349 High Street, Chestertown, MD 21620-1309 $395,000

Interior Sq. Ft: 3,664
Acreage: 0.13
Age:125 years
Style:
Victorian
Subdivision: Historic District Chestertown
Design/Type:
End of Row/Townhouse
Description
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 commercial uses—making it an ideal candidate for those looking to merge lifestyle, business, and history. 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.
Home Assoc: No
Condo Assoc: No
Basement: N
Pool: No Pool
Features
Utilities
Radiator Heating, Oil, Window Unit(s) Cooling, Electric, Hot Water - Electric, Public Water, Public Sewer
Garage/Parking
On Street
Exterior
Pillar/Post/Pier Foundation, Frame Exterior
Contact Information
Schedule an Appointment to See this Home
Request more information
or call me now at 302-429-4500
Listing Courtesy of: Coldwell Banker Chesapeake Real Estate Company
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Listing data as of 6/25/2025.