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    Winchester, KY Triplexes for Sale

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    Brandenburg, KY Lexington, KY N Middletown, KY
    Winchester Triplex with Commercial Space
    $360,000
    4,798 SF

    Winchester Triplex with Commercial Space

    502 W Lexington Avenue, Winchester, KY 40391

    Brick triplex with commercial space and two apartments in Winchester.

    • High visibility commercial space with Lexington Avenue frontage.
    • Triplex with commercial space and two apartments provides diverse income streams.
    • Enjoy peace of mind with two new HVAC units and a new roof within the last 2 years.
    • Approximately 16 parking spaces.
    • Laundry hook‑ups in all 3 units.
    Updated: May 8
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    Multifamily Investment Opportunity in Winchester
    $308,500
    3,637 SF

    Multifamily Investment Opportunity in Winchester

    144 Holly Avenue, Winchester, KY 40391

    Two income-producing buildings on one lot, great investment opportunity.

    • Priced below recent appraisal of $320,000, offering immediate equity.
    • Two buildings (triplex and duplex) on one lot, providing five total income‑producing units.
    • Excellent investment opportunity for portfolio expansion with multiple units in a single purchase.
    • Triplex includes a studio/office‑style apartment, offering flexible usage options.
    • Diverse heating and cooling systems, including forced air, heat pump, central air, and wall units.
    Updated: Feb 14
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    Winchester Tri-Plex Investment Opportunity
    $239,900
    3,007 SF

    Winchester Tri-Plex Investment Opportunity

    Fully occupied tri-plex in Winchester with instant cash flow.

    221 S Highland Street, Winchester, KY 40391
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    Downtown Winchester Triplex For Sale
    $265,000
    2,445 SF

    Downtown Winchester Triplex For Sale

    Turnkey triplex with tenants in place in downtown Winchester.

    130 E Broadway Street, Winchester, KY 40391
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    Based on your search, we've compiled 8 Potential Opportunities for your consideration. Besides 4 Active listings in Winchester, KY, we suggest exploring several alternatives: 4 properties in Nearby Cities

    Opportunities in Nearby Cities

    Here are 4 Similar properties we found in Nearby Locations for your consideration.

    New Triplex Investment Opportunity
    $625,000
    3,600 SF

    New Triplex Investment Opportunity

    Turnkey triplex built in 2023 with income potential.

    192 Fairway Lane, Somerset, KY 42503
    View details
    New Triplex Investment Opportunity
    $625,000
    3,600 SF

    New Triplex Investment Opportunity

    New construction triplex with income potential in Somerset, Kentucky.

    194 Fairway Lane, Somerset, KY 42503
    View details
    Lexington Triplex Investment Opportunity
    $682,500
    3,564 SF

    Lexington Triplex Investment Opportunity

    Triplex in Lexington with strong income potential in prime location.

    1205, 1207, 1209 Reva Ridge Way, Lexington, KY 40517
    View details
    Historic Triplex in Woodward Heights
    $639,900
    3,109 SF

    Historic Triplex in Woodward Heights

    Three apartments near downtown Lexington, suitable for Airbnb or conversion.

    311 Madison Place, Lexington, KY 40508
    View details

    Winchester, KY Triplexes Investment Opportunities Market Analysis

    Explore 4 triplexes for sale in Winchester, KY, showcased through 4 active listings on our real estate platform. These investment opportunities span a total of 13,887 square feet of properties for sale, with an estimated market value of $1,173,400.

    Sale prices for three-family homes in Winchester, KY start at $239,900, averaging $293,350, and reaching up to $360,000 — offering options for a variety of budgets and business needs. Daily updated analytics ensure you stay ahead with the latest data and market trends.

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