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

169 communities near Milton

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The Village at Northridge
$500ks - $600ks
The Village at Northridge, North Reading, MA
Resale Only | 55+ age-restricted | 56 homes
The Village at Shepley Hi...
$900ks
The Village at Shepley Hi..., Groton, MA
New and Resale | 55+ age-restricted | Built 2023 - present | 26 homes
Stone Castle Estates
$200ks - $600ks
Stone Castle Estates, Methuen, MA
Resale Only | 55+ age-restricted | Built 2005 - 2018 | 89 homes
English Commons at Topsfi...
$800ks - $900ks
English Commons at Topsfi..., Topsfield, MA
Resale Only | 55+ age-restricted | Built 2010 - 2014 | 49 homes
WestRidge
$700ks
WestRidge, Hudson, MA
Resale Only | 55+ age-restricted | Built 2009 - 2016 | 136 homes
Want to learn more about 55+ communities in Milton? 55places can help!
Questions? Call us: (857) 314-6642
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Regency at Assabet Ridge
$500ks - $600ks
Regency at Assabet Ridge, Marlborough, MA
Resale Only | 55+ age-restricted | Built 2010 - 2015 | 69 homes
Angell Brook Village
$300ks
Angell Brook Village, West Boylston, MA
Resale Only | 55+ age-restricted | Built 2005 - 2012 | 132 homes
Pheasant Hill
$300ks - $400ks
Pheasant Hill, Northborough, MA
Resale Only | 55+ age-restricted | Built 2005 - 2006 | 48 homes
Whitestone Village
$400ks - $500ks
Whitestone Village, Groveland, MA
Resale Only | 55+ age-restricted | Built 2002 - 2005 | 100 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.
Stonebridge Commons
$500ks
Stonebridge Commons, Hanson, MA
Resale Only | 55+ age-restricted | Built 2007 - 2018 | 121 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.
Red Mill Village
$400ks - $600ks
Red Mill Village, Norton, MA
Resale Only | 55+ age-restricted | Built 2012 - 2014 | 156 homes
Regency at Emerald Pines
$600ks - $900ks
Regency at Emerald Pines, Methuen, MA
Resale Only | 55+ age-restricted | Built 2015 - 2018 | 140 homes
The Village at Westminste...
$400ks - $500ks
The Village at Westminste..., Holden, MA
New and Resale | 55+ age-restricted | Built 2006 - present | 125 homes
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New England Commons
$200ks - $300ks
New England Commons, Webster, MA
New and Resale | 55+ age-restricted | Built 2005 - present | 100 homes
Blue Heron Pond
$500ks
Blue Heron Pond, Lancaster, MA
Resale Only | 55+ age-restricted | Built 2006 - 2014 | 58 homes
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Questions? Call us: (857) 314-6642
Adams Farm
$700ks - $800ks
Adams Farm, Shrewsbury, MA
Resale Only | 55+ age-restricted | Built 2005 - 2013 | 90 homes
Westbrook Crossing
$400ks - $500ks
Westbrook Crossing, Dedham, MA
Resale Only | 55+ age-restricted | Built 2003 - 2004 | 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.
Quail Ridge
$600ks - $700ks
Quail Ridge, Acton, MA
Resale Only | 55+ age-restricted | Built 2015 - present | 153 homes
Villages at Weathervane
$800ks - $1Ms
Villages at Weathervane, Weymouth, MA
Resale Only | 55+ age-restricted | Built 2003 - 2010 | 149 homes
Woodstone Crossing
$300ks - $400ks
Woodstone Crossing, Weymouth, MA
Resale Only | Age-targeted | Built 2015 - 2019 | 200 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.
Reading Woods
$400ks - $600ks
Reading Woods, Reading, MA
Resale Only | 55+ age-restricted | Built 2011 - 2016 | 424 homes
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Questions? Call us: (857) 314-6642
Holliston Woods
$500ks - $700ks
Holliston Woods, Holliston, MA
Resale Only | 55+ age-restricted | Built 2016 - 2018 | 66 homes
Summer Reach
$400ks - $500ks
Summer Reach, Plymouth, MA
Resale Only | 55+ age-restricted | Built 2017 - 2020 | 114 homes
The Villages at Crane Mea...
$400ks
The Villages at Crane Mea..., Marlborough, MA
Resale Only | 55+ age-restricted | Built 2001 - 2005 | 91 homes
The Village at Auburnvill...
$300ks - $400ks
The Village at Auburnvill..., Whitman, MA
Resale Only | 55+ age-restricted | Built 2004 - 2014 | 92 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.
The Seasons at Salisbury
$400ks - $500ks
The Seasons at Salisbury, Holden, MA
Resale Only | 55+ age-restricted | Built 2002 - 2006 | 91 homes
Duxbury Estates
$700ks - $800ks
Duxbury Estates, Duxbury, MA
Resale Only | 55+ age-restricted | Built 2008 - 2013 | 44 homes
Peregrine Woods
$400ks - $600ks
Peregrine Woods, Marshfield, MA
Resale Only | 55+ age-restricted | Built 2002 - 2005 | 32 homes
Tara Woods
$400ks
Tara Woods, Plymouth, MA
Resale Only | 55+ age-restricted | Built 2007 - 2015 | 38 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!
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.
Donovan Farm
$500ks - $700ks
Donovan Farm, Norwell, MA
Resale Only | 55+ age-restricted | Built 2001 - 2003 | 40 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
Balancing Rock
$500ks - $600ks
Balancing Rock, Holliston, MA
Resale Only | 55+ age-restricted | Built 2006 - 2008 | 49 homes
Bigelow Farm
$500ks - $600ks
Bigelow Farm, Northborough, MA
Resale Only | 55+ age-restricted | Built 2006 - 2013 | 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.
Chilton Park Village
$400ks
Chilton Park Village, Plymouth, MA
Resale Only | 55+ age-restricted | Built 2006 - 2015 | 25 homes
Want to learn more about 55+ rental communities in Milton? 55places can help!
Questions? Call us: (857) 314-6642
Cranberry Grove
$200ks - $300ks
Cranberry Grove, Wareham, MA
Resale Only | 55+ age-restricted | Built 2001 - 2001 | 36 homes
Kensington at The Pinehil...
$500ks
Kensington at The Pinehil..., Plymouth, MA
New Construction | Age-targeted | Built 2017 - present | 17 homes
Arbor Hills
$400ks - $500ks
Arbor Hills, Kingston, MA
Resale Only | 55+ age-restricted | Built 2003 - 2005 | 54 homes
Want to learn more about 55+ 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
North Meadow Village
$500ks - $800ks
North Meadow Village, Middleton, MA
Resale Only | 55+ age-restricted | Built 2012 - 2015 | 42 homes
New Great Island 4 WOODSONG, PLYMOUTH, MA, 02360, Plymouth, MA 02360
$975,000

2 beds

|

2 baths

|

2,113 sq ft

|

House

4 WOODSONG, PLYMOUTH, MA, 02360
Community: Great Island
New Orchard Hill 14 GILMORE FARM RD 14, WESTBOROUGH, MA, ..., Westborough, MA 01581
$739,900

2 beds

|

3 baths

|

3,325 sq ft

|

Condo

14 GILMORE FARM RD 14, WESTBOROUGH, MA, ...
Community: Orchard Hill
New Riverside Woods 2 FRANCIS DR 405, ANDOVER, MA, 01810, Andover, MA 01810
$549,900

2 beds

|

2 baths

|

1,135 sq ft

|

Condo

2 FRANCIS DR 405, ANDOVER, MA, 01810
Community: Riverside Woods
New Orchard Hill 14 BALDWIN CT 14, WESTBOROUGH, MA, 01581, Westborough, MA 01581
$730,000

2 beds

|

3 baths

|

2,225 sq ft

|

Condo

14 BALDWIN CT 14, WESTBOROUGH, MA, 01581
Community: Orchard Hill
New Riverside Woods 2 FRANCIS DR 301, ANDOVER, MA, 01810, Andover, MA 01810
$599,900

2 beds

|

2 baths

|

1,490 sq ft

|

Condo

2 FRANCIS DR 301, ANDOVER, MA, 01810
Community: Riverside Woods
Want to learn more about 55+ communities in Milton? 55places can help!
Questions? Call us: (857) 314-6642
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Questions? Call us: (857) 314-6642
New Del Webb Chauncy Lake 6312 PETERS FARM WAY 6312, WESTBOROUGH, ..., Westborough, MA 01581
$645,000

2 beds

|

2 baths

|

1,469 sq ft

|

Condo

6312 PETERS FARM WAY 6312, WESTBOROUGH, ...
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
New 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
Del Webb Chauncy Lake 1411 PETERS FARM WAY 1411, WESTBOROUGH, ..., Westborough, MA 01581
$575,000

2 beds

|

2 baths

|

1,326 sq ft

|

Condo

1411 PETERS FARM WAY 1411, WESTBOROUGH, ...
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 16 GREY HAWK DR 16, MASHPEE, MA, 02649, Mashpee, MA 02649
$639,000

2 beds

|

3 baths

|

1,416 sq ft

|

Condo

16 GREY HAWK DR 16, MASHPEE, MA, 02649
Community: Southport
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.
Sawyer's Reach 51 MARINERS WAY 51, PLYMOUTH, MA, 02360, Plymouth, MA 02360
$850,000

2 beds

|

3 baths

|

1,871 sq ft

|

Condo

51 MARINERS WAY 51, PLYMOUTH, MA, 02360
Community: Sawyer's Reach
Martins Landing 300 MARTINS LNDG 505, NORTH READING, MA,..., North Reading, MA 01864
$650,000

2 beds

|

2 baths

|

1,221 sq ft

|

Condo

300 MARTINS LNDG 505, NORTH READING, MA,...
Community: Martins Landing
Martins Landing 260 MARTINS LNDG 102, NORTH READING, MA,..., North Reading, MA 01864
$569,900

1 beds

|

1 baths

|

1,027 sq ft

|

Condo

260 MARTINS LNDG 102, NORTH READING, MA,...
Community: Martins Landing
Want to learn more about 55+ communities in Milton? 55places can help!
Questions? Call us: (857) 314-6642
Woodcrest Run 635 OLD POST RD 2-203, SHARON, MA, 02067, Sharon, MA 02067
$499,900

2 beds

|

2 baths

|

1,056 sq ft

|

Condo

635 OLD POST RD 2-203, SHARON, MA, 02067
Community: Woodcrest Run
Bates Quarry 10 WEATHERVANE DR 20, WALPOLE, MA, 02081, Walpole, MA 02081
$864,999

2 beds

|

3 baths

|

2,301 sq ft

|

House

10 WEATHERVANE DR 20, WALPOLE, MA, 02081
Community: Bates Quarry
Want to learn more about 55+ rental communities in Milton? 55places can help!
Questions? Call us: (857) 314-6642
Del Webb Chauncy Lake 1109 PETERS FARM WAY 1109, WESTBOROUGH, ..., Westborough, MA 01581
$449,000

1 beds

|

1 baths

|

1,030 sq ft

|

Condo

1109 PETERS FARM WAY 1109, WESTBOROUGH, ...
Martins Landing 320 MARTINS LNDG 310, NORTH READING, MA,..., North Reading, MA 01864
$604,995

1 beds

|

1 baths

|

1,129 sq ft

|

Condo

320 MARTINS LNDG 310, 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.
Martins Landing 320 MARTINS LNDG 211, NORTH READING, MA,..., North Reading, MA 01864
$576,995

1 beds

|

1 baths

|

1,027 sq ft

|

Condo

320 MARTINS LNDG 211, NORTH READING, MA,...
Community: Martins Landing
Harmony Place 15 FIDELITY DR 70, RUTLAND, MA, 01543, Rutland, MA 01543
$489,000

2 beds

|

2 baths

|

1,447 sq ft

|

Condo

15 FIDELITY DR 70, RUTLAND, MA, 01543
Community: Harmony Place
Harmony Place 4 FIDELITY DR 2, RUTLAND, MA, 01543, Rutland, MA 01543
$498,000

2 beds

|

2 baths

|

1,582 sq ft

|

Condo

4 FIDELITY DR 2, RUTLAND, MA, 01543
Community: Harmony Place
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 Preserve at Hunters Hill R42 CLUBHOUSE DR R42, DIGHTON, MA, 02715, Dighton, MA 02715
$709,900

2 beds

|

2 baths

|

1,775 sq ft

|

House

R42 CLUBHOUSE DR R42, DIGHTON, MA, 02715
Want to learn more about 55+ communities in Milton? 55places can help!
Questions? Call us: (857) 314-6642
Summer Reach 40 DANFORTH LN 40, PLYMOUTH, MA, 02360, Plymouth, MA 02360
$795,000

2 beds

|

3 baths

|

1,848 sq ft

|

Condo

40 DANFORTH LN 40, PLYMOUTH, MA, 02360
Community: Summer Reach
Sawyer's Reach 62 MARINERS WAY 301, PLYMOUTH, MA, 02360, Plymouth, MA 02360
$675,000

2 beds

|

2 baths

|

1,386 sq ft

|

Condo

62 MARINERS WAY 301, PLYMOUTH, MA, 02360
Community: Sawyer's Reach
Willis Brook at Lynnfield 1 STABLEOFORD CT 13, LYNNFIELD, MA, 0194..., Lynnfield, MA 01940
$1,499,000

2 beds

|

2 baths

|

1,900 sq ft

|

Condo

1 STABLEOFORD CT 13, LYNNFIELD, MA, 0194...
Regency at Glen Ellen 124 GLEN ELLEN BLVD 124, MILLIS, MA, 020..., Millis, MA 02054
$1,150,000

2 beds

|

2 baths

|

1,797 sq ft

|

Condo

124 GLEN ELLEN BLVD 124, MILLIS, MA, 020...
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.
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
Rockwood Meadows 63 ROCKWOOD LN 63, UPTON, MA, 01568, Upton, MA 01568
$949,900

2 beds

|

3 baths

|

2,392 sq ft

|

Condo

63 ROCKWOOD LN 63, UPTON, MA, 01568
Community: Rockwood Meadows
Sawyer's Reach 1 MARINERS WAY 204, PLYMOUTH, MA, 02360, Plymouth, MA 02360
$580,000

1 beds

|

2 baths

|

1,113 sq ft

|

Condo

1 MARINERS WAY 204, PLYMOUTH, MA, 02360
Community: Sawyer's Reach
Del Webb Chauncy Lake 5 PETERS FARM WAY 107, WESTBOROUGH, MA, ..., Westborough, MA 01581
$649,995

2 beds

|

2 baths

|

1,512 sq ft

|

Condo

5 PETERS FARM WAY 107, WESTBOROUGH, MA, ...
Martins Landing 320 MARTINS LANDING WAY 502, NORTH READI..., North Reading, MA 01864
$549,995

1 beds

|

1 baths

|

1,027 sq ft

|

Condo

320 MARTINS LANDING WAY 502, NORTH READI...
Community: Martins Landing
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.
Martins Landing 320 MARTINS LNDG 2410, NORTH READING, MA..., North Reading, MA 01864
$724,995

2 beds

|

2 baths

|

1,450 sq ft

|

Condo

320 MARTINS LNDG 2410, NORTH READING, MA...
Community: Martins Landing
Bates Quarry 3 WEATHERVANE DR 1, WALPOLE, MA, 02081, Walpole, MA 02081
$998,069

2 beds

|

3 baths

|

2,144 sq ft

|

Condo

3 WEATHERVANE DR 1, WALPOLE, MA, 02081
Community: Bates Quarry
Del Webb Chauncy Lake 5 PETERS FARM WAY 201, WESTBOROUGH, MA, ..., Westborough, MA 01581
$674,995

2 beds

|

2 baths

|

1,496 sq ft

|

Condo

5 PETERS FARM WAY 201, WESTBOROUGH, MA, ...
The Village at Orchard Meadows 47 ORCHARD MEADOW DR 47, SHREWSBURY, MA,..., Shrewsbury, MA 01545
$525,000

2 beds

|

2 baths

|

1,370 sq ft

|

Condo

47 ORCHARD MEADOW DR 47, SHREWSBURY, MA,...
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.
Seton Highlands at The Pinehills 18 ABERDEEN 18, PLYMOUTH, MA, 02360, Plymouth, MA 02360
$879,900

2 beds

|

3 baths

|

4,054 sq ft

|

Condo

18 ABERDEEN 18, PLYMOUTH, MA, 02360
Want to learn more about 55+ rental communities in Milton? 55places can help!
Questions? Call us: (857) 314-6642
Del Webb Chauncy Lake 2306 TALBOT WAY 2306, WESTBOROUGH, MA, 0..., Westborough, MA 01581
$599,000

2 beds

|

2 baths

|

1,469 sq ft

|

Condo

2306 TALBOT WAY 2306, WESTBOROUGH, MA, 0...
30 Coppersmith 30 COPPERSMITH WAY # 309, CANTON, MA, 02..., Canton, MA 02021
$560,995

1 beds

|

1 baths

|

1,119 sq ft

|

Condo

30 COPPERSMITH WAY # 309, CANTON, MA, 02...
Community: 30 Coppersmith
30 Coppersmith 30 COPPERSMITH WAY 506, CANTON, MA, 0202..., Canton, MA 02021
$865,915

2 beds

|

2 baths

|

1,582 sq ft

|

Condo

30 COPPERSMITH WAY 506, CANTON, MA, 0202...
Community: 30 Coppersmith
Want to learn more about 55+ communities in Milton? 55places can help!
Questions? Call us: (857) 314-6642
Del Webb Chauncy Lake 5 PETERS FARM WAY 111, WESTBOROUGH, MA, ..., Westborough, MA 01581
$469,995

1 beds

|

1 baths

|

1,030 sq ft

|

Condo

5 PETERS FARM WAY 111, WESTBOROUGH, MA, ...
Preserve at Emerald Pines 40 PHOEBE ST 101, METHUEN, MA, 01844, Methuen, MA 01844
$859,900

3 beds

|

3 baths

|

2,654 sq ft

|

Condo

40 PHOEBE ST 101, METHUEN, MA, 01844

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