Call us at (508) 231-4659 to learn more about active adult communities near Ashland
Ashland, MA 55+ active adult communities & homes for sale
24 communities near Ashland
34 homes near Ashland
Sort by:
Relevance
$500Ks
- $700Ks
The Lanterns at Warren Wo..., Ashland, MA
Resale Only
|
55+ age-restricted
|
Built 2016 - 2020
|
93 homes
$300Ks
- $800Ks
Del Webb Chauncy Lake, Westborough, MA
New Construction
|
55+ age-restricted
|
Built 2018 - present
|
700 homes
$800Ks
- $1Ms
Regency at Glen Ellen, Millis, MA
New Construction
|
55+ age-restricted
|
Built 2017 - present
|
324 homes
$800Ks
- $1Ms
The Trails, Hopkinton, MA
New Construction
|
55+ age-restricted
|
Built 2017 - present
|
170 homes
$600Ks
- $600Ks
Upton Ridge, Upton, MA
New Construction
|
55+ age-restricted
|
Built 2019 - present
|
139 homes
Want to learn more about 55+ communities in Ashland?
55places can help!
Questions? Call us:
(508) 231-4659
$700Ks
- $1Ms
WestRidge, Hudson, MA
Resale Only
|
55+ age-restricted
|
Built 2009 - 2016
|
136 homes
$1Ms
- $1Ms
Millwood Preserve, Framingham, MA
New Construction
|
55+ age-restricted
|
Built 2020 - present
|
129 homes
$600Ks
- $600Ks
Orchard Hill, Westborough, MA
Resale Only
|
55+ age-restricted
|
Built 2002 - 2010
|
100 homes
$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.
$400Ks
- $400Ks
The Villages at Crane Mea..., Marlborough, MA
Resale Only
|
55+ age-restricted
|
Built 2001 - 2005
|
91 homes
$500Ks
- $600Ks
Regency at Assabet Ridge, Marlborough, MA
Resale Only
|
55+ age-restricted
|
Built 2010 - 2015
|
69 homes
$500Ks
- $700Ks
Holliston Woods, Holliston, MA
Resale Only
|
55+ age-restricted
|
Built 2016 - 2018
|
66 homes
$600Ks
- $700Ks
Brooksmont, Holliston, MA
Resale Only
|
55+ age-restricted
|
Built 2017 - 2020
|
66 homes
$800Ks
- $1Ms
Enclave at Hudson, Hudson, MA
New Construction
|
55+ age-restricted
|
Built 2021 - present
|
64 homes
Want to learn more about 55+ communities in Ashland?
55places can help!
Questions? Call us:
(508) 231-4659
$600Ks
- $700Ks
Northside Meadows, Framingham, MA
Resale Only
|
55+ age-restricted
|
Built 2017 - 2019
|
60 homes
$600Ks
- $700Ks
Rockwood Meadows, Upton, MA
New Construction
|
55+ age-restricted
|
Built 2016 - present
|
58 homes
$500Ks
- $600Ks
Balancing Rock, Holliston, MA
Resale Only
|
55+ age-restricted
|
Built 2006 - 2008
|
49 homes
$300Ks
- $400Ks
Pheasant Hill, Northborough, MA
Resale Only
|
55+ age-restricted
|
Built 2005 - 2006
|
48 homes
$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.
$600Ks
- $1Ms
Northwoods at Sudbury, Sudbury, MA
Resale Only
|
55+ age-restricted
|
Built 1999 - 2019
|
43 homes
$500Ks
- $600Ks
Bigelow Farm, Northborough, MA
Resale Only
|
55+ age-restricted
|
Built 2006 - 2013
|
41 homes
$900Ks
- $900Ks
59 North Main, Sherborn, MA
New Construction
|
55+ age-restricted
|
Built 2019 - present
|
12 homes
Del Webb Chauncy Lake
![11101 PETERS FARM WAY # 101, WESTBOROUGH..., Westborough, MA 01581]()
2 beds
|2 baths
|1,469 sq ft
|Condo
11101 PETERS FARM WAY # 101, WESTBOROUGH...
Community: Del Webb Chauncy Lake
MLS 73438484 • Compass, Dee Kerner
Forest Glen
![100 SPRING HILL DR # 100, UXBRIDGE, MA, ..., Uxbridge, MA 01569]()
2 beds
|2 baths
|1,694 sq ft
|Condo
100 SPRING HILL DR # 100, UXBRIDGE, MA, ...
Community: Forest Glen
MLS 73449018 • Keller Williams Elite, Anthony Rug...
New
Del Webb Chauncy Lake
![2 CODMAN WAY 411, WESTBOROUGH, MA, 01581, Westborough, MA 01581]()
2 beds
|2 baths
|1,375 sq ft
|Condo
2 CODMAN WAY 411, WESTBOROUGH, MA, 01581
Community: Del Webb Chauncy Lake
MLS 73452782 • Pulte Homes of New England, Erin S...
Regency at Glen Ellen
![18 LANSING WAY # 18, MILLIS, MA, 02054, Millis, MA 02054]()
2 beds
|3 baths
|2,306 sq ft
|Condo
18 LANSING WAY # 18, MILLIS, MA, 02054
Community: Regency at Glen Ellen
MLS 73424107 • Berkshire Hathaway HomeServices Co...
New
The Villages at Walker Meadow
![3 DOVER WAY # 3, WESTBOROUGH, MA, 01581, Westborough, MA 01581]()
2 beds
|2 baths
|1,874 sq ft
|Condo
3 DOVER WAY # 3, WESTBOROUGH, MA, 01581
Community: The Villages at Walker Meadow
MLS 73452352 • Mathieu Newton Sotheby's Internati...
Want to learn more about 55+ communities in Ashland?
55places can help!
Questions? Call us:
(508) 231-4659
Del Webb Chauncy Lake
![5 PETERS FARM WAY # 412, WESTBOROUGH, MA..., Westborough, MA 01581]()
2 beds
|2 baths
|1,512 sq ft
|Condo
5 PETERS FARM WAY # 412, WESTBOROUGH, MA...
Community: Del Webb Chauncy Lake
MLS 73436343 • Pulte Homes of New England, Erin S...
Del Webb Chauncy Lake
![2 CODMAN WAY 5103, WESTBOROUGH, MA, 0158..., Westborough, MA 01581]()
1 beds
|1 baths
|972 sq ft
|Condo
2 CODMAN WAY 5103, WESTBOROUGH, MA, 0158...
Community: Del Webb Chauncy Lake
MLS 73432617 • Pulte Homes of New England, Erin S...
Regency at Glen Ellen
![6 GLEN ELLEN BLVD # 6, MILLIS, MA, 02054, Millis, MA 02054]()
3 beds
|3 baths
|2,656 sq ft
|Condo
6 GLEN ELLEN BLVD # 6, MILLIS, MA, 02054
Community: Regency at Glen Ellen
MLS 73437375 • Vesta Real Estate Group, Inc., Ves...
Regency at Assabet Ridge
![13 WILSHIRE WAY # 13, MARLBOROUGH, MA, 0..., Marlborough, MA 01752]()
2 beds
|2 baths
|1,584 sq ft
|Condo
13 WILSHIRE WAY # 13, MARLBOROUGH, MA, 0...
Community: Regency at Assabet Ridge
MLS 73424705 • Colby Hunter Realty, John Jewett
The Trails
![13 BIRKDALE LN # 13, HOPKINTON, MA, 0174..., Hopkinton, MA 01748]()
2 beds
|3 baths
|2,277 sq ft
|Condo
13 BIRKDALE LN # 13, HOPKINTON, MA, 0174...
Community: The Trails
MLS 73430544 • Keller Williams Elite, Sue Sindoni
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 Glen Ellen
![27 RICHARDSON DR # 27, MILLIS, MA, 02054, Millis, MA 02054]()
2 beds
|3 baths
|2,485 sq ft
|Condo
27 RICHARDSON DR # 27, MILLIS, MA, 02054
Community: Regency at Glen Ellen
MLS 73390614 • Redfin Corp., Shelly A. Armstrong
Brooksmont
![104 BROOKSMONT DR # 104, HOLLISTON, MA, ..., Holliston, MA 01746]()
2 beds
|2 baths
|1,516 sq ft
|Condo
104 BROOKSMONT DR # 104, HOLLISTON, MA, ...
Community: Brooksmont
MLS 73414911 • Engel & Volkers Wellesley, Cindy L...
Del Webb Chauncy Lake
![4403 PETERS FARM WAY 403, WESTBOROUGH, M..., Westborough, MA 01581]()
1 beds
|1 baths
|956 sq ft
|Condo
4403 PETERS FARM WAY 403, WESTBOROUGH, M...
Community: Del Webb Chauncy Lake
MLS 73446787 • Boucher Real Estate, Inc., Duane B...
Del Webb Chauncy Lake
![3103 PETERS FARM WAY # 3103, WESTBOROUGH..., Westborough, MA 01581]()
1 beds
|1 baths
|956 sq ft
|Condo
3103 PETERS FARM WAY # 3103, WESTBOROUGH...
Community: Del Webb Chauncy Lake
MLS 73415011 • Berkshire Hathaway HomeServices Co...
Millwood Preserve
![9 HAWK LN # 28, FRAMINGHAM, MA, 01701, Framingham, MA 01701]()
2 beds
|3 baths
|2,306 sq ft
|Condo
9 HAWK LN # 28, FRAMINGHAM, MA, 01701
Community: Millwood Preserve
MLS 73449723 • Andrew J. Abu Inc., REALTORS®, Li...
Want to learn more about 55+ communities in Ashland?
55places can help!
Questions? Call us:
(508) 231-4659
Del Webb Chauncy Lake
![11302 PETERS FARM WAY # 11302, WESTBOROU..., Westborough, MA 01581]()
1 beds
|1 baths
|956 sq ft
|Condo
11302 PETERS FARM WAY # 11302, WESTBOROU...
Community: Del Webb Chauncy Lake
MLS 73443694 • Century 21 Custom Home Realty, Lau...
Del Webb Chauncy Lake
![3112 PETERS FARM WAY # 112, WESTBOROUGH,..., Westborough, MA 01581]()
1 beds
|1 baths
|1,021 sq ft
|Condo
3112 PETERS FARM WAY # 112, WESTBOROUGH,...
Community: Del Webb Chauncy Lake
MLS 73441080 • LAER Realty Partners, Debi Malone
Del Webb Chauncy Lake
![2 TALBOT WAY 2103, WESTBOROUGH, MA, 0158..., Westborough, MA 01581]()
1 beds
|1 baths
|956 sq ft
|Condo
2 TALBOT WAY 2103, WESTBOROUGH, MA, 0158...
Community: Del Webb Chauncy Lake
MLS 73446186 • Lamacchia Realty, Inc., Martha Con...
Orchard Hill
![5 BLOSSOM CT # 5, WESTBOROUGH, MA, 01581, Westborough, MA 01581]()
3 beds
|4 baths
|3,373 sq ft
|Condo
5 BLOSSOM CT # 5, WESTBOROUGH, MA, 01581
Community: Orchard Hill
MLS 73437675 • Berkshire Hathaway HomeServices Co...
Del Webb Chauncy Lake
![2 CODMAN WAY 402, WESTBOROUGH, MA, 01581, Westborough, MA 01581]()
1 beds
|1 baths
|972 sq ft
|Condo
2 CODMAN WAY 402, WESTBOROUGH, MA, 01581
Community: Del Webb Chauncy Lake
MLS 73448601 • Pulte Homes of New England, Erin S...
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
![133 BROOKSMONT DR # 43, HOLLISTON, MA, 0..., Holliston, MA 01746]()
2 beds
|3 baths
|2,160 sq ft
|Condo
133 BROOKSMONT DR # 43, HOLLISTON, MA, 0...
Community: Brooksmont
MLS 73447828 • Coldwell Banker Realty - Canton, M...
The Villages at Walker Meadow
![9 SHAKER WAY # 9, WESTBOROUGH, MA, 01581, Westborough, MA 01581]()
2 beds
|2 baths
|2,090 sq ft
|Condo
9 SHAKER WAY # 9, WESTBOROUGH, MA, 01581
Community: The Villages at Walker Meadow
MLS 73429776 • Mathieu Newton Sotheby's Internati...
Regency at Glen Ellen
![3 JAMESON DR # 3, MILLIS, MA, 02054, Millis, MA 02054]()
2 beds
|3 baths
|1,832 sq ft
|Condo
3 JAMESON DR # 3, MILLIS, MA, 02054
Community: Regency at Glen Ellen
MLS 73447013 • Coldwell Banker Realty - Needham, ...
Del Webb Chauncy Lake
![3102 PETERS FARM WAY # 102, WESTBOROUGH,..., Westborough, MA 01581]()
1 beds
|1 baths
|956 sq ft
|Condo
3102 PETERS FARM WAY # 102, WESTBOROUGH,...
Community: Del Webb Chauncy Lake
MLS 73416001 • Guardian Realty Group, Barton Fink
The Trails
![4 WATERVILLE LN # 4, HOPKINTON, MA, 0174..., Hopkinton, MA 01748]()
2 beds
|3 baths
|2,510 sq ft
|Condo
4 WATERVILLE LN # 4, HOPKINTON, MA, 0174...
Community: The Trails
MLS 73406944 • Realty Executives Boston West, Phi...
Want to learn more about 55+ communities in Ashland?
55places can help!
Questions? Call us:
(508) 231-4659
Regency at Glen Ellen
![20 JAMESON DR # 20, MILLIS, MA, 02054, Millis, MA 02054]()
3 beds
|3 baths
|2,581 sq ft
|Condo
20 JAMESON DR # 20, MILLIS, MA, 02054
Community: Regency at Glen Ellen
MLS 73422515 • Coldwell Banker Realty - Needham, ...
Del Webb Chauncy Lake
![5 PETERS FARM WAY # 101, WESTBOROUGH, MA..., Westborough, MA 01581]()
2 beds
|2 baths
|1,496 sq ft
|Condo
5 PETERS FARM WAY # 101, WESTBOROUGH, MA...
Community: Del Webb Chauncy Lake
MLS 73436336 • Pulte Homes of New England, Erin S...
The Trails
![71 WESTON LN # 71, HOPKINTON, MA, 01748, Hopkinton, MA 01748]()
2 beds
|4 baths
|3,258 sq ft
|Condo
71 WESTON LN # 71, HOPKINTON, MA, 01748
Community: The Trails
MLS 73444675 • RE/MAX Executive Realty, Erika Ste...
Del Webb Chauncy Lake
![12302 PETERS FARM WAY # 302, WESTBOROUGH..., Westborough, MA 01581]()
1 beds
|1 baths
|956 sq ft
|Condo
12302 PETERS FARM WAY # 302, WESTBOROUGH...
Community: Del Webb Chauncy Lake
MLS 73416795 • Century 21 North East, MG Group
Del Webb Chauncy Lake
![5 PETERS FARM WAY # 205, WESTBOROUGH, MA..., Westborough, MA 01581]()
2 beds
|2 baths
|1,166 sq ft
|Condo
5 PETERS FARM WAY # 205, WESTBOROUGH, MA...
Community: Del Webb Chauncy Lake
MLS 73433417 • Pulte Homes of New England, Erin S...
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
![9 BALDWIN CT # 9, WESTBOROUGH, MA, 01581, Westborough, MA 01581]()
3 beds
|3 baths
|2,793 sq ft
|Condo
9 BALDWIN CT # 9, WESTBOROUGH, MA, 01581
Community: Orchard Hill
MLS 73440395 • Mathieu Newton Sotheby's Internati...
Millwood Preserve
![11 EAGLE LN 105, FRAMINGHAM, MA, 01701, Framingham, MA 01701]()
2 beds
|4 baths
|3,503 sq ft
|Condo
11 EAGLE LN 105, FRAMINGHAM, MA, 01701
Community: Millwood Preserve
MLS 73440251 • Andrew J. Abu Inc., REALTORS®, Li...
The Trails
![10 WATERVILLE LN # 10, HOPKINTON, MA, 01..., Hopkinton, MA 01748]()
2 beds
|3 baths
|2,274 sq ft
|Condo
10 WATERVILLE LN # 10, HOPKINTON, MA, 01...
Community: The Trails
MLS 73410711 • Realty Executives Boston West, Kar...
Millwood Preserve
![18 EAGLE LN # 21, FRAMINGHAM, MA, 01701, Framingham, MA 01701]()
2 beds
|3 baths
|2,454 sq ft
|Condo
18 EAGLE LN # 21, FRAMINGHAM, MA, 01701
Community: Millwood Preserve
MLS 73429114 • Coldwell Banker Realty - Wellesley...
Frequently Asked Questions
In Ashland, there is 1 small community with less than 500 homes.
The smallest 55+ community in Ashland has 93 homes, the largest has 93 homes, and the average community consists of 93 homes.
No, there are no gated 55+ communities in Ashland.
Want more information about active adult communities around Ashland?
Want to learn more about 55+ communities in Ashland?
24
communities
near Ashland
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.
© 2025 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: Nov 08, 2025.
This application does not include information on all of the properties available for sale at this time.
