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    Winchester, KY Apartment Buildings for Sale

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    Bowling Green, KY Paducah, KY Somerset, KY
    Mixed-Use Building in Winchester, KY
    $750,000
    6,110 SF

    Mixed-Use Building in Winchester, KY

    218 S Maple Street, Winchester, KY 40391

    Two-story building with office, apartments, and ample parking.

    • Two‑story building suitable for commercial and residential use.
    • Main floor configured as a 'ready to go' office space.
    • Two large apartments on the second floor with separate outside entry.
    • Detached 3‑bay garage and large asphalt parking lot (25+ vehicles).
    • Zoned heating and cooling with heat pump system.
    Updated: Mar 2
    View details
    Winchester Multifamily and Office Investment
    $1,575,000
    26,124 SF

    Winchester Multifamily and Office Investment

    2 N Main Street, Winchester, KY 40391

    Historical landmark with 18 apartments and 2 offices.

    • Significant CAPEX investments in 2022 & 2024, including facade transformation and full restoration.
    • Strong income potential: Current $168,000 annual rent with a $4,000/month upside, exceeding the 1% rule.
    • 20 income‑producing units: 18 LIHTC apartments and 2 renovated ground‑floor offices.
    • Located in the Kerr Building, the largest downtown historical landmark, with structural repairs and new roofing.
    • Turn‑key and stabilized property in a thriving downtown Winchester location.
    Updated: Aug 9, 2025
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    Winchester Multi-Family Development Opportunity
    $800,000
    4.87 Acres

    Winchester Multi-Family Development Opportunity

    Large multi-family development opportunity in Winchester, across from Legacy Grove Park.

    1108 W Lexington Avenue, Winchester, KY 40391
    View details
    Based on your search, we've compiled 11 Potential Opportunities for your consideration. Besides 3 Active listings in Winchester, KY, we suggest exploring several alternatives: 4 properties in Nearby Cities, plus 4 Land Listings that present a potential for development.

    Explore Opportunities in Nearby Cities

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

    Historic Income Property in Paris
    $1,650,000
    10,362 SF

    Historic Income Property in Paris

    Historic mixed-use property with multiple income streams in downtown Paris.

    339 Main Street unit: 1-5, Paris, KY 40361
    View details
    Luxury Chevy Chase Multifamily Property
    $5,100,000
    23,216 SF

    Luxury Chevy Chase Multifamily Property

    High-end 24-unit property in Lexington's desirable Chevy Chase neighborhood.

    319 Duke Rd, Lexington, KY 40502
    View details
    Lexington Chevy Chase Multifamily Opportunity
    $5,100,000

    Lexington Chevy Chase Multifamily Opportunity

    24-unit property in Lexington's Chevy Chase neighborhood, built in 2020.

    319 Duke Rd, Lexington, KY 40502
    View details
    Paris, KY Townhome Apartments
    $920,000
    8,800 SF

    Paris, KY Townhome Apartments

    Eight-unit townhome-style apartment complex in Paris, Kentucky.

    117 Bradford Dr, Paris, KY 40361
    View details

    Potential Development Sites for Consideration

    Can't find the perfect fit? These Land listings present an alternative path: the potential to develop a property for your specific goals.

    Important: These AI-suggestions are a starting point, not a guarantee of permitted use. All zoning, permitting, and land use information must be independently verified by you with the appropriate local authorities before making any commitments.

    Asheville Development Opportunity: 5.94 Acres
    $2,500,000
    5.94 Acres

    Asheville Development Opportunity: 5.94 Acres

    5.94-acre parcel zoned RM6, ideal for multi-family development.

    215 N Bear Creek Road, Asheville, NC 28806
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    Greenville Development Opportunity: 1.33 Acres
    $699,900
    1.33 Acres

    Greenville Development Opportunity: 1.33 Acres

    1.33 acre parcel suitable for multi-family development near downtown.

    71 Salters Road, Greenville, SC 29607
    View details
    Multifamily Development Opportunity in Charlotte
    $559,700
    0.47 Acres

    Multifamily Development Opportunity in Charlotte

    Prime 0.47-acre parcel zoned for multifamily development near UNC Charlotte.

    4312 Tantilla Circle, Charlotte, NC 28215
    View details
    Land Near Shepherd University
    $650,000
    3.70 Acres

    Land Near Shepherd University

    Prime land near Shepherd University with development potential.

    8285 MARTINSBURG Pike, Shepherdstown, WV 25443
    View details

    Winchester, KY Apartment Buildings Investment Opportunities Market Analysis

    Explore 3 apartment buildings for sale in Winchester, KY, showcased through 3 active listings on our real estate platform. These investment opportunities span a total of 252,082 square feet of properties for sale, with an estimated market value of $3,125,000.

    Sale prices for two-family homes in Winchester, KY start at $750,000, averaging $1,041,666, and reaching up to $1,575,000 — 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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