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    Winchester, KY Quadplexes for Sale

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    Bowling Green, KY Louisville, KY Paducah, KY
    Updated Quadplex in Downtown Winchester
    $479,000
    5,058 SF

    Updated Quadplex in Downtown Winchester

    265 S Highland Street, Winchester, KY 40391

    Turn-key quadplex with strong rental potential near downtown amenities.

    • Turn‑key quadplex, updated throughout and ready for tenants.
    • Strong rental potential in downtown Winchester location close to amenities.
    • Each unit has 2 bedrooms, 1 bathroom, full kitchen, and private laundry.
    • Utilities are separately metered for each unit.
    • Total of 8 bedrooms and 4 bathrooms within 5058 sq ft.
    Updated: Mar 12
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    Renovated 4-Plex in Downtown Winchester
    $600,000
    5,046 SF

    Renovated 4-Plex in Downtown Winchester

    101 S Burns Avenue, Winchester, KY 40391

    Restored 4-unit building with modern updates in prime location.

    • Fully renovated 4‑plex in a restored historic building (renovated in 2021).
    • Prime downtown Winchester location, walkable to shops, dining, and attractions.
    • Each unit is spacious (approximately 1,296 sq ft) with modern updates and appliances included.
    • New roof installed in 2021.
    • Strong rental potential in a growing market.
    Updated: Nov 10, 2025
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    Based on your search, we've compiled 6 Potential Opportunities for your consideration. Besides 2 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.

    Turn-Key Lexington Fourplex Investment
    $675,000
    3,585 SF

    Turn-Key Lexington Fourplex Investment

    Fully leased fourplex in Lexington's thriving Jefferson Corridor.

    509 W 3rd Street, Lexington, KY 40508
    View details
    Paris, KY Multifamily Property
    $450,000
    3,780 SF

    Paris, KY Multifamily Property

    Multifamily property for sale in Paris, Kentucky.

    117-123 Bradford Drive, Paris, KY 40361
    View details
    Paris, KY Multifamily Property
    $450,000
    4,704 SF

    Paris, KY Multifamily Property

    Multifamily property in Paris, Kentucky, totaling 4,704 square feet.

    125-131 Bradford Drive, Paris, KY 40361
    View details
    Downtown Lexington Investment Opportunity
    $525,000
    4,300 SF

    Downtown Lexington Investment Opportunity

    4-plex with additional single-unit home near dining and parks.

    367 N Martin Luther King Boulevard, Lexington, KY 40508
    View details

    Winchester, KY Quadplexes Investment Opportunities Market Analysis

    Explore 2 quadplexes for sale in Winchester, KY on our real estate platform. These investment opportunities span a total of 10,104 square feet of properties for sale, with an estimated market value of $1,079,000.

    Sale prices for four-unit buildings in Winchester, KY start at $479,000, averaging $539,500, and reaching up to $600,000 — 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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