Winchester, KY Homes

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  /2

  $100,000

  • Land
  • 29,620 Sq Ft
  • $147,059 per Acre

  100 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

  100 Duclair Dr, Winchester, KY 40391
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  /2

  $224,900

  Sold May 08, 2026

  11 Shelley Dr, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,188 Sq Ft
  • Built 1970

  Last Sold Summary

  • $189/SF

  Current Estimated Value $227,114

  Last Listing Agent Mark Wallace Transactionbroker.com

  11 Shelley Dr, Winchester, KY 40391
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  /47

  Est $364,262

  Not Listed For Sale

  113 S Burns Ave, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 3,299 Sq Ft
  • Built 1895

  113 S Burns Ave, Winchester, KY 40391

  Last Sold Summary

  • 1 Day On Market
• 

  

  

  /65

  $759,000

  $66K PRICE DROP

  • 2 Beds
  • 2.5 Baths
  • 2,361 Sq Ft

  455 Davis Ln, Winchester, KY 40391

  Hunter's Paradise! This beautiful 85 acre farm is nestled in the heart of Clark County. Wildlife is abundant as you travel throughout the property. The home is very spacious with a full mother in law suite. Entertain friends at the full bar, while enjoying the wood burning stove. A functioning greenhouse expands the possibilities for year round gardening. If you are looking for little piece of

  Dale Hatton Dream Maker Realty, LLC

  455 Davis Ln, Winchester, KY 40391
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  /30

  $254,000

  Sold Dec 02, 2025

  312 Forest Ave, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,550 Sq Ft
  • Built 1962

  Last Sold Summary

  • 6% Below List Price
  • $164/SF
  • 52 Days On Market

  Current Estimated Value $255,194

  Last Listing Agent Michelle Blackburn RE/MAX Creative, Winchester

  312 Forest Ave, Winchester, KY 40391
• 

  

  /35

  Est $334,908

  Not Listed For Sale

  123 W Hickman St, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 2,498 Sq Ft
  • Built 1940

  123 W Hickman St, Winchester, KY 40391

  Last Sold Summary

  • 1 Day On Market
• 

  

  /12

  $249,900

  $95K PRICE DROP

  • 4 Beds
  • 4 Baths
  • 2,072 Sq Ft

  1128 Dale Dr, Winchester, KY 40391

  Duplex. Both units are being sold together. Great income-producing potential. Each side offers a nice sized vaulted Great room that opens to the kitchen, 2 bedrooms, 1.5 baths, a laundry room, and a 1-car garage. Nice private backyard for side with lots of trees. 1130 has a new HVAC. Selling As Is Inspections Welcome.

  Brian Hatfield Coldwell Banker McMahan

  1128 Dale Dr, Winchester, KY 40391
• 

  

  /75

  $410,000

  Sold Nov 21, 2025

  291 Log Lick Rd, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 2,600 Sq Ft
  • Built 2007

  Last Sold Summary

  • 6% Below List Price
  • $158/SF
  • 3 Days On Market

  Current Estimated Value $421,284

  Last Listing Agent Joyce Ratliff Tom Goebel & Company

  291 Log Lick Rd, Winchester, KY 40391
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  /49

  Est $257,098

  Not Listed For Sale

  115 Olde Potomac Ave, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 2,018 Sq Ft
  • Built 1940

  115 Olde Potomac Ave, Winchester, KY 40391

  Last Sold Summary

  • 3 Days On Market
• 

  /2

  $110,000

  $10K PRICE INCREASE

  • Land
  • 12,632 Sq Ft
  • $379,310 per Acre

  160 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

  160 Duclair Dr, Winchester, KY 40391
• 

  

  /4

  $101,000

  Sold Jul 14, 2025

  2058 Athens Boonesboro Rd, Winchester, KY 40391

  • Land
  • 4.02 Acres
  • $25,124 per Acre

  Last Sold Summary

  • 7% Below List Price
  • 86 Days On Market

  Last Listing Agent Megan McCoy Keller Williams Legacy Group

  2058 Athens Boonesboro Rd, Winchester, KY 40391
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  /36

  Est $243,202

  Not Listed For Sale

  242 W Lexington Ave, Winchester, KY 40391

  • 3 Beds
  • 1.5 Baths
  • 1,755 Sq Ft
  • Built 1940

  242 W Lexington Ave, Winchester, KY 40391

  Last Sold Summary

  • 49 Days On Market
• 

  

  /29

  $329,500

  $10K PRICE DROP Pending

  • 3 Beds
  • 2 Baths
  • 1,719 Sq Ft

  374 N Middletown Rd, Winchester, KY 40391

  Investment Opportunity! This is the Parent Listing. 2 Parcels listed for $339,500 (MLS listing #s 25005575 and 25005577). 2 (titled) Manufactured double-wide homes on permanent foundations sitting on ten acres in Clark County KY. Both properties, 374 and 360 N. Middletown Rd., are being offered together. (Child listing is 360 N. Middletown Rd). Mature garden and LOTS of potential. You could

  Danielle Haggard Keller Williams Commonwealth

  374 N Middletown Rd, Winchester, KY 40391
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  /36

  $257,400

  Sold Nov 21, 2025

  103 Hampton Ave, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,715 Sq Ft
  • Built 1958

  Last Sold Summary

  • 10% Below List Price
  • $150/SF
  • 4 Days On Market

  Current Estimated Value $270,095

  Last Listing Agent Brett Bussell Turf Town Properties

  103 Hampton Ave, Winchester, KY 40391
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  /41

  Est $286,940

  Not Listed For Sale

  21 Beckner St, Winchester, KY 40391

  • 6 Beds
  • 3.5 Baths
  • 3,072 Sq Ft
  • Built 1940

  21 Beckner St, Winchester, KY 40391

  Last Sold Summary

  • 17 Days On Market
• 

  

  /3

  $645,000

  New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,526 Sq Ft

  106 Bella Shae Way, Winchester, KY 40391

  Welcome Home to the Claiborne Floor Plan by CP Builders. This stunning 4-bedroom, 2.5-bathroom home offers a luxurious and spacious living experience. The first floor features a magnificent primary suite complete with a spacious ensuite bathroom, a walk-in closet, and direct access to the backyard. The open floor plan seamlessly connects the living, dining, and kitchen areas, creating a warm and

  Shane Underwood Keller Williams Commonwealth

  106 Bella Shae Way, Winchester, KY 40391
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  /58

  $460,000

  Sold Jul 11, 2025

  150 Stone Crest Rd, Winchester, KY 40391

  • 4 Beds
  • 4 Baths
  • 4,448 Sq Ft
  • Built 1978

  Last Sold Summary

  • 6% Below List Price
  • $103/SF
  • 18 Days On Market

  Last Listing Agent Brenda Murphy Murphy Realty Group

  150 Stone Crest Rd, Winchester, KY 40391
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  /51

  Est $384,003

  Not Listed For Sale

  200 College St, Winchester, KY 40391

  • 4 Beds
  • 2 Baths
  • 3,227 Sq Ft
  • Built 1887

  200 College St, Winchester, KY 40391

  Last Sold Summary

  • 137 Days On Market
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  /9

  $199,500

  $11K PRICE DROP Pending

  • Land
  • 7.77 Acres
  • $25,676 per Acre

  368 Flanagan Station Rd, Winchester, KY 40391

  Build your dream retreat on this beautiful 7.77-acre parcel nestled in a peaceful rural setting just outside Winchester. The gently rolling terrain provides a serene backdrop for your custom home, hobby farm, or equestrian space, offering plenty of room to roam, garden, or simply enjoy the privacy. With easy access from Flanagan Station Road, this property combines a quiet country feel with

  Shari Frasure Keller Williams Commonwealth

  368 Flanagan Station Rd, Winchester, KY 40391
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  /32

  $175,000

  Sold Dec 29, 2025

  200 Madison Ave, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,124 Sq Ft
  • Built 1996

  Last Sold Summary

  • 2% Below List Price
  • $156/SF
  • 19 Days On Market

  Current Estimated Value $180,564

  Last Listing Agent Silvia Torres Tru Life Real Estate

  200 Madison Ave, Winchester, KY 40391

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