349 & 351 High St, Chestertown, MD 21620
Local realty services provided by:O'BRIEN REALTY ERA POWERED
349 & 351 High St,Chestertown, MD 21620
$395,000
- 6 Beds
- - Baths
- 3,664 sq. ft.
- Multi-family
- Pending
Listed by: cheryl hurt
Office: coldwell banker chesapeake real estate company
MLS#:MDKE2003720
Source:BRIGHTMLS
Price summary
- Price:$395,000
- Price per sq. ft.:$107.81
About this home
A Rare Opportunity in the Heart of Historic Chestertown
Discover a truly special offering in the vibrant core of Chestertown’s Historic and Arts & Entertainment Districts. Owned by the same family for over 50 years, this multi-family property sits on a generous double lot known historically as the Laurence Lots—featured on original town maps and steeped in local heritage.
Brimming with character and potential, the property currently features a townhouse on one side and two apartments on the other, offering a flexible layout ideal for renovation, income generation, or a creative reimagining. Whether you're envisioning a stately single-family residence, a dynamic live/work space, or a thoughtfully restored multi-unit investment, the possibilities are as expansive as the lot itself.
That said, this is not a turnkey property. Significant settling has occurred over the years, and a substantial renovation will be required to bring it back to life. Offered strictly as-is, this is a true fixer-upper for the visionary buyer ready to take on a transformative project.
Situated within both the Arts & Entertainment District and Enterprise Zone, this location supports both residential and business uses—making it an ideal candidate for those looking to merge lifestyle, business, and history. **See updated zoning info and description from town office in Documents.
Bring your vision, creativity, and tools—and seize the chance to breathe new life into a piece of Chestertown’s storied past. Opportunities like this don’t come along often.
Schedule your showing today and imagine the future you can build here.
Contact an agent
Home facts
- Year built:1900
- Listing ID #:MDKE2003720
- Added:682 day(s) ago
- Updated:February 11, 2026 at 08:32 AM
Rooms and interior
- Bedrooms:6
- Living area:3,664 sq. ft.
Heating and cooling
- Cooling:Window Unit(s)
- Heating:Oil, Radiator
Structure and exterior
- Year built:1900
- Building area:3,664 sq. ft.
- Lot area:0.13 Acres
Utilities
- Water:Public
- Sewer:Public Sewer
Finances and disclosures
- Price:$395,000
- Price per sq. ft.:$107.81
- Tax amount:$5,442 (2024)
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