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    Chestertown, MD Residential Income Properties for Sale

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    Worton, MD Church Hill, MD Kennedyville, MD
    Turnkey Investment Property in Chestertown
    $2,300,000
    Turnkey Investment Property in Chestertown

    200 HIGH St, Chestertown, MD 21620

    Profitable mixed-use property with apartments and storefronts in downtown Chestertown.
    • Turnkey, profitable investment property with no vacancies since 2022 renovation.
    • Solid leases in place for 5 apartments and 3 storefronts in downtown Chestertown.
    • Generous property tax credit through 2032 (buyer to verify transferability).
    • Complete renovation to the studs in 2022 with new electric, plumbing, water heaters, appliances, foundation, windows, insulation, roof (rear), water/sewer lines, and rear egress.
    • Two storefronts rented to a local arts non‑profit with a yoga/pilates studio moving into the third.
    Updated: Apr 24
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    Updated Apartment Building in Chestertown
    $1,469,900
    Updated Apartment Building in Chestertown

    104 MAPLE Ave, Chestertown, MD 21620

    Turnkey, stabilized apartment building near downtown and Washington College.
    • Turnkey, stabilized asset with strong fundamentals.
    • Well‑balanced unit mix with a 3‑bedroom and five 2‑bedroom units.
    • Updated units feature hardwood flooring, quartz countertops (select units), LED lighting, and in‑unit washer/dryers (most units).
    • Significant building‑wide improvements completed in 2019.
    • Located in Chestertown's historic, walkable community near downtown restaurants, waterfront, and shopping.
    Updated: Apr 24
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    Historic Chestertown Mixed-Use Property
    $1,300,000
    1,300 SF
    Historic Chestertown Mixed-Use Property

    Mixed-use property with commercial kitchen and residential apartment in Chestertown.

    327 CANNON St, Chestertown, MD 21620

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    Historic Chestertown Multi-Family Opportunity
    $395,000
    3,664 SF
    Historic Chestertown Multi-Family Opportunity

    Multi-family property in Chestertown's Historic and Arts & Entertainment Districts.

    349 & 351 HIGH STREET, Chestertown, MD 21620

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    Based on your search, we've compiled 12 Potential Opportunities for your consideration. Besides 4 Active listings in Chestertown, MD, 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.

    Live-Work Duplex with Rental Potential
    $339,000
    2,236 SF
    Live-Work Duplex with Rental Potential

    Move-in-ready duplex offering flexible live-work or multi-unit income, with fenced parking for up to six vehicles.

    11955 AUGUSTINE HERMAN Highway, Kennedyville, MD 21645

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    Multifamily Property with Office Space
    $629,900
    Multifamily Property with Office Space

    Four residential units plus office space, fully rented.

    310 MAIN St, Marydel, MD 21649

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    Updated Apartment Building Investment Opportunity
    $620,000
    3,600 SF
    Updated Apartment Building Investment Opportunity

    Updated four-unit apartment building with potential rental income.

    310 Main Street, Marydel, MD 21649

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    Live-Work Duplex with Private Entrances
    $339,000
    2,236 SF
    Live-Work Duplex with Private Entrances

    Flexible two-unit home offers live-work capability with potential storefront space and on-site parking for up to six vehicles.

    11955 Augustine Herman Highway, Kennedyville, MD 21645

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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.

    87 Acres Residential Development Land
    $3,000,000
    87.34 Acres
    87 Acres Residential Development Land

    87-acre residential development land annexed to Chestertown, Maryland.

    CROMWELL CLARK Road, Chestertown, MD 21620

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    Partially Wooded Village-Zoned Land
    $49,000
    1.09 Acres
    Partially Wooded Village-Zoned Land

    Over an acre in a Village zoning district with confirmed utility hookup allocation, supporting a range of residential and limited commercial uses.

    LAMBS MEADOW Road, Worton, MD 21678

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    Unimproved Land in Chestertown
    Contact for pricing
    0.69 Acres
    Unimproved Land in Chestertown

    0.69 acre of unimproved land in Kent County, Maryland.

    23683 L Rd, Chestertown, MD 21620

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    50 Acres Mixed-Use Development Land
    $1,250,000
    49.83 Acres
    50 Acres Mixed-Use Development Land

    50 acres in Rock Hall, MD, ideal for mixed-use development.

    ROCK HALL Road, Rock Hall, MD 21661

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    Chestertown, MD Residential Income Properties Investment Opportunities Market Analysis

    Explore 4 residential income properties for sale in Chestertown, MD, showcased through 4 active listings on our real estate platform. These investment opportunities span a total of 4,964 square feet of properties for sale, with an estimated market value of $1,695,000.

    Sale prices for residential income properties in Chestertown, MD start at $395,000, averaging $847,500, and reaching up to $1,300,000 — 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 3
    Apartment buildings 2

    Demographics Overview

    Population 14K
    Population Growth (5Y) +2.9%
    Median Household Income $76,094
    College Educated 32.4%

    High-Yield Neighborhoods for Investment

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

    Neighborhood Average Price
    21620 $1.4M

    Taxes & Financing

    Tax Rate (average for all types) 1.34%
    Property Tax per SF $23.81 per SF
    Tax Rate vs County Average 0.07 pp above county avg
    Average Loan-to-Value 65.0%

    Listings Trend

    New vs delisted commercial listings in Kent County

    New Delisted

    Property Size Breakdown

    The majority of commercial real estate listings in Chestertown fall within the 10,000 to 25,000 square foot range.

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