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    Chestertown, MD
    Residential Income

    Chestertown, MD Residential Income Properties for Sale

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    Worton, MD Church Hill, MD Still Pond, MD Rock Hall, MD Millington, MD Betterton, MD Sudlersville, MD Centreville, MD
    Six-Unit Apartment Building
    Updated: Jul 27
    Six-Unit Apartment Building

    104 MAPLE AVENUE, Chestertown, MD 21620

    $650,000
    7,296 sqft
    Six apartments across multiple levels
    7,296 SF apartment building built in 1927
    Seven electric meters and seven electric panels
    Three forced hot air units plus central A/C and mini‑split systems
    Unfinished basement with utilities and storage
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    Mixed-Use Income Property with Retail
    Updated: Jul 10
    Mixed-Use Income Property with Retail

    200204 High Street, Chestertown, MD 21620

    $2,300,000
    1860‑built downtown Chestertown building with 5 apartments and 3 storefronts
    Renovated to the studs in 2022; since renovations, no vacancies reported
    Replaced major systems in 2022: new electric service, wiring, plumbing (PEX), water and septic lines, and energy‑efficient water heaters and appliances
    New windows, insulation, and air sealing; monitored fire alarm system and rebuilt foundation
    Roof work includes new rear portions roof (front 50‑year cedar roof replaced in early 2000s)
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    Updated Apartment Building in Chestertown
    Updated Apartment Building in Chestertown

    104 MAPLE Ave, Chestertown, MD 21620

    $1,350,000

    Turnkey, stabilized apartment building near downtown and Washington College.

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    Turn a Listing Into an Investment Snapshot Cap Rate, Potential NOI, Demand score for every listing. Go To Analytics Center
    Historic Chestertown Multi-Family Opportunity
    Historic Chestertown Multi-Family Opportunity

    349 & 351 HIGH STREET, Chestertown, MD 21620

    $395,000
    3,664 sqft 0.13 AC lot

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

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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.

    Duplex Near Historic Chestertown
    Duplex Near Historic Chestertown

    12712 and 12714 STILL POND Road, Still Pond, MD 21667

    $549,000
    4,305 sqft 0.43 AC lot

    Duplex offers income potential near Chestertown and Betterton Beach.

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    Duplex-Configured Residence with Split Entrances
    Duplex-Configured Residence with Split Entrances

    2507 ISLAND VIEW Road, Essex, MD 21221

    $565,000
    2,970 sqft 0.23 AC lot

    Duplex-designed home with two exterior entrances, high-end finishes, and split HVAC units throughout.

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    Modern Farmhouse Duplex Opportunity
    Modern Farmhouse Duplex Opportunity

    2507 ISLAND VIEW ROAD, Essex, MD 21221

    $565,000
    2,970 sqft 0.23 AC lot

    Custom-built home with two en-suites and two exterior entrances, designed as a duplex with flexible in-law or rental potential.

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    Corner Retail and Residential Income
    Corner Retail and Residential Income

    26622 Medders Road, Still Pond, MD 21667

    $425,000
    7,566 sqft

    Mixed-use property with a corner retail storefront and three rented apartments under separate zoning designations.

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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.

    Flex-Use Land in Village District
    Flex-Use Land in Village District

    LAMBS MEADOW Road, Worton, MD 21678

    $49,000
    1.09 AC lot

    Partially wooded Village-zoned land with confirmed water utility allocation hookup.

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    50 Acres Mixed-Use Development Land
    50 Acres Mixed-Use Development Land

    ROCK HALL Road, Rock Hall, MD 21661

    $1,250,000
    49.83 AC lot

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

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    Goldsboro Wooded Homesite with Pond
    Goldsboro Wooded Homesite with Pond

    5.281 ACRES SCHULYER RD, Goldsboro, MD 21636

    $159,900
    5.28 AC lot

    5.28-acre wooded homesite with wildlife pond views in Goldsboro, MD.

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    Grasonville Land for Sale
    Grasonville Land for Sale

    110 James Lane, Grasonville, MD 21638

    $175,000
    0.50 AC lot

    Half-acre lot zoned for commercial/residential use in Grasonville, MD.

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    Chestertown, MD Residential Income Properties Market Trends and Statistics

    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 10,960 square feet of properties for sale, with an estimated market value of $4,695,000.

    Sale prices for residential income properties in Chestertown, MD start at $395,000, averaging $1,173,750, and reaching up to $2,300,000 — 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 4
    Apartment buildings 3

    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 $1.2M

    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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