349 High St, Chestertown, MD 21620
Local realty services provided by:Better Homes and Gardens Real Estate Community Realty
349 High St,Chestertown, MD 21620
$395,000
- 7 Beds
- 4 Baths
- 3,664 sq. ft.
- Townhouse
- Pending
Listed by: cheryl hurt
Office: coldwell banker chesapeake real estate company
MLS#:MDKE2004076
Source:BRIGHTMLS
Price summary
- Price:$395,000
- Price per sq. ft.:$107.81
About this home
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.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
Contact an agent
Home facts
- Year built:1900
- Listing ID #:MDKE2004076
- Added:534 day(s) ago
- Updated:November 20, 2025 at 08:43 AM
Rooms and interior
- Bedrooms:7
- Total bathrooms:4
- Full bathrooms:3
- Half bathrooms:1
- 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)
New listings near 349 High St
- New
$89,500Active3.92 AcresGeorgetown Rd, CHESTERTOWN, MD 21620
MLS# MDKE2005844Listed by: CHESAPEAKE REAL ESTATE ASSOCIATES, LLC - New
$375,000Active4 beds 3 baths1,936 sq. ft.108 Flying Cloud Dr, CHESTERTOWN, MD 21620
MLS# MDKE2005928Listed by: CROSS STREET REALTORS LLC - Coming Soon
$265,000Coming Soon3 beds 1 baths7521 Pine Ave, CHESTERTOWN, MD 21620
MLS# MDKE2005920Listed by: CHESAPEAKE REAL ESTATE ASSOCIATES, LLC - New
$635,000Active0.09 Acres108 Little Harbor Way, CHESTERTOWN, MD 21620
MLS# MDKE2005902Listed by: GUNTHER-MCCLARY REAL ESTATE - New
$88,900Active0.48 AcresEast St, CHESTERTOWN, MD 21620
MLS# MDQA2015588Listed by: SELECT LAND & HOMES, LLC - New
$399,000Active3 beds 3 baths2,034 sq. ft.121 Primrose Rd, CHESTERTOWN, MD 21620
MLS# MDQA2015570Listed by: COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY - New
$299,000Active2 beds 2 baths920 sq. ft.611 Cannon St, CHESTERTOWN, MD 21620
MLS# MDKE2005906Listed by: SELECT LAND & HOMES, LLC - New
$1,459,000Active3 beds 3 baths2,231 sq. ft.Little Harbor Way #1, CHESTERTOWN, MD 21620
MLS# MDKE2005768Listed by: GUNTHER-MCCLARY REAL ESTATE - New
$799,900Active3 beds 4 baths2,092 sq. ft.106 Landing Ln, CHESTERTOWN, MD 21620
MLS# MDKE2005892Listed by: GUNTHER-MCCLARY REAL ESTATE - New
$849,900Active3 beds 3 baths1,980 sq. ft.104 Little Harbor Way, CHESTERTOWN, MD 21620
MLS# MDKE2005894Listed by: GUNTHER-MCCLARY REAL ESTATE