Chestertown, MD Apartment buildings 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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$395,000

Historic Chestertown Multifamily Renovation Opportunity

349 High St, Chestertown, MD 21620

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

Rare double lot in the heart of Chestertown's Historic and Arts & Entertainment Districts.
Multi‑family property with flexible layout suitable for renovation or redevelopment.
Located within both the Arts & Entertainment District and Enterprise Zone, supporting residential and commercial uses.
Historically significant property, known as the Laurence Lots, featured on original town maps.
Potential for income generation through apartments or creative reimagining.

Updated: Jun 3, 2024

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$1,195,000

Chestertown Multifamily Investment Opportunity

Multifamily property for sale in Chestertown, Maryland.

23393 Cacaway Farm Ln, Chestertown, MD 21620

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Based on your search, we've compiled 7 Potential Opportunities for your consideration. Besides 3 Active listings in Chestertown, MD, we suggest exploring several alternatives: 4 properties in Nearby Cities

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Cozy Condo with Granite Kitchen

Two-bedroom condo featuring granite countertops and in-unit laundry.

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Light-Filled Penthouse Condo in Baltimore

Top-floor condo with updates, convenient location in White Marsh.

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Chestertown, MD Apartment Buildings Investment Opportunities Market Analysis

Explore 3 apartment buildings for sale in Chestertown, MD, showcased through 3 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 two-family homes 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.

Chestertown, MD Apartment Buildings for Sale

Historic Chestertown Multi-Family Renovation Opportunity

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

Historic Chestertown Multifamily Renovation Opportunity

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

Chestertown Multifamily Investment Opportunity