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Milton, MA 55+ active adult communities & homes for sale - Page 3

167 communities near Milton

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Forest Hills of Londonder...
$400Ks
Forest Hills of Londonder..., Londonderry, NH
Resale Only | 55+ age-restricted | Built 2001 - 2006 | 65 homes
Clearwater Estates
$300Ks - $400Ks
Clearwater Estates, Raymond, NH
Resale Only | 55+ age-restricted | Built 2005 - 2019 | 64 homes
Enclave at Hudson
$800Ks - $1Ms
Enclave at Hudson, Hudson, MA
New Construction | 55+ age-restricted | Built 2021 - present | 64 homes
30 Coppersmith
$400Ks - $800Ks
30 Coppersmith, Canton, MA
New Construction | 55+ age-restricted | Built 2025 - present | 63 homes
Sawyer Green
$400Ks - $500Ks
Sawyer Green, Dover, NH
Resale Only | 55+ age-restricted | Built 2009 - 2013 | 62 homes
Want to learn more about 55+ communities in Milton? 55places can help!
Questions? Call us: (857) 314-6642
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Hadleigh Woods
$300Ks
Hadleigh Woods, Windham, NH
Resale Only | 55+ age-restricted | Built 2003 - 2004 | 62 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
Rockland Glen
$300Ks - $500Ks
Rockland Glen, Rockland, MA
Resale Only | 55+ age-restricted | Built 2008 - 2015 | 60 homes
Northside Meadows
$600Ks - $700Ks
Northside Meadows, Framingham, MA
Resale Only | 55+ age-restricted | Built 2017 - 2019 | 60 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.
Westbrook Crossing
$400Ks - $500Ks
Westbrook Crossing, Dedham, MA
Resale Only | 55+ age-restricted | Built 2003 - 2004 | 60 homes
Read the Ultimate 55+ Rental Guide Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
The Village at Hollis Dep...
$300Ks
The Village at Hollis Dep..., Hollis, NH
Resale Only | 55+ age-restricted | Built 2003 - 2003 | 60 homes
Bay Ridge
$600Ks - $800Ks
Bay Ridge, Middletown, RI
Resale Only | 55+ age-restricted | Built 2008 - 2014 | 60 homes
Mission Pointe
$500Ks
Mission Pointe, Hudson, NH
Resale Only | 62+ age-restricted | Built 2006 - 2011 | 58 homes
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Rockwood Meadows
$600Ks - $700Ks
Rockwood Meadows, Upton, MA
New Construction | 55+ age-restricted | Built 2016 - present | 58 homes
Blue Heron Pond
$400Ks - $500Ks
Blue Heron Pond, Lancaster, MA
Resale Only | 55+ age-restricted | Built 2006 - 2014 | 58 homes
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Annandale on The River
$500Ks - $600Ks
Annandale on The River, Litchfield, NH
Resale Only | 55+ age-restricted | Built 2009 - 2011 | 57 homes
The Village at Northridge
$500Ks - $600Ks
The Village at Northridge, North Reading, MA
Resale Only | 55+ age-restricted | 56 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.
Liberty Woods
$600Ks - $700Ks
Liberty Woods, Hanson, MA
New Construction | 55+ age-restricted | Built 2023 - present | 56 homes
Rollins Hill
$500Ks - $700Ks
Rollins Hill, Stratham, NH
Resale Only | 55+ age-restricted | Built 2017 - 2021 | 55 homes
Arbor Hills
$400Ks - $500Ks
Arbor Hills, Kingston, MA
Resale Only | 55+ age-restricted | Built 2003 - 2005 | 54 homes
Read the Ultimate 55+ Rental Guide Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
Trail Ridge at Harvard
$700Ks
Trail Ridge at Harvard, Harvard, MA
Resale Only | 55+ age-restricted | Built 2008 - 2023 | 52 homes
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Silver Lake Estates
$700Ks - $800Ks
Silver Lake Estates, Hollis, NH
Resale Only | 55+ age-restricted | Built 2019 - 2022 | 52 homes
Souhegan River View Villa...
$400Ks - $500Ks
Souhegan River View Villa..., Merrimack, NH
Resale Only | 55+ age-restricted | Built 2001 - 2006 | 51 homes
The Elms of Hanover
$500Ks - $700Ks
The Elms of Hanover, Hanover, MA
Resale Only | 55+ age-restricted | Built 2003 - 2004 | 51 homes
Leddy Fields
$400Ks - $600Ks
Leddy Fields, Epping, NH
Resale Only | 55+ age-restricted | Built 2005 - 2014 | 50 homes
Want to learn more about 55+ rental communities in Milton? 55places can help!
Questions? Call us: (857) 314-6642
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.
Lamplighter Estates
$200Ks - $300Ks
Lamplighter Estates, Kingston, NH
Resale Only | 55+ age-restricted | Built 2001 - 2003 | 50 homes
5 rating (1 reviews) Canberra Village
$400Ks - $500Ks
Canberra Village, Litchfield, NH
Resale Only | 55+ age-restricted | Built 2004 - 2005 | 49 homes
Cahill Place
$200Ks
Cahill Place, Milford, NH
Resale Only | 55+ age-restricted | Built 2006 - 2006 | 49 homes
English Commons at Topsfi...
$800Ks - $900Ks
English Commons at Topsfi..., Topsfield, MA
Resale Only | 55+ age-restricted | Built 2010 - 2014 | 49 homes
Balancing Rock
$500Ks - $600Ks
Balancing Rock, Holliston, MA
Resale Only | 55+ age-restricted | Built 2006 - 2008 | 49 homes
Want to learn more about 55+ communities in Milton? 55places can help!
Questions? Call us: (857) 314-6642
Read the Ultimate 55+ Rental Guide Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
Pheasant Hill
$300Ks - $400Ks
Pheasant Hill, Northborough, MA
Resale Only | 55+ age-restricted | Built 2005 - 2006 | 48 homes
Mill Pond Crossing
$300Ks - $400Ks
Mill Pond Crossing, Brentwood, NH
Resale Only | 55+ age-restricted | Built 2008 - 2013 | 47 homes
Gilcreast Farms
$300Ks
Gilcreast Farms, Litchfield, NH
Resale Only | 55+ age-restricted | Built 2003 - 2005 | 47 homes
Prescott Crossing
$400Ks
Prescott Crossing, Raymond, NH
Resale Only | 55+ age-restricted | Built 2003 - 2004 | 46 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.
Stone Bridge Estates of S...
$600Ks
Stone Bridge Estates of S..., Salem, NH
Resale Only | 55+ age-restricted | Built 2015 - 2020 | 46 homes
Want to learn more about 55+ rental communities in Milton? 55places can help!
Questions? Call us: (857) 314-6642
Rolling Mill
$600Ks - $700Ks
Rolling Mill, Plymouth, MA
Resale Only | 55+ age-restricted | Built 2018 - 2021 | 46 homes
Runnells Landing
$300Ks
Runnells Landing, Hollis, NH
Resale Only | 55+ age-restricted | Built 2002 - 2004 | 45 homes
Harvest Village
$300Ks - $400Ks
Harvest Village, Londonderry, NH
Resale Only | 55+ age-restricted | Built 1995 - 1999 | 45 homes
Want to learn more about 55+ communities in Milton? 55places can help!
Questions? Call us: (857) 314-6642
Cohas Landing
$300Ks
Cohas Landing, Londonderry, NH
Resale Only | 55+ age-restricted | Built 1991 - 1997 | 44 homes
Braemoor Commons
$300Ks - $400Ks
Braemoor Commons, Salem, NH
Resale Only | 55+ age-restricted | Built 2014 - 2015 | 44 homes
New 30 Coppersmith 30 COPPERSMITH WAY # 408, CANTON, MA, 02..., Canton, MA 02021
$622,995

2 beds

|

2 baths

|

1,425 sq ft

|

Condo

30 COPPERSMITH WAY # 408, CANTON, MA, 02...
Community: 30 Coppersmith
Oak Point 3402 ISLAND DR, MIDDLEBORO, MA, 02346, Middleboro, MA 02346
$349,900

3 beds

|

2 baths

|

1,344 sq ft

|

House

3402 ISLAND DR, MIDDLEBORO, MA, 02346
Community: Oak Point
Southport 10 KETTLE LN # 10, MASHPEE, MA, 02649, Mashpee, MA 02649
$535,000

2 beds

|

3 baths

|

1,685 sq ft

|

Condo

10 KETTLE LN # 10, MASHPEE, MA, 02649
Community: Southport
Southport 181 LEISURE GREEN DR # 181, MASHPEE, MA,..., Mashpee, MA 02649
$449,000

2 beds

|

2 baths

|

1,338 sq ft

|

Condo

181 LEISURE GREEN DR # 181, MASHPEE, MA,...
Community: Southport
Del Webb Chauncy Lake 11101 PETERS FARM WAY # 101, WESTBOROUGH..., Westborough, MA 01581
$599,000

2 beds

|

2 baths

|

1,469 sq ft

|

Condo

11101 PETERS FARM WAY # 101, WESTBOROUGH...
Want to learn more about 55+ communities in Milton? 55places can help!
Questions? Call us: (857) 314-6642
Want to learn more about 55+ rental communities in Milton? 55places can help!
Questions? Call us: (857) 314-6642
Southport 15 PEBBLE BEACH AVE # 2005-103, MASHPEE,..., Mashpee, MA 02649
$549,000

2 beds

|

3 baths

|

1,685 sq ft

|

Condo

15 PEBBLE BEACH AVE # 2005-103, MASHPEE,...
Community: Southport
Millwood Preserve 9 HAWK LN # 28, FRAMINGHAM, MA, 01701, Framingham, MA 01701
$1,175,000

2 beds

|

3 baths

|

2,306 sq ft

|

Condo

9 HAWK LN # 28, FRAMINGHAM, MA, 01701
Community: Millwood Preserve
New Del Webb Chauncy Lake 2 CODMAN WAY 408, WESTBOROUGH, MA, 01581, Westborough, MA 01581
$589,999

2 beds

|

2 baths

|

1,375 sq ft

|

Condo

2 CODMAN WAY 408, WESTBOROUGH, MA, 01581
New Tara Woods 6 STERLING BLVD # 6, PLYMOUTH, MA, 02360, Plymouth, MA 02360
$680,000

2 beds

|

2 baths

|

1,500 sq ft

|

Condo

6 STERLING BLVD # 6, PLYMOUTH, MA, 02360
Community: Tara Woods
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.
30 Coppersmith 30 COPPERSMITH WAY # 301, CANTON, MA, 02..., Canton, MA 02021
$733,995

2 beds

|

2 baths

|

1,582 sq ft

|

Condo

30 COPPERSMITH WAY # 301, CANTON, MA, 02...
Community: 30 Coppersmith
Read the Ultimate 55+ Rental Guide Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
Southport 23 SEA SPRAY AVE # 563, MASHPEE, MA, 026..., Mashpee, MA 02649
$759,000

2 beds

|

4 baths

|

2,455 sq ft

|

Condo

23 SEA SPRAY AVE # 563, MASHPEE, MA, 026...
Community: Southport
New 30 Coppersmith 30 COPPERSMITH WAY # 207, CANTON, MA, 02..., Canton, MA 02021
$692,995

2 beds

|

2 baths

|

1,582 sq ft

|

Condo

30 COPPERSMITH WAY # 207, CANTON, MA, 02...
Community: 30 Coppersmith
30 Coppersmith 30 COPPERSMITH WAY # 103, CANTON, MA, 02..., Canton, MA 02021
$496,550

1 beds

|

1 baths

|

1,027 sq ft

|

Condo

30 COPPERSMITH WAY # 103, CANTON, MA, 02...
Community: 30 Coppersmith
Want to learn more about 55+ communities in Milton? 55places can help!
Questions? Call us: (857) 314-6642
New Del Webb Chauncy Lake 4 PETERS FARM WAY # 203, WESTBOROUGH, MA..., Westborough, MA 01581
$470,000

1 beds

|

1 baths

|

945 sq ft

|

Condo

4 PETERS FARM WAY # 203, WESTBOROUGH, MA...
Seton Highlands at The Pinehills 17 ABERDEEN # 17, PLYMOUTH, MA, 02360, Plymouth, MA 02360
$949,000

3 beds

|

3 baths

|

2,690 sq ft

|

Condo

17 ABERDEEN # 17, PLYMOUTH, MA, 02360
Want to learn more about 55+ rental communities in Milton? 55places can help!
Questions? Call us: (857) 314-6642
Great Island 16 REBECCAS LNDG # 16, PLYMOUTH, MA, 023..., Plymouth, MA 02360
$799,000

2 beds

|

2 baths

|

1,814 sq ft

|

Condo

16 REBECCAS LNDG # 16, PLYMOUTH, MA, 023...
Community: Great Island
New Harmony Place 10 FIDELITY DR # 5, RUTLAND, MA, 01543, Rutland, MA 01543
$498,000

2 beds

|

2 baths

|

1,582 sq ft

|

Condo

10 FIDELITY DR # 5, RUTLAND, MA, 01543
Community: Harmony Place
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.
Harmony Place 12 FIDELITY DR # 6, RUTLAND, MA, 01543, Rutland, MA 01543
$498,000

2 beds

|

2 baths

|

1,582 sq ft

|

Condo

12 FIDELITY DR # 6, RUTLAND, MA, 01543
Community: Harmony Place
New Harmony Place 210 FIDELITY DR 84, RUTLAND, MA, 01543, Rutland, MA 01543
$498,000

2 beds

|

2 baths

|

1,582 sq ft

|

Condo

210 FIDELITY DR 84, RUTLAND, MA, 01543
Community: Harmony Place
Center Commons 29 LIBERTY DR # 29, PEMBROKE, MA, 02359, Pembroke, MA 02359
$619,900

2 beds

|

3 baths

|

1,966 sq ft

|

Condo

29 LIBERTY DR # 29, PEMBROKE, MA, 02359
Community: Center Commons
Read the Ultimate 55+ Rental Guide Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
Martins Landing 320 MARTINS LNDG APT 210, NORTH READING,..., North Reading, MA 01864
$594,995

1 beds

|

1 baths

|

1,129 sq ft

|

Condo

320 MARTINS LNDG APT 210, NORTH READING,...
Community: Martins Landing
Want to learn more about 55+ communities in Milton? 55places can help!
Questions? Call us: (857) 314-6642
Martins Landing 320 MARTINS LNDG 410, NORTH READING, MA,..., North Reading, MA 01864
$734,995

2 beds

|

2 baths

|

1,450 sq ft

|

Condo

320 MARTINS LNDG 410, NORTH READING, MA,...
Community: Martins Landing
Martins Landing 320 MARTINS LNDG 107, NORTH READING, MA,..., North Reading, MA 01864
$749,995

2 beds

|

2 baths

|

1,579 sq ft

|

Condo

320 MARTINS LNDG 107, NORTH READING, MA,...
Community: Martins Landing
New Martins Landing 320 MARTINS LNDG 401, NORTH READING, MA,..., North Reading, MA 01864
$849,999

2 beds

|

2 baths

|

1,586 sq ft

|

Condo

320 MARTINS LNDG 401, NORTH READING, MA,...
Community: Martins Landing
The Villages at Crane Meadow 11 WHISPERING BROOK RD # 55, MARLBOROUGH..., Marlborough, MA 01752
$569,900

2 beds

|

3 baths

|

1,830 sq ft

|

Condo

11 WHISPERING BROOK RD # 55, MARLBOROUGH...
Want to learn more about 55+ rental communities in Milton? 55places can help!
Questions? Call us: (857) 314-6642
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 Del Webb Chauncy Lake 5 PETERS FARM WAY # 207, WESTBOROUGH, MA..., Westborough, MA 01581
$706,855

2 beds

|

2 baths

|

1,512 sq ft

|

Condo

5 PETERS FARM WAY # 207, WESTBOROUGH, MA...
New Del Webb Chauncy Lake 5 PETERS FARM WAY # 5205, WESTBOROUGH, M..., Westborough, MA 01581
$603,795

2 beds

|

2 baths

|

1,166 sq ft

|

Condo

5 PETERS FARM WAY # 5205, WESTBOROUGH, M...
New Del Webb Chauncy Lake 5 PETERS FARM WAY # 101, WESTBOROUGH, MA..., Westborough, MA 01581
$680,285

2 beds

|

2 baths

|

1,496 sq ft

|

Condo

5 PETERS FARM WAY # 101, WESTBOROUGH, MA...
The Trails 71 WESTON LN # 71, HOPKINTON, MA, 01748, Hopkinton, MA 01748
$1,025,000

2 beds

|

4 baths

|

3,258 sq ft

|

Condo

71 WESTON LN # 71, HOPKINTON, MA, 01748
Community: The Trails
The Trails 30 WATERVILLE LN # 30, HOPKINTON, MA, 01..., Hopkinton, MA 01748
$1,199,000

2 beds

|

3 baths

|

2,510 sq ft

|

Condo

30 WATERVILLE LN # 30, HOPKINTON, MA, 01...
Community: The Trails
Want to learn more about 55+ communities in Milton? 55places can help!
Questions? Call us: (857) 314-6642
Read the Ultimate 55+ Rental Guide Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
New Martins Landing 320 MARTINS LANDING WAY 102, NORTH READI..., North Reading, MA 01864
$499,999

1 beds

|

1 baths

|

1,027 sq ft

|

Condo

320 MARTINS LANDING WAY 102, NORTH READI...
Community: Martins Landing
New Martins Landing 320 MARTINS LNDG APT 209, NORTH READING,..., North Reading, MA 01864
$589,995

1 beds

|

1 baths

|

1,115 sq ft

|

Condo

320 MARTINS LNDG APT 209, NORTH READING,...
Community: Martins Landing
The Preserve at Hunters Hill 3051 CLUBHOUSE DR 78, DIGHTON, MA, 02715, Dighton, MA 02715
$829,225

2 beds

|

2 baths

|

2,266 sq ft

|

House

3051 CLUBHOUSE DR 78, DIGHTON, MA, 02715
The Villages at Walker Meadow 9 SHAKER WAY # 9, WESTBOROUGH, MA, 01581, Westborough, MA 01581
$700,000

2 beds

|

2 baths

|

2,090 sq ft

|

Condo

9 SHAKER WAY # 9, WESTBOROUGH, MA, 01581
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.
Southport 18 EXECUTIVE DR # 18, MASHPEE, MA, 02649, Mashpee, MA 02649
$450,000

2 beds

|

2 baths

|

1,338 sq ft

|

Condo

18 EXECUTIVE DR # 18, MASHPEE, MA, 02649
Community: Southport
Want to learn more about 55+ rental communities in Milton? 55places can help!
Questions? Call us: (857) 314-6642
Seton Highlands at The Pinehills 105 SETON HIGHLANDS # 105, PLYMOUTH, MA,..., Plymouth, MA 02360
$849,000

2 beds

|

3 baths

|

2,186 sq ft

|

Condo

105 SETON HIGHLANDS # 105, PLYMOUTH, MA,...
Southport 20 TWIN OAKS DR # 20, MASHPEE, MA, 02649, Mashpee, MA 02649
$524,900

2 beds

|

2 baths

|

1,491 sq ft

|

Condo

20 TWIN OAKS DR # 20, MASHPEE, MA, 02649
Community: Southport
Riverside Woods 4 FRANCIS DR 207, ANDOVER, MA, 01810, Andover, MA 01810
$620,000

2 beds

|

2 baths

|

1,490 sq ft

|

Condo

4 FRANCIS DR 207, ANDOVER, MA, 01810
Community: Riverside Woods
Want to learn more about 55+ communities in Milton? 55places can help!
Questions? Call us: (857) 314-6642
30 Coppersmith 50 COPPERSMITH WAY UNIT 211, CANTON, MA,..., Canton, MA 02021
$899,000

2 beds

|

2 baths

|

1,831 sq ft

|

Condo

50 COPPERSMITH WAY UNIT 211, CANTON, MA,...
Community: 30 Coppersmith
Regency at Glen Ellen 18 LANSING WAY # 18, MILLIS, MA, 02054, Millis, MA 02054
$799,000

2 beds

|

3 baths

|

2,306 sq ft

|

Condo

18 LANSING WAY # 18, MILLIS, MA, 02054

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