Change Real Estate Presents:

349 & 351 High Street
Chestertown MD 21620

For Sale: $395,000.00 Active Under Contract

List Date: 2024-04-19

Chestertown
3,664 build ft2
5,737 land ft2

About This Property

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.

Listing Agent: Cheryl Hurt. Coldwell Banker Chesapeake Real Estate Company 619-755-7730 cherylh@cbchesapeake.com

Property Features

Location Information
County:
Subdivision: None
Interior Features
Appliances:
Interior:
Laundry:
Furnished: None
Flooring:
Water: Public
Cooling: Window Unit(s)
Heating: Radiator
Fireplaces: 1
Windows:
Utilities:
Sewer: Public Sewer
Exterior Features
Year Built: 1900
Schools
Elementary School: None
Junior High School: None
High School: None

IDXListing Courtesy of Cheryl Hurt. Coldwell Banker Chesapeake Real Estate Company 619-755-7730 cherylh@cbchesapeake.com

Property Photos [Click to enlarge]

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