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
      144 Holly Avenue, Winchester, KY 40391
      144 Holly Avenue, Winchester, KY 40391
      $319,500
      8beds
      5bath
      3,637sqft
      0.22acres
      House for Sale

      144 Holly Avenue, Winchester, KY 40391

      Listing by: Keller Williams Commonwealth
      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
      144 Holly Avenue, Winchester, KY 40391
      144 Holly Avenue, Winchester, KY 40391
      144 Holly Avenue, Winchester, KY 40391
      144 Holly Avenue, Winchester, KY 40391
      144 Holly Avenue, Winchester, KY 40391
      144 Holly Avenue, Winchester, KY 40391
      144 Holly Avenue, Winchester, KY 40391
      144 Holly Avenue, Winchester, KY 40391
      144 Holly Avenue, Winchester, KY 40391
      144 Holly Avenue, Winchester, KY 40391
      144 Holly Avenue, Winchester, KY 40391
      144 Holly Avenue, Winchester, KY 40391
      144 Holly Avenue, Winchester, KY 40391
      144 Holly Avenue, Winchester, KY 40391
      144 Holly Avenue, Winchester, KY 40391
      144 Holly Avenue, Winchester, KY 40391
      144 Holly Avenue, Winchester, KY 40391
      144 Holly Avenue, Winchester, KY 40391
      144 Holly Avenue, Winchester, KY 40391
      144 Holly Avenue, Winchester, KY 40391
      144 Holly Avenue, Winchester, KY 40391
      144 Holly Avenue, Winchester, KY 40391
      144 Holly Avenue, Winchester, KY 40391
      144 Holly Avenue, Winchester, KY 40391
      144 Holly Avenue, Winchester, KY 40391
      144 Holly Avenue, Winchester, KY 40391
      144 Holly Avenue, Winchester, KY 40391
      144 Holly Avenue, Winchester, KY 40391
      144 Holly Avenue, Winchester, KY 40391
      144 Holly Avenue, Winchester, KY 40391
      144 Holly Avenue, Winchester, KY 40391
      144 Holly Avenue, Winchester, KY 40391
      144 Holly Avenue, Winchester, KY 40391
      144 Holly Avenue, Winchester, KY 40391
      144 Holly Avenue, Winchester, KY 40391
      144 Holly Avenue, Winchester, KY 40391
      144 Holly Avenue, Winchester, KY 40391
      144 Holly Avenue, Winchester, KY 40391
      144 Holly Avenue, Winchester, KY 40391
      144 Holly Avenue, Winchester, KY 40391
      144 Holly Avenue, Winchester, KY 40391
      144 Holly Avenue, Winchester, KY 40391
      144 Holly Avenue, Winchester, KY 40391
      144 Holly Avenue, Winchester, KY 40391
      144 Holly Avenue, Winchester, KY 40391
      144 Holly Avenue, Winchester, KY 40391
      144 Holly Avenue, Winchester, KY 40391
      144 Holly Avenue, Winchester, KY 40391
      144 Holly Avenue, Winchester, KY 40391
      144 Holly Avenue, Winchester, KY 40391
      144 Holly Avenue, Winchester, KY 40391
      144 Holly Avenue, Winchester, KY 40391
      144 Holly Avenue, Winchester, KY 40391
      144 Holly Avenue, Winchester, KY 40391
      144 Holly Avenue, Winchester, KY 40391
      144 Holly Avenue, Winchester, KY 40391
      144 Holly Avenue, Winchester, KY 40391
      144 Holly Avenue, Winchester, KY 40391
      144 Holly Avenue, Winchester, KY 40391
      144 Holly Avenue, Winchester, KY 40391
      144 Holly Avenue, Winchester, KY 40391
      144 Holly Avenue, Winchester, KY 40391
      $319,500
      8beds
      5full,half bath
      3,637sqft
      0.22acres

      144 Holly Avenue, Winchester, KY 40391

      House for Sale by Shane T UnderwoodKeller Williams Commonwealth.

      Data checked -. Listing last updated 33 days ago.
      1. Overview
      2. Details
      3. More 

      Excellent investment opportunity featuring two income-producing buildings on one lot, offered together as a package deal. This unique multifamily property includes a triplex and a separate duplex, making it ideal for investors looking to expand their portfolio with multiple units in one purchase. The triplex (Building A) consists of three units: Unit A-1: 2 bedrooms, 1 bathroom Unit A-2: 1 bedroom, 1 bathroom Unit A-3: Office/studio-style apartment with 1 bedroom and 1 bathroom The duplex (Building B) offers two additional units: Unit B-1: 2 bedrooms, 1 bathroom Unit B-2: 2 bedrooms, 1 bathroom With five total units, this property provides strong income potential and flexibility for a variety of investment strategies. A recent appraisal came in at $320,000, and the property is priced below appraised value, creating built-in equity from day one.Great opportunity for investors seeking a solid multifamily asset with upside. Call today to schedule your private showing.

      Details
        Property type
      Residential Income
        Year built
      2001
        Heating
      Baseboard, Electric, Forced Air, Heat Pump, Natural Gas, Other
        Cooling
      Central Air, Ceiling Fan(s), Electric, Heat Pump, Window Unit(s), Wall Unit(s)
        Garage
      No
        Parking spots
      5
      26002633
      MLS ID
      Active
      Status
      02-14-2026
      On market date
        Laundry features
        Fireplace
      No
        Architectural Style
        Basement
        View
      Interior features
      Exterior features
      Lot features
      Appliances included
      Construction materials
      Flooring
      Monthly taxes
      -
      Yearly taxes
      -
      School district
      Clark County - 7
      Schools
      Conkwright, Robert Campbell, GRC
      Senior community
      No
      Open Houses
      In-Person
      No upcoming in-person open houses
      Virtual
      No upcoming virtual open houses
      Contact Agent
      Listing By:
      Shane T Underwood
      Shane T Underwood
      Terra Long
      Terra Long
      Shane T Underwood
      Shane T Underwood
      REALTOR® Salesperson, Keller Williams Commonwealth
       
       
      Terra Long
      Terra Long
      REALTOR® Salesperson, Keller Williams Commonwealth
       
       
      Location
      From Winchester, take N. Maple St. Turn left onto Holly Ave. Property is located on the left-hand side, just after cherry St.
      For Sale Nearby
      No nearby homes are For Sale Nearby.
      Recently Sold
      No nearby homes have been Recently Sold.
      144 Holly Avenue, Winchester, KY 40391, is a 8 bedroom, 5 bathroom, 3637 sqft. Quadruplex built in 2001. This property is currently available for sale and was listed on Imagine Your Home on 2-14-2026. The MLS# for this Quadruplex is MLS# 26002633.
      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