Chestertown : Maryland

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What it's Like to Retire in Chestertown

Chestertown is small town of about 5,000 that is east of Baltimore on the Delmarva Peninsula, northeast of Annapolis on the Chester River.  The population is growing as more people consider it a quiet alternative to places like St. Michaels. In the mid-eighteenth century Chestertown was considered Maryland's second leading port after Annapolis. Chestertown is home to Washington College, the 10th oldest college in the U.S. The College has a large campus as you enter town. Then the charming downtown is set around a square and the Courthouse. Beautiful brick and wood houses are close together along some very cute streets. Chestertown was named  to the 2007 list of America's Dozen Distinctive Destinations by the National Trust for Historic Preservation. Photo of Chestertown harbor and river courtesy of Wikipedia and Yassie.


Where to Retire in Chestertown and Home Prices

There are active adult communities in the area (see link at top right). The median sales price of a home in mid-2016 was $227,000 according to Zillow.


What is special about Chestertown

Chestertown is a beautiful old river town with a rich history and many historic homes and buildings. The town was named as one of America's best rural places to live. The Chestertown Tea Festival celebrates Chestertown's colonial heritage with  events including a re-enactment of the legendary Tea Party that was held shortly after the Boston Tea Party.

What is not special about Chestertown

It's expensive to live in Chestertown.

Who will like retirement in Chestertown

People who like small towns with a lot of history and access to the water might like Chestertown. Washington College offers the Academy of Lifelong Learning for adults with many classes from which to choose and volunteer opportunities.


Local economy is driven by

There is some tourism in Chestertown. Many people commute to other places.

Climate and Physical Environment

Chestertown is on the Chester River on the east side of the Chesapeake from Baltimore and Annapolis.The average July high temperature is 88 and the average January low is 25. September is the wettest  month with over 3" of rain.

Restaurants & Cultural Scene

The Chestertown Tea Festival is a big annual event. Washington College contributes to the cultural life of the town.


The Chestertown crime rate is similar to the U.S. Average.

Medical facilities

Kent and Queen Hospital is located in Chestertown. Other hospitals are 25 miles away in Baltimore.


Chestertown is convenient to BWI International Airport in Baltimore.

Valuable Links

The Chestertown Tea Festival
Maryland retirement guide
Progressive Farmer award for Best Rural Place

Washington College Academy of Lifelong Learning


What people are saying about Chestertown

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  • State: MD
  • Environment: College Town,Small Town,Boating Community,
  • City Population: 10,000-25,000
  • Median age of Population: 25-44
  • Avg Jan Temperature: 21-40
  • Avg July Temperature: 60-80
  • Median HH Income: 20,001-40,000
  • Average Home Price (MLS): $200,001-$300,000
  • Annual Property Tax on a $200,000 house: 2000-4000
  • Total Crime Index: 91-100 (slightly below average)
  • Cost of Living Index: 101-110 (slightly above average)
  • Culture Index: 111-120 (high)
  • State Sales Tax: Yes
  • State Income Tax: Yes
  • Name of the Guide: boomer

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Chestertown retirement communities
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