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Upton, MA 55+ active adult communities & homes for sale - Page 2

Living in Upton

Located about 30 miles southeast of Boston, Upton provides peaceful small town living while still being within easy reach of large city amenities. Upton is a beautiful area which…

Located about 30 miles southeast of Boston, Upton provides peaceful small town living while still being within easy reach of large city amenities. Upton is a beautiful area which includes several picturesque lakes and forests that are perfect for outdoor enthusiasts. The town's quaint downtown area is filled with unique shops, restaurants, and cafes. With a population of just under 8,000 Upton is known for its close-knit friendly community. 

Affordability and Cost of Living 

Compared to some other areas on the east coast Upton is less expensive but its cost of living is still 35 percent higher than the national average. Much of the higher cost of living is due to housing costs which are almost double that of the national average. Healthcare costs are a little lower than average. However, groceries, utilities, and transportation costs are between 5 and 15 percent higher than the national average. Property taxes in Upton are high, the average property tax in Worcester County where Upton is located is 1.1 percent of fair market value. There are no county or city sales taxes but the state sales tax for Massachusetts is 6.25 percent.

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 exempt but all other forms of retirement income are subject to tax. Massachusetts does have estate tax but no inheritance taxes.

Climate and Geography 

The Upton area sees about 50 inches of rain per year, much of it falling during the months of May and June. Average winter temperatures range from 20 to 35 degrees. Summer in Upton is warm and humid with summer temperatures averaging between 60 and 80 degrees with 70 percent humidity. Average snowfall in Upton is 51 inches with the highest chance of snow during the month of February. 

Upton's scenery is characterized by its rolling hills, forests, and lakes. Upton State Forest is a popular destination for hikers, mountain bikers, and birdwatchers, boasting over 2,600 acres of trails, streams, and lakes. Lake Wildwood, located in the northeast corner of the town, provides a great spot for fishing, swimming, and boating. The town also has a number of conservation areas, such as Warren Brook and Whitehall State Park, which offer stunning views of the area's natural landscape and wildlife.

Recreation, Shopping, and Entertainment 

Upton, MA offers a wide range of recreational activities, cultural events, shopping, and entertainment options for visitors and residents alike. From hiking and biking to museums and historical sites, there is something for everyone to enjoy in this charming town.

Golf and Racquet Sports

  • Blissful Meadows Golf Club
  • Hopedale Country Club
  • Pickleball courts at Kiwanis Beach and Memorial Park
  • Tennis courts at Kiwanis Beach

Hiking, Biking and Boating

  • Upton State Forest
  • Warren Brook Watershed Conservation Area
  • West Hill Dam and Recreation Area
  • Lake Wildwood

Museums and Historical Sites

  • Nipmuc Indian Museum
  • Grafton and Upton Railroad Depot
  • Upton Historical Society

Performing Arts

  • Encore Theater Company
  • Hopkinton Center for the Arts
  • Alternatives Whitin Mill

Parks and Gardens

  • Blackstone River and Canal Heritage State Park
  • Southwick's Zoo
  • Tower Hill Botanic Garden
  • Whitehall State Park

Festivals and Fairs

  • Upton Annual Harvest Fair
  • Grafton Celebrates the Holidays
  • Upton Summerfest
  • Westborough Spring Festival

Health and Wellness 

Upton is conveniently located near several major medical centers, including UMass Memorial Medical Center in Worcester, Milford Regional Medical Center, and Marlborough Hospital. These centers offer a range of specialized services and advanced treatments for various medical conditions. 

There are several local options for self-care, including spas, and fitness centers, where residents can take advantage of various wellness services, such as massages and personal training. The Westborough Tennis and Swim Club is located just a short drive from Upton and offers a range of fitness classes, including yoga, Pilates, and Zumba, as well as swimming and tennis facilities. The YMCA of Central Massachusetts, which has several locations in the area also offers various fitness classes, swimming, and wellness programs. 

Recommended Itinerary for Visiting Area 55+ Communities

If you are considering retiring to Upton, MA, it's a good idea to visit the area to get a sense of what it's like to live there. Here's a suggested itinerary to help you make the most of a two day trip:

Day One

Morning:

  • Start your day with breakfast at the famous Dunkin, which serves delicious donuts, breakfast sandwiches, and coffee.
  • After breakfast, head to the beautiful Upton State Forest for a morning hike or walk. With over 2,500 acres of forest, trails, and ponds, this is a great place to enjoy nature and get some exercise.

Afternoon:

  • For lunch, head to Red Rock Grill & Bar for a tasty sandwich or wrap and a cold drink.
  • In the afternoon, take a scenic drive to Southwick's Zoo, one of the top-rated zoos in New England, featuring over 115 animal species from around the world.

Evening:

  • For dinner, enjoy the cozy and welcoming atmosphere of Galliford's Restaurant and Tavern, which serves delicious American cuisine and offers a variety of beers on tap.

Day Two

Morning:

  • Start your day with breakfast at Breakfast at Stephanies, a popular local spot for pancakes, omelets, and coffee.
  • Meet with your local 55places expert retirement community partner agent to learn more about the area's retirement communities and available properties.

Afternoon:

Evening:

  • End your day with dinner at the beautiful and romantic Rustic Kitchen, which serves delicious Italian cuisine and has a great wine list.

Getting to Upton, MA

Upton is conveniently located near several major highways, making it easily accessible by car. Visitors driving from Boston can take the Massachusetts Turnpike (I-90) west to I-495 south, which will bring them to Upton. From the north, visitors can take I-495 south to exit 21, and from the south, they can take I-495 north to exit 21A.

For those traveling by air, the closest major airport is Boston Logan International Airport, located approximately 45 miles east of Upton. Many major airlines fly into Boston Logan, including American, Delta, United, JetBlue, and Southwest. From the airport, visitors can rent a car or take a taxi or rideshare service to Upton.

Additionally, visitors can take the commuter rail from Boston to nearby towns, such as Grafton or Worcester, and then take a taxi or rideshare service to Upton. The closest Amtrak station is in Worcester, which is approximately 20 miles south of Upton. For visitors arriving by bus, several regional and national bus companies, including Greyhound and Peter Pan, provide service to Worcester.

 

Frequently Asked Questions


41 communities near Upton

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Want to learn more about 55+ communities in Upton? 55places can help!
Questions? Call us: (508) 603-7097
The Villages at Crane Mea...
$400ks
The Villages at Crane Mea..., Marlborough, MA
Resale Only | 55+ age-restricted | Built 2001 - 2005 | 91 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.
New Regency at Glen Ellen 29 HENRY WAY 29, MILLIS, MA, 02054, Millis, MA 02054
$899,000

2 beds

|

3 baths

|

2,432 sq ft

|

Condo

29 HENRY WAY 29, MILLIS, MA, 02054
New The Village at Westminster Place 9 SETTLERS LN 583, HOLDEN, MA, 01520, Holden, MA 01520
$649,000

3 beds

|

3 baths

|

1,877 sq ft

|

Condo

9 SETTLERS LN 583, HOLDEN, MA, 01520
New 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...
New Del Webb Chauncy Lake 8 PETERS FARM WAY 206, WESTBOROUGH, MA, ..., Westborough, MA 01581
$654,995

2 beds

|

2 baths

|

1,496 sq ft

|

Condo

8 PETERS FARM WAY 206, WESTBOROUGH, MA, ...
New Bates Quarry 11 BATES QUARRY LN 48, WALPOLE, MA, 0208..., Walpole, MA 02081
$922,995

2 beds

|

2 baths

|

1,501 sq ft

|

House

11 BATES QUARRY LN 48, WALPOLE, MA, 0208...
Community: Bates Quarry
Want to learn more about 55+ communities in Upton? 55places can help!
Questions? Call us: (508) 603-7097
New 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
New Harmony Place 136 FIDELITY DR 6, RUTLAND, MA, 01543, Rutland, MA 01543
$550,000

2 beds

|

2 baths

|

1,582 sq ft

|

Condo

136 FIDELITY DR 6, RUTLAND, MA, 01543
Community: Harmony Place
Garrison Place 13 GARRISON WAY 13, CARLISLE, MA, 01741, Carlisle, MA 01741
$1,098,000

2 beds

|

3 baths

|

2,385 sq ft

|

House

13 GARRISON WAY 13, CARLISLE, MA, 01741
Community: Garrison Place
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
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
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.
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
$559,995

2 beds

|

2 baths

|

1,166 sq ft

|

Condo

5 PETERS FARM WAY 7405, WESTBOROUGH, MA,...
Del Webb Chauncy Lake 5305 PETERS FARM WAY 7305, WESTBOROUGH, ..., Westborough, MA 01581
$529,995

2 beds

|

2 baths

|

1,166 sq ft

|

Condo

5305 PETERS FARM WAY 7305, WESTBOROUGH, ...
Pennington Crossing 1102 PENNINGTON DR 1102, WALPOLE, MA, 02..., Walpole, MA 02081
$529,900

1 beds

|

1 baths

|

955 sq ft

|

Condo

1102 PENNINGTON DR 1102, WALPOLE, MA, 02...
Community: Pennington Crossing
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
Want to learn more about 55+ communities in Upton? 55places can help!
Questions? Call us: (508) 603-7097
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...
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...
Bates Quarry 16 TIGER TER 29, WALPOLE, MA, 02081, Walpole, MA 02081
$948,999

2 beds

|

2 baths

|

2,509 sq ft

|

Condo

16 TIGER TER 29, WALPOLE, MA, 02081
Community: Bates Quarry
Cindy Certified
12 TIGER TER 28, WALPOLE, MA, 02081, Walpole, MA 02081
$863,999

2 beds

|

2 baths

|

1,501 sq ft

|

Condo

12 TIGER TER 28, WALPOLE, MA, 02081
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.
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
Garrison Place 1 GARRISON WAY 1, CARLISLE, MA, 01741, Carlisle, MA 01741
$1,138,000

2 beds

|

4 baths

|

3,230 sq ft

|

Condo

1 GARRISON WAY 1, CARLISLE, MA, 01741
Community: Garrison Place
Woodcrest Run 635 OLD POST RD 109, SHARON, MA, 02067, Sharon, MA 02067
$479,900

2 beds

|

2 baths

|

1,056 sq ft

|

Condo

635 OLD POST RD 109, SHARON, MA, 02067
Community: Woodcrest Run
Woodcrest Run 635 OLD POST RD 302, SHARON, MA, 02067, Sharon, MA 02067
$489,900

2 beds

|

2 baths

|

1,187 sq ft

|

Condo

635 OLD POST RD 302, SHARON, MA, 02067
Community: Woodcrest Run
Brooksmont 65 BROOKSMONT DR 15, HOLLISTON, MA, 0174..., Holliston, MA 01746
$785,000

2 beds

|

3 baths

|

2,360 sq ft

|

Condo

65 BROOKSMONT DR 15, HOLLISTON, MA, 0174...
Community: Brooksmont
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...
Want to learn more about 55+ communities in Upton? 55places can help!
Questions? Call us: (508) 603-7097
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
$584,900

2 beds

|

2 baths

|

1,512 sq ft

|

Condo

1213 CODMAN WAY 1213, WESTBOROUGH, MA, 0...
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.
Brierly Pond Village 37 HORNE WAY 37, MILLBURY, MA, 01527, Millbury, MA 01527
$479,900

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 79, WESTBOROU..., Westborough, MA 01581
$700,000

2 beds

|

2 baths

|

2,090 sq ft

|

Condo

14 WESSONVILLE VILLAGE WAY 79, WESTBOROU...
Pennington Crossing 1211 PENNINGTON DR 1211, WALPOLE, MA, 02..., Walpole, MA 02081
$575,000

1 beds

|

1 baths

|

1,030 sq ft

|

Condo

1211 PENNINGTON DR 1211, WALPOLE, MA, 02...
Community: Pennington Crossing
Regency at Glen Ellen 112 GLEN ELLEN BLVD 112, MILLIS, MA, 020..., Millis, MA 02054
$1,299,950

3 beds

|

4 baths

|

4,483 sq ft

|

Condo

112 GLEN ELLEN BLVD 112, MILLIS, MA, 020...
Cindy Certified
180 U:202 OLD POST RD 202, SHARON, MA, 0..., Sharon, MA 02067
$887,900

2 beds

|

3 baths

|

1,431 sq ft

|

Condo

180 U:202 OLD POST RD 202, SHARON, MA, 0...
The Seasons at Salisbury 148 FIRESIDE LN 148, HOLDEN, MA, 01520, Holden, MA 01520
$685,000

2 beds

|

3 baths

|

2,601 sq ft

|

Condo

148 FIRESIDE LN 148, HOLDEN, MA, 01520
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
Harmony Place 21 FIDELITY DR 73, RUTLAND, MA, 01543, Rutland, MA 01543
$489,000

2 beds

|

2 baths

|

1,582 sq ft

|

Condo

21 FIDELITY DR 73, RUTLAND, MA, 01543
Community: Harmony Place
Want to learn more about 55+ communities in Upton? 55places can help!
Questions? Call us: (508) 603-7097
Harmony Place 23 FIDELITY DR 74, RUTLAND, MA, 01543, Rutland, MA 01543
$489,000

2 beds

|

2 baths

|

1,582 sq ft

|

Condo

23 FIDELITY DR 74, RUTLAND, MA, 01543
Community: Harmony Place
Harmony Place 19 FIDELITY DR 72, RUTLAND, MA, 01543, Rutland, MA 01543
$498,000

2 beds

|

2 baths

|

1,582 sq ft

|

Condo

19 FIDELITY DR 72, RUTLAND, MA, 01543
Community: Harmony Place
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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