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    Winchester, KY Multifamily Properties for Sale

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    Brandenburg, KY Lexington, KY N Middletown, KY
    10 results
    Winchester Triplex with Commercial Space
    $360,000
    4,798 SF

    Winchester Triplex with Commercial Space

    502 W Lexington Avenue, Winchester, KY 40391

    Brick triplex with commercial space and two apartments in Winchester.

    • High visibility commercial space with Lexington Avenue frontage.
    • Triplex with commercial space and two apartments provides diverse income streams.
    • Enjoy peace of mind with two new HVAC units and a new roof within the last 2 years.
    • Approximately 16 parking spaces.
    • Laundry hook‑ups in all 3 units.
    Updated: May 8
    View details
    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
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    Multifamily Investment Opportunity in Winchester
    $308,500
    3,637 SF

    Multifamily Investment Opportunity in Winchester

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

    144 Holly Avenue, 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
    View details
    Winchester Tri-Plex Investment Opportunity
    $239,900
    3,007 SF

    Winchester Tri-Plex Investment Opportunity

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

    221 S Highland Street, Winchester, KY 40391
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    Renovated 4-Plex in Downtown Winchester
    $600,000
    5,046 SF

    Renovated 4-Plex in Downtown Winchester

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

    101 S Burns Avenue, 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 Street, Winchester, KY 40391
    View details
    Winchester Multifamily and Office Investment
    $1,575,000
    26,124 SF

    Winchester Multifamily and Office Investment

    Historical landmark with 18 apartments and 2 offices.

    2 N Main Street, Winchester, KY 40391
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    Winchester, KY Duplex For Sale
    $269,500
    2,072 SF

    Winchester, KY Duplex For Sale

    Income-producing duplex with garages and private backyards in Winchester, KY.

    1128-1130 Dale Drive, Winchester, KY 40391
    View details
    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 18 Potential Opportunities for your consideration. Besides 10 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.

    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
    View details
    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
    View details
    Duplex and Warehouse Investment Opportunity
    $240,000
    1,800 SF

    Duplex and Warehouse Investment Opportunity

    Duplex, warehouse, and additional lot offer income potential.

    149 Richmond Avenue, Mt Sterling, KY 40353
    View details
    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 Drive, Mt Sterling, KY 40353
    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.

    Campton, KY Land For Sale
    $35,000
    2.35 Acres

    Campton, KY Land For Sale

    2.35 acre lot near Red River Gorge.

    Lower HollerTop Road lot: 31, Campton, KY 41301
    View details
    Prime Land Off US HWY
    $345,500
    2.27 Acres

    Prime Land Off US HWY

    2.27 acres with excellent visibility and easy access.

    Briar Creek lot: #1, Lawrenceburg, KY 40342
    View details
    Recreational Land with Babbling Brook
    $60,000
    10.00 Acres

    Recreational Land with Babbling Brook

    10 acres of recreational land with endless possibilities.

    869 N Hwy 708, Beattyville, KY 41311
    View details
    Land For Sale in McKee
    Contact for pricing
    1.60 Acres

    Land For Sale in McKee

    1.6 acre tract with utilities and road frontage.

    Mc Kee, KY 40447
    View details

    Winchester, KY Multifamily Properties Investment Opportunities Market Analysis

    Explore 10 multifamily properties for sale in Winchester, KY, showcased through 10 active listings on our real estate platform. These investment opportunities span a total of 58,297 square feet of properties for sale, with an estimated market value of $4,846,900.

    Sale prices for multifamily properties in Winchester, KY start at $239,900, averaging $538,544, 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

    Triplexes 4
    Apartment buildings 3
    Duplexes 2
    Quadplexes 2

    Demographics Overview

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

    High-Yield Neighborhoods for Strategic Investment

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

    Neighborhood Average Price
    40391 $587.4K

    Taxes & Financing

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

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