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    Winchester, KY
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    Winchester, KY Multifamily Properties for Sale

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    Two-Story Medical Office and Apartments
    Updated: Mar 2
    Two-Story Medical Office and Apartments

    218 S Maple Street, Winchester, KY 40391

    $750,000
    6,110 sqft · 0.70 AC lot
    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.
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    This listing looks promising.

    Here's a quick look at some key insights for

    218 S Maple Street, Winchester, KY 40391

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    • Est. Cap Rate

      8.6%
      Above avg (5.9%)

    • Est. NOI

      $65K
      Annual

    • Price @ 7% Cap

      $925K
      Above asking
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    Triplex with Back Parking
    Updated: Jul 2
    Triplex with Back Parking

    221 S Highland Street, Winchester, KY 40391

    $239,000
    3,007 sqft · 0.16 AC lot
    Triplex near downtown Winchester with three separate units: main‑level 2BR/1BA, upstairs 2BR/1BA, and lower‑level 1BR/1BA
    Current rents: main level $1,299/mo, upper unit $895/mo, and lower unit $799/mo when rented
    Main level unit includes 2 bedrooms, 1 full bath, 2 living areas, a large eat‑in kitchen, and a laundry room
    Upstairs unit features 2 bedrooms, 1 full bath, a living room, and an eat‑in kitchen
    Lower level unit offers 1 bedroom, 1 full bathroom, a large living room, and an eat‑in kitchen
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    Fully Leased Fourplex
    Fully Leased Fourplex

    23 Wheeler Avenue, Winchester, KY 40391

    $389,900
    4,687 sqft · 0.23 AC lot

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

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    Brick Mixed-Use Triplex
    Brick Mixed-Use Triplex

    502 W Lexington Avenue, Winchester, KY 40391

    $350,000
    4,798 sqft · 0.18 AC lot

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

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    Turn Any Listing Into an Investment Snapshot Owner equity, real caprate, demand score for every listing. Go To Analytics Center
    Downtown Triplex Income Property
    Downtown Triplex Income Property

    130 E Broadway Street, Winchester, KY 40391

    $250,000
    2,445 sqft · 0.17 AC lot

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

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    Updated Quadplex in Downtown Winchester
    Updated Quadplex in Downtown Winchester

    265 S Highland Street, Winchester, KY 40391

    $479,000
    5,058 sqft · 0.14 AC lot

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

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    Two-Unit Duplex with Garages
    Two-Unit Duplex with Garages

    1128-1130 Dale Drive, Winchester, KY 40391

    $249,900
    2,072 sqft · 0.15 AC lot

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

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    Based on your search, we've compiled 15 Potential Opportunities for your consideration. Besides 7 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
    Mixed-Use Properties in Mt. Sterling

    4-12 Court Street, Mt Sterling, KY 40353

    $540,000
    4,196 sqft · 0.06 AC lot

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

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    Updated Quadplex Investment Property
    Updated Quadplex Investment Property

    125 Howard Avenue, Mt Sterling, KY 40353

    $339,000
    3,792 sqft · 0.26 AC lot

    Well-maintained quadplex with multiple system upgrades, offering a turn-key residential income option with fewer major replacements remaining.

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    32 Acres Multi-Unit Commercial Opportunity
    32 Acres Multi-Unit Commercial Opportunity

    1429 Brush Creek Road, Clay City, KY 40312

    $1,400,000
    11,378 sqft · 32.00 AC lot

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

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    Clay City Commercial Opportunity
    Clay City Commercial Opportunity

    1429 Brush Creek Road, Clay City, KY 40312

    $1,400,000
    11,378 sqft · 32.00 AC lot

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

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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.

    Campton, KY Land For Sale
    Campton, KY Land For Sale

    Lower HollerTop Road lot: 31, Campton, KY 41301

    $35,000
    2.35 AC lot

    2.35 acre lot near Red River Gorge.

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    Prime Land Off US HWY
    Prime Land Off US HWY

    Briar Creek lot: #1, Lawrenceburg, KY 40342

    $345,500
    2.27 AC lot

    2.27 acres with excellent visibility and easy access.

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    Recreational Land with Babbling Brook
    Recreational Land with Babbling Brook

    869 N Hwy 708, Beattyville, KY 41311

    $60,000
    10.00 AC lot

    10 acres of recreational land with endless possibilities.

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    Land For Sale in McKee
    Land For Sale in McKee

    Mc Kee, KY 40447

    Contact for pricing
    1.60 AC lot

    1.6 acre tract with utilities and road frontage.

    View details

    Winchester, KY Multifamily Properties Market Trends and Statistics

    Explore 7 multifamily properties for sale in Winchester, KY, showcased through 7 active listings on our real estate platform. These investment opportunities span a total of 28,177 square feet of properties for sale, with an estimated market value of $2,707,800.

    Sale prices for multifamily properties in Winchester, KY start at $239,000, averaging $386,828, and reaching up to $750,000 — 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

    Triplexes 3
    Quadplexes 2
    Apartment buildings 1
    Duplexes 1

    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 $577.7K

    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)

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