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Massachusetts 55+ active adult communities & homes for sale

Living in Massachusetts

From the suburbs of the Greater Boston area and MetroWest to the coastal towns of the South Shore near Plymouth and seaside villages across Cape Cod, Massachusetts combines…
From the suburbs of the Greater Boston area and MetroWest to the coastal towns of the South Shore near Plymouth and seaside villages across Cape Cod, Massachusetts combines world-class medical infrastructure with classic New England living. The state's tax environment offers significant benefits for retirees: Social Security benefits and government pensions are completely exempt from state income tax, while private retirement withdrawals are taxed at a flat 5.0%. Additionally, qualifying homeowners 65 and older can leverage the Senior Circuit Breaker credit for up to $2,820 in property tax relief.Massachusetts features 152 active adult communities—headlined by Oak Point in Middleborough, the state's largest master plan, alongside resort-style condominium developments like Del Webb Chauncy Lake in Westborough, Southport in Mashpee, and luxury coastal enclaves in Scituate. Real estate choices span low-maintenance active adult condos to single-family coastal homes. At 55places, we comprehensively profile every Massachusetts active adult neighborhood with verified pricing, real resident reviews, and direct access to trusted local 55+ real estate experts.

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152 communities near Massachusetts

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5 rating (3 reviews) Oak Point
$300ks - $400ks
Oak Point, Middleborough, MA
New and Resale | 55+ age-restricted | Built 1999 - present | 1,150 homes
Martins Landing
$400ks - $700ks
Martins Landing, North Reading, MA
New Construction | 55+ age-restricted | Built 2018 - present | 450 homes
Villages at Weathervane
$800ks - $1Ms
Villages at Weathervane, Weymouth, MA
Resale Only | 55+ age-restricted | Built 2003 - 2010 | 149 homes
Del Webb Chauncy Lake
$400ks - $600ks
Del Webb Chauncy Lake, Westborough, MA
New Construction | 55+ age-restricted | Built 2018 - present | 700 homes
Southport
$400ks - $600ks
Southport, Mashpee, MA
New and Resale | 55+ age-restricted | Built 1989 - present | 730 homes
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Blue Heron Pond
$500ks
Blue Heron Pond, Lancaster, MA
Resale Only | 55+ age-restricted | Built 2006 - 2014 | 58 homes
New England Commons
$200ks - $300ks
New England Commons, Webster, MA
New and Resale | 55+ age-restricted | Built 2005 - present | 100 homes
Quail Ridge
$600ks - $700ks
Quail Ridge, Acton, MA
Resale Only | 55+ age-restricted | Built 2015 - present | 153 homes
Regency at Glen Ellen
$700ks - $900ks
Regency at Glen Ellen, Millis, MA
New Construction | 55+ age-restricted | Built 2017 - present | 324 homes
Lake Point Village
$400ks - $600ks
Lake Point Village, Lakeville, MA
New Construction | 55+ age-restricted | Built 2020 - present | 66 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.
Great Island
$600ks
Great Island, Plymouth, MA
Resale Only | 55+ age-restricted | Built 2002 - 2015 | 600 homes
The Preserve at Hunters H...
$400ks - $500ks
The Preserve at Hunters H..., Dighton, MA
New and Resale | 55+ age-restricted | Built 2006 - present | 140 homes
Upton Ridge
$400ks - $600ks
Upton Ridge, Upton, MA
New Construction | 55+ age-restricted | Built 2019 - present | 139 homes
Harmony Place
$400ks - $500ks
Harmony Place, Rutland, MA
New Construction | 55+ age-restricted | Built 2023 - present | 142 homes
Preserve at Emerald Pines
$700ks - $900ks
Preserve at Emerald Pines, Methuen, MA
Resale Only | 55+ age-restricted | Built 2017 - 2024 | 192 homes
Sawyer's Reach
$400ks - $900ks
Sawyer's Reach, Plymouth, MA
New and Resale | 55+ age-restricted | Built 2017 - present | 224 homes
Want to learn more about 55+ communities in Massachusetts? 55places can help!
Questions? Call us: (888) 625-4885
30 Coppersmith
$700ks
30 Coppersmith, Canton, MA
New Construction | 55+ age-restricted | Built 2025 - present | 63 homes
Riverside Woods
$400ks - $600ks
Riverside Woods, Andover, MA
Resale Only | 55+ age-restricted | Built 2017 - present | 200 homes
The Trails
$500ks - $700ks
The Trails, Hopkinton, MA
New Construction | 55+ age-restricted | Built 2017 - present | 170 homes
The Pines at Hathaway Pon...
$300ks - $500ks
The Pines at Hathaway Pon..., Rochester, MA
Resale Only | 55+ age-restricted | Built 2006 - 2014 | 61 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.
Pennington Crossing
$300ks - $600ks
Pennington Crossing, Walpole, MA
New Construction | 55+ age-restricted | Built 2018 - present | 172 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
Woodstone Crossing
$300ks - $400ks
Woodstone Crossing, Weymouth, MA
Resale Only | Age-targeted | Built 2015 - 2019 | 200 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
Willis Brook at Lynnfield
$1Ms
Willis Brook at Lynnfield, Lynnfield, MA
New Construction | 55+ age-restricted | Built 2026 - present | 100 homes
Orchard Hill
$500ks
Orchard Hill, Westborough, MA
Resale Only | 55+ age-restricted | Built 2002 - 2010 | 100 homes
Garrison Place
$900ks - $1Ms
Garrison Place, Carlisle, MA
Resale Only | 55+ age-restricted | Built 2018 - 2019 | 16 homes
Want to learn more about 55+ communities in Massachusetts? 55places can help!
Questions? Call us: (888) 625-4885
Reading Woods
$400ks - $600ks
Reading Woods, Reading, MA
Resale Only | 55+ age-restricted | Built 2011 - 2016 | 424 homes
4 rating (2 reviews) Regency at Methuen
$500ks - $600ks
Regency at Methuen, Methuen, MA
Resale Only | 55+ age-restricted | Built 2011 - 2015 | 240 homes
Seton Highlands at The Pi...
$600ks - $700ks
Seton Highlands at The Pi..., Plymouth, MA
New and Resale | 55+ age-restricted | Built 2008 - present | 120 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.
Woodcrest Run
$400ks - $600ks
Woodcrest Run, Sharon, MA
New Construction | 55+ age-restricted | Built 2019 - present | 25 homes
The Village at Auburnvill...
$300ks - $400ks
The Village at Auburnvill..., Whitman, MA
Resale Only | 55+ age-restricted | Built 2004 - 2014 | 92 homes
Brierly Pond Village
$300ks - $400ks
Brierly Pond Village, Millbury, MA
Resale Only | 55+ age-restricted | Built 2003 - 2013 | 199 homes
The Village at Northridge
$500ks - $600ks
The Village at Northridge, North Reading, MA
Resale Only | 55+ age-restricted | 56 homes
Rockland Glen
$300ks - $500ks
Rockland Glen, Rockland, MA
Resale Only | 55+ age-restricted | Built 2008 - 2015 | 60 homes
Rolling Green at Topsfiel...
$600ks - $800ks
Rolling Green at Topsfiel..., Topsfield, MA
Resale Only | 55+ age-restricted | Built 2014 - 2014 | 30 homes
Bigelow Farm
$500ks - $600ks
Bigelow Farm, Northborough, MA
Resale Only | 55+ age-restricted | Built 2006 - 2013 | 41 homes
Hatter's Point
$600ks - $700ks
Hatter's Point, Amesbury, MA
Resale Only | 55+ age-restricted | Built 2004 - 2017 | 88 homes
Want to learn more about 55+ communities in Massachusetts? 55places can help!
Questions? Call us: (888) 625-4885
The Seasons at Salisbury
$400ks - $500ks
The Seasons at Salisbury, Holden, MA
Resale Only | 55+ age-restricted | Built 2002 - 2006 | 91 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.
123...4
New Oak Point 5006 OAK POINT DR, MIDDLEBORO, MA, 02346, Middleboro, MA 02346
$434,000

3 beds

|

2 baths

|

1,568 sq ft

|

House

5006 OAK POINT DR, MIDDLEBORO, MA, 02346
Community: Oak Point
New Oak Point 602 WAVERLY RD, MIDDLEBORO, MA, 02346, Middleboro, MA 02346
$449,000

3 beds

|

2 baths

|

1,462 sq ft

|

House

602 WAVERLY RD, MIDDLEBORO, MA, 02346
Community: Oak Point
New 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...
New The Villages at Walker Meadow 4 WESSONVILLE VILLAGE WAY 4, WESTBOROUGH..., Westborough, MA 01581
$750,000

2 beds

|

2 baths

|

2,090 sq ft

|

Condo

4 WESSONVILLE VILLAGE WAY 4, WESTBOROUGH...
New 30 Coppersmith 30 COPPERSMITH WAY 502, CANTON, MA, 0202..., Canton, MA 02021
$544,995

1 beds

|

1 baths

|

1,027 sq ft

|

Condo

30 COPPERSMITH WAY 502, CANTON, MA, 0202...
Community: 30 Coppersmith
Want to learn more about 55+ communities in Massachusetts? 55places can help!
Questions? Call us: (888) 625-4885
New 30 Coppersmith 30 COPPERSMITH WAY 306, CANTON, MA, 0202..., Canton, MA 02021
$689,995

2 beds

|

2 baths

|

1,582 sq ft

|

Condo

30 COPPERSMITH WAY 306, CANTON, MA, 0202...
Community: 30 Coppersmith
New
Cindy Certified
150 LIZOTTE DR 311, MARLBOROUGH, MA, 017..., Marlborough, MA 01752
$503,305

2 beds

|

3 baths

|

1,425 sq ft

|

Condo

150 LIZOTTE DR 311, MARLBOROUGH, MA, 017...
New Del Webb Chauncy Lake 11 PETERS FARM WAY 310, WESTBOROUGH, MA,..., Westborough, MA 01581
$499,900

2 beds

|

2 baths

|

1,326 sq ft

|

Condo

11 PETERS FARM WAY 310, WESTBOROUGH, MA,...
New The Village at Northridge 19 NORTHRIDGE DR 19, NORTH READING, MA, ..., North Reading, MA 01864
$589,900

2 beds

|

2 baths

|

1,426 sq ft

|

Condo

19 NORTHRIDGE DR 19, NORTH READING, MA, ...
New
Cindy Certified
6 MUIRFIELD 6, PLYMOUTH, MA, 02360, Plymouth, MA 02360
$869,000

2 beds

|

2 baths

|

2,296 sq ft

|

Condo

6 MUIRFIELD 6, PLYMOUTH, MA, 02360
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 Great Island 3 AUTUMN GLN, PLYMOUTH, MA, 02360, Plymouth, MA 02360
$759,000

2 beds

|

3 baths

|

2,447 sq ft

|

House

3 AUTUMN GLN, PLYMOUTH, MA, 02360
Community: Great Island
New Sawyer's Reach 3 MARINERS WAY 305, PLYMOUTH, MA, 02360, Plymouth, MA 02360
$475,000

1 beds

|

1 baths

|

804 sq ft

|

Condo

3 MARINERS WAY 305, PLYMOUTH, MA, 02360
Community: Sawyer's Reach
New Woodstone Crossing 90 TROTTER RD 3404, WEYMOUTH, MA, 02190, Weymouth, MA 02190
$469,900

1 beds

|

1 baths

|

965 sq ft

|

Condo

90 TROTTER RD 3404, WEYMOUTH, MA, 02190
Community: Woodstone Crossing
New Del Webb Chauncy Lake 8106 PETERS FARM WAY 106, WESTBOROUGH, M..., Westborough, MA 01581
$599,995

2 beds

|

2 baths

|

1,496 sq ft

|

Condo

8106 PETERS FARM WAY 106, WESTBOROUGH, M...
New
Cindy Certified
150 LIZOTTE DR 312, MARLBOROUGH, MA, 017..., Marlborough, MA 01752
$556,995

2 beds

|

3 baths

|

1,582 sq ft

|

Condo

150 LIZOTTE DR 312, MARLBOROUGH, MA, 017...
Rolling Green at Topsfield 470 BOSTON ST 21, TOPSFIELD, MA, 01983, Topsfield, MA 01983
$994,000

2 beds

|

4 baths

|

2,949 sq ft

|

House

470 BOSTON ST 21, TOPSFIELD, MA, 01983
Want to learn more about 55+ communities in Massachusetts? 55places can help!
Questions? Call us: (888) 625-4885
Red Mill Village 30 CODDING RD 30, NORTON, MA, 02766, Norton, MA 02766
$925,000

3 beds

|

3 baths

|

2,387 sq ft

|

Condo

30 CODDING RD 30, NORTON, MA, 02766
Community: Red Mill Village
Cindy Certified
200 MARTINS LNDG 107, NORTH READING, MA,..., North Reading, MA 01864
$645,000

2 beds

|

2 baths

|

1,470 sq ft

|

Condo

200 MARTINS LNDG 107, NORTH READING, MA,...
Cindy Certified
20 AUDUBON WAY 409, CANTON, MA, 02021, Canton, MA 02021
$824,900

2 beds

|

3 baths

|

1,421 sq ft

|

Condo

20 AUDUBON WAY 409, CANTON, MA, 02021
Cindy Certified
20 AUDUBON WAY 109, CANTON, MA, 02021, Canton, MA 02021
$719,900

2 beds

|

3 baths

|

1,421 sq ft

|

Condo

20 AUDUBON WAY 109, CANTON, MA, 02021
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.
Cindy Certified
20 AUDUBON WAY 101, CANTON, MA, 02021, Canton, MA 02021
$749,900

2 beds

|

3 baths

|

1,471 sq ft

|

Condo

20 AUDUBON WAY 101, CANTON, MA, 02021
Cindy Certified
20 AUDUBON WAY 202, CANTON, MA, 02021, Canton, MA 02021
$699,900

2 beds

|

3 baths

|

1,440 sq ft

|

Condo

20 AUDUBON WAY 202, CANTON, MA, 02021
Willis Brook at Lynnfield 10 FAIRWAY LN 64, LYNNFIELD, MA, 01940, Lynnfield, MA 01940
$1,549,000

2 beds

|

2 baths

|

1,913 sq ft

|

Condo

10 FAIRWAY LN 64, LYNNFIELD, MA, 01940
Orchard Hill 19 IMPERIAL CT 19, WESTBOROUGH, MA, 0158..., Westborough, MA 01581
$579,000

2 beds

|

3 baths

|

2,523 sq ft

|

Condo

19 IMPERIAL CT 19, WESTBOROUGH, MA, 0158...
Community: Orchard Hill
Oak Point 5111 PHEASANT, MIDDLEBORO, MA, 02346, Middleboro, MA 02346
$459,900

2 beds

|

2 baths

|

1,674 sq ft

|

House

5111 PHEASANT, MIDDLEBORO, MA, 02346
Community: Oak Point
Woodstone Crossing 70 TROTTER RD 203, WEYMOUTH, MA, 02190, Weymouth, MA 02190
$445,000

1 beds

|

1 baths

|

955 sq ft

|

Condo

70 TROTTER RD 203, WEYMOUTH, MA, 02190
Community: Woodstone Crossing
Great Island 37 WEATHERVANE, PLYMOUTH, MA, 02360, Plymouth, MA 02360
$725,000

2 beds

|

2 baths

|

1,548 sq ft

|

House

37 WEATHERVANE, PLYMOUTH, MA, 02360
Community: Great Island
Want to learn more about 55+ communities in Massachusetts? 55places can help!
Questions? Call us: (888) 625-4885
Great Island 26 CROSS WIND, PLYMOUTH, MA, 02360, Plymouth, MA 02360
$800,000

2 beds

|

3 baths

|

2,382 sq ft

|

House

26 CROSS WIND, PLYMOUTH, MA, 02360
Community: Great Island
Del Webb Chauncy Lake 4206 PETERS FARM WAY 206, WESTBOROUGH, M..., Westborough, MA 01581
$539,000

2 beds

|

2 baths

|

1,469 sq ft

|

Condo

4206 PETERS FARM WAY 206, WESTBOROUGH, M...
Regency at Methuen 106 SHERWOOD DR 1, METHUEN, MA, 01844, Methuen, MA 01844
$749,900

2 beds

|

2 baths

|

1,797 sq ft

|

Condo

106 SHERWOOD DR 1, METHUEN, MA, 01844
Community: Regency at Methuen
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.
Cindy Certified
150 LIZOTTE DR 201, MARLBOROUGH, MA, 017..., Marlborough, MA 01752
$516,995

2 beds

|

3 baths

|

1,582 sq ft

|

Condo

150 LIZOTTE DR 201, MARLBOROUGH, MA, 017...
Great Island 22 PICKET FENCE, PLYMOUTH, MA, 02360, Plymouth, MA 02360
$900,000

3 beds

|

4 baths

|

4,085 sq ft

|

House

22 PICKET FENCE, PLYMOUTH, MA, 02360
Community: Great Island
Del Webb Chauncy Lake 8 PETERS FARM WAY 307, WESTBOROUGH, MA, ..., Westborough, MA 01581
$663,995

2 beds

|

2 baths

|

1,512 sq ft

|

Condo

8 PETERS FARM WAY 307, WESTBOROUGH, MA, ...
Southport 10 CHIPPERS LN 10, MASHPEE, MA, 02649, Mashpee, MA 02649
$625,000

2 beds

|

3 baths

|

2,007 sq ft

|

Condo

10 CHIPPERS LN 10, MASHPEE, MA, 02649
Community: Southport
Martins Landing 320 MARTINS LNDG 508, NORTH READING, MA,..., North Reading, MA 01864
$649,995

2 beds

|

2 baths

|

1,450 sq ft

|

Condo

320 MARTINS LNDG 508, NORTH READING, MA,...
Community: Martins Landing
Orchard Hill 5 GILMORE FARM RD 5, WESTBOROUGH, MA, 01..., Westborough, MA 01581
$608,000

2 beds

|

3 baths

|

2,183 sq ft

|

Condo

5 GILMORE FARM RD 5, WESTBOROUGH, MA, 01...
Community: Orchard Hill
Rockland Glen 4 MIDFIELD DR 4, ROCKLAND, MA, 02370, Rockland, MA 02370
$699,900

2 beds

|

3 baths

|

2,857 sq ft

|

Condo

4 MIDFIELD DR 4, ROCKLAND, MA, 02370
Community: Rockland Glen
Westbrook Crossing 989 E ST 115, DEDHAM, MA, 02026, Dedham, MA 02026
$530,000

2 beds

|

2 baths

|

1,485 sq ft

|

Condo

989 E ST 115, DEDHAM, MA, 02026
Community: Westbrook Crossing
Want to learn more about 55+ communities in Massachusetts? 55places can help!
Questions? Call us: (888) 625-4885
The Preserve at Hunters Hill 65 CLUB HOUSE DR, DIGHTON, MA, 02715, Dighton, MA 02715
$739,900

2 beds

|

2 baths

|

1,775 sq ft

|

House

65 CLUB HOUSE DR, DIGHTON, MA, 02715
Seton Highlands at The Pinehills 15 ABERDEEN 15, PLYMOUTH, MA, 02360, Plymouth, MA 02360
$895,000

3 beds

|

4 baths

|

3,703 sq ft

|

Condo

15 ABERDEEN 15, PLYMOUTH, MA, 02360
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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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: Nov 06, 2026.
This application does not include information on all of the properties available for sale at this time.

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