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Massachusetts 55+ active adult communities & homes for sale

Living in Massachusetts

From the high-demand suburbs of the Greater Boston area and MetroWest to the coastal towns of the South Shore 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
Want to learn more about 55+ communities in Massachusetts? 55places can help!
Questions? Call us: (888) 625-4885
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.
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
Great Island
$600ks
Great Island, Plymouth, MA
Resale Only | 55+ age-restricted | Built 2002 - 2015 | 600 homes
Preserve at Emerald Pines
$800ks - $900ks
Preserve at Emerald Pines, Methuen, MA
Resale Only | 55+ age-restricted | Built 2017 - 2024 | 192 homes
Riverside Woods
$400ks - $600ks
Riverside Woods, Andover, MA
Resale Only | 55+ age-restricted | Built 2017 - present | 200 homes
30 Coppersmith
$700ks
30 Coppersmith, Canton, MA
New Construction | 55+ age-restricted | Built 2025 - present | 63 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
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
Upton Ridge
$400ks - $600ks
Upton Ridge, Upton, MA
New Construction | 55+ age-restricted | Built 2019 - present | 139 homes
The Gardens of Wilbraham
$200ks - $400ks
The Gardens of Wilbraham, Wilbraham, MA
New and Resale | 55+ age-restricted | Built 2005 - present | 108 homes
The Trails
$500ks - $700ks
The Trails, Hopkinton, MA
New Construction | 55+ age-restricted | Built 2017 - present | 170 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.
Reading Woods
$400ks - $600ks
Reading Woods, Reading, MA
Resale Only | 55+ age-restricted | Built 2011 - 2016 | 424 homes
WestRidge
$700ks
WestRidge, Hudson, MA
Resale Only | 55+ age-restricted | Built 2009 - 2016 | 136 homes
Brierly Pond Village
$300ks - $400ks
Brierly Pond Village, Millbury, MA
Resale Only | 55+ age-restricted | Built 2003 - 2013 | 199 homes
Orchard Hill
$500ks
Orchard Hill, Westborough, MA
Resale Only | 55+ age-restricted | Built 2002 - 2010 | 100 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
Harmony Place
$400ks - $500ks
Harmony Place, Rutland, MA
New Construction | 55+ age-restricted | Built 2023 - present | 142 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
Want to learn more about 55+ communities in Massachusetts? 55places can help!
Questions? Call us: (888) 625-4885
Woodcrest Run
$400ks - $600ks
Woodcrest Run, Sharon, MA
New Construction | 55+ age-restricted | Built 2019 - present | 25 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
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.
Chilton Park Village
$400ks
Chilton Park Village, Plymouth, MA
Resale Only | 55+ age-restricted | Built 2006 - 2015 | 25 homes
Woodstone Crossing
$300ks - $400ks
Woodstone Crossing, Weymouth, MA
Resale Only | Age-targeted | Built 2015 - 2019 | 200 homes
The Village at Auburnvill...
$300ks - $400ks
The Village at Auburnvill..., Whitman, MA
Resale Only | 55+ age-restricted | Built 2004 - 2014 | 92 homes
Pennington Crossing
$300ks - $600ks
Pennington Crossing, Walpole, MA
New Construction | 55+ age-restricted | Built 2018 - present | 172 homes
Hatter's Point
$600ks - $700ks
Hatter's Point, Amesbury, MA
Resale Only | 55+ age-restricted | Built 2004 - 2017 | 88 homes
North Meadow Village
$500ks - $800ks
North Meadow Village, Middleton, MA
Resale Only | 55+ age-restricted | Built 2012 - 2015 | 42 homes
Stonebridge Commons
$500ks
Stonebridge Commons, Hanson, MA
Resale Only | 55+ age-restricted | Built 2007 - 2018 | 121 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
Stone Castle Estates
$200ks - $600ks
Stone Castle Estates, Methuen, MA
Resale Only | 55+ age-restricted | Built 2005 - 2018 | 89 homes
Regency at Emerald Pines
$600ks - $900ks
Regency at Emerald Pines, Methuen, MA
Resale Only | 55+ age-restricted | Built 2015 - 2018 | 140 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.
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New Oak Point 408 GREEN ST, MIDDLEBORO, MA, 02346, Middleboro, MA 02346
$389,000

3 beds

|

2 baths

|

1,344 sq ft

|

House

408 GREEN ST, MIDDLEBORO, MA, 02346
Community: Oak Point
New Riverside Woods 2 FRANCIS DR 401, ANDOVER, MA, 01810, Andover, MA 01810
$619,000

2 beds

|

2 baths

|

1,490 sq ft

|

Condo

2 FRANCIS DR 401, ANDOVER, MA, 01810
Community: Riverside Woods
New Great Island 6 CLAM PUDDING, PLYMOUTH, MA, 02360, Plymouth, MA 02360
$850,000

3 beds

|

3 baths

|

2,580 sq ft

|

House

6 CLAM PUDDING, PLYMOUTH, MA, 02360
Community: Great Island
New Seton Highlands at The Pinehills 24 INVERNESS 24, PLYMOUTH, MA, 02360, Plymouth, MA 02360
$923,000

3 beds

|

3 baths

|

2,719 sq ft

|

Condo

24 INVERNESS 24, PLYMOUTH, MA, 02360
New Reading Woods 31 JACOB WAY 31, READING, MA, 01867, Reading, MA 01867
$879,000

3 beds

|

3 baths

|

2,089 sq ft

|

Condo

31 JACOB WAY 31, READING, MA, 01867
Community: Reading Woods
Want to learn more about 55+ communities in Massachusetts? 55places can help!
Questions? Call us: (888) 625-4885
New 30 Coppersmith 30 COPPERSMITH WAY 403, CANTON, MA, 0202..., Canton, MA 02021
$603,995

1 beds

|

1 baths

|

1,027 sq ft

|

Condo

30 COPPERSMITH WAY 403, CANTON, MA, 0202...
Community: 30 Coppersmith
New Del Webb Chauncy Lake 5 PETERS FARM WAY 411, WESTBOROUGH, MA, ..., Westborough, MA 01581
$654,995

2 beds

|

2 baths

|

1,375 sq ft

|

Condo

5 PETERS FARM WAY 411, WESTBOROUGH, MA, ...
New Del Webb Chauncy Lake 5 PETERS FARM WAY 410, WESTBOROUGH, MA, ..., Westborough, MA 01581
$594,995

2 beds

|

2 baths

|

1,375 sq ft

|

Condo

5 PETERS FARM WAY 410, WESTBOROUGH, MA, ...
New Del Webb Chauncy Lake 5 PETERS FARM WAY 7303, WESTBOROUGH, MA,..., Westborough, MA 01581
$429,995

1 beds

|

1 baths

|

972 sq ft

|

Condo

5 PETERS FARM WAY 7303, WESTBOROUGH, MA,...
New Del Webb Chauncy Lake 5312 PETERS FARM WAY 312, WESTBOROUGH, M..., Westborough, MA 01581
$699,995

2 beds

|

2 baths

|

1,512 sq ft

|

Condo

5312 PETERS FARM WAY 312, WESTBOROUGH, M...
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 Oak Point 6406 OAK PT, MIDDLEBORO, MA, 02346, Middleboro, MA 02346
$399,000

3 beds

|

2 baths

|

1,456 sq ft

|

House

6406 OAK PT, MIDDLEBORO, MA, 02346
Community: Oak Point
Great Island 5 HIGHBANK TRL, PLYMOUTH, MA, 02360, Plymouth, MA 02360
$721,050

2 beds

|

3 baths

|

2,074 sq ft

|

House

5 HIGHBANK TRL, PLYMOUTH, MA, 02360
Community: Great Island
Stone Castle Estates 4 TILBURY RD 4, METHUEN, MA, 01844, Methuen, MA 01844
$324,424

1 beds

|

2 baths

|

1,128 sq ft

|

Condo

4 TILBURY RD 4, METHUEN, MA, 01844
Orchard Hill 9 BALDWIN CT 9, WESTBOROUGH, MA, 01581, Westborough, MA 01581
$600,000

3 beds

|

3 baths

|

2,793 sq ft

|

Condo

9 BALDWIN CT 9, WESTBOROUGH, MA, 01581
Community: Orchard Hill
Preserve at Emerald Pines 3 HUMMINGBIRD WAY 3, METHUEN, MA, 01844, Methuen, MA 01844
$879,000

3 beds

|

3 baths

|

2,642 sq ft

|

Condo

3 HUMMINGBIRD WAY 3, METHUEN, MA, 01844
Regency at Glen Ellen 43 JAMESON DR 43, MILLIS, MA, 02054, Millis, MA 02054
$1,299,900

3 beds

|

3 baths

|

2,873 sq ft

|

Condo

43 JAMESON DR 43, MILLIS, MA, 02054
Want to learn more about 55+ communities in Massachusetts? 55places can help!
Questions? Call us: (888) 625-4885
Riverside Woods 2 FRANCIS DR 203, ANDOVER, MA, 01810, Andover, MA 01810
$449,900

1 beds

|

1 baths

|

955 sq ft

|

Condo

2 FRANCIS DR 203, ANDOVER, MA, 01810
Community: Riverside Woods
Regency at Methuen 14 HARTSHORNE WAY 14, METHUEN, MA, 01844, Methuen, MA 01844
$799,900

3 beds

|

3 baths

|

2,407 sq ft

|

Condo

14 HARTSHORNE WAY 14, METHUEN, MA, 01844
Community: Regency at Methuen
Seton Highlands at The Pinehills 17 ABERDEEN 17, PLYMOUTH, MA, 02360, Plymouth, MA 02360
$889,000

3 beds

|

3 baths

|

2,690 sq ft

|

Condo

17 ABERDEEN 17, PLYMOUTH, MA, 02360
Del Webb Chauncy Lake 2306 TALBOT WAY 2306, WESTBOROUGH, MA, 0..., Westborough, MA 01581
$559,000

2 beds

|

2 baths

|

1,469 sq ft

|

Condo

2306 TALBOT WAY 2306, WESTBOROUGH, MA, 0...
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.
Angell Brook Village 10 ANGELL BROOK DR 10, WEST BOYLSTON, MA..., West Boylston, MA 01583
$540,000

3 beds

|

2 baths

|

2,228 sq ft

|

Condo

10 ANGELL BROOK DR 10, WEST BOYLSTON, MA...
Preserve at Emerald Pines 53 PHOEBE ST 31, METHUEN, MA, 01844, Methuen, MA 01844
$940,000

2 beds

|

4 baths

|

2,985 sq ft

|

Condo

53 PHOEBE ST 31, METHUEN, MA, 01844
Millwood Preserve 5 BAITING BROOK RD 5, FRAMINGHAM, MA, 01..., Framingham, MA 01701
$1,429,000

2 beds

|

4 baths

|

3,396 sq ft

|

Condo

5 BAITING BROOK RD 5, FRAMINGHAM, MA, 01...
Community: Millwood Preserve
Bartlett Hill 19 PLUMROSE CT 19, PORTLAND, CT, 06480, Portland, CT 06480
$500,000

2 beds

|

3 baths

|

1,503 sq ft

19 PLUMROSE CT 19, PORTLAND, CT, 06480
Community: Bartlett Hill
The Preserve at Hunters Hill 72 CLUB HOUSE DR, DIGHTON, MA, 02715, Dighton, MA 02715
$799,900

2 beds

|

2 baths

|

1,600 sq ft

|

House

72 CLUB HOUSE DR, DIGHTON, MA, 02715
Quail Ridge 20 PARKLAND LN 20, ACTON, MA, 01720, Acton, MA 01720
$925,000

2 beds

|

2 baths

|

2,149 sq ft

|

Condo

20 PARKLAND LN 20, ACTON, MA, 01720
Community: Quail Ridge
The Preserve at Hunters Hill 127 CLUBHOUSE DR, DIGHTON, MA, 02715, Dighton, MA 02715
$756,275

2 beds

|

2 baths

|

1,815 sq ft

|

House

127 CLUBHOUSE DR, DIGHTON, MA, 02715
Want to learn more about 55+ communities in Massachusetts? 55places can help!
Questions? Call us: (888) 625-4885
Riverside Woods 1 FRANCIS DR 405, ANDOVER, MA, 01810, Andover, MA 01810
$529,900

2 beds

|

2 baths

|

1,135 sq ft

|

Condo

1 FRANCIS DR 405, ANDOVER, MA, 01810
Community: Riverside Woods
Martins Landing 320 MARTINS LNDG 509, NORTH READING, MA,..., North Reading, MA 01864
$799,995

2 beds

|

2 baths

|

1,450 sq ft

|

Condo

320 MARTINS LNDG 509, NORTH READING, MA,...
Community: Martins Landing
Martins Landing 320 MARTINS LNDG 307, NORTH READING, MA,..., North Reading, MA 01864
$774,995

2 beds

|

2 baths

|

1,579 sq ft

|

Condo

320 MARTINS LNDG 307, NORTH READING, MA,...
Community: Martins Landing
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.
The Gardens of Wilbraham 79 CHERRY DR 79, WILBRAHAM, MA, 01095, Wilbraham, MA 01095
$435,000

2 beds

|

2 baths

|

1,376 sq ft

|

Condo

79 CHERRY DR 79, WILBRAHAM, MA, 01095
The Village at Orchard Meadows 79 ORCHARD MEADOWS DR 79, SHREWSBURY, MA..., Shrewsbury, MA 01545
$534,900

2 beds

|

2 baths

|

1,370 sq ft

|

Condo

79 ORCHARD MEADOWS DR 79, SHREWSBURY, MA...
Oak Point 307 BLUEBERRY CIR, MIDDLEBORO, MA, 02346, Middleboro, MA 02346
$450,000

3 beds

|

2 baths

|

1,700 sq ft

|

House

307 BLUEBERRY CIR, MIDDLEBORO, MA, 02346
Community: Oak Point
The Pines at Hathaway Pond 14 HATHAWAY POND CIR 14, ROCHESTER, MA, ..., Rochester, MA 02770
$685,000

2 beds

|

3 baths

|

1,776 sq ft

|

Condo

14 HATHAWAY POND CIR 14, ROCHESTER, MA, ...
WestRidge 68 HASTINGS RD 68, HUDSON, MA, 01749, Hudson, MA 01749
$850,000

3 beds

|

3 baths

|

2,264 sq ft

|

Condo

68 HASTINGS RD 68, HUDSON, MA, 01749
Community: WestRidge
Southport 14 STONY BROOK DR 516, MASHPEE, MA, 0264..., Mashpee, MA 02649
$699,000

2 beds

|

3 baths

|

1,792 sq ft

|

Condo

14 STONY BROOK DR 516, MASHPEE, MA, 0264...
Community: Southport
Pennington Crossing 4402 PENNINGTON DR 4402, WALPOLE, MA, 02..., Walpole, MA 02081
$799,900

2 beds

|

2 baths

|

1,339 sq ft

|

Condo

4402 PENNINGTON DR 4402, WALPOLE, MA, 02...
Community: Pennington Crossing
The Trails 21 BIRKDALE LN 21, HOPKINTON, MA, 01748, Hopkinton, MA 01748
$999,000

2 beds

|

4 baths

|

3,610 sq ft

|

Condo

21 BIRKDALE LN 21, HOPKINTON, MA, 01748
Community: The Trails
Want to learn more about 55+ communities in Massachusetts? 55places can help!
Questions? Call us: (888) 625-4885
Northwoods at Sudbury 10 NORTHWOOD DR 301, SUDBURY, MA, 01776, Sudbury, MA 01776
$649,000

1 beds

|

2 baths

|

1,668 sq ft

|

Condo

10 NORTHWOOD DR 301, SUDBURY, MA, 01776
Sawyer's Reach 62 MARINERS WAY 210, PLYMOUTH, MA, 02360, Plymouth, MA 02360
$504,900

1 beds

|

2 baths

|

910 sq ft

|

Condo

62 MARINERS WAY 210, PLYMOUTH, MA, 02360
Community: Sawyer's Reach
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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© 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.
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This application does not include information on all of the properties available for sale at this time.

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