Cheshire, MA

Berkshire County · Massachusetts

Cheshire, MA Homes for Sale & Real Estate

Free instant estimate · No obligation · Or talk to a local agent →

Cheshire lies in the Hoosac Valley of northern Berkshire County, between Adams and Lanesborough. The town is known for its rolling farmland, Cheshire Reservoir and views of Mount Greylock. Route 8 runs through the small town center, and the Appalachian Trail crosses town on its way north toward Greylock. Cheshire’s dairy history is remembered through its famous mammoth cheese sent to President Jefferson.

Homes in Cheshire include older farmhouses and colonials near the center, capes and ranches in residential neighborhoods, and homes on larger rural lots with mountain views. Some homes sit near the reservoir. Dolan O’Rourke helps buyers explore Cheshire and nearby Berkshire towns and works with sellers to prepare and market their homes.

Living in Cheshire

Cheshire Reservoir

Cheshire Reservoir, also called Hoosac Lake, offers boating, fishing and scenic views of Mount Greylock along Route 8 and the rail trail.

Ashuwillticook Rail Trail

The paved Ashuwillticook Rail Trail runs along the reservoir and the Hoosic River, linking Cheshire with Adams to the north and Lanesborough to the south.

Appalachian Trail

The Appalachian Trail passes right through the town center, and hikers can follow it north over the ridges toward Mount Greylock.

Mammoth cheese

A monument in town recalls the 1801 mammoth cheese that Cheshire’s dairy farmers made and sent to President Thomas Jefferson in Washington.

Berkshire County · Massachusetts

Homes for sale in Cheshire, MA

Search every listing in Cheshire, MA by neighborhood, street, ZIP or MLS number, then save the homes you love.

Popular searches
  • New-listing alerts by email
  • Request a tour in one click
  • Local agents in RI & MA

Just listed

Newest listings in Cheshire, MA

The most recent homes for sale, newest first.

Loading the newest listings…

Getting around and the outdoors

Getting around

Route 8 runs through Cheshire, connecting north to Adams and North Adams and south to Lanesborough and Pittsfield, while Route 116 climbs east toward Savoy and the hill towns. Berkshire Regional Transit Authority buses serve the corridor, and Pittsfield offers Amtrak service and larger shopping areas.

Parks and recreation

The Ashuwillticook Rail Trail and Cheshire Reservoir offer biking, walking, fishing and paddling close to home. The Appalachian Trail and nearby Mount Greylock provide serious hiking, and the town’s farm fields and hillside orchards make for scenic drives in the fall.

Nearby communities

Buying or selling in Cheshire?

Whether you are buying your first home, moving up, downsizing or investing, our agents will guide you from the first conversation to the closing table.

Client reviews

What our clients say

5.0★★★★★9 reviews on Google and Yelp
★★★★★

I had the absolute pleasure of working with John Dolan and Dolan O’Rourke Real Estate Services while selling my mother’s home. We were going through an extremely difficult transition. We were both unfamiliar with the process of selling a home. From day one, John made himself readily available and kindly explained every part of the process to my mother, always making sure she understood each detail. His knowledge and expertise goes far and above what we expected. His constant communication never left us guessing – we felt very involved in every part of the process. I was caring for my mother on my own and he did everything in his power to ease the burden of selling her property. John knew I had great anxiety over our difficult situation and would always tell me not to worry. He always found a resolution to every bump in the road- and now I am finally worry free! John made us feel cared for and safe. We cannot thank him enough for his hard work. He helped us find a deal that we never could’ve imagined and changed our life for the better!  

Molly O.August 2024 · Yelpwith JohnRead full review
★★★★★

John was amazing with helping us in our home buying journey! His knowledge and patience made things very easy for us as first time home buyers. I highly recommend John to anyone who wants professionalism and someone who’s gonna get the job done! Thanks John!  

DaVaughn G.June 2023 · Googlewith JohnRead full review
★★★★★

We worked with John of Dolan O’Rourke Real Estate Services to purchase our first home in the Greater Boston area. As first time home buyers, John invested a lot of time early on to educate us about what to expect and strategies to consider. Throughout the process John had great communication, listening and advice as we navigated a challenging market. John was approachable, knowledgeable and always fun to be around as we looked at numerous houses, and helped us shape our conversations to really dial in to what we were looking for. We would love to recommend John for future real estate services and are so appreciative of his hard work.

Stephanie C.June 2022 · Googlewith JohnRead full review

Read all 9 reviews →

Thinking about buying or selling in Cheshire?

Ask us anything about buying, selling or renting. A local agent will reply.

Scroll to Top