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    1 home
      1 home available
      221 S Highland Street, Winchester, KY 40391
      Price Reduced $12,400
      221 S Highland Street, Winchester, KY 40391
      $257,500
      5beds
      3bath
      3,007sqft
      0.16acres
      House for Sale

      221 S Highland Street, Winchester, KY 40391

      Listing by: The Brokerage
      1 - 1 of 1 results
      © 2025 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
      221 S Highland Street, Winchester, KY 40391
      221 S Highland Street, Winchester, KY 40391
      221 S Highland Street, Winchester, KY 40391
      221 S Highland Street, Winchester, KY 40391
      221 S Highland Street, Winchester, KY 40391
      221 S Highland Street, Winchester, KY 40391
      221 S Highland Street, Winchester, KY 40391
      221 S Highland Street, Winchester, KY 40391
      221 S Highland Street, Winchester, KY 40391
      221 S Highland Street, Winchester, KY 40391
      221 S Highland Street, Winchester, KY 40391
      221 S Highland Street, Winchester, KY 40391
      221 S Highland Street, Winchester, KY 40391
      Price Reduced $12,400
      $257,500 $12,400 
      5beds
      3full,half bath
      3,007sqft
      0.16acres

      221 S Highland Street, Winchester, KY 40391

      House for Sale by Joshua LynchThe Brokerage.

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

      INVESTOR SPECIAL, could be a great option for an end of year cost seg study and bonus depreciation. You have the opportunity to purchase a fully occupied tri-plex in the heart of Winchester with instant cash flow. Main level unit is a large 2 bed, one bath. Upstairs unit is also a 2 bed, one bath, and lower level is a 1 bed, one bath unit. There is street parking and alley access with parking in the rear. All units have their own exterior entrance. Some utilities are metered together, landlord does cover utility expenses. Please call with any questions, please do not disturb the tenants!

      Details
        Property type
      Residential Income
        Year built
      1930
        Heating
      Baseboard, Floor Furnace, Other
        Cooling
      Electric, Window Unit(s)
        Garage
      No
        Parking spots
      5
      25504956
      MLS ID
      Active
      Status
      10-29-2025
      On market date
        Laundry features
      Electric Dryer Hookup, Washer Hookup
        Flooring
        Fireplace
      No
        Architectural Style
        Basement
        View
      Interior features
      Exterior features
      Lot features
      Appliances included
      Construction materials
      Monthly taxes
      -
      Yearly taxes
      -
      Community Features
      -
      School district
      Clark County - 7
      Schools
      GRC
      Senior community
      No
      Open Houses
      In-Person
      No upcoming in-person open houses
      Virtual
      No upcoming virtual open houses
      Contact Agent
      Listing By:
      Joshua Lynch
      Joshua Lynch
      Michael Martin
      Michael Martin
      Joshua Lynch
      Joshua Lynch
      REALTOR® Salesperson, The Brokerage
       
       
      Michael Martin
      Michael Martin
      REALTOR® Salesperson, The Brokerage
       
       
      Location
      Main St. to S. Highland Park. Home will be on the left.
      For Sale Nearby
      No nearby homes are For Sale Nearby.
      Recently Sold
      No nearby homes have been Recently Sold.
      221 S Highland Street, Winchester, KY 40391, is a 5 bedroom, 3 bathroom, 3007 sqft. Triplex built in 1930. This property is currently available for sale and was listed on Imagine Your Home on 10-29-2025. The MLS# for this Triplex is MLS# 25504956.
      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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