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349 & 351 High Street

CHESTERTOWN, MD 21620
  • $395,000
  • STATUS: Active Under Contract
  • ON SITE: 624 Days
  • ID#: MDKE2003720
Under Contract
UPDATED: 22 min ago
$395,000
  • 0
    BEDS
  • 0.13
    ACRES
  • 0
    BATHS
  • 0
    1/2 BATHS
  • 3,664
    SQFT
  • $108
    $/SQFT
Type:
Multi-Family
Built:
1900
County:

School Ratings & Info

School District:

Description

A Rare Opportunity in the Heart of Historic ChestertownDiscover 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.

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©2025 Bright MLS, All Rights Reserved. IDX information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale may no longer be available because they are for instance, under contract, sold, or are no longer being offered for sale. Information is deemed reliable but is not guaranteed accurate by the MLS or The Lisa Mathena Group. Some real estate firms do not participate in IDX and their listings do not appear on this website. Some properties listed with participating firms do not appear on this website at the request of the seller. Data last updated: 2025-12-14T13:52:12.507.
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349 & 351 High Street CHESTERTOWN, MD 21620

  • Price: $395,000
  • Status: Active Under Contract
  • On Site: 624 Days
  • Updated: 22 min ago
  • ID#: MDKE2003720
0
Beds
0
Baths
0
½ Baths
0.13
Acres
3,664
SQFT
$108
$/SQFT
1900
Built
County:
Kent
School District:
Kent County Public Schools
Property Description
A Rare Opportunity in the Heart of Historic ChestertownDiscover 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.
Exterior Features

Architectural Style Victorian Construction Materials Frame Garage YN No Parking Types On Street Pool No Pool Water Access YN No Water View YN No Waterfront YN No

Interior Features

Above Grade Fin SQFT 3664 Basement YN No Below Grade Finished Area 0 Below Grade Unfinished Area 0 Cooling Window Unit(s) Fireplace YN Yes Fireplaces Total 1 Heating Radiator Heating YN Yes Rooms Total 17 Single Room Units 0 Spa YN No Three Bedroom Units 1 Two Bedroom Units 1 Units Furnished None

Property Features

Acceptable Financing CashConventional Accessibility Features None Central Air YN No Cooling Fuel Electric Cross Street Mill Foundation Details Pilings Heating Fuel Oil Historic YN No Hot Water Tankless Municipality Chestertown Navigable Water YN N New Construction YN No Number Of Units Total 2 Original MLSNumber 802931689104 Ownership Interest Fee Simple Property Sub Type Duplex Rent Control YN No Sale Type Standard Sewer Public Sewer Structure Design Type End of Row/Townhouse Tax Annual Amount 5442.00 Vacation Rental YN No Water Source Public Zoning RB PROFESSIONAL OFFICE Zoning Description See attached document from relevant portion of the zoning ordinance.

Listing courtesy of Coldwell Banker Chesapeake Real Estate Company: .


©2025 Bright MLS, All Rights Reserved. IDX information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale may no longer be available because they are for instance, under contract, sold, or are no longer being offered for sale. Information is deemed reliable but is not guaranteed accurate by the MLS or The Lisa Mathena Group. Some real estate firms do not participate in IDX and their listings do not appear on this website. Some properties listed with participating firms do not appear on this website at the request of the seller. Data last updated: 2025-12-14T13:52:12.507.
 
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