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    Winchester, KY Residential Income Properties for Sale

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    Brandenburg, KY Paris, KY Richmond, KY
    12 listings
    Winchester Mixed-Use Commercial Opportunity
    $500,000
    5,054 SF
    Winchester Mixed-Use Commercial Opportunity

    808 Bypass Road, Winchester, KY 40391

    Versatile property with commercial space, apartment, and expansion potential.
    • High‑visibility location minutes from I‑64 with strong traffic exposure.
    • Fully equipped commercial space (currently a bakery) with kitchen, service counter, dining/event space, drive‑thru, outdoor seating, and parking.
    • Private‑entry apartment attached to the commercial space for rental income or owner occupancy.
    • Unfinished area plumbed for a second one‑bedroom apartment, offering future expansion potential.
    • Versatile property suitable for various businesses: cafe, restaurant, retail, office, etc.
    Updated: Apr 21
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    Two-Story Medical Office and Apartments
    $750,000
    6,110 SF
    Two-Story Medical Office and Apartments

    218 S Maple Street, Winchester, KY 40391

    Main-floor physician-ready office with two walkup apartments above, plus basement storage and a detached three-bay garage.
    • 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
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    Fully Leased Fourplex
    $389,900
    4,687 SF
    Fully Leased Fourplex

    Fully leased fourplex with long-term tenants and utilities paid by residents, positioned across from a park with ample parking.

    23 Wheeler Avenue, Winchester, KY 40391

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    Brick Mixed-Use Triplex
    $350,000
    4,798 SF
    Brick Mixed-Use Triplex

    Brick triplex combines an on-site storefront with two-bedroom apartments and dedicated laundry hook-ups in every unit.

    502 W Lexington Avenue, Winchester, KY 40391

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    Single-Family Residence with 10-Foot Ceilings
    $339,900
    4,456 SF
    Single-Family Residence with 10-Foot Ceilings

    Spacious Winchester home offers 5 bedrooms, 4 baths, and flexible interior space for living or income use.

    410 W Lexington Avenue, 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 Street, Winchester, KY 40391

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    Downtown Triplex Income Property
    $250,000
    2,445 SF
    Downtown Triplex Income Property

    Turnkey triplex with two updated units and a third unit occupied by a long-term tenant.

    130 E Broadway Street, Winchester, KY 40391

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    Updated Quadplex in Downtown Winchester
    $479,000
    5,058 SF
    Updated Quadplex in Downtown Winchester

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

    265 S Highland Street, Winchester, KY 40391

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    Renovated Multi-Family with Office Units
    $1,575,000
    26,124 SF
    Renovated Multi-Family with Office Units

    Renovated income property with 18 apartments and 2 ground-floor offices, supported by central HVAC and secure key-fob access.

    2 N Main Street, Winchester, KY 40391

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    Two-Unit Duplex with Garages
    $249,900
    2,072 SF
    Two-Unit Duplex with Garages

    Duplex sold together, featuring two bedrooms, 1.5 baths, laundry space, and a 1-car garage per unit.

    1128-1130 Dale Drive, Winchester, KY 40391

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    Spacious Investment Property in Winchester
    $209,000
    2,683 SF
    Spacious Investment Property in Winchester

    Updated investment property with large living spaces and endless possibilities.

    217 S Highland Street, 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 Road, Winchester, KY 40391

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    Based on your search, we've compiled 20 Potential Opportunities for your consideration. Besides 12 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.

    Opportunities in Nearby Cities

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

    Mixed-Use Properties in Mt. Sterling
    $540,000
    4,196 SF
    Mixed-Use Properties in Mt. Sterling

    Mixed-use properties with commercial and residential spaces in downtown Mt. Sterling.

    4-12 Court Street, Mt Sterling, KY 40353

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    32 Acres Multi-Unit Commercial Opportunity
    $1,400,000
    11,378 SF
    32 Acres Multi-Unit Commercial Opportunity

    Multi-unit commercial property on 32 acres near Red River Gorge.

    1429 Brush Creek Road, Clay City, KY 40312

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    Clay City Commercial Opportunity
    $1,400,000
    11,378 SF
    Clay City Commercial Opportunity

    32-acre property with multi-unit potential near Red River Gorge.

    1429 Brush Creek Road, Clay City, KY 40312

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    Downtown Mt Sterling Mixed-Use Property
    $275,500
    2,040 SF
    Downtown Mt Sterling Mixed-Use Property

    Well-maintained mixed-use property with commercial and residential units.

    4-8 Court St, Mt Sterling, KY 40353

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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.

    Winchester Land Investment Opportunity
    $550,500
    20.78 Acres
    Winchester Land Investment Opportunity

    20+ acre residential land tract near Winchester Country Club.

    1395 Two Mile Road, Winchester, KY 40391

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    Winchester Land For Development
    $2,500,000
    148.00 Acres
    Winchester Land For Development

    148 acres of land suitable for residential development.

    1395 Two Mile Road, Winchester, KY 40391

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    Winchester, KY Land Opportunity
    $1,200,000
    24.15 Acres
    Winchester, KY Land Opportunity

    24-acre residential land in Winchester, zoned for planned development.

    1395 Two Mile Road, Winchester, KY 40391

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    148 Acres Winchester Development Land
    $2,500,000
    148.00 Acres
    148 Acres Winchester Development Land

    148 acres of land zoned for planned development.

    1395 Two Mile Road, Winchester, KY 40391

    View details

    Winchester, KY Residential Income Properties Market Trends and Statistics

    Explore 12 residential income properties for sale in Winchester, KY, showcased through 12 active listings on our real estate platform. These investment opportunities span a total of 69,939 square feet of properties for sale, with an estimated market value of $6,148,700.

    Sale prices for residential income properties in Winchester, KY start at $209,000, averaging $512,391, 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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    Top Commercial Asset Segments

    Commercial property segments ranked by active listings on the market

    Multifamily properties 7
    Single family properties 3
    Apartment buildings 2
    Quadplexes 2
    Triplexes 2

    Demographics Overview

    Population 37K
    Population Growth (5Y) +3.5%
    Median Household Income $67,910
    College Educated 15.1%

    High-Yield Neighborhoods for Investment

    Identify Winchester submarkets with the highest inventory density on the market and evaluate the average listing prices of real estate assets

    Neighborhood Average Price
    40391 $486.9K

    Taxes & Financing

    Tax Rate (average for all types) 0.91%
    Property Tax per SF $10.57 per SF
    Average Loan-to-Value 65.0%

    Listings Trend

    New vs delisted commercial listings in Clark County

    New Delisted

    Total CRE Inventory on Market (SF)

    Average Property Price per SF

    For-sale pricing trends across core commercial property types in Clark County

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