Winchester, KY Homes

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  /39

  $239,000

  Pending

  • 6 Beds
  • 3 Baths
  • 3,007 Sq Ft

  221 S Highland St, Winchester, KY 40391

  Excellent investment opportunity!!! A triplex near downtown Winchester. Close to everything. The main level features a unit with 3 bedrooms, 1 full bath, 2 living areas, a large eat-in kitchen and a laundry room. The upstairs unit features 2 bedrooms, 1 full bath, a living room, and an eat-in kitchen. The lower level features a 1 bedroom, 1 full bathroom, a large living room and an eat-in

  Libby VanMeter Marshall Lane Real Estate - Lexington

  221 S Highland St, 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 $255,742

  Last Listing Agent Michelle Blackburn RE/MAX Creative, Winchester

  312 Forest Ave, Winchester, KY 40391
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  /49

  Est $248,301

  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

  Last Listing Agent Christa Joynt Keller Williams Commonwealth
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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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  /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 $420,513

  Last Listing Agent Joyce Ratliff Tom Goebel & Company

  291 Log Lick Rd, Winchester, KY 40391
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  /36

  Est $244,594

  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

  Last Listing Agent Danny Hudnall Thwaites Realtors LLC
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  /73

  $724,950

  $100K 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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  /34

  $200,000

  Sold Aug 03, 2026

  190 Privacy Ln, Winchester, KY 40391

  • Land
  • 6.08 Acres
  • $32,895 per Acre

  Last Sold Summary

  • 27% Below List Price
  • 136 Days On Market

  Current Estimated Value $242,250

  Last Listing Agent Jason Joseph Keller Williams Commonwealth

  190 Privacy Ln, Winchester, KY 40391
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  /12

  Est $247,734

  Not Listed For Sale

  217 College St, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,650 Sq Ft
  • Built 1940

  217 College St, Winchester, KY 40391

  Last Sold Summary

  • 72 Days On Market

  Last Listing Agent Angie Conley Dixon Dixon Properties
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  /37

  $286,000

  $10K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,386 Sq Ft

  33 Bon-Haven Ave, Winchester, KY 40391

  Welcome home to this beautifully renovated home in the desirable Bon Haven subdivision! From the moment you step inside, you'll appreciate the bright and inviting living room that flows seamlessly into the updated kitchen, creating a warm and functional space for everyday living. The main level features two spacious bedrooms and two full bathrooms, while the second floor offers a private third

  Erika Beatty Plum Tree Realty

  33 Bon-Haven Ave, 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 $273,553

  Last Listing Agent Brett Bussell Turf Town Properties

  103 Hampton Ave, Winchester, KY 40391
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  /54

  Est $360,507

  Not Listed For Sale

  308 W Hickman St, Winchester, KY 40391

  • 5 Beds
  • 3 Baths
  • 2,681 Sq Ft
  • Built 1940

  308 W Hickman St, Winchester, KY 40391

  Last Sold Summary

  • 136 Days On Market

  Last Listing Agent Dalis Alvarez GSP Homes
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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
• 

  

  /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 $180,403

  Last Listing Agent Silvia Torres Tru Life Real Estate

  200 Madison Ave, Winchester, KY 40391
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  /86

  Est $304,862

  Not Listed For Sale

  112 Olde Potomac Ave, Winchester, KY 40391

  • 4 Beds
  • 3 Baths
  • 3,220 Sq Ft
  • Built 1935

  112 Olde Potomac Ave, Winchester, KY 40391

  Last Sold Summary

  • 2 Days On Market

  Last Listing Agent Josh Wood Freedom Realty & Property Management
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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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  /82

  $392,000

  Sold Dec 19, 2025

  397 Calmes Blvd, Winchester, KY 40391

  • 4 Beds
  • 3.5 Baths
  • 2,637 Sq Ft
  • Built 1992

  Last Sold Summary

  • 11% Below List Price
  • $149/SF
  • 62 Days On Market

  Current Estimated Value $400,468

  Last Listing Agent Omar Shalash Tru Life Real Estate

  397 Calmes Blvd, Winchester, KY 40391
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  /30

  Est $235,229

  Not Listed For Sale

  302 W Lexington Ave, Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,939 Sq Ft
  • Built 1935

  302 W Lexington Ave, Winchester, KY 40391

  Last Sold Summary

  • 16 Days On Market

  Last Listing Agent Heather Justice Rector Hayden Realtors
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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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  /24

  $265,000

  Sold Feb 25, 2026

  120 Sunset Heights, Winchester, KY 40391

  • 3 Beds
  • 2 Baths
  • 1,440 Sq Ft
  • Built 1999

  Last Sold Summary

  • 4% Below List Price
  • $184/SF
  • 32 Days On Market

  Current Estimated Value $262,240

  Last Listing Agent Keith Wilson Coldwell Banker McMahan

  120 Sunset Heights, Winchester, KY 40391

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