Call us at (508) 231-4659 to learn more about active adult communities in Ashland
Ashland, MA 55+ active adult communities & homes for sale
24 communities near Ashland
32 homes near Ashland
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$400ks
- $600ks
Del Webb Chauncy Lake, Westborough, MA
New Construction
|
55+ age-restricted
|
Built 2018 - present
|
700 homes
$700ks
- $900ks
Regency at Glen Ellen, Millis, MA
New Construction
|
55+ age-restricted
|
Built 2017 - present
|
324 homes
$500ks
- $600ks
Regency at Assabet Ridge, Marlborough, MA
Resale Only
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55+ age-restricted
|
Built 2010 - 2015
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69 homes
$500ks
- $700ks
The Trails, Hopkinton, MA
New Construction
|
55+ age-restricted
|
Built 2017 - present
|
170 homes
$500ks
Orchard Hill, Westborough, MA
Resale Only
|
55+ age-restricted
|
Built 2002 - 2010
|
100 homes
Want to learn more about 55+ communities in Ashland?
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(508) 231-4659
$500ks
Northwoods at Sudbury, Sudbury, MA
Resale Only
|
55+ age-restricted
|
Built 1999 - 2019
|
43 homes
$700ks
- $800ks
Millwood Preserve, Framingham, MA
New Construction
|
55+ age-restricted
|
Built 2020 - present
|
129 homes
$400ks
- $600ks
Brooksmont, Holliston, MA
Resale Only
|
55+ age-restricted
|
Built 2017 - 2020
|
66 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.
$300ks
- $400ks
Pheasant Hill, Northborough, MA
Resale Only
|
55+ age-restricted
|
Built 2005 - 2006
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48 homes
$400ks
The Villages at Crane Mea..., Marlborough, MA
Resale Only
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55+ age-restricted
|
Built 2001 - 2005
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91 homes
$500ks
- $600ks
Bigelow Farm, Northborough, MA
Resale Only
|
55+ age-restricted
|
Built 2006 - 2013
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41 homes
$600ks
- $700ks
The Villages at Walker Me..., Westborough, MA
Resale Only
|
55+ age-restricted
|
Built 1999 - 2000
|
100 homes
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Questions? Call us:
(508) 231-4659
$600ks
- $700ks
Northside Meadows, Framingham, MA
Resale Only
|
55+ age-restricted
|
Built 2017 - 2019
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60 homes
$800ks
- $1Ms
Enclave at Hudson, Hudson, MA
New Construction
|
55+ age-restricted
|
Built 2021 - present
|
64 homes
$1Ms
- $2Ms
Village at Silver Hill, Weston, MA
New Construction
|
55+ age-restricted
|
Built 2021 - present
|
8 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.
$500ks
- $700ks
Holliston Woods, Holliston, MA
Resale Only
|
55+ age-restricted
|
Built 2016 - 2018
|
66 homes
$500ks
- $600ks
Balancing Rock, Holliston, MA
Resale Only
|
55+ age-restricted
|
Built 2006 - 2008
|
49 homes
$600ks
- $700ks
Rockwood Meadows, Upton, MA
New Construction
|
55+ age-restricted
|
Built 2016 - present
|
58 homes
$400ks
- $600ks
Upton Ridge, Upton, MA
New Construction
|
55+ age-restricted
|
Built 2019 - present
|
139 homes
Want to learn more about 55+ communities in Ashland?
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Questions? Call us:
(508) 231-4659
$500ks
- $700ks
The Lanterns at Warren Wo..., Ashland, MA
Resale Only
|
55+ age-restricted
|
Built 2016 - 2020
|
93 homes
$900ks
59 North Main, Sherborn, MA
New Construction
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55+ age-restricted
|
Built 2019 - present
|
12 homes
New
Northwoods at Sudbury
![20 NORTHWOOD DR 303, SUDBURY, MA, 01776, Sudbury, MA 01776]()
1 beds
|2 baths
|1,616 sq ft
|Condo
20 NORTHWOOD DR 303, SUDBURY, MA, 01776
Community: Northwoods at Sudbury
MLS 73499458 • Jin Chung Realty LLC, Jin H. Chung
New
Del Webb Chauncy Lake
![4 PETERS FARM WAY 206, WESTBOROUGH, MA, ..., Westborough, MA 01581]()
2 beds
|2 baths
|1,469 sq ft
|Condo
4 PETERS FARM WAY 206, WESTBOROUGH, MA, ...
Community: Del Webb Chauncy Lake
MLS 73499155 • eXp Realty, Natasha Koryak
New
Millwood Preserve
![11 BAITING BROOK RD 11, FRAMINGHAM, MA, ..., Framingham, MA 01701]()
3 beds
|3 baths
|2,559 sq ft
|Condo
11 BAITING BROOK RD 11, FRAMINGHAM, MA, ...
Community: Millwood Preserve
MLS 73497980 • The Greene Realty Group, Derek Gre...
Del Webb Chauncy Lake
![5 PETERS FARM WAY 312, WESTBOROUGH, MA, ..., Westborough, MA 01581]()
2 beds
|2 baths
|1,512 sq ft
|Condo
5 PETERS FARM WAY 312, WESTBOROUGH, MA, ...
Community: Del Webb Chauncy Lake
MLS 73495769 • Pulte Homes of New England, Erin S...
Del Webb Chauncy Lake
![5 PETERS FARM WAY 109, WESTBOROUGH, MA, ..., Westborough, MA 01581]()
1 beds
|1 baths
|1,030 sq ft
|Condo
5 PETERS FARM WAY 109, WESTBOROUGH, MA, ...
Community: Del Webb Chauncy Lake
MLS 73495766 • Pulte Homes of New England, Erin S...
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Questions? Call us:
(508) 231-4659
Del Webb Chauncy Lake
![4403 PETERS FARM WAY 4403, WESTBOROUGH, ..., Westborough, MA 01581]()
1 beds
|1 baths
|956 sq ft
|Condo
4403 PETERS FARM WAY 4403, WESTBOROUGH, ...
Community: Del Webb Chauncy Lake
MLS 73495616 • Lamacchia Realty, Inc., Martha Con...
Del Webb Chauncy Lake
![12308 PETERS FARM WAY 308, WESTBOROUGH, ..., Westborough, MA 01581]()
2 beds
|2 baths
|1,326 sq ft
|Condo
12308 PETERS FARM WAY 308, WESTBOROUGH, ...
Community: Del Webb Chauncy Lake
MLS 73495030 • ERA Key Realty Services - Distinct...
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 73493124 • Mathieu Newton Sotheby's Internati...
Regency at Assabet Ridge
![13 WILSHIRE WAY 13, MARLBOROUGH, MA, 017..., Marlborough, MA 01752]()
2 beds
|2 baths
|1,584 sq ft
|Condo
13 WILSHIRE WAY 13, MARLBOROUGH, MA, 017...
Community: Regency at Assabet Ridge
MLS 73491917 • Colby Hunter Realty, John Jewett
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
![14 CALLAHAN DR 14, FRAMINGHAM, MA, 01701, Framingham, MA 01701]()
2 beds
|3 baths
|2,454 sq ft
|Condo
14 CALLAHAN DR 14, FRAMINGHAM, MA, 01701
Community: Millwood Preserve
MLS 73491798 • Compass, Bell Property Partners
Del Webb Chauncy Lake
![5 PETERS FARM WAY 309, WESTBOROUGH, MA, ..., Westborough, MA 01581]()
2 beds
|2 baths
|1,375 sq ft
|Condo
5 PETERS FARM WAY 309, WESTBOROUGH, MA, ...
Community: Del Webb Chauncy Lake
MLS 73489742 • Pulte Homes of New England, Erin S...
Del Webb Chauncy Lake
![5 PETERS FARM WAY 104, WESTBOROUGH, MA, ..., Westborough, MA 01581]()
1 beds
|1 baths
|972 sq ft
|Condo
5 PETERS FARM WAY 104, WESTBOROUGH, MA, ...
Community: Del Webb Chauncy Lake
MLS 73489727 • Pulte Homes of New England, Erin S...
The Trails
![28 WATERVILLE LN 28, HOPKINTON, MA, 0174..., Hopkinton, MA 01748]()
2 beds
|3 baths
|2,510 sq ft
|Condo
28 WATERVILLE LN 28, HOPKINTON, MA, 0174...
Community: The Trails
MLS 73489252 • Realty Executives Boston West, Phi...
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55places can help!
Questions? Call us:
(508) 231-4659
Regency at Glen Ellen
![86 GLEN ELLEN BLVD 86, MILLIS, MA, 02054, Millis, MA 02054]()
3 beds
|3 baths
|3,060 sq ft
|Condo
86 GLEN ELLEN BLVD 86, MILLIS, MA, 02054
Community: Regency at Glen Ellen
MLS 73488324 • Flip and Hold Realty LLC, Christop...
Balancing Rock
![20 GLACIER WAY 20, HOLLISTON, MA, 01746, Holliston, MA 01746]()
2 beds
|3 baths
|2,084 sq ft
|Condo
20 GLACIER WAY 20, HOLLISTON, MA, 01746
Community: Balancing Rock
MLS 73487872 • Vesta Real Estate Group, Inc., Ves...
Del Webb Chauncy Lake
![1105 PETERS FARM WAY 105, WESTBOROUGH, M..., Westborough, MA 01581]()
1 beds
|1 baths
|945 sq ft
|Condo
1105 PETERS FARM WAY 105, WESTBOROUGH, M...
Community: Del Webb Chauncy Lake
MLS 73487816 • Mathieu Newton Sotheby's Internati...
Regency at Glen Ellen
![8 GLEN ELLEN BLVD 8, MILLIS, MA, 02054, Millis, MA 02054]()
2 beds
|4 baths
|4,247 sq ft
|Condo
8 GLEN ELLEN BLVD 8, MILLIS, MA, 02054
Community: Regency at Glen Ellen
MLS 73487461 • William Raveis R.E. & Home Service...
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
![5 PETERS FARM WAY 305, WESTBOROUGH, MA, ..., Westborough, MA 01581]()
2 beds
|2 baths
|1,175 sq ft
|Condo
5 PETERS FARM WAY 305, WESTBOROUGH, MA, ...
Community: Del Webb Chauncy Lake
MLS 73486054 • Pulte Homes of New England, Erin S...
Orchard Hill
![14 BALDWIN CT 14, WESTBOROUGH, MA, 01581, Westborough, MA 01581]()
2 beds
|3 baths
|2,225 sq ft
|Condo
14 BALDWIN CT 14, WESTBOROUGH, MA, 01581
Community: Orchard Hill
MLS 73481699 • Mathieu Newton Sotheby's Internati...
Del Webb Chauncy Lake
![6312 PETERS FARM WAY 6312, WESTBOROUGH, ..., Westborough, MA 01581]()
2 beds
|2 baths
|1,469 sq ft
|Condo
6312 PETERS FARM WAY 6312, WESTBOROUGH, ...
Community: Del Webb Chauncy Lake
MLS 73481383 • Keller Williams Pinnacle MetroWest...
Del Webb Chauncy Lake
![1109 PETERS FARM WAY 1109, WESTBOROUGH, ..., Westborough, MA 01581]()
1 beds
|1 baths
|1,030 sq ft
|Condo
1109 PETERS FARM WAY 1109, WESTBOROUGH, ...
Community: Del Webb Chauncy Lake
MLS 73480122 • Oak Realty, Pamela Bathen
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Regency at Glen Ellen
![124 GLEN ELLEN BLVD 124, MILLIS, MA, 020..., Millis, MA 02054]()
2 beds
|2 baths
|1,797 sq ft
|Condo
124 GLEN ELLEN BLVD 124, MILLIS, MA, 020...
Community: Regency at Glen Ellen
MLS 73478697 • Coldwell Banker Realty - Needham, ...
Del Webb Chauncy Lake
![5 PETERS FARM WAY 107, WESTBOROUGH, MA, ..., Westborough, MA 01581]()
2 beds
|2 baths
|1,512 sq ft
|Condo
5 PETERS FARM WAY 107, WESTBOROUGH, MA, ...
Community: Del Webb Chauncy Lake
MLS 73477940 • Pulte Homes of New England, Erin S...
Del Webb Chauncy Lake
![2306 TALBOT WAY 2306, WESTBOROUGH, MA, 0..., Westborough, MA 01581]()
2 beds
|2 baths
|1,469 sq ft
|Condo
2306 TALBOT WAY 2306, WESTBOROUGH, MA, 0...
Community: Del Webb Chauncy Lake
MLS 73477125 • Lamacchia Realty, Inc., Martha Con...
Forest Glen
![61 SPRING HILL DR 61, UXBRIDGE, MA, 0156..., Uxbridge, MA 01569]()
2 beds
|2 baths
|1,525 sq ft
|Condo
61 SPRING HILL DR 61, UXBRIDGE, MA, 0156...
Community: Forest Glen
MLS 73475598 • Century 21 Custom Home Realty, Rob...
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
![59 BROOKSMONT DR 59, HOLLISTON, MA, 0174..., Holliston, MA 01746]()
2 beds
|3 baths
|2,360 sq ft
|Condo
59 BROOKSMONT DR 59, HOLLISTON, MA, 0174...
Community: Brooksmont
MLS 73474124 • Homes-R-Us Realty of MA, Inc., Nat...
Regency at Glen Ellen
![13 HATTIE LN 13, MILLIS, MA, 02054, Millis, MA 02054]()
2 beds
|3 baths
|2,627 sq ft
|Condo
13 HATTIE LN 13, MILLIS, MA, 02054
Community: Regency at Glen Ellen
MLS 73474095 • Compass, Bell Property Partners
Del Webb Chauncy Lake
![1102 PETERS FARM WAY 1102, WESTBOROUGH, ..., Westborough, MA 01581]()
1 beds
|1 baths
|956 sq ft
|Condo
1102 PETERS FARM WAY 1102, WESTBOROUGH, ...
Community: Del Webb Chauncy Lake
MLS 73473722 • Redfin Corp., Shelly A. Armstrong
Regency at Assabet Ridge
![28 BOWOOD LN 28, MARLBOROUGH, MA, 01752, Marlborough, MA 01752]()
3 beds
|3 baths
|2,205 sq ft
|Condo
28 BOWOOD LN 28, MARLBOROUGH, MA, 01752
Community: Regency at Assabet Ridge
MLS 73469241 • Coldwell Banker Realty - Sudbury, ...
The Trails
![14 WATERVILLE LN # 14, HOPKINTON, MA, 01..., Hopkinton, MA 01748]()
2 beds
|3 baths
|2,274 sq ft
|Condo
14 WATERVILLE LN # 14, HOPKINTON, MA, 01...
Community: The Trails
MLS 73460639 • Realty Executives Boston West, Kar...
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Questions? Call us:
(508) 231-4659
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
![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
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?
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REIN updates its listings on a daily basis. Data last updated: Apr 10, 2026.
This application does not include information on all of the properties available for sale at this time.
