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Milton, MA 55+ active adult communities & homes for sale - Page 4

167 communities near Milton

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King's Landing
$300Ks - $400Ks
King's Landing, Kingston, NH
Resale Only | 55+ age-restricted | Built 2015 - 2017 | 44 homes
Forest Glen
$400Ks - $500Ks
Forest Glen, Uxbridge, MA
New Construction | 55+ age-restricted | Built 2018 - present | 44 homes
Seaside at Scituate - The...
$900Ks - $1Ms
Seaside at Scituate - The..., Scituate, MA
New Construction | 55+ age-restricted | Built 2019 - present | 44 homes
Duxbury Estates
$500Ks - $700Ks
Duxbury Estates, Duxbury, MA
Resale Only | 55+ age-restricted | Built 2008 - 2013 | 44 homes
Center Commons
$500Ks - $600Ks
Center Commons, Pembroke, MA
Resale Only | 55+ age-restricted | Built 2004 - 2009 | 44 homes
Want to learn more about 55+ communities in Milton? 55places can help!
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Northwoods at Sudbury
$600Ks - $1Ms
Northwoods at Sudbury, Sudbury, MA
Resale Only | 55+ age-restricted | Built 1999 - 2019 | 43 homes
North Meadow Village
$500Ks - $800Ks
North Meadow Village, Middleton, MA
Resale Only | 55+ age-restricted | Built 2012 - 2015 | 42 homes
Pine Creek
$300Ks
Pine Creek, Litchfield, NH
Resale Only | 55+ age-restricted | Built 2007 - 2014 | 42 homes
Webster Woods
$300Ks - $400Ks
Webster Woods, Hooksett, NH
Resale Only | 55+ age-restricted | Built 2005 - 2007 | 41 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.
Bigelow Farm
$500Ks - $600Ks
Bigelow Farm, Northborough, MA
Resale Only | 55+ age-restricted | Built 2006 - 2013 | 41 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.
Donovan Farm
$500Ks - $700Ks
Donovan Farm, Norwell, MA
Resale Only | 55+ age-restricted | Built 2001 - 2003 | 40 homes
Buttrick Village
$400Ks - $500Ks
Buttrick Village, Londonderry, NH
Resale Only | 55+ age-restricted | Built 1997 - 2000 | 40 homes
Whispering Winds
$300Ks - $700Ks
Whispering Winds, Windham, NH
Resale Only | 55+ age-restricted | Built 2001 - 2001 | 40 homes
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The Villages of Pelham
$300Ks - $400Ks
The Villages of Pelham, Pelham, NH
Resale Only | 55+ age-restricted | Built 2016 - 2018 | 40 homes
Thompson's Preserve
$500Ks
Thompson's Preserve, Nashua, NH
Resale Only | 55+ age-restricted | Built 2019 - 2020 | 39 homes
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Spring Meadow
$700Ks
Spring Meadow, Hanover, MA
Resale Only | 55+ age-restricted | Built 2004 - 2007 | 39 homes
Tara Woods
$400Ks
Tara Woods, Plymouth, MA
Resale Only | 55+ age-restricted | Built 2007 - 2015 | 38 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.
Little Mill Woods
$300Ks - $400Ks
Little Mill Woods, Sandown, NH
Resale Only | 55+ age-restricted | Built 2005 - 2012 | 38 homes
Stone Sled Farm
$500Ks - $600Ks
Stone Sled Farm, Bow, NH
Resale Only | 55+ age-restricted | Built 2005 - 2013 | 38 homes
Brandywyne
$700Ks - $800Ks
Brandywyne, South Kingstown, RI
Resale Only | 55+ age-restricted | Built 2011 - 2013 | 37 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.
Parrish Hills
$300Ks - $500Ks
Parrish Hills, Londonderry, NH
Resale Only | 55+ age-restricted | Built 2001 - 2003 | 37 homes
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Questions? Call us: (857) 314-6642
Hayden Green
$500Ks
Hayden Green, Nashua, NH
Resale Only | 55+ age-restricted | Built 2013 - 2015 | 37 homes
Country Hills
$600Ks
Country Hills, East Kingston, NH
Resale Only | 55+ age-restricted | Built 2005 - 2005 | 36 homes
Bailey Brook
$600Ks - $700Ks
Bailey Brook, Middletown, RI
Resale Only | 55+ age-restricted | Built 2018 - 2024 | 36 homes
Benjamin Chase Mill
$400Ks - $500Ks
Benjamin Chase Mill, Derry, NH
Resale Only | 55+ age-restricted | Built 2005 - 2015 | 36 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.
Cranberry Grove
$200Ks - $300Ks
Cranberry Grove, Wareham, MA
Resale Only | 55+ age-restricted | Built 2001 - 2001 | 36 homes
Lexington Place
$400Ks
Lexington Place, Hudson, NH
Resale Only | 55+ age-restricted | Built 1999 - 1999 | 34 homes
Rowell Estates
$300Ks - $400Ks
Rowell Estates, Kingston, NH
Resale Only | 55+ age-restricted | Built 2004 - 2004 | 33 homes
Sugarplum Hill
$300Ks - $400Ks
Sugarplum Hill, Londonderry, NH
Resale Only | 55+ age-restricted | Built 2006 - 2012 | 33 homes
Peregrine Woods
$400Ks - $600Ks
Peregrine Woods, Marshfield, MA
Resale Only | 55+ age-restricted | Built 2002 - 2005 | 32 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.
The Cottages at Lebaron H...
$500Ks - $600Ks
The Cottages at Lebaron H..., Lakeville, MA
New Construction | 55+ age-restricted | Built 2019 - present | 32 homes
Brookside Village
$700Ks
Brookside Village, Walpole, MA
Resale Only | 55+ age-restricted | Built 2018 - 2018 | 30 homes
Rolling Green at Topsfiel...
$600Ks - $800Ks
Rolling Green at Topsfiel..., Topsfield, MA
Resale Only | 55+ age-restricted | Built 2014 - 2014 | 30 homes
Village at Oakwood
$600Ks - $700Ks
Village at Oakwood, Derry, NH
Resale Only | 55+ age-restricted | Built 2019 - 2021 | 30 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.
Brookedge Village Condomi...
$300Ks - $400Ks
Brookedge Village Condomi..., South Kingstown, RI
Resale Only | 55+ age-restricted | Built 2007 - 2007 | 28 homes
Want to learn more about 55+ rental communities in Milton? 55places can help!
Questions? Call us: (857) 314-6642
Mattapoisett Landing
$400Ks - $500Ks
Mattapoisett Landing, Mattapoisett, MA
Resale Only | 55+ age-restricted | Built 2012 - 2015 | 27 homes
Wyman Farms
$500Ks - $900Ks
Wyman Farms, Shrewsbury, MA
New Construction | 55+ age-restricted | Built 2017 - present | 26 homes
Del Ray Place
$700Ks - $800Ks
Del Ray Place, Windham, NH
New Construction | 55+ age-restricted | Built 2019 - present | 26 homes
Want to learn more about 55+ communities in Milton? 55places can help!
Questions? Call us: (857) 314-6642
The Cottages at Spruce Wo...
$400Ks - $500Ks
The Cottages at Spruce Wo..., Durham, NH
Resale Only | 55+ age-restricted | Built 1999 - 2014 | 25 homes
Woodcrest Run
$400Ks
Woodcrest Run, Sharon, MA
New Construction | 55+ age-restricted | Built 2019 - present | 25 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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