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Westborough, MA 55+ active adult communities & homes for sale

Living in Westborough

Westborough, MA is a picturesque New England town with a charming town square as well as numerous nearby outdoor recreational opportunities. The town is situated in a beautiful…

Westborough, MA is a picturesque New England town with a charming town square as well as numerous nearby outdoor recreational opportunities. The town is 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 55+ 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, as well as 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.

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. Additionally the state has an estate tax, however there is 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, therefore 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 are undoubtedly 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.

Westborough 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. On the other hand 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. Moreover, 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 in the

Westborough Area

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

Shopping

  • Westborough Shopping Center
  • DownTown Crossing
  • Northborough Crossing

Parks

  • 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 in Westborough

Westborough 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. Additionally there are 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

Westborough 55+ Communities

Day One

Morning:

  • 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.

Afternoon:

  • 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.

Evening:

  • 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

Morning:

  • 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 and tour 55+ community options in the area.

Afternoon:

  • 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.

Evening:

  • 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

Westborough 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.

Frequently Asked Questions


25 communities near Westborough

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Del Webb Chauncy Lake
$400ks - $600ks
Del Webb Chauncy Lake, Westborough, MA
New Construction | 55+ age-restricted | Built 2018 - present | 700 homes
Brierly Pond Village
$300ks - $400ks
Brierly Pond Village, Millbury, MA
Resale Only | 55+ age-restricted | Built 2003 - 2013 | 199 homes
Upton Ridge
$400ks - $600ks
Upton Ridge, Upton, MA
New Construction | 55+ age-restricted | Built 2019 - present | 139 homes
The Trails
$500ks - $700ks
The Trails, Hopkinton, MA
New Construction | 55+ age-restricted | Built 2017 - present | 170 homes
The Village at Orchard Me...
$400ks - $500ks
The Village at Orchard Me..., Shrewsbury, MA
Resale Only | 55+ age-restricted | Built 2002 - 2007 | 114 homes
Want to learn more about 55+ communities in Westborough? 55places can help!
Questions? Call us: (774) 512-3099
Bigelow Farm
$500ks - $600ks
Bigelow Farm, Northborough, MA
Resale Only | 55+ age-restricted | Built 2006 - 2013 | 41 homes
WestRidge
$700ks
WestRidge, Hudson, MA
Resale Only | 55+ age-restricted | Built 2009 - 2016 | 136 homes
Enclave at Hudson
$800ks - $1Ms
Enclave at Hudson, Hudson, MA
New Construction | 55+ age-restricted | Built 2021 - present | 64 homes
Regency at Assabet Ridge
$500ks - $600ks
Regency at Assabet Ridge, Marlborough, MA
Resale Only | 55+ age-restricted | Built 2010 - 2015 | 69 homes
Orchard Hill
$500ks
Orchard Hill, Westborough, MA
Resale Only | 55+ age-restricted | Built 2002 - 2010 | 100 homes
Download the Ultimate 55+ Homebuying Guide Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.
The Villages at Walker Me...
$600ks - $700ks
The Villages at Walker Me..., Westborough, MA
Resale Only | 55+ age-restricted | Built 1999 - 2000 | 100 homes
Northside Meadows
$600ks - $700ks
Northside Meadows, Framingham, MA
Resale Only | 55+ age-restricted | Built 2017 - 2019 | 60 homes
Brooksmont
$400ks - $600ks
Brooksmont, Holliston, MA
Resale Only | 55+ age-restricted | Built 2017 - 2020 | 66 homes
Forest Glen
$400ks - $500ks
Forest Glen, Uxbridge, MA
New Construction | 55+ age-restricted | Built 2018 - present | 44 homes
Pheasant Hill
$300ks - $400ks
Pheasant Hill, Northborough, MA
Resale Only | 55+ age-restricted | Built 2005 - 2006 | 48 homes
Blue Heron Pond
$500ks
Blue Heron Pond, Lancaster, MA
Resale Only | 55+ age-restricted | Built 2006 - 2014 | 58 homes
Want to learn more about 55+ communities in Westborough? 55places can help!
Questions? Call us: (774) 512-3099
Adams Farm
$700ks - $800ks
Adams Farm, Shrewsbury, MA
Resale Only | 55+ age-restricted | Built 2005 - 2013 | 90 homes
Wyman Farms
$500ks - $900ks
Wyman Farms, Shrewsbury, MA
New Construction | 55+ age-restricted | Built 2017 - present | 26 homes
Angell Brook Village
$300ks
Angell Brook Village, West Boylston, MA
Resale Only | 55+ age-restricted | Built 2005 - 2012 | 132 homes
Holliston Woods
$500ks - $700ks
Holliston Woods, Holliston, MA
Resale Only | 55+ age-restricted | Built 2016 - 2018 | 66 homes
Download the Ultimate 55+ Homebuying Guide Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.
The Villages at Crane Mea...
$400ks
The Villages at Crane Mea..., Marlborough, MA
Resale Only | 55+ age-restricted | Built 2001 - 2005 | 91 homes
Balancing Rock
$500ks - $600ks
Balancing Rock, Holliston, MA
Resale Only | 55+ age-restricted | Built 2006 - 2008 | 49 homes
Rockwood Meadows
$600ks - $700ks
Rockwood Meadows, Upton, MA
New Construction | 55+ age-restricted | Built 2016 - present | 58 homes
The Lanterns at Warren Wo...
$500ks - $700ks
The Lanterns at Warren Wo..., Ashland, MA
Resale Only | 55+ age-restricted | Built 2016 - 2020 | 93 homes
Millwood Preserve
$1Ms
Millwood Preserve, Framingham, MA
Resale Only | 55+ age-restricted | Built 2020 - 2024 | 129 homes
New WestRidge 33 HASTINGS 33, HUDSON, MA, 01749, Hudson, MA 01749
$599,999

2 beds

|

3 baths

|

1,758 sq ft

|

Condo

33 HASTINGS 33, HUDSON, MA, 01749
Community: WestRidge
New Enclave at Hudson 38 BARNES BLVD 23, HUDSON, MA, 01749, Hudson, MA 01749
$1,125,000

2 beds

|

3 baths

|

2,544 sq ft

|

Condo

38 BARNES BLVD 23, HUDSON, MA, 01749
Community: Enclave at Hudson
New Bigelow Farm 5 LYDIA'S WAY 5, NORTHBOROUGH, MA, 01532, Northborough, MA 01532
$799,900

2 beds

|

3 baths

|

2,556 sq ft

|

Condo

5 LYDIA'S WAY 5, NORTHBOROUGH, MA, 01532
Community: Bigelow Farm
New Del Webb Chauncy Lake 3 PETERS FARM WAY 107, WESTBOROUGH, MA, ..., Westborough, MA 01581
$560,000

2 beds

|

2 baths

|

1,469 sq ft

|

Condo

3 PETERS FARM WAY 107, WESTBOROUGH, MA, ...
New The Trails 38 WESTON LN 38, HOPKINTON, MA, 01748, Hopkinton, MA 01748
$999,900

2 beds

|

3 baths

|

2,274 sq ft

|

Condo

38 WESTON LN 38, HOPKINTON, MA, 01748
Community: The Trails
Want to learn more about 55+ communities in Westborough? 55places can help!
Questions? Call us: (774) 512-3099
The Trails 10 WATERVILLE LN 10, HOPKINTON, MA, 0174..., Hopkinton, MA 01748
$999,900

2 beds

|

3 baths

|

2,274 sq ft

|

Condo

10 WATERVILLE LN 10, HOPKINTON, MA, 0174...
Community: The Trails
Del Webb Chauncy Lake 8310 PETERS FARM WAY 310, WESTBOROUGH, M..., Westborough, MA 01581
$564,995

2 beds

|

2 baths

|

1,375 sq ft

|

Condo

8310 PETERS FARM WAY 310, WESTBOROUGH, M...
The Village at Orchard Meadows 4 BLOSSOM TREE DR 4, SHREWSBURY, MA, 015..., Shrewsbury, MA 01545
$599,900

2 beds

|

2 baths

|

1,580 sq ft

|

Condo

4 BLOSSOM TREE DR 4, SHREWSBURY, MA, 015...
Brierly Pond Village 22 HORNE WAY 22, MILLBURY, MA, 01527, Millbury, MA 01527
$459,900

2 beds

|

2 baths

|

1,746 sq ft

|

Condo

22 HORNE WAY 22, MILLBURY, MA, 01527
The Lanterns at Warren Woods 20 FERN XING 20, ASHLAND, MA, 01721, Ashland, MA 01721
$850,000

2 beds

|

3 baths

|

2,290 sq ft

|

Condo

20 FERN XING 20, ASHLAND, MA, 01721
Download the Ultimate 55+ Homebuying Guide Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.
Regency at Assabet Ridge 23 AVEBURY LN 23, MARLBOROUGH, MA, 01752, Marlborough, MA 01752
$800,000

4 beds

|

4 baths

|

3,561 sq ft

|

Condo

23 AVEBURY LN 23, MARLBOROUGH, MA, 01752
Upton Ridge 16 LINKSIDE CT 16, NORTHBRIDGE, MA, 0153..., Northbridge, MA 01534
$649,900

2 beds

|

3 baths

|

2,030 sq ft

|

Condo

16 LINKSIDE CT 16, NORTHBRIDGE, MA, 0153...
Community: Upton Ridge
Del Webb Chauncy Lake 4 PETERS FARM WAY 409, WESTBOROUGH, MA, ..., Westborough, MA 01581
$539,900

2 beds

|

2 baths

|

1,326 sq ft

|

Condo

4 PETERS FARM WAY 409, WESTBOROUGH, MA, ...
Del Webb Chauncy Lake 5 PETERS FARM WAY 7405, WESTBOROUGH, MA,..., Westborough, MA 01581
$539,995

2 beds

|

2 baths

|

1,166 sq ft

|

Condo

5 PETERS FARM WAY 7405, WESTBOROUGH, MA,...
Brierly Pond Village 97 HORNE WAY 97, MILLBURY, MA, 01527, Millbury, MA 01527
$450,000

2 beds

|

3 baths

|

1,746 sq ft

|

Condo

97 HORNE WAY 97, MILLBURY, MA, 01527
Del Webb Chauncy Lake 8113 PETERS FARM WAY 113, WESTBOROUGH, M..., Westborough, MA 01581
$639,995

2 beds

|

2 baths

|

1,512 sq ft

|

Condo

8113 PETERS FARM WAY 113, WESTBOROUGH, M...
Want to learn more about 55+ communities in Westborough? 55places can help!
Questions? Call us: (774) 512-3099
Del Webb Chauncy Lake 8103 PETERS FARM WAY 103, WESTBOROUGH, M..., Westborough, MA 01581
$414,995

1 beds

|

2 baths

|

972 sq ft

|

Condo

8103 PETERS FARM WAY 103, WESTBOROUGH, M...
Upton Ridge 126 CLUBHOUSE LN 126, NORTHBRIDGE, MA, 0..., Northbridge, MA 01534
$639,000

3 beds

|

3 baths

|

2,130 sq ft

|

Condo

126 CLUBHOUSE LN 126, NORTHBRIDGE, MA, 0...
Community: Upton Ridge
The Trails 30 WATERVILLE LN 30, HOPKINTON, MA, 0174..., Hopkinton, MA 01748
$1,069,900

2 beds

|

3 baths

|

2,510 sq ft

|

Condo

30 WATERVILLE LN 30, HOPKINTON, MA, 0174...
Community: The Trails
Del Webb Chauncy Lake 8106 PETERS FARM WAY 106, WESTBOROUGH, M..., Westborough, MA 01581
$619,995

2 beds

|

2 baths

|

1,496 sq ft

|

Condo

8106 PETERS FARM WAY 106, WESTBOROUGH, M...
Download the Ultimate 55+ Homebuying Guide Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.
Del Webb Chauncy Lake 8108 PETERS FARM WAY 108, WESTBOROUGH, M..., Westborough, MA 01581
$469,995

1 beds

|

2 baths

|

1,058 sq ft

|

Condo

8108 PETERS FARM WAY 108, WESTBOROUGH, M...
Del Webb Chauncy Lake 8 PETERS FARM WAY 105, WESTBOROUGH, MA, ..., Westborough, MA 01581
$449,995

1 beds

|

2 baths

|

958 sq ft

|

Condo

8 PETERS FARM WAY 105, WESTBOROUGH, MA, ...
Del Webb Chauncy Lake 1213 CODMAN WAY 1213, WESTBOROUGH, MA, 0..., Westborough, MA 01581
$569,900

2 beds

|

2 baths

|

1,512 sq ft

|

Condo

1213 CODMAN WAY 1213, WESTBOROUGH, MA, 0...
Brierly Pond Village 37 HORNE WAY 37, MILLBURY, MA, 01527, Millbury, MA 01527
$450,000

2 beds

|

3 baths

|

1,746 sq ft

|

Condo

37 HORNE WAY 37, MILLBURY, MA, 01527
The Villages at Walker Meadow 14 WESSONVILLE VILLAGE WAY 14, WESTBOROU..., Westborough, MA 01581
$650,000

2 beds

|

2 baths

|

2,090 sq ft

|

Condo

14 WESSONVILLE VILLAGE WAY 14, WESTBOROU...
Northside Meadows 11 TOLLAND WAY 11, FRAMINGHAM, MA, 01701, Framingham, MA 01701
$1,195,000

2 beds

|

3 baths

|

2,607 sq ft

|

Condo

11 TOLLAND WAY 11, FRAMINGHAM, MA, 01701
Community: Northside Meadows
The Village at Orchard Meadows 79 ORCHARD MEADOWS DR 79, SHREWSBURY, MA..., Shrewsbury, MA 01545
$534,900

2 beds

|

2 baths

|

1,370 sq ft

|

Condo

79 ORCHARD MEADOWS DR 79, SHREWSBURY, MA...
Want to learn more about 55+ communities in Westborough? 55places can help!
Questions? Call us: (774) 512-3099
Upton Ridge 56 SHANNON WAY 56, UPTON, MA, 01568, Upton, MA 01568
$669,000

2 beds

|

3 baths

|

1,950 sq ft

|

Condo

56 SHANNON WAY 56, UPTON, MA, 01568
Community: Upton Ridge
Orchard Hill 19 IMPERIAL CT 19, WESTBOROUGH, MA, 0158..., Westborough, MA 01581
$579,000

2 beds

|

3 baths

|

2,183 sq ft

|

Condo

19 IMPERIAL CT 19, WESTBOROUGH, MA, 0158...
Community: Orchard Hill
Del Webb Chauncy Lake 3202 PETERS FARM WAY 202, WESTBOROUGH, M..., Westborough, MA 01581
$425,000

1 beds

|

1 baths

|

956 sq ft

|

Condo

3202 PETERS FARM WAY 202, WESTBOROUGH, M...
Download the Ultimate 55+ Homebuying Guide Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.
The Trails 9 WATERVILLE LN 9, HOPKINTON, MA, 01748, Hopkinton, MA 01748
$999,900

2 beds

|

3 baths

|

2,274 sq ft

|

Condo

9 WATERVILLE LN 9, HOPKINTON, MA, 01748
Community: The Trails
Del Webb Chauncy Lake 3405 PETERS FARM WAY 3405, WESTBOROUGH, ..., Westborough, MA 01581
$523,500

2 beds

|

2 baths

|

1,121 sq ft

|

Condo

3405 PETERS FARM WAY 3405, WESTBOROUGH, ...
The Village at Orchard Meadows 70 ORCHARD MEADOW DR 70, SHREWSBURY, MA,..., Shrewsbury, MA 01545
$648,900

2 beds

|

3 baths

|

1,896 sq ft

|

Condo

70 ORCHARD MEADOW DR 70, SHREWSBURY, MA,...
Del Webb Chauncy Lake 4 PETERS FARM WAY 311, WESTBOROUGH, MA, ..., Westborough, MA 01581
$549,000

2 beds

|

2 baths

|

1,326 sq ft

|

Condo

4 PETERS FARM WAY 311, WESTBOROUGH, MA, ...
Upton Ridge 87 SHANNON WAY 86, UPTON, MA, 01568, Upton, MA 01568
$699,900

2 beds

|

3 baths

|

1,950 sq ft

|

Condo

87 SHANNON WAY 86, UPTON, MA, 01568
Community: Upton Ridge
Del Webb Chauncy Lake 12101 PETERS FARM WAY 12101, WESTBOROUGH..., Westborough, MA 01712
$574,444

2 beds

|

2 baths

|

1,459 sq ft

|

Condo

12101 PETERS FARM WAY 12101, WESTBOROUGH...
Del Webb Chauncy Lake 11 PETERS FARM WAY 310, WESTBOROUGH, MA,..., Westborough, MA 01581
$519,900

2 beds

|

2 baths

|

1,326 sq ft

|

Condo

11 PETERS FARM WAY 310, WESTBOROUGH, MA,...
Brierly Pond Village 6 ASHTON LN 6, MILLBURY, MA, 01527, Millbury, MA 01527
$512,900

2 beds

|

4 baths

|

2,256 sq ft

|

Condo

6 ASHTON LN 6, MILLBURY, MA, 01527
Want to learn more about 55+ communities in Westborough? 55places can help!
Questions? Call us: (774) 512-3099
Del Webb Chauncy Lake 4 PETERS FARM WAY 206, WESTBOROUGH, MA, ..., Westborough, MA 01581
$549,000

2 beds

|

2 baths

|

1,469 sq ft

|

Condo

4 PETERS FARM WAY 206, WESTBOROUGH, MA, ...
Del Webb Chauncy Lake 12308 PETERS FARM WAY 308, WESTBOROUGH, ..., Westborough, MA 01581
$525,000

2 beds

|

2 baths

|

1,326 sq ft

|

Condo

12308 PETERS FARM WAY 308, WESTBOROUGH, ...
Download the Ultimate 55+ Homebuying Guide Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.

Frequently Asked Questions


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