The Guide to Living in Chestertown, Maryland
On Maryland’s Eastern Shore, a historic small town with maritime heritage
CHESTERTOWN, MARYLAND
The History of Chestertown, Maryland
Chestertown, Maryland, was established in 1706 and quickly became an important colonial port town on the Chester River.
Originally part of Kent County, it served as a commercial hub for tobacco cultivation and later expanded to other trade goods. The town thrived during the 18th century, with its waterfront bustling with merchant ships. Chestertown, Maryland is notable for its historic architecture, including many well-preserved Georgian-style buildings, reflecting its prosperous past.
In the 19th and 20th centuries, Chestertown, Maryland retained its small-town charm while preserving its colonial heritage. Today, it is recognized for its cultural festivals and as home to Washington College, one of the oldest colleges in the United States.
THE HOMES COLLECTION
Chestertown Modern
A modern waterfront residence of Maryland’s Eatern Shore
CHESTERTOWN, MARYLAND
Frequently Asked Questions
Explore common questions about life in Chestertown, Maryland, including the best restaurants, neighborhoods, and more.
IS CHESTERTOWN, MARYLAND A GOOD PLACE TO LIVE?
Regarded as one of the most desirable waterfront communities in the United States, Chestertown, Maryland offers a blend coastal-town living with accessible urban amenities.
HOW MUCH DOES IT COST TO BUY A HOME IN CHESTERTOWN, MARYLAND?
The median sale price for a detached single family home in Chestertown, Maryland is $330,000, which is roughly in line the national average of $308,980. Ready to buy the home of your dreams? Browse homes for sale in Chestertown, Maryland presented by Sotheby’s International Realty.
HOW MANY PEOPLE LIVE IN CHESTERTOWN, MARYLAND?
According to the 2020 Census data, Chestertown, Maryland has a population of 16,141 people, including a median age of 42 and a median household income of $63,484.
WHAT ARE THE BEST RESTAURANTS IN CHESTERTOWN, MARYLAND?
Chestertown, Maryland has some of the best restaurants on Maryland’s Eastern Shore.
WHAT IS THE SCHOOL DISTRICT FOR CHESTERTOWN, MARYLAND?
Residents of Chestertown, Maryland attend Kent County Public Schools, including…
WHAT IS THE PROPERTY TAX RATE FOR CHESTERTOWN, MARYLAND?
Property taxes for Chestertown, Maryland are calculated per every $100 of assessed value and are broken out into three separate segments. For 2024, the county rate is $0.6105, the state rate is $0.1120, and the municipal rate is $0.520.
IS CHESTERTOWN, MARYLAND ON THE WATER?
Located along a gracious bend of the Chester River, Chestertown, Maryland offers access to nearby waterways, including the Chesapeake Bay.
HOW FAR IS CHESTERTOWN, MARYLAND FROM WASHINGTON, D.C.?
Chestertown, Maryland is approximately 75 miles east of downtown Washington, D.C. The most common way to get to Washington, D.C. from Chestertown, Maryland is via car, which requires transit across the Chesapeake Bay Bridge.
THE RAPPAHANNOCK RIVER COMPANY
Find a Trusted Design Professional in Chestertown, Maryland
Explore the very best Residential Architects, Custom Home Builders, Interior Designers, and Landscape Architects near Chestertown, Maryland, including members of our Partner Network
Chestertown Modern of Chestertown, Maryland. Image courtesy of Durston Saylor.
CHESTERTOWN, MARYLAND
South Fork Studio
South Fork Studio is a Landscape Architecture Firm in Chestertown, Maryland
Magothy River Modern of Arnold, Maryland. Image courtesy of David Burroughs.
Maxmore Creek Colonial of Easton, Maryland. Image courtesy of Keyanna Bowen, East & Lane.
EASTON, MARYLAND
Charles Paul Goebel
Charles Paul Goebel is a Residential Architect in Easton, Maryland
THE RAPPAHANNOCK RIVER COMPANY
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