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    221 S Highland St Winchester, KY 40391

    New
    For Sale
    $257,500

    MULTI_FAMILY - Winchester, KY

    Property size:
    3,007 SF
    Lot size:
    0.16 Acres
    Days on Market:
    7
    Last Refresh:
    Dec 6 at 1:06 pm

    Property Features for 221 S Highland St

    General Information

    Property type
    Residential Multi Family
    Property subtype
    Other
    Standard status
    Active
    Zoning
    R-1C
    Rooms
    Bathroom 2, Bathroom 3, Bedroom 3, Bedroom 1, Bedroom 5, Laundry Room, Bedroom 4, Bathroom 1, Bedroom 2
    Bedrooms
    5
    Bathrooms
    3
    APN
    054-3012-016-00
    Parking
    5
    Size
    3,007 SF
    Lot size
    0.16 Acres

    Utilities

    Heating system
    Floor Furnace, Baseboard
    Cooling system
    Window Unit(s), Electric

    Building Details

    Year built
    1930
    Floors in Building
    1
    Number of units
    3
    Roof type
    Shingle

    The Brokerage (859) 983-5870 [email protected]

    Listing agent Joshua Lynch (859) 428-6379

    Listing date Nov 30, 2025

    MLS# 25504956 Listing URL

    Copyright © 2025 ImagineMLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.

    Overview

    Winchester Triplex: Investor Opportunity

    This is an opportunity to purchase a fully occupied triplex in Winchester. The property features a main level unit with two bedrooms and one bathroom, an upstairs unit also with two bedrooms and one bathroom, and a lower level unit with one bedroom and one bathroom. All units have their own exterior entrance. The property is located in the heart of Winchester. It is situated on a 0.16-acre lot. The building has a total area of 3,007 square feet. Zoning is R-1C. There is street parking and alley access with parking in the rear. Some utilities are metered together, and the landlord covers utility expenses. This property could be a great option for an end-of-year cost segregation study and bonus depreciation, offering instant cash flow.
    Property Profile Location Intelligence

    Current Use by Public Records

    Triplexes

    Suggested Use

    Realty agency Restaurant Law Firm Spa & Massage Dental Office Hair Salon Nail Salon Building Supply Clothing Store Auto Repair Shop

    Zoning and permitted uses should be independently verified with local authorities.

    Location Insight

    • Map
    • Local Demand
    City
    Winchester
    County
    Clark
    State
    Kentucky
    Longitude
    -84.176817
    Latitude
    37.989228

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    FAQs

    What type of property is this?
    Triplex - Fully occupied triplex in Winchester with immediate cash flow.
    Where is this triplex located?
    The property is located at 221 S Highland St Winchester, KY.
    What is the asking price?
    The asking price for this property is $257,500.
    What are key features of this property?
    This property features: - Fully occupied tri-plex providing instant cash flow.; - Opportunity for cost segregation study and bonus depreciation.; - Three separate units: two 2-bed, 1-bath units and one 1-bed, 1-bath unit.
    (859) 428-6379
    Request Owner's contact information
    221 S Highland St Winchester, KY 40391
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    Realmo Value Estimation

    Realmo estimates a property’s market value using a proprietary methodology that incorporates public data and user-submitted information. This cumulative value is generated by integrating a variety of conventional and innovative methods. 

    Disclaimer

    These figures are not official appraisals and should not be used as a substitute for a valuation performed by a licensed appraiser.

    Actual market value may differ due to factors not captured in the data. Estimates are offered for informational purposes only, and users should conduct independent research before making financial or investment decisions.

    By using this feature, you acknowledge that Realmo is not responsible for actions taken based on these estimates.

    AI approach

    Realmo AI Method estimates property value using machine learning models trained on millions of comparable listings, transactions, and market signals. It analyzes property features, location intelligence data, and current market dynamics to predict the most probable market value in real time.

    Cap approach

    Capitalization Method calculates value based on estimated net operating income (NOI) and applying a market-based capitalization rate (cap rate), we estimate what a typical investor might be willing to pay for it.

    Comparable approach

    Comparable estimate is based on recent sales of similar nearby properties, adjusted for factors like size, condition, and location.

    Relative

    Relative property class coefficient uses factors that account for typical price differences between various asset types (e.g., retail vs. industrial) to provide a more accurate market-aligned estimate.

    Geo

    Comparable Sales Method, enhanced by Geo coefficients — location-based adjustment factors that reflect differences in price levels across neighborhoods, cities, or regions ensuring a more accurate, market-sensitive valuation.

    Alternative use

    Estimate considers the property’s potential value if used for a different purpose-based on zoning, demand, and market feasibility.

    More about this property
    221 S Highland St Winchester, KY 40391
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