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    Chestertown, MD Multifamily Properties for Sale

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    Baltimore, MD Salisbury, MD Hagerstown, MD
    Historic Chestertown Multi-Family Opportunity
    $395,000
    3,664 SF

    Historic Chestertown Multi-Family Opportunity

    349 & 351 HIGH STREET, Chestertown, MD 21620

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

    • Rare opportunity to own a multi‑family property on a double lot in the heart of Chestertown's Historic and Arts & Entertainment Districts.
    • Flexible layout suitable for renovation into a single‑family home, live/work space, or multi‑unit investment property.
    • Located within both the Arts & Entertainment District and Enterprise Zone, supporting residential and business uses.
    • Property is steeped in local heritage, known historically as the Laurence Lots and featured on original town maps.
    • Generous double lot offers expansive possibilities for development and reimagining.
    Updated: Mar 16
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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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    Based on your search, we've compiled 10 Potential Opportunities for your consideration. Besides 2 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.

    Explore Opportunities in Nearby Cities

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

    Grasonville Multifamily Investment Opportunity
    $250,000
    2,655 SF

    Grasonville Multifamily Investment Opportunity

    Five-unit apartment building in Grasonville, Maryland, with upside potential.

    5122 MAIN Street, Grasonville, MD 21638
    View details
    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
    View details
    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
    View details
    Beach Harbor Lot with Amenities
    $60,000

    Beach Harbor Lot with Amenities

    Private, gated campground lot with amenities on Chester River.

    111 SADDLER WAY, Grasonville, MD 21638
    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.

    Land Subdivision with Mobile Potential
    $125,000

    Land Subdivision with Mobile Potential

    Land with subdivision potential, suitable for "Class C" mobiles.

    Lot 2 Seashore Highway, Bridgeville, DE 19933
    View details
    Income-Producing Triplex on 3 Acres
    $425,000
    2,475 SF

    Income-Producing Triplex on 3 Acres

    Fully occupied triplex with land and business potential in Freeland.

    21525 YORK Road, Freeland, MD 21053
    View details
    Land for Sale
    Contact for pricing

    Land for Sale

    Land available on Mine Road, Kinzers, PA.

    5153-D Mine Rd, Kinzers, PA 17535
    View details
    HORNTOWN Land with Camping Amenities
    $163,500
    0.16 Acres

    HORNTOWN Land with Camping Amenities

    Land with access to pool, clubhouse, boat ramp, and more.

    354-355* SEA BASS DR, Horntown, VA 23395
    View details

    Chestertown, MD Multifamily Properties Investment Opportunities Market Analysis

    Explore 2 multifamily properties for sale in Chestertown, MD on our real estate platform. These investment opportunities span a total of 3,664 square feet of properties for sale, with an estimated market value of $395,000.

    Sale prices for multifamily properties in Chestertown, MD start at $395,000, averaging $395,000, and reaching up to $395,000 — 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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