Williamstown, Massachusetts: Morning view of shops along Spring Street in the downtown district, via DenisTangneyJr / iStock.com

12 Top-Ranked Towns in Massachusetts for Retirees

Boasting some of the world's best hospitals, top-notch public education (crucial for lifelong learners), and excellent access to both mountains and the sea, it's no surprise that the personal finance publication WalletHub ranked Massachusetts as the Best State to Live in for 2023. Massachusetts is a haven for history buffs, being the landing place of the Pilgrims. Although it's not the cheapest option, the best things in life are seldom free, as the saying goes. If you're considering Massachusetts for retirement, explore these 12 top-ranked towns for retirees.

Westborough

Westborough, Massachusetts: Exterior of the Arcade Building in downtown Westborough
Westborough, Massachusetts: Exterior of the Arcade Building in downtown Westborough, via quiggyt4 / Shutterstock.com

Westborough offers nearly everything an empty-nester could want. It boasts excellent accessibility, with a stop on the MBTA Commuter Rail linking it to Boston, which is only about 34 miles away. In roughly 40 minutes, you can reach one of the world's premier hospital cities. For pet owners, the Cummings School of Veterinary Medicine is just 4 miles away. The town features great shopping at local stores, beautiful streets for strolling, and scenic hiking spots like the Westborough Reservoir Loop. Additionally, Westborough is rated “A” for ethnic and economic diversity by Niche.com and has a significant senior population, constituting 27% of its residents.

Sharon

Sharon, Massachusetts, town center
Sharon, Massachusetts, town center

Sharon is appealing for its natural beauty, centered around spring-fed Lake Massapoag, and offers ample opportunities for outdoor adventures. It's a safe choice too, being one of Massachusetts's 20 Safest Cities according to Safewise. For those with a sweet tooth, Crescent Ridge Dairy, with its milk ice cream sourced from their own 44-acre farm, is a highlight. While Sharon has a fair selection of shops and restaurants, Boston is just a 30-minute drive away. Seniors make up 31% of the town’s population, offering a community where you can easily connect and share experiences.

West Yarmouth

West Yarmouth, Cape Cod, Massachusetts.
West Yarmouth, Cape Cod, Massachusetts.

West Yarmouth, and its surrounding area, is noted for its relative affordability. For instance, according to Redfin, the median home price in West Yarmouth was $345,000 in December 2023, compared to Boston's median of $830,000 – offering a significant saving of $485,000. This price point allows seniors to enjoy the attractions of Cape Cod, including some of the most beautiful beaches. The Cape Cod National Seashore is just a 30-minute drive away. The median age in West Yarmouth is 48, suggesting that an empty-nester would find it easy to fit in and find social support. The area also offers excellent healthcare access, with nearby Cape Cod Hospital in Hyannis, just 2 miles away, winning several awards, including the Coronary Intervention Excellence Award.

Manchester-by-the-Sea

Seaside homes in Manchester-by-the-Sea.
Seaside homes in Manchester-by-the-Sea.

Manchester-by-the-Sea, a quaint and charming town with lovely parks, is an ideal retirement location. It's 8 miles from Gloucester, a world-class boating venue, and 14 miles from Marblehead, known as the birthplace of the American Navy. According to Niche.com, seniors comprise 38% of the population, creating a close-knit community. Furthermore, 34% of the population holds a master’s degree or higher, indicating a highly educated community and the potential for engaging intellectual conversations. While home prices are relatively high, the town is only about a half-hour's drive from Boston, offering access to big-city adventures and amenities.

Wayland

Aerial view of the historic town center of Wayland, Massachusetts.
Aerial view of the historic town center of Wayland, Massachusetts.

Safety is a key consideration in retirement, and Wayland is ranked as Massachusetts’ safest city by Safewise. As a suburb of Boston, located just 20 miles away, Wayland provides access to all the benefits of the capital, including world-class hospitals like Massachusetts General Hospital. The town offers a sparse suburban feel, and nearly everyone (92%) is a homeowner, according to Niche.com. Seniors account for 36% of Wayland’s population, ensuring a robust community of peers. For nature enthusiasts, Cochituate State Park is nearby, perfect for enjoying birdwatching or sunsets.

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Williamstown

Spring Street in Williamstown, home of Williams College
Spring Street in Williamstown, home of Williams College, via Adam Gladstone / Shutterstock.com

Eastern Massachusetts often receives a lot of attention, but the Berkshires region, known internationally for its surreal beauty, offers a captivating alternative. Williamstown is a prime example of this. The town offers numerous outdoor attractions that are both rejuvenating and accessible. Additionally, it's budget-friendly. As of December 2023, Williamstown's median home price was $410,000 according to Redfin, considerably lower than both the Boston area and the state average. In terms of medical access, the town is conveniently located near several facilities, including Southwestern Vermont Medical Center, only 11 miles away, known for its Outstanding Patient Experience Award. Furthermore, Berkshire Community College’s Osher Lifelong Learning Institute, just minutes from town, offers courses like Practical Self-Defense, The Five Composers that Changed Classical Music, and The History of the English Language.

Leverett

Intersection of Shutesbury Road and Cushman Road, East Leverett Massachusetts
Intersection of Shutesbury Road and Cushman Road, East Leverett Massachusetts

The area around Amherst, including the town of Leverett, offers appealing features for retirees. Leverett is laid back, quaint, and peaceful, catering well to the retiree demographic. Despite its small size, with a population of less than 2,000, Leverett is conveniently located just a 10-minute drive from Amherst, which provides a range of amenities and services. One of the area’s highlights is the University of Massachusetts Amherst, one of New England's largest campuses. The Amherst Senior Center, offering wellness, recreational activities, and counseling, enhances the appeal. Medical facilities are easily accessible, with Cooley Dickinson Hospital in Northampton, recommended by 74% of its patients, only 7 miles away. With seniors constituting about 43% of Leverett's population, a vibrant, age-appropriate social scene is expected.

Northampton

A street in Northampton, Massachusetts.
A street in Northampton, Massachusetts. Editorial credit: EQRoy / Shutterstock.com

In Northampton, 35% of the population is seniors, according to Niche.com, suggesting a strong community of peers for retirees. Similarly, the percentage of residents with a master’s degree or higher is noteworthy, indicating a community that is both witty and well-informed. The presence of Hampshire College adds to the town's vibrancy and youthful spirit, appealing to those who wish to stay young at heart. Northampton boasts a decent art scene, walkability, and proximity to towns like Holyoke, Amherst, Greenfield, and Springfield. For healthcare needs, Cooley Dickinson Hospital in Northampton is readily available, with several more medical facilities within a 30-minute drive.

Sandwich

Glass Museum in Sandwich, Massachusetts
Glass Museum in Sandwich, Massachusetts Wikimedia Commons

As of December 2023, the median home price in Sandwich was $555,000 according to Redfin. Though this may seem high, it is actually a great bargain considering its location less than an hour's drive from Boston. Seniors aged 55 and above make up a significant 45% of the town’s population, creating an environment akin to a seniors' reunion. This high percentage of empty-nesters suggests strong social support. The town’s motto, "After so many shipwrecks, a haven," resonates well with the senior community. Located on Cape Cod, Sandwich offers access to some of the most beautiful beaches in the world. Additionally, medical facilities in nearby towns such as Hyannis, Wareham, Plymouth, and Falmouth are all within a 20-minute drive.

Lenox

View of a street in Lenox, Massachusetts.
View of a street in Lenox, Massachusetts. Editorial credit: Richard Cavalleri / Shutterstock.com

Lenox, located in the Berkshires, is another appealing town for retirees, known for its breathtaking beauty. The town has a dense suburban feel with 68% homeownership. The presence of a large senior population, with 52% of residents aged 55 and above, indicates a robust social support network. Lenox offers diverse activities, including skiing in winter, hiking in fall, and enjoying summer concerts. Nearby towns like Pittsfield, just 7 miles away, and Great Barrington, 12 miles away, provide additional amenities. Hospitals such as Berkshire Medical Center in Pittsfield and Fairview Hospital in Great Barrington – which 90% of patients recommend and is recognized for both the Outstanding Patient Experience and Pulmonary Care Excellence Awards – are easily accessible. The median sale price of a home in Lenox was $758,000 as per recent data.

Auburn

Auburn Town Offices and Merriam Library, Auburn Massachusetts
Auburn Town Offices and Merriam Library, Auburn Massachusetts, By John Phelan - Own work, CC BY 3.0, Wikimedia Commons

Auburn, with its connotations of a rich, reddish-brown hue, is another prime choice for retirees in Massachusetts. The town has a peaceful suburban atmosphere, and according to Niche.com, 84% of residents are homeowners. With one in three residents being a senior aged 55 and above, it's easy for seniors to find peers. Its proximity to Worcester, just 5 miles away, is advantageous for those seeking access to big-city amenities. Worcester is home to top-notch hospitals, including Umass Memorial Medical Center, recognized for the Cardiac Surgery Excellence Award. Auburn is also quite affordable; the median home price was $420,000 in December 2023 according to Redfin, making it an accessible option for retirees.

Hingham

Street view in Hingham, Massachusetts
Street view in Hingham, Massachusetts

Incorporated in 1635, Hingham quickly developed into a bustling industrial town, noted for coopering and toy-making. Remarkably, the toy shop at Hersey Farm remains the only pre-industrial toymaker’s shop still operating in the United States. Situated on an inlet of Massachusetts Bay, just 21 miles from Boston, Hingham ranks as one of the best places to live in Massachusetts, contributing to its high demand. This is reflected in the town’s median home price of $1.1 million as of December 2023. According to Niche.com, 82% of Hingham's residents own their homes, and seniors constitute 37% of the population. The town is celebrated for its beautiful parks and impressive seascapes. Its strategic location offers easy access to numerous hospitals. Additionally, being located on the water, Hingham provides ample opportunities for summer activities and adventures.

The Takeaway

Massachusetts, consistently ranked as one of the best states to live in the United States, offers a plethora of appeals for retirees. From the stunning mountains in the Berkshires to the captivating waterfront views in the east, the Bay State is also renowned for its rich history. Living in Massachusetts means being part of a legacy that includes notable figures such as Samuel Adams, John F. Kennedy, and poet E.E. Cummings, known for "I Carry Your Heart with Me." For those seeking retirement destinations, towns like Sharon, West Yarmouth, Wayland, and Williamstown stand out as excellent choices in Massachusetts.

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