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    Chestertown, MD Residential Income Properties for Sale

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

    Historic Chestertown Multi-Family Renovation Opportunity

    349 High St, Chestertown, MD 21620

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

    • Rare 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 steeped in local history, known as the Laurence Lots, featured on original town maps.
    • Victorian architectural style with fireplace.
    Updated: Dec 9, 2025
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    Land in Chestertown, Maryland
    Contact for pricing
    0.34 Acres

    Land in Chestertown, Maryland

    Cogar Rd, Chestertown, MD 21620

    Residential land with clubhouse and marina access in Chestertown.

    • Generous 15,000 sq ft lot
    • Access to a fabulous clubhouse
    • Access to a picturesque marina
    • Serene retreat
    • Charming Chestertown, MD location
    Updated: Nov 13, 2025
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    Land in Chestertown, Maryland
    Contact for pricing
    0.34 Acres

    Land in Chestertown, Maryland

    Residential land with clubhouse and marina access in Chestertown.

    Tonopah Rd, Chestertown, MD 21620
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    Meticulously Maintained Waterfront Townhome
    $559,000

    Meticulously Maintained Waterfront Townhome

    Elegant 2-bedroom townhome in Chester River Landing community.

    103 Landing Ln, Chestertown, MD 21620
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    Historic Chestertown Multifamily Renovation Opportunity
    $395,000

    Historic Chestertown Multifamily Renovation Opportunity

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

    349 High St, Chestertown, MD 21620
    View details
    Historic Chestertown Multi-Family Renovation Opportunity
    $395,000

    Historic Chestertown Multi-Family Renovation Opportunity

    Multi-family property in historic Chestertown, ideal for renovation.

    349 High St, Chestertown, MD 21620
    View details
    Chestertown Multifamily Investment Opportunity
    $1,195,000

    Chestertown Multifamily Investment Opportunity

    Multifamily property for sale in Chestertown, Maryland.

    23393 Cacaway Farm Ln, Chestertown, MD 21620
    View details
    Based on your search, we've compiled 11 Potential Opportunities for your consideration. Besides 7 Active listings in Chestertown, MD, we suggest exploring several alternatives: 4 properties in Nearby Cities

    Explore Opportunities in Nearby Cities

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

    New Construction Duplex in Rock Hall
    $364,900

    New Construction Duplex in Rock Hall

    New construction duplexes with modern finishes in desirable Rock Hall.

    21141 Striper Run, Rock Hall, MD 21661
    View details
    New Construction Duplexes in Rock Hall
    $364,900

    New Construction Duplexes in Rock Hall

    New construction duplexes with modern finishes in desirable Rock Hall.

    21139 Striper Run, Rock Hall, MD 21661
    View details
    Renovated Townhouse in Carrollwood Manor
    $309,900
    1,582 SF

    Renovated Townhouse in Carrollwood Manor

    Move-in ready townhouse with new kitchen, baths, and HVAC.

    627 Kittendale Rd, Baltimore, MD 21220
    View details
    Renovated Mobile Home on Corner
    $98,500

    Renovated Mobile Home on Corner

    Completely renovated mobile home with new features and extra parking.

    1 Hammock Trl, Baltimore, MD 21220
    View details

    Chestertown, MD Residential Income Properties Investment Opportunities Market Analysis

    Explore 7 residential income properties for sale in Chestertown, MD, showcased through 7 active listings on our real estate platform. These investment opportunities span a total of 5,663 square feet of properties for sale, with an estimated market value of $395,000.

    Prices for residential income 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 have the most current data.

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    • 21620

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