Retiring in Massachusetts is attractive, but can be costly


By Sharon Longo
Contributing Writer

The small-town charm of Lenox and scenery of the Berkshire hills are big draws for retirees interested in relocating to the western part of the state.
The small-town charm of Lenox and scenery of the Berkshire hills are big draws for retirees interested in relocating to the western part of the state.

REGION – Massachusetts has its pros and cons when it comes to retiring here. Some data shows it to be an expensive choice, which is no surprise to those who spent their work lives here. Other factors such as certain locations and amenities make it a retirement haven, however.

The Bay State is the most expensive state for retirement in New England with prices for many goods and services, plus home costs, higher than the average in other areas. On the positive side, Social Security income is not taxed, and there are many perks to living in the state. According to, the state has a “booming economy” and is a great place to start up a company or go into a second career. 

Plenty of variety

Massachusetts has a vast array of living choices, with mountains, farmland, beaches and areas that offer museums, art studios, festivals and diverse restaurants, bars and coffee shops. Seafood abounds with fresh fish, clams and lobster, or one can fall in love with the small-town quaintness and charm of areas that offer a wide range of shops and other amenities. There are plenty of opportunities to attend pro sporting events, or take in some outdoor activities like fishing, boating, hiking or skiing. 

Of course, with more free time, you might want to take a class or two for some continuing education. In the western part of the state, with the Five College Learning in Retirement program, seniors can take courses at Amherst College, Mount Holyoke, Smith College, Hampshire College or the University of Massachusetts at Amherst. Harvard University in Cambridge also has a program called the Harvard Institute for Learning in Retirement

What are the best places to live?

Access to 16 different Cape Cod beaches makes Dennis an attractive retirement destination.
Access to 16 different Cape Cod beaches makes Dennis an attractive retirement destination.

Of the 2022 ten best places in Massachusetts to retire according to, there are several that have a population of under 6,000 while boasting many retirees, with many of them on Cape Cod, a longtime retirement destination for state residents.

West Dennis, a village in Dennis on the Cape, has a median home price of about $397,300. It has been described as tranquil, with tree-lined streets, while the town of Dennis offers 16 beaches on Nantucket Sound or Cape Cod Bay. There is also some historic charm to Dennis, which was a whaling and seafaring town, and it is home to The Cape Playhouse, said to be the oldest professional summer theater in the US.  

North Falmouth is a quaint tourist town, with a median home price of $550,200. The historic village within Falmouth on Cape Cod has beaches on Buzzards Bay and Vineyard Sound. For some scenic activities, consider biking, hiking, or in the winter, cross country skiing along the 10.7 miles of the Shining Sea Bikeway. 

East Sandwich has a rural feel, with the median home price at $496,800. The historic charm abounds in the area with many museums and older home tours, as well as a grist mill. Beaches are on Cape Cod Bay, and there is also a fish hatchery and many other amenities to provide some fun or exploration.

The Pinehills, a quaint and charming area of Plymouth, boasts two of the top-ranked golf courses with a median home price at $569,300, and finally, Orleans, with beaches on the Atlantic Ocean and Cape Cod Bay, has its median home price at $639,500. 

Towns with a population between 6,000 and 10,000, yet with a rural or “sparse suburban” feel, include Chatham and Brewster. Both have many retirees, the former containing a wildlife refuge which is the home to many migratory birds. Chatham also has a median home price of $668,500. Brewster, with a median home price of $450,200, is an interesting location which includes Brewster Flats. This area has many tidal pools and sections filled with sea life as Cape Cod Bay ebbs and flows. 

Finally, Wayland and Yarmouth, with populations of 13,823 and 23,292, also have many retirees. The median home price in Yarmouth is $551,283, with Wayland coming in at the highest at about $733,300. Yarmouth, the second oldest town on Cape Cod, has many of the amenities of Cape Cod living, and Wayland, ranked number 2 by Niche for “Best Suburbs to Live in Massachusetts,” has a quiet feel, yet as a part of the MetroWest region it’s close enough to partake in the city offerings of Boston. North of Boston, the coastal town of Newburyport also gets high grades for retirees, as does Lenox in the mountainous Berkshire region of Western Massachusetts.

What about health care?

One concern for seniors looking for a place to retire is whether or not there are good nearby healthcare facilities, and Massachusetts has some of the best in the country. Massachusetts General Hospital in Boston came in at number 3 on Newsweek’s best 100 hospitals, as well as Brigham and Women’s Hospital in Boston ranking number 17 and Beth Israel Deaconess Medical Center in Boston at #97. There are also many others throughout the 10,565 square miles of the state.

Where to live in retirement can be a daunting decision, taking many factors into consideration. But if it meets your budget, Massachusetts could still be a good choice after your working years are over or you have downsized your career to part-time work or a different encore pursuit.



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