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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


65 homes near Upton

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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
Harmony Place
$400ks - $500ks
Harmony Place, Rutland, MA
New Construction | 55+ age-restricted | Built 2023 - present | 142 homes
Upton Ridge
$400ks - $600ks
Upton Ridge, Upton, MA
New Construction | 55+ age-restricted | Built 2019 - present | 139 homes
Brierly Pond Village
$300ks - $400ks
Brierly Pond Village, Millbury, MA
Resale Only | 55+ age-restricted | Built 2003 - 2013 | 199 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 Upton? 55places can help!
Questions? Call us: (508) 603-7097
Regency at Glen Ellen
$700ks - $900ks
Regency at Glen Ellen, Millis, MA
New Construction | 55+ age-restricted | Built 2017 - present | 324 homes
Pennington Crossing
$300ks - $600ks
Pennington Crossing, Walpole, MA
New Construction | 55+ age-restricted | Built 2018 - present | 172 homes
Woodcrest Run
$400ks - $600ks
Woodcrest Run, Sharon, MA
New Construction | 55+ age-restricted | Built 2019 - present | 25 homes
The Trails
$500ks - $700ks
The Trails, Hopkinton, MA
New Construction | 55+ age-restricted | Built 2017 - present | 170 homes
Garrison Place
$900ks - $1Ms
Garrison Place, Carlisle, MA
Resale Only | 55+ age-restricted | Built 2018 - 2019 | 16 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.
Bates Quarry
Bates Quarry, Walpole, MA
New Construction | 55+ age-restricted | Built 2025 - present | 100 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
Regency at Assabet Ridge
$500ks - $600ks
Regency at Assabet Ridge, Marlborough, MA
Resale Only | 55+ age-restricted | Built 2010 - 2015 | 69 homes
The Village at Westminste...
$400ks - $500ks
The Village at Westminste..., Holden, MA
New and Resale | 55+ age-restricted | Built 2006 - present | 125 homes
Quail Ridge
$600ks - $700ks
Quail Ridge, Acton, MA
Resale Only | 55+ age-restricted | Built 2015 - present | 153 homes
The Seasons at Salisbury
$400ks - $500ks
The Seasons at Salisbury, Holden, MA
Resale Only | 55+ age-restricted | Built 2002 - 2006 | 91 homes
Want to learn more about 55+ communities in Upton? 55places can help!
Questions? Call us: (508) 603-7097
Orchard Hill
$500ks
Orchard Hill, Westborough, MA
Resale Only | 55+ age-restricted | Built 2002 - 2010 | 100 homes
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
Northwoods at Sudbury
$500ks
Northwoods at Sudbury, Sudbury, MA
Resale Only | 55+ age-restricted | Built 1999 - 2019 | 43 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.
Brooksmont
$400ks - $600ks
Brooksmont, Holliston, MA
Resale Only | 55+ age-restricted | Built 2017 - 2020 | 66 homes
Holliston Woods
$500ks - $700ks
Holliston Woods, Holliston, MA
Resale Only | 55+ age-restricted | Built 2016 - 2018 | 66 homes
Village at Silver Hill
$1Ms - $2Ms
Village at Silver Hill, Weston, MA
New Construction | 55+ age-restricted | Built 2021 - present | 8 homes
Forest Glen
$400ks - $500ks
Forest Glen, Uxbridge, MA
New Construction | 55+ age-restricted | Built 2018 - present | 44 homes
Adams Farm
$700ks - $800ks
Adams Farm, Shrewsbury, MA
Resale Only | 55+ age-restricted | Built 2005 - 2013 | 90 homes
Trail Ridge at Harvard
$700ks
Trail Ridge at Harvard, Harvard, MA
Resale Only | 55+ age-restricted | Built 2008 - 2023 | 52 homes
Brookside Village
$700ks
Brookside Village, Walpole, MA
Resale Only | 55+ age-restricted | Built 2018 - 2018 | 30 homes
Want to learn more about 55+ communities in Upton? 55places can help!
Questions? Call us: (508) 603-7097
Blue Heron Pond
$500ks
Blue Heron Pond, Lancaster, MA
Resale Only | 55+ age-restricted | Built 2006 - 2014 | 58 homes
Enclave at Hudson
$800ks - $1Ms
Enclave at Hudson, Hudson, MA
New Construction | 55+ age-restricted | Built 2021 - present | 64 homes
Wyman Farms
$500ks - $900ks
Wyman Farms, Shrewsbury, MA
New Construction | 55+ age-restricted | Built 2017 - present | 26 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 England Commons
$200ks - $300ks
New England Commons, Webster, MA
New and Resale | 55+ age-restricted | Built 2005 - present | 100 homes
Pheasant Hill
$300ks - $400ks
Pheasant Hill, Northborough, MA
Resale Only | 55+ age-restricted | Built 2005 - 2006 | 48 homes
59 North Main
$900ks
59 North Main, Sherborn, MA
New Construction | 55+ age-restricted | Built 2019 - present | 12 homes
Angell Brook Village
$300ks
Angell Brook Village, West Boylston, MA
Resale Only | 55+ age-restricted | Built 2005 - 2012 | 132 homes
WestRidge
$700ks
WestRidge, Hudson, MA
Resale Only | 55+ age-restricted | Built 2009 - 2016 | 136 homes
Bella Vista
$300ks - $400ks
Bella Vista, Glocester, RI
Resale Only | 55+ age-restricted | Built 2015 - 2021 | 70 homes
Balancing Rock
$500ks - $600ks
Balancing Rock, Holliston, MA
Resale Only | 55+ age-restricted | Built 2006 - 2008 | 49 homes
Bigelow Farm
$500ks - $600ks
Bigelow Farm, Northborough, MA
Resale Only | 55+ age-restricted | Built 2006 - 2013 | 41 homes
Want to learn more about 55+ communities in Upton? 55places can help!
Questions? Call us: (508) 603-7097
Millwood Preserve
$1Ms
Millwood Preserve, Framingham, MA
Resale Only | 55+ age-restricted | Built 2020 - 2024 | 129 homes
Rockwood Meadows
$600ks - $700ks
Rockwood Meadows, Upton, MA
New Construction | 55+ age-restricted | Built 2016 - present | 58 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.
1...2
Harmony Place 17 FIDELITY DR 71, RUTLAND, MA, 01543, Rutland, MA 01543
$498,000

2 beds

|

2 baths

|

1,582 sq ft

|

Condo

17 FIDELITY DR 71, RUTLAND, MA, 01543
Community: Harmony Place
Regency at Glen Ellen 43 JAMESON DR 43, MILLIS, MA, 02054, Millis, MA 02054
$1,199,000

3 beds

|

3 baths

|

2,873 sq ft

|

Condo

43 JAMESON DR 43, MILLIS, MA, 02054
Quail Ridge 20 PARKLAND LN 20, ACTON, MA, 01720, Acton, MA 01720
$899,900

2 beds

|

2 baths

|

2,149 sq ft

|

Condo

20 PARKLAND LN 20, ACTON, MA, 01720
Community: Quail Ridge
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...
Pennington Crossing 4402 PENNINGTON DR 4402, WALPOLE, MA, 02..., Walpole, MA 02081
$750,000

2 beds

|

2 baths

|

1,339 sq ft

|

Condo

4402 PENNINGTON DR 4402, WALPOLE, MA, 02...
Community: Pennington Crossing
Want to learn more about 55+ communities in Upton? 55places can help!
Questions? Call us: (508) 603-7097
Northwoods at Sudbury 10 NORTHWOOD DR 301, SUDBURY, MA, 01776, Sudbury, MA 01776
$649,000

1 beds

|

2 baths

|

1,668 sq ft

|

Condo

10 NORTHWOOD DR 301, SUDBURY, MA, 01776
Upton Ridge 56 SHANNON WAY 56, UPTON, MA, 01568, Upton, MA 01568
$689,000

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
$560,000

2 beds

|

3 baths

|

2,183 sq ft

|

Condo

19 IMPERIAL CT 19, WESTBOROUGH, MA, 0158...
Community: Orchard Hill
Brierly Pond Village 168 HORNE WAY 168, MILLBURY, MA, 01527, Millbury, MA 01527
$414,000

2 beds

|

3 baths

|

1,735 sq ft

|

Condo

168 HORNE WAY 168, MILLBURY, MA, 01527
Upton Ridge 204 SAND TRAP CT 204, NORTHBRIDGE, MA, 0..., Northbridge, MA 01534
$625,000

3 beds

|

3 baths

|

2,170 sq ft

|

Condo

204 SAND TRAP CT 204, NORTHBRIDGE, MA, 0...
Community: Upton Ridge
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 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...
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
Woodcrest Run 635 OLD POST RD 2-303, SHARON, MA, 02067, Sharon, MA 02067
$675,000

2 beds

|

3 baths

|

2,400 sq ft

|

Condo

635 OLD POST RD 2-303, SHARON, MA, 02067
Community: Woodcrest Run
Cindy Certified
180/208 OLD POST RD 208, SHARON, MA, 020..., Sharon, MA 02067
$1,094,900

2 beds

|

3 baths

|

1,653 sq ft

|

Condo

180/208 OLD POST RD 208, SHARON, MA, 020...
Cindy Certified
5 ABBY LN 5, SHREWSBURY, MA, 01545, Shrewsbury, MA 01545
$759,900

3 beds

|

3 baths

|

2,188 sq ft

|

Condo

5 ABBY LN 5, SHREWSBURY, MA, 01545
Del Webb Chauncy Lake 3405 PETERS FARM WAY 3405, WESTBOROUGH, ..., Westborough, MA 01581
$524,500

2 beds

|

2 baths

|

1,121 sq ft

|

Condo

3405 PETERS FARM WAY 3405, WESTBOROUGH, ...
Want to learn more about 55+ communities in Upton? 55places can help!
Questions? Call us: (508) 603-7097
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
$559,000

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...
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 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
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
$539,900

2 beds

|

2 baths

|

1,326 sq ft

|

Condo

12308 PETERS FARM WAY 308, WESTBOROUGH, ...
Harmony Place 4 FIDELITY DR 2, RUTLAND, MA, 01543, Rutland, MA 01543
$498,000

2 beds

|

2 baths

|

1,582 sq ft

|

Condo

4 FIDELITY DR 2, RUTLAND, MA, 01543
Community: Harmony Place

Frequently Asked Questions


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