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    Winchester, KY Single Family Properties for Sale

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    Brandenburg, KY Lexington, KY N Middletown, KY
    Historic Building in Downtown Winchester
    $415,000
    3,538 SF

    Historic Building in Downtown Winchester

    39 S Main Street, Winchester, KY 40391

    Renovated commercial building with restaurant and apartment in Winchester.

    • Renovated historic building in Downtown Winchester.
    • Restaurant space with full hood system and commercial kitchen.
    • Live/work layout potential with apartment upstairs.
    • Booming Downtown Winchester location.
    • Hardwood floors and tin ceiling.
    Updated: Jul 9, 2025
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    Spacious Investment Property in Winchester
    $209,000
    2,683 SF

    Spacious Investment Property in Winchester

    217 S Highland Street, Winchester, KY 40391

    Updated investment property with large living spaces and endless possibilities.

    • Fresh updates throughout the home.
    • Large living spaces.
    • Natural Gas heating.
    • Cable Available.
    • Shingle roof.
    Updated: Dec 9, 2025
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    Turnkey Waterfront Restaurant with Apartment
    $531,000
    5,012 SF

    Turnkey Waterfront Restaurant with Apartment

    Renovated restaurant with indoor-outdoor dining and spacious upstairs apartment.

    220 Athens Boonsboro Road, Winchester, KY 40391
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    Based on your search, we've compiled 7 Potential Opportunities for your consideration. Besides 3 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.

    Historic Frankfort Commercial Building For Sale
    $325,000
    3,420 SF

    Historic Frankfort Commercial Building For Sale

    Two-story brick building in downtown Frankfort with income potential.

    225 W Main Street, Frankfort, KY 40601
    View details
    Lexington Investment Property For Sale
    $117,000
    3,780 SF

    Lexington Investment Property For Sale

    Turnkey investment opportunity with immediate cash flow in Lexington.

    415 Chestnut Street, Lexington, KY 40508
    View details
    Lexington Multi-Family Investment Opportunity
    $179,900
    2,100 SF

    Lexington Multi-Family Investment Opportunity

    Turnkey investment property generating $1,500 monthly rental income.

    1346 Ohio Terrace, Lexington, KY 40508
    View details
    Frankfort Multifamily Investment Opportunity
    $325,000

    Frankfort Multifamily Investment Opportunity

    Four properties, six units, ideal for rental portfolio expansion.

    814 Holmes Street, Frankfort, KY 40601
    View details

    Winchester, KY Single Family Properties Investment Opportunities Market Analysis

    Explore 3 single family properties for sale in Winchester, KY, showcased through 3 active listings on our real estate platform. These investment opportunities span a total of 11,233 square feet of properties for sale, with an estimated market value of $1,155,000.

    Sale prices for single family properties in Winchester, KY start at $209,000, averaging $385,000, and reaching up to $531,000 — 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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