spring St, Winchester, KY 40391
• 

  

  /31

  $315,000

  Sold Aug 10, 2026

  110 Powe Dr, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,010 Sq Ft
  • Built 2007

  Last Sold Summary

  • 9% Below List Price
  • $157/SF
  • 93 Days On Market

  Current Estimated Value $330,792

  Last Listing Agent Michael Hilario The Agency

  110 Powe Dr, Winchester, KY 40391
• 

  

  /28

  Est $237,856

  Not Listed For Sale

  1112 Ironworks Rd, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,176 Sq Ft
  • Built 2006

  1112 Ironworks Rd, Winchester, KY 40391

  Last Sold Summary

  • 116 Days On Market

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

  

  /116

  $1,595,000

  $100K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 4,518 Sq Ft

  3166 Colby Rd, Winchester, KY 40391

  NEW PRICE!!! Not sure what you are looking for, but see if this property checks enough boxes for you. This beautiful 33± acre estate offers the perfect blend of country charm, modern comfort, and endless opportunity. The stately historical home, built in 1919, offers a rare opportunity to own a true piece of Kentucky history . Enjoy stunning mountain views — perched at one of the highest points

  Alyssa M Boley Coldwell Banker McMahan

  3166 Colby Rd, Winchester, KY 40391
• 

  

  /31

  $379,717

  Sold Mar 27, 2026

  300 Calmes Blvd, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 2,636 Sq Ft
  • Built 1989

  Last Sold Summary

  • 5% Below List Price
  • $144/SF
  • 111 Days On Market

  Current Estimated Value $389,069

  Last Listing Agent Darrell Tackett Dream Maker Realty, LLC

  300 Calmes Blvd, Winchester, KY 40391

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