Holliston, MA 55+ Active Adult Retirement Communities

Holliston, MA is a charming New England town located in Middlesex County, just 25 miles west of Boston. It is a great place for those looking for an 55+ active adult community due to its quaint downtown area, scenic beauty, and community-focused atmosphere. Holliston is surrounded by beautiful parks and natural areas, has many historical sites, and a growing arts community. 

Holliston, MA is a charming New England town located in Middlesex County, just 25 miles west of Boston. It is a great place for those looking for an 55+ active adult community due to its quaint downtown area, scenic beauty, and community-focused atmosphere. Holliston is surrounded by beautiful parks and natural areas, has many historical sites, and a growing arts community. 

If you are considering a move to Holliston, MA, be sure to check out the following local resources: Holliston's official website provides information on town services and events while the Holliston Patch provides local news about the town and surrounding areas. In addition the Holliston Public Library offers a variety of programs and resources for residents.

The cost of living in Holliston is slightly higher than the national average, with the overall cost of living index at 138.2 compared to the national average of 100. Housing is the biggest contributor to the high cost of living in Holliston. The median home price in Holliston is around $613,100, which is significantly higher than the national median home price of $338,100. The cost of groceries and transportation is also higher than the national average although healthcare costs are lower than both the state and national averages. Holliston is in Middlesex County where average property taxes are high at 1.04 percent. There are some tax credits available to senior or low income homeowners.

Massachusetts has a state income tax of a flat 5 percent although taxable income over $1 million is subject to an additional 4 percent. Social Security and government pensions are not taxed but all other forms of retirement income are taxed. Massachusetts does have estate tax but no inheritance taxes. Sales tax is 6.25 percent. 

Climate and Geography 

Holliston has a humid continental climate with four distinct seasons. The summers are warm and humid, with temperatures averaging around 80 degrees during the day and 60 degrees at night. Snowfall is common in winter, with daytime temperatures ranging from 15 degrees to 30 degrees. The spring and fall seasons are transitional seasons with mild temperatures and occasional precipitation.

The town is located in the MetroWest region of Massachusetts and is surrounded by rolling hills, forests, and a number of lakes. Hopkinton State Park borders the town on the eastern edge, and there are several conservation areas and green spaces, such as Holliston Meadows State Park, known for its picturesque Charles River views. With its easy access to rural and urban areas, Holliston is a perfect place for those who enjoy outdoor activities and natural beauty. Several major highways are close to the town, making it easy to travel to other parts of the state, such as Boston, Worcester, and Providence.

Recreation, Shopping, and Entertainment 

With its picturesque scenery and rich history, Holliston offers an array of recreational activities, cultural events, shopping, and entertainment options. Here are some of the top things to do and places to visit in Holliston:

Golf and Racquet Sports

  • Pinecrest Golf Club
  • Holliston Tennis Club
  • Patoma Park Pickleball Courts
  • Weston Racquet Club

Hiking, Biking, and Boating

  • Holliston Rail Trail
  • Lake Winthrop
  • Upper Charles Trail
  • Holliston Conservation Land

Museums and Historical Sites

  • Historical Society of Holliston Museum
  • Placentino-Millmore House
  • Casey-Boylston House
  • Mary Brooke Casadonte Education Center and Archives

Performing Arts

  • Holliston Community Theatre
  • Prana Center
  • New England Symphony Orchestra
  • Holliston Summer Concert Series


  • Holliston Superette
  • Outpost Farm
  • Fiske's General Store
  • The Cottage

Parks and Gardens

  • Goodwill Park
  • Wenakeening Woods
  • Stoddard Park
  • Holliston Community Garden

Festivals and Fairs

  • Newcomers Club's Annual Craft Fair
  • Historical Society's Harvest Fair
  • Lions Club's Agricultural Fair
  • Celebrate Holliston

Whether you are looking to golf, bike, or simply relax in a beautiful park, there is something for everyone in this charming town.

Health and Wellness 

Holliston has a variety of resources to support and promote healthy living. The Holliston Parks and Recreation Department offers fitness classes and activities, such as yoga, Pilates, and Zumba. For those looking to improve or maintain cognitive and mental health, the Holliston Public Library offers various resources, including book clubs, mindfulness workshops, and stress management classes. Holliston's farmers market provides fresh organic produce for those looking to improve health through nutrition.

The town is also located near several major medical centers such as Beth Israel Deaconess Medical Center and Massachusetts General Hospital, both located in Boston. These hospitals provide world class medical care and are just a short drive from Holliston.

Recommended Itinerary for Visiting Holliston 55+ Communities

Day One


Grab breakfast at Coffee Haven, a cozy cafe in the heart of downtown Holliston known for their delicious coffee and pastries.

Head over to Stoddard Park, a beautiful public park situated on Lake Winthrop. Take a walk around the lake, enjoy the views, and perhaps even rent a kayak or paddleboard for a fun activity on the water.

Visit the Holliston Historical Society Museum to learn about the town's rich history and see artifacts from the past.


Grab lunch at Anthony's on the Green, a popular restaurant located at Pinecrest Golf Club, known for their delicious sandwiches, salads, and burgers.

Take a stroll through the Holliston Upper Charles Rail Trail, a scenic trail that runs through town and is perfect for a leisurely walk or bike ride.


Have dinner at Casey's Pub, a local favorite that offers a large variety of chicken wing flavors, burgers, and craft beers.

Catch a show at the Prana Center, a community theater that hosts a variety of performances throughout the year.

Day Two


Start the day with breakfast at The Holliston Grill, a casual restaurant known for their hearty breakfast plates and delicious pancakes.

Meet with a local 55places expert retirement community partner agent to learn more about retirement communities in the area. Take tours of communities of interest and see what amenities and activities are offered.


Grab lunch at The Corner Market, a cozy restaurant that serves a variety of sandwiches, salads, and pizza.

Visit the Holliston Town Forest, a scenic park with hiking trails and a beautiful pond.


Have dinner at T.C. Lando's, a local restaurant that offers a variety of Italian and American cuisine.

Getting to Holliston, MA

Holliston is located in eastern Massachusetts, approximately 30 miles southwest of Boston. The most convenient ways to get there are by car or plane.


Holliston can be easily reached by car via major highways. If coming from the north or south, take I-95/Route 128 and then take the exit for Route 16 west towards Holliston. If coming from the east or west, take the Massachusetts Turnpike (I-90) and then take exit 12 towards Route 9 east. Follow Route 9 east until you reach Route 126 and then take Route 126 south towards Holliston.


The nearest major airport is Boston Logan International Airport (BOS), which is approximately 30 miles east of Holliston. Many major airlines operate flights to Boston Logan, including American Airlines, Delta Air Lines, United Airlines, and JetBlue Airways. The airport has four terminals and is a hub for Delta Air Lines and JetBlue Airways. 

Communities Near Holliston

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3 communities near Holliston

0 Homes for Sale

Holliston Woods - Holliston, MA

Holliston Woods

For Sale
  • High $500ks - Low $700ks
  • 66 Homes
  • 55+ Age Restriction
  • Resale Homes Only
  • 2016 - 2018
  • No Reviews
Brooksmont - Holliston, MA


For Sale
  • High $400ks - Mid $600ks
  • 66 Homes
  • 55+ Age Restriction
  • Resale Homes Only
  • 2017 - 2020
  • No Reviews

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Balancing Rock

For Sale
  • Low $500ks - Mid $600ks
  • 49 Homes
  • 55+ Age Restriction
  • Resale Homes Only
  • 2006 - 2008
  • No Reviews

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