10 Best Places To Retire In Massachusetts

Folks fault Massachusetts for being an expensive place to retire, but considering that the Bay State boasts some of the most top-rated hospitals in North America, a copious array of world-famous academic institutions and universities, and an epic cultural scene with several theatres, museums, and indie bookshops, this New England gem offers great value for money. And as if that is not enough, Massachusetts is not a drab place with zero outdoor elegance. From the Berkshires to the picturesque coastline, you will always be blown away by the incredibly gorgeous landscape. But which are the finest spots? Starting with Westborough, the following are the 10 best small towns in Massachusetts to retire.

Lenox

Lenox is another cool spot to retire in the Berkshires, a region of beautiful rolling scenery with colorfully adorned hills and valleys. One of the things that sets Lenox apart is the median age of 64, meaning the area is essentially a get-together location for retirees. The social support system, therefore, should be unmatched. Keep in mind that Pittsfield is just 7 miles down the road, with Great Barrington an additional 5, which means you can access a broad range of desirable amenities on a whim, including the Berkshire Medical Center in Pittsfield. October Mountain State Forest is in your backyard and offers a good variety of hiking and biking trails, as well as peaceful ponds for calm and clarity. It is the largest state forest in Massachusetts. You can observe beavers and other wildlife at Mass Audubon's Pleasant Valley Wildlife Sanctuary or occasionally kill time at Ventfort Hall Gilded Age Mansion & Museum. The median listing home price in Lenox was $549,000 in September 2025.

Westborough

Although it may appear like a big town, especially with its population of about 22,000, Westborough always has an endearing small-town feel that many empty nesters will find irresistible. Moreover, Downtown Westborough is beautiful with small businesses lining the streets, and shopping and food are never too far. With Worcester just 11 miles west and Boston just over 30 miles east, this town is conveniently sandwiched between two big locations with an epic cultural scene. UMass Memorial Medical Center in Worcester has been recognized as the number one hospital in Massachusetts for surviving a heart attack, while the immaculately groomed Westborough Golf Club is a fantastic 9-hole track with tees for all levels.

The Willows at Westborough is an awesome retirement community that offers religious services, musical performances, daily exercise, and card games. Meanwhile, outdoor lovers have a decent number of options to work with, including the Westborough Reservoir Loop. The median listing home price in Westborough was $709,000 in September 2025, significantly lower than the statewide median of $739,500.

Sharon

Sharon is a safe and peaceful location with trees, a spring-fed Lake in its center, and countryside scenery. Lake Massapoag makes for a great summer with family, especially for its delightful range of outdoor recreational opportunities. There are weekly bands in summer to enjoy, welcoming restaurants for a spontaneous brunch, and, of course, Crescent Ridge, regularly ranked among the best ice cream spots in the United States. Wards Berry Farm offers a wide selection of fresh fruits and vegetables, while the nearby Boston Medical Center - South is one of only 5 hospitals in Massachusetts to be recognized by Healthgrades with a 2025 Patient Safety Excellence Award. Take note that CareOne at Sharon offers compassion and kindness at reasonable price points, although you can opt for your own home. Houses fetch a median listing price of $749,900, which is within a reasonable range of the state median.

Williamstown

Leaf peepers will find a slice of heaven in the Berkshires, the wider region within which Williamstown is located. The whole area has spectacular scenery, especially with all the lushness and mind-rousing greenery. The median listing home price in Williamstown was $525,000 in August 2025, a pocket-friendly price point that comes with access to Berkshire Medical Center in nearby Pittsfield, recently named among U.S. News & World Report's 2025-2026 Best Hospitals edition as a High Performing hospital for Pneumonia and Kidney Disease care.

Avid golfers have the Taconic Golf Club, routinely ranked among the best courses in the entire state. This green gem has hosted three different USGA championships: the 1956 U.S. Junior Amateur, 1963 U.S. Women’s Amateur, and 1996 U.S. Senior Amateur. There's Williams College, where you can enroll in an interesting major and keep your brain razor-sharp, and Sweetwood of Williamstown, a comfortable retirement community that offers a range of amenities designed to enrich a retiree's everyday experiences.

Auburn

Besides enjoying immediate access to the picturesque Pakachoag Hiking Trail, which should make for a regular, early-morning routine, empty nesters in Auburn are surrounded by amenities like the award-winning Umass Memorial Medical Center in Worcester, outdoor recreational spots like Pakachoag Golf Course ( it's a decent 9-hole), and fantastic cultural gems like the phenomenal Blackstone Valley 14 Cinema de Lux in nearby Millbury, a great choice for a movie night, especially given its central location and plenty of parking space. Moreover, it is perfectly situated right at The Shoppes in Millbury, meaning you can enjoy some shopping and dining right before or after a show. In August 2025, the median listing home price in Auburn was $589,000, way better than the statewide median of $739,500.

West Yarmouth

West Yarmouth is another solid retirement venue for several reasons, including the relative affordability of the area, the amenities that you can access without prior plans, and the area's modest range of both indoor and outdoor recreational opportunities. In September 2025, the median listing home price in West Yarmouth was $599,000, way better than the statewide median. Cape Cod National Seashore, a scintillating outdoor beauty that draws vacationers from every nook of the state, is just 30 minutes down the road. Cape Cod Hospital — Hyannis, which has previously been recognized for the Coronary Intervention Excellence Award, is also just around the corner. There is Maplewood at Mayflower Place, an assisted-living facility that offers genuine care and compassion to empty nesters in the area, and Whydah Pirate Museum, a cool place to kill an afternoon while soaking up interesting pirate history.

Northampton

Northampton may not be the place in the world to retire on its own, but the doorstep proximity to Amherst immeasurably tips the scales in its favour. The University of Massachusetts Amherst, which you can access in a heartbeat, has the distinction of being the largest public research university in New England. And there are several others within a few miles. Cultural attractions include places like Smith College Museum of Art, which boasts over four floors of galleries and a cafe, and the Botanic Garden of Smith College, a blissful space with several unique and wonderful plants to look at.

Outdoor lovers have Elwell State Park, a wooded waterfront site with trails that sits on the shores of the Connecticut River. In August 2025, the median listing home price in Northampton was $547,000, a package that includes easy access to Cooley Dickinson Hospital, a recipient of the 2024 'Get With The Guidelines' quality achievement award from the American Heart Association.

Amherst

Amherst is in a region evocatively known as Happy Valley in rural western Massachusetts. It is on the edge of the beautiful Berkshire Mountains and offers access to several decent colleges, including Amherst College, the University of Massachusetts at Amherst, and Hampshire College. Therefore, expect a location whose collegiate character and abundant cultural opportunities draw empty nesters from far and wide. Yet, Amherst is surprisingly cheap, especially considering what it offers. Houses in the area fetch a median listing price of just $475,000, less than the statewide median. You can kill time at the Emily Dickinson Museum, a space that honors one of America’s most celebrated poets, the city's public library, which houses special collections of Amherst authors, and Amherst Cinema, where you can enjoy an afternoon matinee in a fun, light-hearted environment. For any resilient flu, Cooley Dickinson Hospital, a member of Mass General Brigham, provides exceptional care to residents of the Western Massachusetts region.

Gardner

Even if you have gripes with Massachusetts, Gardner’s convenient proximity to Worcester, which is home to the highly rated UMass Memorial Medical Center, and Boston, which offers a much larger cultural scene, makes it such a comfortable place to retire. This north-central Massachusetts jewel is just 37 miles northwest of Worcester and 60 miles northwest of Boston. Fitness enthusiasts will enjoy peddling their bikes along the North Central Pathway, a paved trail that winds through Gardner into Winchendon, or taking a refreshing dip at Dunn State Park, a quiet spot with well-maintained trails and delicious views. Meanwhile, Crystal Lake is perfect for a mid-morning walk or a family picnic, while Gardner Cinemas is the go-to place for a mood-lifting show. In September 2025, the median listing home price in Gardner was $385,000.

Great Barrington

Great Barrington is a nice town; beautiful, cozy, and fun in every direction. Although it is a small town with just about 7,000 residents, it serves as the hub of Southern Berkshire County and boasts a vibrant Main Street, along with side streets lined with shops and inviting restaurants. Instead of brooding indoors, you can always enjoy some comic relief at Mahaiwe Performing Arts Center, an intimate space with interesting shows, float down the Housatonic River (or hit up the waterfront trails around it), or spend the whole day at Lake Mansfield Beach and Conservation Forest Trails, either swimming, walking, or just enjoying the scenery and the all-round soothing atmosphere. The median listing home price in Great Barrington was $710,000 in September 2025, slightly lower than the statewide median.

So, while you may not be excited by the cost of living in Massachusetts, sometimes you have to sacrifice a bit to enjoy some of life’s comforts and conveniences. The Bay State is regularly ranked among the best places to retire, and you will spend your golden years here amid world-class medical facilities, Ivy League universities, and an epic cultural landscape to suit almost every type of hobby in the world. Not to be outdone, the outdoor scenery here is also one for the books. You will find dreamy landscapes with rolling hills on one side, and white-sand beaches with nautical charm on the other.