Winchester, KY Homes

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  /36

  $98,500

  $27K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,152 Sq Ft

  16 Denny Ave, Winchester, KY 40391

  Well priced and well located, 16 Denny Avenue is conveniently located near Eugene Gay Splash Park, downtown Winchester, shopping and schools. Home features 1152 sq ft with 3 bedrooms, 1 full bath, eat in kitchen and living room. Enclosed porch is located on front of house. Upgrades include laminate flooring, ductless heating and cooling and roof. Property has been tenant occupied and is sold as

  ROBIN TRIMBLE HomeFirst Real Estate

  16 Denny Ave, Winchester, KY 40391
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  /40

  $310,000

  Sold Jul 06, 2026

  305 Abbeywood Dr, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 1,899 Sq Ft
  • Built 2003

  Last Sold Summary

  • 2% Below List Price
  • $163/SF
  • 2 Days On Market

  Current Estimated Value $312,905

  Last Listing Agent Shevawn Akers Firefly Realty & Investments

  305 Abbeywood Dr, Winchester, KY 40391
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  /32

  Est $250,623

  Not Listed For Sale

  13 Euclid Ave, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,893 Sq Ft
  • Built 1917

  13 Euclid Ave, Winchester, KY 40391

  Last Sold Summary

  • 75 Days On Market

  Last Listing Agent Jim Woodrum RE/MAX Creative, Winchester
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  /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
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  /64

  $349,000

  Sold Jul 28, 2026

  411 Boone Ave, Winchester, KY 40391

  • 4 Beds
  • 2.5 Baths
  • 3,405 Sq Ft
  • Built 1945

  Last Sold Summary

  • $102/SF
  • 3 Days On Market

  Current Estimated Value $356,078

  Last Listing Agent Cathy Mattingly Indigo & Co

  411 Boone Ave, Winchester, KY 40391
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  /45

  Est $431,457

  Not Listed For Sale

  142 College St, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 3,012 Sq Ft
  • Built 1940

  142 College St, Winchester, KY 40391

  Last Sold Summary

  • 87 Days On Market

  Last Listing Agent Patrick Arvin Keller Williams Commonwealth
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  /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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  /24

  $277,000

  Sold Mar 25, 2026

  149 Winn Ave, Winchester, KY 40391

  • 12 Beds
  • 4 Baths
  • 4,010 Sq Ft
  • Built 1940

  Last Sold Summary

  • 4% Below List Price
  • $69/SF
  • 51 Days On Market

  Current Estimated Value $285,159

  Last Listing Agent Libby VanMeter Marshall Lane Real Estate - Lexington

  149 Winn Ave, Winchester, KY 40391
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  /32

  Est $213,016

  Not Listed For Sale

  8 Nunnelly Ct, Winchester, KY 40391

  • 2 Beds
  • 1.5 Baths
  • 1,255 Sq Ft
  • Built 1940

  8 Nunnelly Ct, Winchester, KY 40391

  Last Sold Summary

  • 33 Days On Market

  Last Listing Agent Timothy Saylor Threshold Real Estate Services
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  /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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  /37

  $260,000

  Sold Feb 20, 2026

  313 Carolina Ave, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 1,855 Sq Ft
  • Built 1962

  Last Sold Summary

  • $140/SF
  • 4 Days On Market

  Current Estimated Value $264,120

  Last Listing Agent Kenneth DeGrant High Point Realty & Auction

  313 Carolina Ave, Winchester, KY 40391
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  /82

  Est $305,354

  Not Listed For Sale

  111 S Burns Ave, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 2,994 Sq Ft
  • Built 1920

  111 S Burns Ave, Winchester, KY 40391

  Last Sold Summary

  • 202 Days On Market

  Last Listing Agent Melodie Lincavage Berkshire Hathaway HomeServices Foster Realtors
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  /27

  $280,000

  $10K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,752 Sq Ft

  198 Hilltop Dr, Winchester, KY 40391

  Excellent location! 4 bedroom, 2 bath. This home offers one level living on the edge of town and close to the interstate! AMAZING VIEWS of country side! Two living room spaces! Split bedroom design. Covered back patio. NEW LVP flooring. NEW electric service panel and meter base. Freshly painted throughout. NEW appliances. Fully fenced backyard. This home is move in ready. Come see today!

  Stephanie Hacker Kentucky Residential Real Estate, LLC

  198 Hilltop Dr, Winchester, KY 40391
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  /38

  $293,000

  Sold Mar 06, 2026

  6261 Ironworks Rd, Winchester, KY 40391

  • Land
  • 15.79 Acres
  • $18,556 per Acre

  Last Sold Summary

  • 2% Below List Price
  • 5 Days On Market

  Last Listing Agent Kyle McPeck Coldwell Banker McMahan

  6261 Ironworks Rd, Winchester, KY 40391
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  /47

  Est $376,946

  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

  Last Listing Agent Ginger Mccoy Kentucky Residential Real Estate, LLC
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  /25

  $165,000

  • 3 Beds
  • 1 Bath
  • 1,249 Sq Ft

  209 E Washington St, Winchester, KY 40391

  Conveniently located in Winchester, this one-story home offers three bedrooms, one bath, and plenty of potential for a first-time buyer or investment property. Inside, you'll find laminate and vinyl flooring throughout, a spacious kitchen, and a separate laundry room. The bathroom received new fixtures in 2025, while the roof is approximately 1.5 years old, taking care of two worthwhile updates

  Michelle Blackburn RE/MAX Creative, Winchester

  209 E Washington St, Winchester, KY 40391
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  /98

  $750,000

  Sold Dec 10, 2025

  3900 (Mt) Mount Sterling Rd, Winchester, KY 40391

  • 6 Beds
  • 5 Baths
  • 4,843 Sq Ft
  • Built 2004

  Last Sold Summary

  • 9% Below List Price
  • $155/SF
  • 42 Days On Market

  Last Listing Agent Teresa Richmond Freedom Realty & Property Management

  3900 (Mt) Mount Sterling Rd, Winchester, KY 40391
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  /27

  Est $210,904

  Not Listed For Sale

  139 W Hickman St, Winchester, KY 40391

  • 3 Beds
  • 1.5 Baths
  • 1,348 Sq Ft
  • Built 1940

  139 W Hickman St, Winchester, KY 40391

  Last Sold Summary

  • 18 Days On Market

  Last Listing Agent Clay David Sutherland ERA Select Real Estate
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  /24

  $329,500

  $10K PRICE DROP Pending

  • 3 Beds
  • 2 Baths
  • 1,792 Sq Ft

  360 N Middletown Rd, Winchester, KY 40391

  Investment Opportunity! This is the Child 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

  360 N Middletown Rd, Winchester, KY 40391
• 

  

  /39

  $395,000

  Sold Jun 12, 2026

  233 Cunningham Ln, Winchester, KY 40391

  • 3 Beds
  • 2.5 Baths
  • 2,258 Sq Ft
  • Built 2007

  Last Sold Summary

  • 12% Below List Price
  • $175/SF
  • 116 Days On Market

  Current Estimated Value $411,817

  Last Listing Agent Amanda Marcum Berkshire Hathaway HomeServices Foster Realtors

  233 Cunningham Ln, Winchester, KY 40391

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