$395,000
 $2,120 est/mo Sourced by Back At You

349 High St,CHESTERTOWN, MD 21620

CHESTERTOWN, MD 21620

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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 Lotsfeatured 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 usesmaking it an ideal candidate for those looking to merge lifestyle, business, and history. Bring your vision, creativity, and toolsand 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.

Details

MLS #MDKE2004076
Listing TypeFor Sale
StyleTown House
Sub-TypeResale
StatusActive-bright
Year1900
Days On Site382
Listing Provided ByColdwell Banker Chesapeake Real Estate Company | Cheryl Hurt

Features

Bed(s)7
Bath(s) 4 Total
SQ Feet3,664
Story(s)3
ZoningC-2
Acreage0.13

Interior

CoolingWindow Unit(s)
Heating Yes / NoYes
HeatingRadiator
FurnishedNo
Fireplace Yes / NoNo

Exterior

Construction MaterialsFrame
Foundation DetailsPillar/Post/Pier

Parking

Garage Yes / NoNo

Utilities

SewerPublic Sewer

Taxes

Tax Year2024
Tax Annual Amount5442

Market Activity 21620

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Learn More About This Property

StateMD
CountyKENT MD
CityCHESTERTOWN
Zip Code21620
AreaKENT MD
Community NameHISTORIC DISTRICT CHESTERTOWN
School DistrictKENT COUNTY PUBLIC SCHOOLS
Listing VS Median (in HISTORIC DISTRICT CHESTERTOWN)
Price:
$395,000
low | high
Med:
$395,000
50% of Average
SqFt:
3,664
low | high
Med:
3,664
50% of Average
$ / SqFt:
$108
low | high
Med:
$108
50% of Average
On site:
382
low | high
Med:
382.000000
100% of Average
Sourced by Back At You
Nearby Listings (Within 1/10 mile)
Price: $296K - $493K
SqFt: 2,500 - 4,500
Nearby Listings Property ImageNearby Listings Details
349 & 351 HIGH ST Property Photo 1
$395,000
349 & 351 High St
Chestertown, MD 21620
Listing Updated: June 9, 2025 at 12:33:26 PM PDT