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    1 home
      1 home available
      229 S Highland Street, Winchester, KY 40391
      229 S Highland Street, Winchester, KY 40391
      $180,000
      4beds
      3bath
      3,462sqft
      0.11acres
      House for Sale

      229 S Highland Street, Winchester, KY 40391

      Listing by: RE/MAX Creative, Winchester
      1 - 1 of 1 results
      © 2026 Imagine MLS
      Display of MLS Data is usually deemed reliable but is NOT guaranteed accurate by the MLS. Buyers are responsible for verifying the accuracy of all information and should investigate the data themselves or retain appropriate professionals.
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      Imagine Your Home
      229 S Highland Street, Winchester, KY 40391
      229 S Highland Street, Winchester, KY 40391
      229 S Highland Street, Winchester, KY 40391
      229 S Highland Street, Winchester, KY 40391
      229 S Highland Street, Winchester, KY 40391
      229 S Highland Street, Winchester, KY 40391
      229 S Highland Street, Winchester, KY 40391
      229 S Highland Street, Winchester, KY 40391
      229 S Highland Street, Winchester, KY 40391
      229 S Highland Street, Winchester, KY 40391
      229 S Highland Street, Winchester, KY 40391
      229 S Highland Street, Winchester, KY 40391
      229 S Highland Street, Winchester, KY 40391
      229 S Highland Street, Winchester, KY 40391
      $180,000
      4beds
      3full,half bath
      3,462sqft
      0.11acres

      229 S Highland Street, Winchester, KY 40391

      House for Sale by Michelle R BlackburnRE/MAX Creative, Winchester.

      Data checked -. Listing last updated 5 days ago.
      1. Overview
      2. Details
      3. More 

      Investor special with historic charm on corner lot! Opportunity awaits with this spacious 5 bedroom, 3 full bath home offering 3,462 sq ft of potential. Situated on a corner lot and walkable to downtown, this classic 2 story property is rich in character, featuring original hardwood floors, detailed woodwork, a welcoming front porch with columns, and a striking staircase with stained glass accents. The home has been partially gutted, with the kitchen, bathrooms, and several rooms ready for renovation, making it an ideal project for investors, flippers, or buyers looking to customize their dream home. With solid bones and timeless architectural details throughout, this property is primed to be transformed into a true showpiece. Cash or renovation financing required. Inspections welcome but selling AS-IS. Bring your vision and unlock the full potential of this one of a kind property.

      Details
        Property type
      Residential
        Year built
      1930
        Heating
      Forced Air, Natural Gas
        Cooling
      Electric
        Garage
      Yes (1 space)
        Parking spots
      -
      26008701
      MLS ID
      Active
      Status
      04-22-2026
      On market date
        Laundry features
        Fireplace
      Yes
        Architectural Style
      Colonial
        Basement
      Crawl Space, Interior Entry, Walk-Out Access
        View
      Interior features
      Exterior features
      Lot features
      Appliances included
      Refrigerator
      Construction materials
      HardiPlank Type, Wood Siding
      Flooring
      Hardwood
      Monthly taxes
      -
      Yearly taxes
      -
      School district
      Clark County - 7
      Schools
      Shearer, Robert Campbell, GRC
      Senior community
      No
      Open Houses
      In-Person
      No upcoming in-person open houses
      Virtual
      No upcoming virtual open houses
      Contact Agent
      Michelle R Blackburn
      Michelle R Blackburn
      REALTOR® Salesperson, RE/MAX Creative, Winchester
       
       
      Location
      From I64, take Maple Expressway towards town. Left on Lexington Ave. Go thru light and make a right on Highland St. Go thru stop sign. House will be on left on corner of Highland and Calloway.
      For Sale Nearby
      No nearby homes are For Sale Nearby.
      Recently Sold
      No nearby homes have been Recently Sold.
      229 S Highland Street, Winchester, KY 40391, is a 4 bedroom, 3 bathroom, 3462 sqft. Single Family Residence built in 1930. This property is currently available for sale and was listed on Imagine Your Home on 4-22-2026. The MLS# for this Single Family Residence is MLS# 26008701.
      Display of MLS Data is usually deemed reliable but is NOT guaranteed accurate by the MLS. Buyers are responsible for verifying the accuracy of all information and should investigate the data themselves or retain appropriate professionals.
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