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Residential Income

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Chestertown, MD Residential Income 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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$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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$1,469,900

Updated Apartment Building in Chestertown

Turnkey, stabilized apartment building near downtown and Washington College.

104 MAPLE Ave, Chestertown, MD 21620

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$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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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.

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

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$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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$60,000

Beach Harbor Lot with Amenities

Private, gated campground lot with amenities on Chester River.

111 SADDLER WAY, Grasonville, MD 21638

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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.

$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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$59,999

1.09 Acres

Worton Land: Versatile Village Zoning

1+ acre lot in Worton, MD, with flexible zoning.

LAMBS MEADOW Road, Worton, MD 21678

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$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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Waterfront Community Homesite with Boat Slip

$147,000

1.00 Acre

Waterfront Community Homesite with Boat Slip

One-acre lot with deeded boat slip in Rock Hall.

LOT 30 HAGY RD, 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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Chestertown, MD Residential Income Properties for Sale

Historic Chestertown Multi-Family Opportunity

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

Turnkey Investment Property in Chestertown

Profitable mixed-use property with apartments and storefronts in downtown Chestertown.