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    Winchester, KY Duplexes for Sale

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    Winchester Multifamily Investment Opportunity
    $269,900
    3,393 SF

    Winchester Multifamily Investment Opportunity

    146 W Lexington Ave, Winchester, KY 40391

    Multifamily property in Downtown Winchester with strong rental potential.

    • Strong rent potential in Downtown Winchester location.
    • Zoned R‑4, allowing for flexible usage.
    • Ideal for house hacking: live in one unit, rent the other.
    • Downstairs unit: 4 bedrooms, 2 bathrooms, currently leased at $1,495/month.
    • Upstairs unit: 3 bedrooms, 1 bathroom, ready for a tenant.
    Updated: Dec 23, 2025
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    Based on your search, we've compiled 5 Potential Opportunities for your consideration. Besides 1 Active listings in Winchester, KY, we suggest exploring several alternatives: 4 properties in Nearby Cities

    Explore Opportunities in Nearby Cities

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

    Versatile Duplex in Mt. Sterling
    $345,000

    Versatile Duplex in Mt. Sterling

    Duplex with owner's suite and tenant lease in Mt. Sterling.

    824-826 Cobbler Ln E, Mt Sterling, KY 40353
    View details
    Mt Sterling Multifamily Investment Property
    $189,000
    2,452 SF

    Mt Sterling Multifamily Investment Property

    Two-unit residential property in Mt Sterling, Kentucky, ideal for investors.

    127 Harrison Ave, Mt Sterling, KY 40353
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    All Brick Duplex with Parking
    Pending
    $299,900
    1,600 SF

    All Brick Duplex with Parking

    All brick duplex with ample parking and endless possibilities.

    537-539 Anniston Dr, Lexington, KY 40505
    View details
    Lexington Duplex Income Opportunity
    $189,900
    1,527 SF

    Lexington Duplex Income Opportunity

    Duplex in Lexington, each unit with two beds and one bath.

    905 Byars Ave, Lexington, KY 40505
    View details

    Winchester, KY Duplexes Investment Opportunities Market Analysis

    Explore 1 duplexes for sale in Winchester, KY on our real estate platform. These investment opportunities span a total of 6,970 square feet of properties for sale, with an estimated market value of $269,900.

    Prices for duplexes in Winchester, KY start at $269,900, averaging $269,900, and reaching up to $269,900 — offering options for a variety of budgets and business needs. Daily updated analytics ensure you have the most current data.

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