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

42 homes near Holliston

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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
Upton Ridge
$400ks - $600ks
Upton Ridge, Upton, MA
New Construction | 55+ age-restricted | Built 2019 - present | 139 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
Regency at Glen Ellen
$700ks - $900ks
Regency at Glen Ellen, Millis, MA
New Construction | 55+ age-restricted | Built 2017 - present | 324 homes
Want to learn more about 55+ communities in Holliston? 55places can help!
Questions? Call us: (508) 893-4855
The Trails
$500ks - $700ks
The Trails, Hopkinton, MA
New Construction | 55+ age-restricted | Built 2017 - present | 170 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
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
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.
Northwoods at Sudbury
$500ks
Northwoods at Sudbury, Sudbury, MA
Resale Only | 55+ age-restricted | Built 1999 - 2019 | 43 homes
Brooksmont
$400ks - $600ks
Brooksmont, Holliston, MA
Resale Only | 55+ age-restricted | Built 2017 - 2020 | 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
Northside Meadows
$600ks - $700ks
Northside Meadows, Framingham, MA
Resale Only | 55+ age-restricted | Built 2017 - 2019 | 60 homes
Enclave at Hudson
$800ks - $1Ms
Enclave at Hudson, Hudson, MA
New Construction | 55+ age-restricted | Built 2021 - present | 64 homes
Holliston Woods
$500ks - $700ks
Holliston Woods, Holliston, MA
Resale Only | 55+ age-restricted | Built 2016 - 2018 | 66 homes
Want to learn more about 55+ communities in Holliston? 55places can help!
Questions? Call us: (508) 893-4855
59 North Main
$900ks
59 North Main, Sherborn, MA
New Construction | 55+ age-restricted | Built 2019 - present | 12 homes
Pheasant Hill
$300ks - $400ks
Pheasant Hill, Northborough, MA
Resale Only | 55+ age-restricted | Built 2005 - 2006 | 48 homes
Regency at Assabet Ridge
$500ks - $600ks
Regency at Assabet Ridge, Marlborough, MA
Resale Only | 55+ age-restricted | Built 2010 - 2015 | 69 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
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.
Millwood Preserve
$1Ms
Millwood Preserve, Framingham, MA
Resale Only | 55+ age-restricted | Built 2020 - 2024 | 129 homes
Village at Silver Hill
$1Ms - $2Ms
Village at Silver Hill, Weston, MA
New Construction | 55+ age-restricted | Built 2021 - present | 8 homes
Rockwood Meadows
$600ks - $700ks
Rockwood Meadows, Upton, MA
New Construction | 55+ age-restricted | Built 2016 - present | 58 homes
Balancing Rock
$500ks - $600ks
Balancing Rock, Holliston, MA
Resale Only | 55+ age-restricted | Built 2006 - 2008 | 49 homes
Brookside Village
$700ks
Brookside Village, Walpole, MA
Resale Only | 55+ age-restricted | Built 2018 - 2018 | 30 homes
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, ...
Want to learn more about 55+ communities in Holliston? 55places can help!
Questions? Call us: (508) 893-4855
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, ...
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.

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REIN updates its listings on a daily basis. Data last updated: Sep 06, 2026.
This application does not include information on all of the properties available for sale at this time.

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