Winchester, KY Homes

• 

  

  

  /51

  $428,000

  Sold Sep 04, 2025

  17 Hampton Ave, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 3,181 Sq Ft
  • Built 1960

  Last Sold Summary

  • 4% Below List Price
  • $135/SF
  • 34 Days On Market

  Current Estimated Value $443,724

  Last Listing Agent Craig Bridgewater Bridgewater Real Estate

  17 Hampton Ave, Winchester, KY 40391
• 

  

  

  /23

  Est $265,265

  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
• 

  

  

  /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
• 

  

  

  /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 $275,539

  Last Listing Agent Michelle Blackburn RE/MAX Creative, Winchester

  402 Harney Dr, Winchester, KY 40391
• 

  

  

  /54

  Est $417,628

  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
• 

  /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
• 

  

  /26

  $239,500

  Sold Jul 15, 2025

  129 Bay Hill Dr, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 2,017 Sq Ft
  • Built 1998

  Last Sold Summary

  • 2% Below List Price
  • $119/SF
  • 26 Days On Market

  Current Estimated Value $247,589

  Last Listing Agent Vickie Skeens RE/MAX Elite Lexington

  129 Bay Hill Dr, Winchester, KY 40391
• 

  

  /70

  Est $283,199

  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
• 

  

  /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
• 

  

  /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 $376,127

  Last Listing Agent Erin Lewis Christies International Real Estate Bluegrass

  110 Hampton Avenue Exd, Winchester, KY 40391
• 

  

  /26

  Est $251,208

  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
• 

  

  /59

  $199,900

  Pending

  • 4 Beds
  • 1 Bath
  • 1,743 Sq Ft

  218 E Washington St, Winchester, KY 40391

  . Charming 4‐Bedroom Home Near Historic Downtown Winchester Freshly painted and move‐in ready, this 4 bedroom, 1 bathroom home offers comfort, convenience, and plenty of bonus space. A large bonus room gives you flexibility for a playroom, office, hobby space, or second living area. Step outside to a fully fenced yard with a wood privacy fence, perfect for pets, kids, or quiet evenings outdoors.

  Justina Rector United Country Re/Cntry Living Spec Inc

  218 E Washington St, 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 $291,397

  Last Listing Agent Jennifer Parsons RE/MAX Elite Lexington

  223 Bartram Ct, Winchester, KY 40391
• 

  

  /28

  Est $250,367

  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
• 

  

  /23

  $324,900

  $45K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 3,868 Sq Ft

  225 Plantations Dr, Winchester, KY 40391

  Welcome to 225 Plantations Drive, a beautifully maintained home in the desirable Royal Oaks Subdivision. This charming three-bedroom, two-and-a-half-bath residence is in wonderful condition and move-in ready! This is home comes with a wonderful floorplan that has a primary bedroom with built-in's on the first floor, Kitchen with granite and stainless appliances and deck has been updated with Trex

  John Wilson Bluegrass Properties Group

  225 Plantations Dr, 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 $401,339

  Last Listing Agent Erin Lewis Christies International Real Estate Bluegrass

  210 College St, Winchester, KY 40391
• 

  

  /41

  Est $250,912

  Not Listed For Sale

  273 Winn Ave, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,982 Sq Ft
  • Built 1880

  273 Winn Ave, Winchester, KY 40391

  Last Sold Summary

  • 38 Days On Market
• 

  

  /40

  $294,900

  $5K PRICE DROP

  • 4 Beds
  • 1 Bath
  • 2,327 Sq Ft

  162 French Ave, Winchester, KY 40391

  Could 162 French Ave., Winchester, KY 40391 be your new address? This stunning, updated Craftsman home feels like it was pulled straight from the pages of Southern Living Magazine, blending modern updates with timeless character and charm. Recent improvements including new windows, doors, wiring, and fresh landscaping enhance the home while preserving its original appeal. This move-in ready

  Jonathan Wood HomeLand Real Estate Inc - Mt Sterling

  162 French Ave, 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 $386,517

  Last Listing Agent Darrell Tackett Dream Maker Realty, LLC

  300 Calmes Blvd, Winchester, KY 40391
• 

  

  /38

  Est $243,518

  Not Listed For Sale

  113 Mary Way, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,050 Sq Ft
  • Built 1996

  113 Mary Way, Winchester, KY 40391

  Last Sold Summary

  • 10 Days On Market
• 

  

  /52

  $449,900

  Pending

  • 4 Beds
  • 3 Baths
  • 3,126 Sq Ft

  207 Hibiscus Ln, Winchester, KY 40391

  Welcome to 207 Hibiscus Ln, will this be your new address? This beautifully maintained home truly checks all the boxes, offering incredible curb appeal with lush landscaping, mature trees for added privacy and shade, and a welcoming covered front porch complete with a swing. The outdoor living spaces are just as impressive, featuring a screened-in porch, spacious deck, rear patio with a custom

  Jonathan Wood HomeLand Real Estate Inc - Mt Sterling

  207 Hibiscus Ln, 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 $421,626

  Last Listing Agent Meredith Walker Bluegrass Sotheby's International Realty

  1857 Ironworks Rd, Winchester, KY 40391
• 

  

  /30

  Est $222,848

  Not Listed For Sale

  306 Sarah Ct, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,092 Sq Ft
  • Built 1998

  306 Sarah Ct, Winchester, KY 40391

  Last Sold Summary

  • 0 Days On Market
• 

  

  /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
• 

  

  /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 $228,229

  Last Listing Agent Alyssa M Boley Coldwell Banker McMahan

  26 Stefanie Ct, Winchester, KY 40391
• 

  

  /25

  Est $252,331

  Not Listed For Sale

  316 Jameson Way, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,625 Sq Ft
  • Built 1990

  316 Jameson Way, Winchester, KY 40391

  Last Sold Summary

  • 140 Days On Market
• 

  

  /20

  $225,000

  $5K PRICE DROP Pending

  • 3 Beds
  • 2 Baths
  • 1,136 Sq Ft

  86 Brink Ave, Winchester, KY 40391

  Welcome Home! Its ready for you! All the updates have been done. You will enjoy a beautiful newly updated kitchen with new appliances, new laminate floors, updated bathrooms , and fresh paint throughout. Enjoy the confidence of a new HVAC, new Hot Water Heater, and young metal roof. This home provides the ease and comfort of a first floor primary and spacious livingroom. Enjoy beautiful evenings

  Jennifer Hukill RE/MAX Elite Lexington

  86 Brink Ave, 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 $362,018

  Last Listing Agent Robin Jones Keller Williams Legacy Group

  114 Mallard Ln, Winchester, KY 40391
• 

  

  /87

  Est $284,789

  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
• 

  /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
• 

  

  /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 $476,985

  Last Listing Agent Robin Jones Keller Williams Legacy Group

  701 Lisletown Ln, Winchester, KY 40391
• 

  

  /38

  Est $201,668

  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
• 

  

  /3

  $42,500

  Pending

  • Land
  • 8,712 Sq Ft
  • $212,500 per Acre

  108 Dorset Ln, Winchester, KY 40391

  The restictions state that if it is a ranch plan, there is a minimun of 1300 sq ft. It it is a 1 1/2 story or two story then 1800 sq ft will be required. A two car garage must be attached. Developer will need to approve plans before starting construction This lot is ideal for a walkout basement. Perfect setting for watching the sunsets

  Jo Gawthrop Keller Williams Bluegrass Realty

  108 Dorset Ln, 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
• 

  

  /14

  Est $202,429

  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
• 

  

  /18

  $169,000

  $10K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,046 Sq Ft

  175 Magnolia St, Winchester, KY 40391

  Two homes on one lot. Informaton in listing is for the home in the front of the lot. Behind this home is a second home consisting of 2 bedrooms, 1, bath, Living room and kitchen. Main home has been completely remodeled but guest home will require major renevations. The home in the front of the property is vacant but there is a tenant in the home in the rear of the property. The lease is month to

  A. Rebecca Woods Woods Realty Group

  175 Magnolia St, 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 $574,504

  Last Listing Agent Jim Woodrum RE/MAX Creative, Winchester

  184 Casa Landa Way, Winchester, KY 40391
• 

  

  /33

  Est $300,877

  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
• 

  

  /7

  $270,000

  $50K PRICE DROP

  • Land
  • 36,590 Sq Ft
  • $321,429 per Acre

  800 Interstate Dr, Winchester, KY 40391

  Visibility, Access, Utilities on site per seller/per plat buyer to verify, zoned B-3. .84 acres located and visible at I-64 exit 96, buyer to verify and satisfy themselves to all aspects and information on property and or inspections sold as is. Buyer to verify water, gas, and electric locations and availability.

  Whitney Ensor Ensor Real Estate, LLC

  800 Interstate Dr, 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 $424,515

  Last Listing Agent Patrick Arvin Keller Williams Commonwealth

  4732 Old Boonesboro Rd, Winchester, KY 40391

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