Chestertown, MD Residential income properties for sale

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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Historic Chestertown Multi-Family Opportunity

$395,000

3,664 SF

Historic Chestertown Multi-Family Opportunity

349 High St, 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.

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Based on your search, we've compiled 6 Potential Opportunities for your consideration. Besides 2 Active listings in Chestertown, MD, we suggest exploring several alternatives: 4 properties in Nearby Cities

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Chestertown, MD Residential Income Properties Investment Opportunities Market Analysis

Explore 2 residential income properties for sale in Chestertown, MD 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.

Sale 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 stay ahead with the latest data and market trends.

Chestertown, MD Residential Income Properties for Sale

Historic Chestertown Multi-Family Renovation Opportunity

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

Historic Chestertown Multi-Family Opportunity

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