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    Winchester, KY Residential Income Properties for Sale

    15 results
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    Renovated 4-Plex in Downtown Winchester
    $600,000
    5,046 SF

    Renovated 4-Plex in Downtown Winchester

    101 4Th St, 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: Mar 11
    View details
    Multifamily Investment Opportunity in Winchester
    $319,500
    3,637 SF

    Multifamily Investment Opportunity in Winchester

    144 Holly Ave, Winchester, KY 40391

    Two income-producing buildings on one lot, great investment opportunity.

    • Priced below recent appraised value of $320,000, offering built‑in 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 (Building A) includes three units: two traditional apartments and one office/studio‑style apartment.
    • Duplex (Building B) provides two additional 2‑bedroom, 1‑bathroom units.
    Updated: Feb 14
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    Winchester Commercial Building with Apartments
    $825,000
    6,110 SF

    Winchester Commercial Building with Apartments

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

    218 S Maple St, Winchester, KY 40391
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    Updated Quadplex in Downtown Winchester
    $505,000
    5,058 SF

    Updated Quadplex in Downtown Winchester

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

    265 S Highland St, Winchester, KY 40391
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    Mixed-Use Property with Residential Income
    $515,000
    1,440 SF

    Mixed-Use Property with Residential Income

    Versatile commercial space with separate income-producing residential home.

    35-37 Hays St, 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 St, Winchester, KY 40391
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    Winchester Tri-Plex Investment Opportunity
    $246,400
    3,007 SF

    Winchester Tri-Plex Investment Opportunity

    Fully occupied tri-plex in Winchester with instant cash flow.

    221 S Highland St, Winchester, KY 40391
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    Historical Landmark Multifamily and Office
    $1,595,000
    26,124 SF

    Historical Landmark Multifamily and Office

    Turn-key, stabilized investment property in thriving downtown Winchester.

    2 N Main St, Winchester, KY 40391
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    Renovated Mixed-Use Building, Winchester, KY
    $299,000
    3,132 SF

    Renovated Mixed-Use Building, Winchester, KY

    Renovated mixed-use building with storefront, apartment, and parking.

    27-29 S Main St, Winchester, KY 40391
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    Winchester Triplex Investment Opportunity
    $388,000
    2,762 SF

    Winchester Triplex Investment Opportunity

    Triplex in Winchester, Kentucky with one and two-bedroom units.

    101 E Lexington Ave, Winchester, KY 40391
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    Winchester Duplex For Sale
    $299,900
    2,072 SF

    Winchester Duplex For Sale

    Income-producing duplex with garages and private backyard.

    1128-1130 Dale Dr, Winchester, KY 40391
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    Spacious Winchester Investment Property
    $229,900
    2,683 SF

    Spacious Winchester Investment Property

    Updated investment property with large living spaces and endless possibilities.

    217 S Highland St, Winchester, KY 40391
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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 Ave, Winchester, KY 40391
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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 Rd, Winchester, KY 40391
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    Winchester Multifamily Investment Opportunity
    $251,000
    2,302 SF

    Winchester Multifamily Investment Opportunity

    Two-unit property with strong income potential in Winchester, Kentucky.

    133 S Highland St, Winchester, KY 40391
    View details
    Based on your search, we've compiled 22 Potential Opportunities for your consideration. Besides 15 Active listings in Winchester, KY, we suggest exploring several alternatives: 4 properties in Nearby Cities, plus 3 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.

    Duplex and Warehouse Investment Opportunity
    $270,000
    1,800 SF

    Duplex and Warehouse Investment Opportunity

    Duplex, warehouse, and additional lot for expansion potential.

    149 Richmond Ave, Mt Sterling, KY 40353
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    Mt Sterling Multifamily Investment Opportunity
    $399,000
    4,366 SF

    Mt Sterling Multifamily Investment Opportunity

    Two duplexes, each with two units, for sale in Mt Sterling.

    503-505 Alexa Dr, Mt Sterling, KY 40353
    View details
    Paris, KY Mixed-Use Property
    $750,000
    3,066 SF

    Paris, KY Mixed-Use Property

    Highly visible mixed-use property with retail and apartment spaces.

    5761 Lexington Rd, Paris, KY 40361
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    Paris, KY Townhome Apartments
    Contact for pricing
    8,800 SF

    Paris, KY Townhome Apartments

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

    117 Bradford Dr, Paris, KY 40361
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    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.

    7.77 Acres in Winchester, KY
    $199,500
    7.77 Acres

    7.77 Acres in Winchester, KY

    7.77-acre parcel in a peaceful rural setting outside Winchester.

    368 Flanagan Station Rd, Winchester, KY 40391
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    Unrestricted Land with Countryside Views
    $189,900
    10.73 Acres

    Unrestricted Land with Countryside Views

    10+ acres of unrestricted land with building sites and views.

    1045 Gay Evans Rd, Winchester, KY 40391
    View details
    Clark County Land by Creek
    $123,000
    11.47 Acres

    Clark County Land by Creek

    11.47 acres in Clark County near Four Mile Creek.

    7950 Four Mile Rd, Winchester, KY 40391
    View details

    Winchester, KY Residential Income Properties Investment Opportunities Market Analysis

    Explore 15 residential income properties for sale in Winchester, KY, showcased through 15 active listings on our real estate platform. These investment opportunities span a total of 403,109 square feet of properties for sale, with an estimated market value of $8,230,600.

    Sale prices for residential income properties in Winchester, KY start at $234,900, averaging $484,152, and reaching up to $1,595,000 — 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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