Imagine Your Home
  • Buy
  • Rent
  • Commercial
  • Find a REALTOR®
  • Our Association
    Price range
    $
    $
    Bedrooms
    Bathrooms
    Property type
    Square feet
    Lot size
    Heating
    Cooling
    Parking spots
    Garage
    Basement
    Year built
    Max HOA
    Tours
    View
    More amenities
    1 home
      1 home available
      133 S Highland Street, Winchester, KY 40391
      Pending
      133 S Highland Street, Winchester, KY 40391
      $251,000
      6beds
      3bath
      2,302sqft
      0.08acres
      House for Sale

      133 S Highland Street, Winchester, KY 40391

      Listing by: Bluegrass Realty Pros, Inc
      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.
      Equal opportunity
      Membio
      Imagine Your Home
      133 S Highland Street, Winchester, KY 40391
      133 S Highland Street, Winchester, KY 40391
      133 S Highland Street, Winchester, KY 40391
      Pending
      $251,000
      6beds
      3full,half bath
      2,302sqft
      0.08acres

      133 S Highland Street, Winchester, KY 40391

      House for Sale by David EspinosaBluegrass Realty Pros, Inc.

      Data checked -. Listing last updated 8 days ago.
      1. Overview
      2. Details
      3. More 

      16 Central Ave, Winchester, KY 40391 Prime multi-family investment in a great Winchester location! This 2-story property features two spacious rental units, both offering strong income potential. The first unit includes 3 bedrooms and 2 bathrooms, while the second unit offers 3 bedrooms and 1 bathroom—ideal for accommodating a range of tenant needs. With an established rental history and close proximity to schools, shopping, and downtown, this property is a smart choice for investors looking to expand their portfolio. Opportunities like this don't come often—schedule your showing today!

      Details
        Property type
      Residential Income
        Year built
      1940
        Heating
      -
        Cooling
        Garage
      No
        Parking spots
      -
      25017462
      MLS ID
      Pending
      Status
      02-24-2026
      On market date
        Laundry features
        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
      Shearer
      Senior community
      No
      Open Houses
      In-Person
      No upcoming in-person open houses
      Virtual
      No upcoming virtual open houses
      Contact Agent
      DE
      David Espinosa
      MLS Only Salesperson 
       
       
      Location
      From downtown Winchester, head north on North Main Street toward Washington Street. Turn right onto Washington Street and continue for about half a mile. Turn left onto Central Avenue and follow it a short distance. The property at 16 Central Avenue will be on your left
      For Sale Nearby
      No nearby homes are For Sale Nearby.
      Recently Sold
      No nearby homes have been Recently Sold.
      133 S Highland Street, Winchester, KY 40391, is a 6 bedroom, 3 bathroom, 2302 sqft. built in 1940. This property is currently available for sale and was listed on Imagine Your Home on 2-24-2026. The MLS# for this is MLS# 25017462.
      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.
      Copyright ©2026