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

41 communities near Upton

Sort by:

Relevance

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

Regency at Glen Ellen

$700ks - $900ks

Regency at Glen Ellen, Millis, MA

New Construction | 55+ age-restricted | Built 2017 - present | 324 homes

The Trails

$500ks - $700ks

The Trails, Hopkinton, MA

New Construction | 55+ age-restricted | Built 2017 - present | 170 homes

Millwood Preserve

$700ks - $800ks

Millwood Preserve, Framingham, MA

New Construction | 55+ age-restricted | Built 2020 - present | 129 homes

Want to learn more about 55+ communities in Upton? 55places can help!

Questions? Call us: (508) 603-7097

Want to learn more about 55+ rental communities in Upton? 55places can help!

Questions? Call us: (508) 603-7097

Brooksmont

$400ks - $600ks

Brooksmont, Holliston, MA

Resale Only | 55+ age-restricted | Built 2017 - 2020 | 66 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

Balancing Rock

$500ks - $600ks

Balancing Rock, Holliston, MA

Resale Only | 55+ age-restricted | Built 2006 - 2008 | 49 homes

Forest Glen

$400ks - $500ks

Forest Glen, Uxbridge, MA

New Construction | 55+ age-restricted | Built 2018 - present | 44 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.

Orchard Hill

$500ks

Orchard Hill, Westborough, MA

Resale Only | 55+ age-restricted | Built 2002 - 2010 | 100 homes

Read the Ultimate 55+ Rental Guide Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.

Quail Ridge

$600ks - $700ks

Quail Ridge, Acton, MA

Resale Only | 55+ age-restricted | Built 2015 - present | 153 homes

Woodcrest Run

$400ks - $600ks

Woodcrest Run, Sharon, MA

New Construction | 55+ age-restricted | Built 2019 - present | 25 homes

Rockwood Meadows

$600ks - $700ks

Rockwood Meadows, Upton, MA

New Construction | 55+ age-restricted | Built 2016 - present | 58 homes

Want to learn more about 55+ communities in Upton? 55places can help!

Questions? Call us: (508) 603-7097

Regency at Assabet Ridge

$500ks - $600ks

Regency at Assabet Ridge, Marlborough, MA

Resale Only | 55+ age-restricted | Built 2010 - 2015 | 69 homes

Northside Meadows

$600ks - $700ks

Northside Meadows, Framingham, MA

Resale Only | 55+ age-restricted | Built 2017 - 2019 | 60 homes

Want to learn more about 55+ rental communities in Upton? 55places can help!

Questions? Call us: (508) 603-7097

Garrison Place

$900ks - $1Ms

Garrison Place, Carlisle, MA

Resale Only | 55+ age-restricted | Built 2018 - 2019 | 16 homes

Northwoods at Sudbury

$500ks

Northwoods at Sudbury, Sudbury, MA

Resale Only | 55+ age-restricted | Built 1999 - 2019 | 43 homes

Wyman Farms

$500ks - $900ks

Wyman Farms, Shrewsbury, MA

New Construction | 55+ age-restricted | Built 2017 - present | 26 homes

Brierly Pond Village

$300ks - $400ks

Brierly Pond Village, Millbury, MA

Resale Only | 55+ age-restricted | Built 2003 - 2013 | 199 homes

59 North Main

$900ks

59 North Main, Sherborn, MA

New Construction | 55+ age-restricted | Built 2019 - present | 12 homes

Pennington Crossing

$300ks - $600ks

Pennington Crossing, Walpole, MA

New Construction | 55+ age-restricted | Built 2018 - present | 172 homes

Want to learn more about 55+ communities in Upton? 55places can help!

Questions? Call us: (508) 603-7097

Upton Ridge

$400ks - $600ks

Upton Ridge, Upton, MA

New Construction | 55+ age-restricted | Built 2019 - present | 139 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

Enclave at Hudson

$800ks - $1Ms

Enclave at Hudson, Hudson, MA

New Construction | 55+ age-restricted | Built 2021 - present | 64 homes

Village at Silver Hill

$1Ms - $2Ms

Village at Silver Hill, Weston, MA

New Construction | 55+ age-restricted | Built 2021 - present | 8 homes

Want to learn more about 55+ rental communities in Upton? 55places can help!

Questions? Call us: (508) 603-7097

New England Commons

$200ks - $300ks

New England Commons, Webster, MA

New and Resale | 55+ age-restricted | Built 2005 - present | 100 homes

Bella Vista

$300ks - $400ks

Bella Vista, Glocester, RI

Resale Only | 55+ age-restricted | Built 2015 - 2021 | 70 homes

Brookside Village

$700ks

Brookside Village, Walpole, MA

Resale Only | 55+ age-restricted | Built 2018 - 2018 | 30 homes

Bates Quarry

Bates Quarry, Walpole, MA

New Construction | 55+ age-restricted | Built 2025 - present | 100 homes

WestRidge

$700ks

WestRidge, Hudson, MA

Resale Only | 55+ age-restricted | Built 2009 - 2016 | 136 homes

Want to learn more about 55+ communities in Upton? 55places can help!

Questions? Call us: (508) 603-7097

Angell Brook Village

$300ks

Angell Brook Village, West Boylston, MA

Resale Only | 55+ age-restricted | Built 2005 - 2012 | 132 homes

Pheasant Hill

$300ks - $400ks

Pheasant Hill, Northborough, MA

Resale Only | 55+ age-restricted | Built 2005 - 2006 | 48 homes

The Village at Westminste...

$400ks - $500ks

The Village at Westminste..., Holden, MA

New and Resale | 55+ age-restricted | Built 2006 - present | 125 homes

Blue Heron Pond

$500ks

Blue Heron Pond, Lancaster, MA

Resale Only | 55+ age-restricted | Built 2006 - 2014 | 58 homes

Adams Farm

$700ks - $800ks

Adams Farm, Shrewsbury, MA

Resale Only | 55+ age-restricted | Built 2005 - 2013 | 90 homes

Want to learn more about 55+ rental communities in Upton? 55places can help!

Questions? Call us: (508) 603-7097

Holliston Woods

$500ks - $700ks

Holliston Woods, Holliston, MA

Resale Only | 55+ age-restricted | Built 2016 - 2018 | 66 homes

The Villages at Crane Mea...

$400ks

The Villages at Crane Mea..., Marlborough, MA

Resale Only | 55+ age-restricted | Built 2001 - 2005 | 91 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

Bigelow Farm

$500ks - $600ks

Bigelow Farm, Northborough, MA

Resale Only | 55+ age-restricted | Built 2006 - 2013 | 41 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

9 SHAKER WAY 9, WESTBOROUGH, MA, 01581

Community: The Villages at Walker Meadow

Want to learn more about 55+ communities in Upton? 55places can help!

Questions? Call us: (508) 603-7097

Want to learn more about 55+ rental communities in Upton? 55places can help!

Questions? Call us: (508) 603-7097

Del Webb Chauncy Lake

5 PETERS FARM WAY 309, WESTBOROUGH, MA, ..., Westborough, MA 01581

$629,995

2 beds

2 baths

1,375 sq ft

Condo

5 PETERS FARM WAY 309, WESTBOROUGH, MA, ...

Community: Del Webb Chauncy Lake

Del Webb Chauncy Lake

5 PETERS FARM WAY 104, WESTBOROUGH, MA, ..., Westborough, MA 01581

$419,995

1 beds

1 baths

972 sq ft

Condo

5 PETERS FARM WAY 104, WESTBOROUGH, MA, ...

Community: Del Webb Chauncy Lake

Del Webb Chauncy Lake

5 PETERS FARM WAY 5105, WESTBOROUGH, MA,..., Westborough, MA 01581

$399,995

1 beds

1 baths

958 sq ft

Condo

5 PETERS FARM WAY 5105, WESTBOROUGH, MA,...

Community: Del Webb Chauncy Lake

The Trails

28 WATERVILLE LN 28, HOPKINTON, MA, 0174..., Hopkinton, MA 01748

$1,069,000

2 beds

3 baths

2,510 sq ft

Condo

28 WATERVILLE LN 28, HOPKINTON, MA, 0174...

Community: The Trails

Regency at Glen Ellen

86 GLEN ELLEN BLVD 86, MILLIS, MA, 02054, Millis, MA 02054

$1,249,900

3 beds

3 baths

3,060 sq ft

Condo

86 GLEN ELLEN BLVD 86, MILLIS, MA, 02054

Community: Regency at Glen Ellen

Regency at Glen Ellen

6 JAMESON DR 6, MILLIS, MA, 02054, Millis, MA 02054

$1,259,000

3 beds

4 baths

3,106 sq ft

Condo

6 JAMESON DR 6, MILLIS, MA, 02054

Community: Regency at Glen Ellen

Regency at Assabet Ridge

25 AVEBURY LN 22, MARLBOROUGH, MA, 01752, Marlborough, MA 01752

$725,000

3 beds

3 baths

2,264 sq ft

Condo

25 AVEBURY LN 22, MARLBOROUGH, MA, 01752

Community: Regency at Assabet Ridge

Balancing Rock

20 GLACIER WAY 20, HOLLISTON, MA, 01746, Holliston, MA 01746

$685,000

2 beds

3 baths

2,084 sq ft

Condo

20 GLACIER WAY 20, HOLLISTON, MA, 01746

Community: Balancing Rock

Want to learn more about 55+ communities in Upton? 55places can help!

Questions? Call us: (508) 603-7097

Del Webb Chauncy Lake

1105 PETERS FARM WAY 105, WESTBOROUGH, M..., Westborough, MA 01581

$389,900

1 beds

1 baths

945 sq ft

Condo

1105 PETERS FARM WAY 105, WESTBOROUGH, M...

Community: Del Webb Chauncy Lake

Regency at Glen Ellen

8 GLEN ELLEN BLVD 8, MILLIS, MA, 02054, Millis, MA 02054

$1,449,000

2 beds

4 baths

4,247 sq ft

Condo

8 GLEN ELLEN BLVD 8, MILLIS, MA, 02054

Condo

10 FIDELITY DR 5, 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

12 FIDELITY DR 6, RUTLAND, MA, 01543, Rutland, MA 01543

$498,000

2 beds

2 baths

1,582 sq ft

Condo

12 FIDELITY DR 6, RUTLAND, MA, 01543

Community: Harmony Place

Del Webb Chauncy Lake

1109 PETERS FARM WAY 1109, WESTBOROUGH, ..., Westborough, MA 01581

$429,000

1 beds

1 baths

1,030 sq ft

Condo

1109 PETERS FARM WAY 1109, WESTBOROUGH, ...

Community: Del Webb Chauncy Lake

Harmony Place

15 FIDELITY DR 70, RUTLAND, MA, 01543, Rutland, MA 01543

$489,000

2 beds

2 baths

1,447 sq ft

Condo

15 FIDELITY DR 70, RUTLAND, MA, 01543

Community: Harmony Place

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

Condo

2306 TALBOT WAY 2306, WESTBOROUGH, MA, 0...

Community: Del Webb Chauncy Lake

Want to learn more about 55+ communities in Upton? 55places can help!

Questions? Call us: (508) 603-7097

Del Webb Chauncy Lake

5 PETERS FARM WAY 111, WESTBOROUGH, MA, ..., Westborough, MA 01581

$469,995

1 beds

1 baths

1,030 sq ft

Condo

5 PETERS FARM WAY 111, WESTBOROUGH, MA, ...

Community: Del Webb Chauncy Lake

Forest Glen

61 SPRING HILL DR 61, UXBRIDGE, MA, 0156..., Uxbridge, MA 01569

$589,000

2 beds

2 baths

1,525 sq ft

Condo

61 SPRING HILL DR 61, UXBRIDGE, MA, 0156...

Community: Forest Glen

Brooksmont

$724,900

2 beds

3 baths

2,360 sq ft

Condo

59 BROOKSMONT DR 59, HOLLISTON, MA, 0174...

Community: Brooksmont

Regency at Glen Ellen

13 HATTIE LN 13, MILLIS, MA, 02054, Millis, MA 02054

$920,000

2 beds

3 baths

2,627 sq ft

Condo

13 HATTIE LN 13, MILLIS, MA, 02054

Community: Regency at Glen Ellen

Del Webb Chauncy Lake

1102 PETERS FARM WAY 1102, WESTBOROUGH, ..., Westborough, MA 01581

$414,900

1 beds

1 baths

956 sq ft

Condo

1102 PETERS FARM WAY 1102, WESTBOROUGH, ...

Condo

12 FIDELITY DR # 6, RUTLAND, MA, 01543

Community: Harmony Place

Want to learn more about 55+ communities in Upton? 55places can help!

Questions? Call us: (508) 603-7097

The Trails

14 WATERVILLE LN # 14, HOPKINTON, MA, 01..., Hopkinton, MA 01748

$989,000

2 beds

3 baths

2,274 sq ft

Condo

14 WATERVILLE LN # 14, HOPKINTON, MA, 01...

Community: The Trails

Regency at Glen Ellen

3 JAMESON DR 3, MILLIS, MA, 02054, Millis, MA 02054

$1,075,000

2 beds

3 baths

1,832 sq ft

Condo

3 JAMESON DR 3, MILLIS, MA, 02054

Community: Regency at Glen Ellen

Frequently Asked Questions

What size 55+ communities are there in Upton?

In Upton, there are no large communities, no medium communities, and 2 small communities with less than 500 homes.

How many homes are there in the smallest, largest, and average 55+ communities in Upton?

The smallest 55+ communities in Upton has 58 homes, the largest has 139 homes, and the average communities consists of 98 homes.

Are there new 55+ homes available in Upton?

Yes, there are new 55+ homes available in Upton. The most recent communities started in Upton include Upton Ridge, Rockwood Meadows. There are also 2 communities in Upton that offer new construction homes, including Rockwood Meadows, Upton Ridge.

Are there gated 55+ communities in Upton?

No, there are no gated 55+ communities in Upton.

How long do listings in 55+ communities in Upton typically stay on the market, and what is the average price of homes for sale?

On average, listings in 55+ communities in Upton stay on the market for around 36 days. The average price of homes for sale in these communities is approximately $849,450, though prices can range widely based on the size, location, and amenities of the communities. For example, homes in Rockwood Meadows average around $1,049,000, while homes in Upton Ridge average around $649,900.

Want more information about active adult communities around Upton?

Global - Lead Form - Buyer or Renter

First Name

Last Name

Phone/Mobile

Text

I'm looking to:

Rent

Buy

*55places does not provide or maintain community HOA information.

Yes, I want to subscribe to email updates from 55places.com, including newsletters, community announcements, and more.

I agree to receive SMS messages to connect me with a local expert.

By requesting more information, you agree that 55places may call, text, or email you about your inquiry, which may be made with automated means (including recorded voice messages, SMS, or text messages). You understand that your consent is not a prerequisite for buying, selling or renting a property. You may revoke your consent at any time by contacting [email protected]. Message/data rates may apply. You also agree to 55places.com’s Privacy Policy and Terms of Use.

Want to learn more about 55+ communities in Upton?

Call us: (508) 603-7097

41 communities

Remove Boundaries ×

Map Satellite

The listings data displayed on this medium comes in part from the Real Estate Information Network Inc. (REIN) and has been authorized by participating listing Broker Members of REIN for display. REIN's listings are based upon Data submitted by its Broker Members, and REIN therefore makes no representation or warranty regarding the accuracy of the Data. All users of REIN's listings database should confirm the accuracy of the listing information directly with the listing agent.
© 2026 REIN. REIN's listings Data and information is protected under federal copyright laws. Federal law prohibits, among other acts, the unauthorized copying or alteration of, or preparation of derivative works from, all or any part of copyrighted materials, including certain compilations of Data and information. COPYRIGHT VIOLATORS MAY BE SUBJECT TO SEVERE FINES AND PENALTIES UNDER FEDERAL LAW.
REIN updates its listings on a daily basis. Data last updated: Mar 31, 2026.
This application does not include information on all of the properties available for sale at this time.

Call Us Call Us

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

41 communities near Upton

41 homes near Upton

3 beds

3 baths

2,793 sq ft

Condo

2 beds

3 baths

2,956 sq ft

House

2 beds

2 baths

1,584 sq ft

Condo

2 beds

3 baths

2,454 sq ft

Condo

2 beds

2 baths

2,090 sq ft

Condo

2 beds

2 baths

1,375 sq ft

Condo

1 beds

1 baths

972 sq ft

Condo

1 beds

1 baths

958 sq ft

Condo

2 beds

3 baths

2,510 sq ft

Condo

3 beds

3 baths

3,060 sq ft

Condo

3 beds

4 baths

3,106 sq ft

Condo

3 beds

3 baths

2,264 sq ft

Condo

2 beds

3 baths

2,084 sq ft

Condo

1 beds

1 baths

945 sq ft

Condo

2 beds

4 baths

4,247 sq ft

Condo

2 beds

2 baths

1,175 sq ft

Condo

2 beds

3 baths

2,218 sq ft

Condo

2 beds

2 baths

1,056 sq ft

Condo

2 beds

3 baths

2,225 sq ft

Condo

2 beds