Welcome to

Chester

Learn more about Chester

Chester, Maryland, is a charming and scenic community located on the Eastern Shore, in Queen Anne’s County. Positioned along the Chester River, this small town offers a peaceful and picturesque environment with a strong connection to its maritime heritage. Chester is known for its beautiful waterfront views, with many homes offering access to the river and opportunities for boating, fishing, and other water-based activities. The town’s proximity to the Chesapeake Bay provides residents with easy access to stunning natural landscapes and recreational opportunities.

The community in Chester is tight-knit and welcoming, with local events and gatherings that foster a sense of camaraderie among residents. The town features a mix of historic and modern homes, contributing to its charming character. Local amenities include parks, schools, and a variety of small businesses and eateries, providing residents with essential services and a taste of local culture. Chester’s location also offers convenient access to larger towns and cities, such as Annapolis and Easton, where residents can find additional shopping, dining, and entertainment options. With its blend of natural beauty, historical charm, and community spirit, Chester is a delightful place to live on Maryland’s Eastern Shore.

Want the full market report for Chester?

We want to ensure that you have all the information needed to make the best decisions when it comes to your home goals. When you enter your info below you will get instant access to the area's latest market report, complete with sales and demographic trends.

Chester
Market Report

Around The Area

Browse through the top rated businesses that Chester has to offer!

Local News & Advice

Read helpful resources and articles related to the area.

Why You’ll Love Spending the H…

Why You’ll Love Spending the H…

POV: Picture this: Its a crisp winter evening, and your new home is al…

The Best Easton Neighborhoods …

The Best Easton Neighborhoods …

Easton, Maryland, is one of those charming towns that truly comes aliv…

A Timeless Retreat on the East…

A Timeless Retreat on the East…

Imagine this: youre driving down a private, tree-lined road, the air c…