16,242

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
  • /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
    • /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

  • /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
  • /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
    • /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

  • /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
  • /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
    • /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

  • /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
  • /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
    • /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

  • /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
    • /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

  • /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
  • /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
    • /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

  • /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
  • /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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