Berkshire County · Massachusetts
Monterey, MA Homes for Sale & Real Estate
Free instant estimate · No obligation · Or talk to a local agent →
Monterey is a small, rural hill town in southern Berkshire County, east of Great Barrington along Route 23. The town is known for its lakes, especially Lake Garfield and Lake Buel, and for its wooded landscape. The small village center includes a general store, library and church, and much of the town is protected forest.
Homes in Monterey include lake houses and cottages on Lake Garfield and Lake Buel, older farmhouses and capes on rural roads, and contemporary homes on wooded lots. Many properties are second homes, and inventory can be limited. Dolan O’Rourke helps buyers explore Monterey and nearby Berkshire towns and works with sellers to market their homes.
Living in Monterey
Lake Garfield
Lake Garfield is a popular spot for swimming, boating and fishing, with a town beach and homes along its shores.
Beartown State Forest
Beartown State Forest extends into Monterey, offering wooded hiking trails, campsites and Benedict Pond for swimming and paddling in summer.
Bidwell House Museum
The Bidwell House Museum preserves an 18th-century home, with heirloom gardens and walking trails across the wooded grounds that surround it.
Village center
Monterey’s small village center along Route 23 features a general store, a library and a historic church beside the Konkapot River.
Berkshire County · Massachusetts
Homes for sale in Monterey, MA
Search every listing in Monterey, MA by neighborhood, street, ZIP or MLS number, then save the homes you love.
- New-listing alerts by email
- Request a tour in one click
- Local agents in RI & MA
Just listed
Newest listings in Monterey, MA
The most recent homes for sale, newest first.
Getting around and the outdoors
Getting around
Route 23 runs through Monterey, connecting west to Great Barrington and east to Otis and Route 8. The Mass Pike is reachable in Lee, and Route 7 is a short drive west. Great Barrington and Pittsfield offer shopping and services.
Parks and recreation
Lake Garfield, Lake Buel and Beartown State Forest offer swimming, boating, hiking and camping. The Appalachian Trail and nearby Tyringham Cobble offer more trails, and winding country roads are popular for cycling and fall foliage drives through the hills each autumn.
Nearby communities
Buying or selling in Monterey?
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.
- Buyers: Learn about our Buyer Representation Services.
- Sellers: Explore our Seller Representation Services and flexible listing tiers.
- Home value: Find out what your Monterey home is worth.
Client reviews
What our clients say
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!
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!
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.
Thinking about buying or selling in Monterey?
Ask us anything about buying, selling or renting. A local agent will reply.
