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

166 communities near Milton

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Seaside at Scituate - The...
$900Ks - $1Ms
Seaside at Scituate - The..., Scituate, MA
New Construction | 55+ age-restricted | Built 2019 - present | 44 homes
Forest Glen
$400Ks - $500Ks
Forest Glen, Uxbridge, MA
New Construction | 55+ age-restricted | Built 2018 - present | 44 homes
Center Commons
$500Ks - $600Ks
Center Commons, Pembroke, MA
Resale Only | 55+ age-restricted | Built 2004 - 2009 | 44 homes
Duxbury Estates
$500Ks - $700Ks
Duxbury Estates, Duxbury, MA
Resale Only | 55+ age-restricted | Built 2008 - 2013 | 44 homes
Northwoods at Sudbury
$600Ks - $1Ms
Northwoods at Sudbury, Sudbury, MA
Resale Only | 55+ age-restricted | Built 1999 - 2019 | 43 homes
Want to learn more about 55+ communities in Milton? 55places can help!
Questions? Call us: (857) 314-6642
North Meadow Village
$500Ks - $800Ks
North Meadow Village, Middleton, MA
Resale Only | 55+ age-restricted | Built 2012 - 2015 | 42 homes
Pine Creek
$300Ks - $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
Bigelow Farm
$500Ks - $600Ks
Bigelow Farm, Northborough, MA
Resale Only | 55+ age-restricted | Built 2006 - 2013 | 41 homes
Donovan Farm
$500Ks - $700Ks
Donovan Farm, Norwell, MA
Resale Only | 55+ age-restricted | Built 2001 - 2003 | 40 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.
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
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 - $500Ks
Thompson's Preserve, Nashua, NH
Resale Only | 55+ age-restricted | Built 2019 - 2020 | 39 homes
Spring Meadow
$700Ks - $700Ks
Spring Meadow, Hanover, MA
Resale Only | 55+ age-restricted | Built 2004 - 2007 | 39 homes
Want to learn more about 55+ communities in Milton? 55places can help!
Questions? Call us: (857) 314-6642
Tara Woods
$400Ks - $400Ks
Tara Woods, Plymouth, MA
Resale Only | 55+ age-restricted | Built 2007 - 2015 | 38 homes
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
Hayden Green
$500Ks - $500Ks
Hayden Green, Nashua, NH
Resale Only | 55+ age-restricted | Built 2013 - 2015 | 37 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.
Parrish Hills
$300Ks - $500Ks
Parrish Hills, Londonderry, NH
Resale Only | 55+ age-restricted | Built 2001 - 2003 | 37 homes
Country Hills
$600Ks
Country Hills, East Kingston, NH
Resale Only | 55+ age-restricted | Built 2005 - 2005 | 36 homes
Benjamin Chase Mill
$400Ks - $500Ks
Benjamin Chase Mill, Derry, NH
Resale Only | 55+ age-restricted | Built 2005 - 2015 | 36 homes
Bailey Brook
$600Ks - $700Ks
Bailey Brook, Middletown, RI
Resale Only | 55+ age-restricted | Built 2018 - 2024 | 36 homes
Cranberry Grove
$200Ks - $300Ks
Cranberry Grove, Wareham, MA
Resale Only | 55+ age-restricted | Built 2001 - 2001 | 36 homes
Want to learn more about 55+ communities in Milton? 55places can help!
Questions? Call us: (857) 314-6642
Lexington Place
$400Ks - $400Ks
Lexington Place, Hudson, NH
Resale Only | 55+ age-restricted | Built 1999 - 1999 | 34 homes
Sugarplum Hill
$300Ks - $400Ks
Sugarplum Hill, Londonderry, NH
Resale Only | 55+ age-restricted | Built 2006 - 2012 | 33 homes
Rowell Estates
$300Ks - $400Ks
Rowell Estates, Kingston, NH
Resale Only | 55+ age-restricted | Built 2004 - 2004 | 33 homes
Peregrine Woods
$400Ks - $600Ks
Peregrine Woods, Marshfield, MA
Resale Only | 55+ age-restricted | Built 2002 - 2005 | 32 homes
The Cottages at Lebaron H...
$500Ks - $600Ks
The Cottages at Lebaron H..., Lakeville, MA
New Construction | 55+ age-restricted | Built 2019 - present | 32 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.
Brookside Village
$700Ks - $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
Brookedge Village Condomi...
$300Ks - $400Ks
Brookedge Village Condomi..., South Kingstown, RI
Resale Only | 55+ age-restricted | Built 2007 - 2007 | 28 homes
Mattapoisett Landing
$400Ks - $500Ks
Mattapoisett Landing, Mattapoisett, MA
Resale Only | 55+ age-restricted | Built 2012 - 2015 | 27 homes
Want to learn more about 55+ communities in Milton? 55places can help!
Questions? Call us: (857) 314-6642
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
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 - $400Ks
Woodcrest Run, Sharon, MA
New Construction | 55+ age-restricted | Built 2019 - present | 25 homes
Chilton Park Village
$400Ks - $400Ks
Chilton Park Village, Plymouth, MA
Resale Only | 55+ age-restricted | Built 2006 - 2015 | 25 homes
Riverside Woods 4 FRANCIS DR 105, ANDOVER, MA, 01810, Andover, MA 01810
$454,900

1 beds

|

1 baths

|

945 sq ft

|

Condo

4 FRANCIS DR 105, ANDOVER, MA, 01810
Community: Riverside Woods
Southport 14 SANDVIEW TER # 14, MASHPEE, MA, 02649, Mashpee, MA 02649
$414,000

2 beds

|

2 baths

|

1,338 sq ft

|

Condo

14 SANDVIEW TER # 14, MASHPEE, MA, 02649
Community: Southport
Brierly Pond Village 92 HORNE WAY # 92, MILLBURY, MA, 01527, Millbury, MA 01527
$475,000

2 beds

|

2 baths

|

1,420 sq ft

|

Condo

92 HORNE WAY # 92, MILLBURY, MA, 01527
Southport 17 CHADWICK CT # 17, MASHPEE, MA, 02649, Mashpee, MA 02649
$615,000

2 beds

|

2 baths

|

2,325 sq ft

|

Condo

17 CHADWICK CT # 17, MASHPEE, MA, 02649
Community: Southport
Southport 12 KETTLE LN # 31, MASHPEE, MA, 02649, Mashpee, MA 02649
$495,000

2 beds

|

2 baths

|

1,606 sq ft

|

Condo

12 KETTLE LN # 31, MASHPEE, MA, 02649
Community: Southport
Want to learn more about 55+ communities in Milton? 55places can help!
Questions? Call us: (857) 314-6642
Southport 72 GREY HAWK DR # 670, MASHPEE, MA, 0264..., Mashpee, MA 02649
$649,000

2 beds

|

3 baths

|

2,283 sq ft

|

Condo

72 GREY HAWK DR # 670, MASHPEE, MA, 0264...
Community: Southport
Southport 37 PINE HILL BLVD # 30, MASHPEE, MA, 026..., Mashpee, MA 02649
$498,900

2 beds

|

2 baths

|

1,338 sq ft

|

Condo

37 PINE HILL BLVD # 30, MASHPEE, MA, 026...
Community: Southport
Southport 8 CHIPPERS LN # 390, MASHPEE, MA, 02649, Mashpee, MA 02649
$595,000

2 beds

|

3 baths

|

2,527 sq ft

|

Condo

8 CHIPPERS LN # 390, MASHPEE, MA, 02649
Community: Southport
30 Coppersmith 50 COPPERSMITH WAY UNIT 211, CANTON, MA,..., Canton, MA 02021
$949,000

2 beds

|

2 baths

|

1,831 sq ft

|

Condo

50 COPPERSMITH WAY UNIT 211, CANTON, MA,...
Community: 30 Coppersmith
Great Island 31 FOX HOLW, PLYMOUTH, MA, 02360, Plymouth, MA 02360
$719,000

3 beds

|

3 baths

|

2,074 sq ft

|

House

31 FOX HOLW, PLYMOUTH, MA, 02360
Community: Great Island
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 12 WEATHERVANE, PLYMOUTH, MA, 02360, Plymouth, MA 02360
$769,000

2 beds

|

2 baths

|

2,056 sq ft

|

House

12 WEATHERVANE, PLYMOUTH, MA, 02360
Community: Great Island
New Martins Landing 320 MARTINS LNDG APT 403, NORTH READING,..., North Reading, MA 01864
$583,970

1 beds

|

1 baths

|

1,027 sq ft

|

Condo

320 MARTINS LNDG APT 403, NORTH READING,...
Community: Martins Landing
New Great Island 19 RED LEAF, PLYMOUTH, MA, 02360, Plymouth, MA 02360
$765,000

2 beds

|

2 baths

|

1,534 sq ft

|

House

19 RED LEAF, PLYMOUTH, MA, 02360
Community: Great Island
Great Island 25 FOX HOLW, PLYMOUTH, MA, 02360, Plymouth, MA 02360
$699,000

2 beds

|

2 baths

|

1,529 sq ft

|

House

25 FOX HOLW, PLYMOUTH, MA, 02360
Community: Great Island
New Del Webb Chauncy Lake 5 PETERS FARM WAY # 106, WESTBOROUGH, MA..., Westborough, MA 01581
$649,995

2 beds

|

2 baths

|

1,496 sq ft

|

Condo

5 PETERS FARM WAY # 106, WESTBOROUGH, MA...
Want to learn more about 55+ communities in Milton? 55places can help!
Questions? Call us: (857) 314-6642
New Del Webb Chauncy Lake 5 PETERS FARM WAY # 105, WESTBOROUGH, MA..., Westborough, MA 01581
$409,999

1 beds

|

1 baths

|

958 sq ft

|

Condo

5 PETERS FARM WAY # 105, WESTBOROUGH, MA...
New Del Webb Chauncy Lake 2 CODMAN WAY 302, WESTBOROUGH, MA, 01581, Westborough, MA 01581
$389,999

1 beds

|

1 baths

|

972 sq ft

|

Condo

2 CODMAN WAY 302, WESTBOROUGH, MA, 01581
New Del Webb Chauncy Lake 5 PETERS FARM WAY # 212, WESTBOROUGH, MA..., Westborough, MA 01581
$512,995

1 beds

|

1 baths

|

1,058 sq ft

|

Condo

5 PETERS FARM WAY # 212, WESTBOROUGH, MA...
Brooksmont 133 BROOKSMONT DR # 43, HOLLISTON, MA, 0..., Holliston, MA 01746
$709,000

2 beds

|

3 baths

|

2,160 sq ft

|

Condo

133 BROOKSMONT DR # 43, HOLLISTON, MA, 0...
Community: Brooksmont
Garrison Place 1 GARRISON WAY # 1, CARLISLE, MA, 01741, Carlisle, MA 01741
$1,250,000

2 beds

|

4 baths

|

3,230 sq ft

|

House

1 GARRISON WAY # 1, CARLISLE, MA, 01741
Community: Garrison 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.
Regency at Glen Ellen 27 RICHARDSON DR # 27, MILLIS, MA, 02054, Millis, MA 02054
$974,900

2 beds

|

3 baths

|

2,485 sq ft

|

Condo

27 RICHARDSON DR # 27, MILLIS, MA, 02054
Del Webb Chauncy Lake 3102 PETERS FARM WAY # 102, WESTBOROUGH,..., Westborough, MA 01581
$375,000

1 beds

|

1 baths

|

956 sq ft

|

Condo

3102 PETERS FARM WAY # 102, WESTBOROUGH,...
Del Webb Chauncy Lake 2 CODMAN WAY 411, WESTBOROUGH, MA, 01581, Westborough, MA 01581
$599,999

2 beds

|

2 baths

|

1,375 sq ft

|

Condo

2 CODMAN WAY 411, WESTBOROUGH, MA, 01581
Brierly Pond Village 28 BRIERLY CIR # 28, MILLBURY, MA, 01527, Millbury, MA 01527
$519,900

2 beds

|

3 baths

|

2,080 sq ft

|

Condo

28 BRIERLY CIR # 28, MILLBURY, MA, 01527
Great Island 4 MILLERS JOIST, PLYMOUTH, MA, 02360, Plymouth, MA 02360
$725,000

3 beds

|

3 baths

|

2,573 sq ft

|

House

4 MILLERS JOIST, PLYMOUTH, MA, 02360
Community: Great Island
Want to learn more about 55+ communities in Milton? 55places can help!
Questions? Call us: (857) 314-6642
The Preserve at Hunters Hill 3035 CLUBHOUSE DR 4, DIGHTON, MA, 02715, Dighton, MA 02715
$699,900

2 beds

|

2 baths

|

1,775 sq ft

|

House

3035 CLUBHOUSE DR 4, DIGHTON, MA, 02715
The Preserve at Hunters Hill 3035 CLUBHOUSE DR 7, DIGHTON, MA, 02715, Dighton, MA 02715
$779,900

2 beds

|

2 baths

|

2,216 sq ft

|

House

3035 CLUBHOUSE DR 7, DIGHTON, MA, 02715
The Preserve at Hunters Hill 3035 CLUBHOUSE DR 6, DIGHTON, MA, 02715, Dighton, MA 02715
$759,900

2 beds

|

2 baths

|

2,097 sq ft

|

House

3035 CLUBHOUSE DR 6, DIGHTON, MA, 02715
The Preserve at Hunters Hill 3035 CLUBHOUSE DR 5, DIGHTON, MA, 02715, Dighton, MA 02715
$759,900

2 beds

|

2 baths

|

2,097 sq ft

|

House

3035 CLUBHOUSE DR 5, DIGHTON, MA, 02715
The Preserve at Hunters Hill 3035 CLUBHOUSE DR 2, DIGHTON, MA, 02715, Dighton, MA 02715
$739,900

2 beds

|

2 baths

|

1,928 sq ft

|

House

3035 CLUBHOUSE DR 2, DIGHTON, MA, 02715
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 Hill 3035 CLUBHOUSE DR 3, DIGHTON, MA, 02715, Dighton, MA 02715
$739,900

2 beds

|

2 baths

|

1,928 sq ft

|

House

3035 CLUBHOUSE DR 3, DIGHTON, MA, 02715
The Preserve at Hunters Hill 3035 CLUBHOUSE DR, DIGHTON, MA, 02715, Dighton, MA 02715
$699,900

2 beds

|

2 baths

|

1,775 sq ft

|

House

3035 CLUBHOUSE DR, DIGHTON, MA, 02715
The Preserve at Hunters Hill 3057 CLUB HOUSE DR, DIGHTON, MA, 02715, Dighton, MA 02715
$739,900

2 beds

|

2 baths

|

2,044 sq ft

|

House

3057 CLUB HOUSE DR, DIGHTON, MA, 02715
The Preserve at Hunters Hill 3035 CLUBHOUSE DR 1, DIGHTON, MA, 02715, Dighton, MA 02715
$699,900

2 beds

|

2 baths

|

1,775 sq ft

|

House

3035 CLUBHOUSE DR 1, DIGHTON, MA, 02715
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
Want to learn more about 55+ communities in Milton? 55places can help!
Questions? Call us: (857) 314-6642
The Preserve at Hunters Hill 3055 CLUB HOUSE DR # 80, DIGHTON, MA, 02..., Dighton, MA 02715
$743,175

2 beds

|

2 baths

|

1,775 sq ft

|

House

3055 CLUB HOUSE DR # 80, DIGHTON, MA, 02...
Great Island 27 CROSS WIND, PLYMOUTH, MA, 02360, Plymouth, MA 02360
$750,000

3 beds

|

3 baths

|

3,180 sq ft

|

House

27 CROSS WIND, PLYMOUTH, MA, 02360
Community: Great Island
Southport 44 TWIN OAKS DR # 44, MASHPEE, MA, 02649, Mashpee, MA 02649
$519,000

2 beds

|

2 baths

|

1,659 sq ft

|

Condo

44 TWIN OAKS DR # 44, MASHPEE, MA, 02649
Community: Southport
Forest Glen 100 SPRING HILL DR # 100, UXBRIDGE, MA, ..., Uxbridge, MA 01569
$574,900

2 beds

|

2 baths

|

1,694 sq ft

|

Condo

100 SPRING HILL DR # 100, UXBRIDGE, MA, ...
Community: Forest Glen
Great Island 24 WEBSTER REACH, PLYMOUTH, MA, 02360, Plymouth, MA 02360
$739,000

3 beds

|

3 baths

|

2,782 sq ft

|

House

24 WEBSTER REACH, PLYMOUTH, MA, 02360
Community: Great Island
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166 communities near Milton
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