Winchester, KY
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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
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    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
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    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
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    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
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    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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