If you like the sound of Annapolis but can’t swing the price tag, Chestertown is an excellent alternative. Sitting across Chesapeake Bay on the Delmarva Peninsula, Chestertown is another 18th-century port town. In fact, it was second in popularity and wealth only to Annapolis. The benefits of living in Chestertown as opposed to Annapolis are a smaller population and a much cheaper housing market. The median home value here is half of Annapolis’ at around $210,000. The population is 5,000 with 28% of the residents aged 65 or older. The downtown still retains a quaint old-world feel with antique brick and wooden homes. Chestertown is also home to Washington College, the 10th oldest college in the nation. Chestertown’s location on the river and near the bay make this is a good choice for retirees who want a small-town soaked in history with easy access to water activities.
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