Westborough 55+ Active Adult Retirement Communities

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Westborough, MA is a picturesque New England town with a charming town square and numerous nearby outdoor recreational opportunities. Situated in a beautiful area surrounded by plenty of hiking trails and parks to explore, Westborough offers active adult homebuyers a serene setting and proximity to both Worcester and Boston. Westborough also boasts a thriving arts and culture scene, with local galleries and theaters offering a variety of events throughout the year. Overall, Westborough is an excellent choice for 55+ homebuyers who are looking for active adult communities near a small, welcoming town.

Some local resources that may be helpful for those considering moving to Westborough include the town’s official website, the Westborough Community Land Trust, and the Westborough Public Library. These websites offer information on local events, parks and trails, and community resources, providing a comprehensive overview of all that the town has to offer.

Affordability and Cost of Living

Although Massachusetts offers some tax advantages for retirees, retirees need to carefully consider the state’s overall cost of living and housing expenses. Residents of Massachusetts pay a flat income tax rate of 5%, which includes most types of retirement income from pensions and benefits. The state also has an estate tax, but no inheritance tax. Social Security income is also exempt from income taxes, which benefits active adults who want to retire in Westborough. Sales tax is 6.25% across the state and there are occasionally local sales taxes added to that rate.

The overall cost of living in Westborough is more than one-third higher than the national average, which means that retirees pay more for the luxury of living in the area. Residents tend to pay more for groceries, utilities, and miscellaneous goods and services, but housing costs represent the most significant expense. Housing tends to cost more than double the national average. Homeowners in the area pay a property tax of 1.1% among the highest median property taxes in the nation. However, to alleviate the tax burden of retirees, the state offers a refundable tax credit to 65+ homeowners.

Climate and Geography

Residents of Westborough, MA enjoy four distinct seasons. Summers are typically warm and somewhat humid, with average temperatures in the high 70s to low 80s. Winters are cold with average temperatures dipping down into the teens, particularly in January. Westborough receives an average of 45 inches of snowfall each year, according to Best Places, making it a great location for winter sports enthusiasts. In the fall, the town is known for its stunning foliage, with vibrant shades of red, orange, and yellow covering the trees. Spring is a beautiful time of year as well, with blooming flowers and milder temperatures.

Geographically, Westborough is located in a beautiful area of Eastern Massachusetts near rolling hills, scenic forests, and sparkling lakes. The town is located south of Lake Chauncy, which provides opportunities for boating, fishing, and other water activities. The George H. Nichols and Westboro Reservoirs are also nearby. Westborough is located along the eastern edge of the Appalachian Mountains, providing residents with stunning views and access to hiking trails. The geography of Westborough makes it a great location for outdoor enthusiasts, offering a range of recreational activities throughout the year. The town’s natural beauty and varied terrain also make it an excellent place for nature lovers to call home.

Recreation, Shopping, and Entertainment 

Westborough offers a wide range of recreational activities, cultural events, shopping, and entertainment options for 55+ homebuyers living in the area. Below are some of the many attractions active adults can explore and enjoy in and around town.

Golf and Racquet Sports

  • Westborough Country Club
  • Juniper Hill Golf Course
  • Westboro Tennis and Swim Club
  • Pickleball courts at Haskell Field

Hiking, Biking, and Boating

  • Chauncy Lake and Beach
  • Tall Grass Trail
  • Westborough Reservoir Loop
  • George H. Nichols Reservoir

Museums and Historical Sites

  • Westborough Historical Society
  • Willard House and Clock Museum
  • New England Botanic Garden at Tower Hill
  • EcoTarium Museum of Science and Nature

Performing Arts

  • Westborough Players’ Club
  • Donald F. Flanagan Theater
  • Performing Arts Center of MetroWest
  • Fenwick Theatre


  • Westborough Shopping Center
  • DownTown Crossing
  • Northborough Crossing


  • Veterans’ Freedom Park
  • Lake Chauncy Public Beach and Park
  • Whitehall State Park
  • Upton State Forest

Festivals and Fairs

  • Westborough Rotary Spring Festival
  • Westborough Farmers Market
  • Arts In Common
  • Westborough Community Band Concerts

Health and Wellness

Westborough, MA is conveniently located near several major medical centers and hospitals, including UMass Memorial Medical Center in Worcester, which offers a variety of services, including primary care, outpatient specialty care, and inpatient care. Additionally, Saint Vincent Hospital, also located in Worcester, provides a wide range of medical services, including emergency care, cancer treatment, and orthopedic surgery.

For those interested in keeping fit, Westborough offers several local options. The Westborough Public Library provides a range of health and wellness resources, including books, magazines, and online resources. The Westborough Senior Center offers a variety of fitness programs, and there are also several local fitness centers, including Planet Fitness, the MetroWest Yoga Studio and Training Center, and the Westboro Tennis and Swim Club.

Recommended Itinerary for Visiting Area 55+ Communities

Day One


  • Start the day with breakfast at South Street Diner, a cozy local restaurant serving delicious breakfast sandwiches, omelets, benedicts, and coffee.
  • Visit the Westborough Historical Society Museum to learn about the history of the town and its significance in the American Revolution.
  • Take a walk or bike ride around the scenic Westborough Reservoir and enjoy the beautiful natural surroundings.


  • Have lunch at Arturo’s Ristorante, an Italian restaurant known for its fresh pasta dishes and brick oven pizza.
  • Head to the Wayne F. MacCallum Wildlife Management Area, a designated greenspace west of Chauncy Lake.


  • Dine at Ted’s Montana Grill, a steakhouse known for its bison burgers and chops.
  • Take a stroll around the town square, stopping in at various shops along the way.

Day Two


  • Enjoy breakfast at Harry’s Restaurant on Turnpike Road, where locals enjoy hearty breakfast dishes and coffee.
  • Meet with the local 55places expert to discuss 55+ community options in the area.


  • Enjoy lunch at Tavolino, an Italian restaurant with a lively atmosphere and delicious food.
  • Take a walk through a portion of the 28-mile Westborough Charm Bracelet Trail System, which connects many of the area’s open spaces and neighborhoods.


  • Have dinner at Westborough Korean Restaurant, which serves Korean barbecue and various traditional Korean dishes.
  • End the day with a drink at Central House Tavern, a bar and grill with an extensive selection of wine, beer, and spirits.

Recommended places to stay:

Getting to Westborough, MA

Westborough, MA is conveniently located near major highways, making it easily accessible by car. Visitors driving from Boston can take I-90 (also known as the Massachusetts Turnpike) and folks traveling from the north can take I-495. 

The closest major airport is Boston Logan International Airport (BOS), which is approximately 36 miles east of Westborough. Boston Logan is a hub for several airlines, including Delta, JetBlue, and American Airlines, making it easy to find direct flights from major cities across the country. From the airport, visitors can rent a car, take a taxi, or use public transportation to get to Westborough.

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