349 High St

Chestertown, MD 21620
  • $395,000

    Price
  • 7

    Bed
  • 3.5

    Bath
  • 3,664

    SqFt

About the Listing CBCE2 - 3291606

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. 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. **See updated zoning info from the town in documents

Listing Highlights for 349 High St

Status Active With Contingency
Days on Site 519
Property Type Townhome
MLS ® MDKE2004076
Year Built 1900
Total Square Footage 3,664
Lot/Acreage 0.13

Interior Details

  • Bedrooms: 7
  • Bathrooms: 3 Full / 1 Half
  • Appliances:
  • Air Cond: Window Unit(s)
  • Heating: Radiator
  • Fireplaces:
  • Floor:
  • Above Ground Sq Ft: 3664
  • Below Ground Sq Ft: 0
  • Basement:
  • Other: No Pet Restrictions,Pets Allowed,Main Floor Bedrooms: 1
  • Water: Public

Exterior Details

  • Lot Description: Not New Construction,Horse Property: No,In City Limits
  • Garage Capacity: N/A
  • Zoning: See attached relevant section of zoning ordinance.
  • Roof:
  • Others:
  • Sewer: Public Sewer
  • Parking Features: On Street

Financial Details

  • Tax Amount: $5,442
  • Taxes w/Assessments: N/A
  • Tax/Property ID: N/A
  • Tax Year: 2024

Payment Calculator

Monthly Payment

  • in Principal and Interest
  • in Taxes
Years
% Down Payment
% Mortgage Rate

Listing Location

Questions About..

349 High St Chestertown, MD 21620

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Never Miss A New Property

Get notified any time there's a new home on the market in this neighborhood!

Don't worry! We'll never spam you or sell your details. You can unsubscribe whenever you'd like.

Originating MLS: BRIGHT_MAIN

home

Are you buying or selling a home?

Buying
Selling
Both
home

When are you planning on buying a new home?

1-3 Mo
3-6 Mo
6+ Mo
home

Are you pre-approved for a mortgage?

Yes
No
Using Cash
home

Would you like to schedule a consultation now?

Yes
No

When would you like us to call?

Thanks! We’ll give you a call as soon as possible.

home

When are you planning on selling your home?

1-3 Mo
3-6 Mo
6+ Mo

Would you like to schedule a consultation or see your home value?

Schedule Consultation
My Home Value

or another way