Winchester, KY Homes

• 

  

  

  /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 $273,338

  Last Listing Agent Michelle Blackburn RE/MAX Creative, Winchester

  402 Harney Dr, Winchester, KY 40391
• 

  

  

  /87

  Est $273,557

  Not Listed For Sale

  418 Jameson Way, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,680 Sq Ft
  • Built 1996

  418 Jameson Way, 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
• 

  

  

  /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 $362,707

  Last Listing Agent Erin Lewis Christies International Real Estate Bluegrass

  110 Hampton Avenue Exd, Winchester, KY 40391
• 

  

  

  /38

  Est $195,518

  Not Listed For Sale

  412 Jameson Way, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,073 Sq Ft
  • Built 1990

  412 Jameson Way, Winchester, KY 40391

  Last Sold Summary

  • 0 Days On Market

  Last Listing Agent Josh Wood Freedom Realty & Property Management
• 

  /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
• 

  

  /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 $292,001

  Last Listing Agent Jennifer Parsons RE/MAX Elite Lexington

  223 Bartram Ct, Winchester, KY 40391
• 

  

  /14

  Est $199,093

  Not Listed For Sale

  411 Jameson Way, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,000 Sq Ft
  • Built 1990

  411 Jameson Way, Winchester, KY 40391

  Last Sold Summary

  • 19 Days On Market

  Last Listing Agent Jason Szaks EXIT Town & Country Realtors
• 

  

  /38

  $239,900

  Pending

  • 3 Beds
  • 2 Baths
  • 1,164 Sq Ft

  210 Shannon Ct, Winchester, KY 40391

  Welcome home to this beautifully updated all electric, one-story, 3-bedroom, 2-bathroom ranch home, perfectly situated on a quiet cul-de-sac in Winchester. NEW (2026) roof, HVAC, paint, kitchen cabinets, kitchen appliances, bathroom vanities, toilets, flooring and doors. Property qualifies for USDA (Rural Housing) loan, one of just a few areas in Clark county. With its charming blue exterior and

  ROBIN TRIMBLE HomeFirst Real Estate

  210 Shannon Ct, 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 $398,794

  Last Listing Agent Erin Lewis Christies International Real Estate Bluegrass

  210 College St, Winchester, KY 40391
• 

  

  /33

  Est $292,147

  Not Listed For Sale

  137 Summerhill Way, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,284 Sq Ft
  • Built 2003

  137 Summerhill Way, Winchester, KY 40391

  Last Sold Summary

  • 6 Days On Market

  Last Listing Agent Keith Wilson Coldwell Banker McMahan
• 

  

  /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

  $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 $446,514

  Last Listing Agent Jim Woodrum RE/MAX Creative, Winchester

  1478 Donaldson Rd, Winchester, KY 40391
• 

  

  /31

  Est $245,106

  Not Listed For Sale

  121 Summerhill Way, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,302 Sq Ft
  • Built 2002

  121 Summerhill Way, Winchester, KY 40391

  Last Sold Summary

  • 70 Days On Market

  Last Listing Agent Pete doCouto Plum Tree Realty
• 

  

  /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
• 

  

  /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 $289,894

  Last Listing Agent Oliver Winn ERA Select Real Estate

  110 Buckingham Ln, Winchester, KY 40391
• 

  

  /23

  Est $274,375

  Not Listed For Sale

  302 Salem Ave, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,490 Sq Ft
  • Built 2001

  302 Salem Ave, Winchester, KY 40391

  Last Sold Summary

  • 34 Days On Market

  Last Listing Agent Emily Donaldson Keller Williams Commonwealth
• 

  

  /31

  $239,995

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

  22 Apache Trail, Winchester, KY 40391

  Enjoy small town living! 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 for convenience and privacy. Run from the routine of renting and enjoy home ownership in

  Vickie Skeens RE/MAX Elite Lexington

  22 Apache Trail, 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 $381,770

  Last Listing Agent Darrell Tackett Dream Maker Realty, LLC

  300 Calmes Blvd, Winchester, KY 40391
• 

  

  /17

  Est $279,706

  Not Listed For Sale

  218 Bracken Ct, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,292 Sq Ft
  • Built 2005

  218 Bracken Ct, Winchester, KY 40391

  Last Sold Summary

  • 7 Days On Market

  Last Listing Agent Vickie Skeens RE/MAX Elite Lexington
• 

  /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
• 

  

  /64

  $415,000

  Sold Feb 25, 2026

  1857 Ironworks Rd, Winchester, KY 40391

  • 5 Beds
  • 2.5 Baths
  • 2,924 Sq Ft
  • Built 1865

  Last Sold Summary

  • 3% Below List Price
  • $142/SF
  • 70 Days On Market

  Current Estimated Value $421,834

  Last Listing Agent Meredith Walker Bluegrass Sotheby's International Realty

  1857 Ironworks Rd, Winchester, KY 40391
• 

  

  /32

  Est $257,005

  Not Listed For Sale

  200 Bracken Ct, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,252 Sq Ft
  • Built 2002

  200 Bracken Ct, Winchester, KY 40391

  Last Sold Summary

  • 3 Days On Market

  Last Listing Agent Amy Diamond ERA Select Real Estate
• 

  

  /120

  $1,695,000

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

  3166 Colby Rd, Winchester, KY 40391

  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 in Clark

  Alyssa M Boley Coldwell Banker McMahan

  3166 Colby Rd, Winchester, KY 40391
• 

  

  /23

  $225,000

  Sold Aug 21, 2025

  26 Stefanie Ct, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,080 Sq Ft
  • Built 1972

  Last Sold Summary

  • $208/SF
  • 12 Days On Market

  Current Estimated Value $222,687

  Last Listing Agent Alyssa M Boley Coldwell Banker McMahan

  26 Stefanie Ct, Winchester, KY 40391
• 

  

  /37

  Est $306,884

  Not Listed For Sale

  311 Fern Ct, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,326 Sq Ft
  • Built 1999

  311 Fern Ct, Winchester, KY 40391

  Last Sold Summary

  • 8 Days On Market

  Last Listing Agent Robyn Bradley Woods Realty Group
• 

  

  /26

  $234,900

  • 3 Beds
  • 2 Baths
  • 1,904 Sq Ft

  528 Estes Dr, Winchester, KY 40391

  *NEW ROOF!* Welcome home to this well-maintained 3-bedroom, 2-bath brick ranch offering easy one-level living in a convenient location close to shopping, dining, parks, and the community pool. The spacious open family room flows into the kitchen, featuring bamboo wood flooring, a large granite island, newer stainless steel appliances, and a gas range—perfect for everyday living and entertaining.

  Josh Wood Freedom Realty & Property Management

  528 Estes Dr, Winchester, KY 40391
• 

  

  /47

  $365,000

  Sold Apr 20, 2026

  114 Mallard Ln, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 2,105 Sq Ft
  • Built 1970

  Last Sold Summary

  • 4% Below List Price
  • $173/SF
  • 162 Days On Market

  Current Estimated Value $358,863

  Last Listing Agent Robin Jones Keller Williams Legacy Group

  114 Mallard Ln, Winchester, KY 40391
• 

  

  /49

  Est $320,551

  Not Listed For Sale

  317 Fern Ct, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,588 Sq Ft
  • Built 1999

  317 Fern Ct, Winchester, KY 40391

  Last Sold Summary

  • 0 Days On Market

  Last Listing Agent Sherry Stephens Murphy Realty Group
• 

  

  /3

  $1,200

  Pending

  • Land
  • 2.57 Acres
  • $467 per Acre

  507 Tech Dr, Winchester, KY 40391

  For lease-Frontage on Rolling Hills Rd, and Tech Drive.I-64 visibility, ideally located commercial property. Paved driveway and gravel lot.$1200 per .25 acre/per month

  Holly Spradlin KY Realty Co

  507 Tech Dr, Winchester, KY 40391
• 

  

  /50

  $465,000

  Sold Aug 11, 2025

  701 Lisletown Ln, Winchester, KY 40391

  • 2 Beds
  • 2.5 Baths
  • 2,784 Sq Ft
  • Built 2008

  Last Sold Summary

  • $167/SF
  • 2 Days On Market

  Current Estimated Value $481,107

  Last Listing Agent Robin Jones Keller Williams Legacy Group

  701 Lisletown Ln, Winchester, KY 40391
• 

  

  /75

  Est $283,731

  Not Listed For Sale

  314 Fern Ct, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,844 Sq Ft
  • Built 1999

  314 Fern Ct, Winchester, KY 40391

  Last Sold Summary

  • 23 Days On Market

  Last Listing Agent Sherry Stephens Murphy Realty Group
• 

  

  /52

  $449,000

  $16K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,942 Sq Ft

  1024 Flanagan Station Rd, Winchester, KY 40391

  Nestled on 8.9 picturesque acres just off Boonesboro Road, this one-of-a-kind property offers the perfect blend of character, privacy, and endless potential. Whether you're dreaming of a horse farm, hobby farm, or simply room to roam, this beautiful property provides plenty of space for horses, livestock, gardening, or enjoying peaceful country living. Inside, you'll find a spacious open-concept

  Brooke Martin RO&CO Real Estate

  1024 Flanagan Station Rd, Winchester, KY 40391
• 

  /2

  $75,000

  Sold Jan 05, 2026

  1341 Sewell Shop Rd, Winchester, KY 40391

  • Land
  • 5.75 Acres
  • $13,043 per Acre

  Last Sold Summary

  • 6% Below List Price
  • 10 Days On Market

  Last Listing Agent Zella Rosenthal Tom Goebel & Company

  1341 Sewell Shop Rd, Winchester, KY 40391
• 

  

  /35

  Est $259,493

  Not Listed For Sale

  206 Moss Cir, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,773 Sq Ft
  • Built 1997

  206 Moss Cir, Winchester, KY 40391

  Last Sold Summary

  • 20 Days On Market

  Last Listing Agent David Baesler Kentucky Dreams Realty
• 

  

  /29

  $50,000

  • 1 Bed
  • 1 Bath
  • 870 Sq Ft

  141 Coffee Springs Ln, Winchester, KY 40391

  This is a public auction. You are buying as/is. Please come and preview the property. 10% Buyers premium added to the final bid. 10% down night of the sell. This property can be made into a dream home. Where else can you find a property for 50,000.00 dollars? Rony Jo Ballou Auctioneer 859-595-6808 bid at www.goochsells.com. Realtors you are welcome to bring your clients to preview this property.

  Rony Jo Ballou Power House Realty

  141 Coffee Springs Ln, Winchester, KY 40391
• 

  

  /29

  $408,000

  Sold Sep 12, 2025

  4732 Old Boonesboro Rd, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 2,361 Sq Ft
  • Built 1945

  Last Sold Summary

  • 18% Below List Price
  • $173/SF
  • 285 Days On Market

  Current Estimated Value $425,011

  Last Listing Agent Patrick Arvin Keller Williams Commonwealth

  4732 Old Boonesboro Rd, Winchester, KY 40391
• 

  

  /35

  Est $280,622

  Not Listed For Sale

  1896 Mount Sterling Rd, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 1,942 Sq Ft
  • Built 1960

  1896 Mount Sterling Rd, Winchester, KY 40391

  Last Sold Summary

  • 10 Days On Market

  Last Listing Agent Keith Wilson Coldwell Banker McMahan
• 

  /2

  $100,000

  $10K PRICE DROP

  • Land
  • 13,939 Sq Ft
  • $312,500 per Acre

  111 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

  111 Jacob Ct, Winchester, KY 40391
• 

  /2

  $555,000

  Sold Jan 16, 2026

  184 Casa Landa Way, Winchester, KY 40391

  • 4 Beds
  • 3.5 Baths
  • 3,585 Sq Ft
  • Built 1998

  Last Sold Summary

  • 6% Below List Price
  • $155/SF

  Current Estimated Value $575,126

  Last Listing Agent Jim Woodrum RE/MAX Creative, Winchester

  184 Casa Landa Way, Winchester, KY 40391

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