Chester Connecticut
Homes for Sale and Real Estate

Area Description

Chester is a quintessential quaint New England town. Small and rural, it has grown and adapted from its historic beginnings as a shipbuilding and mill town to an enclave for artists and artisans and great restaurants.

Area Highlights

The Neighbors

Friendly, warm


Classic Connecticut town along the Connecticut River with a distinct small-town flavor


Family oriented and quiet. Valley Regional High School, which serves Chester, Deep River and Essex, is top notch.

You'll Love

A picturesque Main Street, miles of hiking trails, thousands of acres of state forest, lakes and cascading waterfalls

Perfect For

Families, enjoying outdoor and nature activities and a great art and restaurant scene.

Around the Area

Quaint is a word often used to describe the town of Chester. Its Main Street lined with antique Colonial homes and  restored quirky old buildings is a unique setting for a vibrant art and restaurant scene. Many of the art galleries and studios are owned by the artists and artisans.

To describe this heady mix, there is everything from a gallery featuring contemporary American Impressionism, a hip French (inspired) restaurant, L&E Restaurant and Good Elephant Bistro, to the River Tavern, which has a distinctly metro feel.

Of special note is the Norma Terris Theatre, also known as the Goodspeed-At-Chester, a sister theater to the Goodspeed Opera House in East Haddam. This intimate theater is housed in an old factory and presents new musicals to get them ready for the “big time.”

Located on the hillside of the Connecticut River, the town has a number of marinas, lakes, hidden streams, cascading waterfalls, thousands of acres of state forest, and hiking trails. Residents cherish the small town way of life.  It is home to Camp Hazen YMCA, which has been providing quality camping experiences for kids, families and school groups for more than 90 years.



Area Map

Area Listings