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

167 communities near Middleton

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Lexington Place
$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
Bella Vista
$300ks - $400ks
Bella Vista, Glocester, RI
Resale Only | 55+ age-restricted | Built 2015 - 2021 | 70 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
Want to learn more about 55+ communities in Middleton? 55places can help!
Questions? Call us: (508) 715-6046
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
Stonebridge Commons
$500ks
Stonebridge Commons, Hanson, MA
Resale Only | 55+ age-restricted | Built 2007 - 2018 | 121 homes
Red Mill Village
$400ks - $600ks
Red Mill Village, Norton, MA
Resale Only | 55+ age-restricted | Built 2012 - 2014 | 156 homes
New England Commons
$200ks - $300ks
New England Commons, Webster, MA
New and Resale | 55+ age-restricted | Built 2005 - present | 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.
Blue Heron Pond
$500ks
Blue Heron Pond, Lancaster, MA
Resale Only | 55+ age-restricted | Built 2006 - 2014 | 58 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
Adams Farm
$700ks - $800ks
Adams Farm, Shrewsbury, MA
Resale Only | 55+ age-restricted | Built 2005 - 2013 | 90 homes
Villages at Weathervane
$800ks - $1Ms
Villages at Weathervane, Weymouth, MA
Resale Only | 55+ age-restricted | Built 2003 - 2010 | 149 homes
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
Want to learn more about 55+ communities in Middleton? 55places can help!
Questions? Call us: (508) 715-6046
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
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
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.
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
Donovan Farm
$500ks - $700ks
Donovan Farm, Norwell, MA
Resale Only | 55+ age-restricted | Built 2001 - 2003 | 40 homes
The Elms of Hanover
$500ks - $700ks
The Elms of Hanover, Hanover, MA
Resale Only | 55+ age-restricted | Built 2003 - 2004 | 51 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
Want to learn more about 55+ communities in Middleton? 55places can help!
Questions? Call us: (508) 715-6046
Chilton Park Village
$400ks
Chilton Park Village, Plymouth, MA
Resale Only | 55+ age-restricted | Built 2006 - 2015 | 25 homes
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
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.
Arbor Hills
$400ks - $500ks
Arbor Hills, Kingston, MA
Resale Only | 55+ age-restricted | Built 2003 - 2005 | 54 homes
Mattapoisett Landing
$400ks - $500ks
Mattapoisett Landing, Mattapoisett, MA
Resale Only | 55+ age-restricted | Built 2012 - 2015 | 27 homes
Hatter's Point
$600ks - $700ks
Hatter's Point, Amesbury, MA
Resale Only | 55+ age-restricted | Built 2004 - 2017 | 88 homes
Rockwood Meadows
$600ks - $700ks
Rockwood Meadows, Upton, MA
New Construction | 55+ age-restricted | Built 2016 - present | 58 homes
Rolling Green at Topsfiel...
$600ks - $800ks
Rolling Green at Topsfiel..., Topsfield, MA
Resale Only | 55+ age-restricted | Built 2014 - 2014 | 30 homes
Spring Meadow
$400ks - $500ks
Spring Meadow, Hanover, MA
Resale Only | 55+ age-restricted | Built 2004 - 2007 | 39 homes
Rockland Glen
$300ks - $500ks
Rockland Glen, Rockland, MA
Resale Only | 55+ age-restricted | Built 2008 - 2015 | 60 homes
Forest Glen
$400ks - $500ks
Forest Glen, Uxbridge, MA
New Construction | 55+ age-restricted | Built 2018 - present | 44 homes
Want to learn more about 55+ communities in Middleton? 55places can help!
Questions? Call us: (508) 715-6046
Trail Ridge at Harvard
$700ks
Trail Ridge at Harvard, Harvard, MA
Resale Only | 55+ age-restricted | Built 2008 - 2023 | 52 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.
New The Villages at Walker Meadow 6 ASHLEY WAY 6, WESTBOROUGH, MA, 01581, Westborough, MA 01581
$649,900

2 beds

|

2 baths

|

1,874 sq ft

|

Condo

6 ASHLEY WAY 6, WESTBOROUGH, MA, 01581
New Preserve at Emerald Pines 38 PHOEBE ST 102, METHUEN, MA, 01844, Methuen, MA 01844
$879,000

3 beds

|

3 baths

|

2,616 sq ft

|

Condo

38 PHOEBE ST 102, METHUEN, MA, 01844
New Del Webb Chauncy Lake 11 PETERS FARM WAY 310, WESTBOROUGH, MA,..., Westborough, MA 01581
$575,000

2 beds

|

2 baths

|

1,326 sq ft

|

Condo

11 PETERS FARM WAY 310, WESTBOROUGH, MA,...
New Wyman Farms 935 MAIN ST 10, SHREWSBURY, MA, 01545, Shrewsbury, MA 01545
$1,195,000

2 beds

|

4 baths

|

2,648 sq ft

|

Condo

935 MAIN ST 10, SHREWSBURY, MA, 01545
Community: Wyman Farms
New Brookside Village 51 FILLMORE LN 51, WALPOLE, MA, 02081, Walpole, MA 02081
$899,000

2 beds

|

3 baths

|

2,180 sq ft

|

Condo

51 FILLMORE LN 51, WALPOLE, MA, 02081
Community: Brookside Village
Want to learn more about 55+ communities in Middleton? 55places can help!
Questions? Call us: (508) 715-6046
New Great Island 9 SADDLEBACK, PLYMOUTH, MA, 02360, Plymouth, MA 02360
$949,000

2 beds

|

3 baths

|

3,542 sq ft

|

House

9 SADDLEBACK, PLYMOUTH, MA, 02360
Community: Great Island
New Great Island 22 PICKET FENCE, PLYMOUTH, MA, 02360, Plymouth, MA 02360
$949,000

3 beds

|

3 baths

|

4,085 sq ft

|

House

22 PICKET FENCE, PLYMOUTH, MA, 02360
Community: Great Island
New Rolling Mill 91 NEWFIELD ST 41, PLYMOUTH, MA, 02360, Plymouth, MA 02360
$750,000

2 beds

|

2 baths

|

1,781 sq ft

|

Condo

91 NEWFIELD ST 41, PLYMOUTH, MA, 02360
Community: Rolling Mill
Bigelow Farm 8 LYDIA'S WAY 8, NORTHBOROUGH, MA, 01532, Northborough, MA 01532
$825,000

2 beds

|

3 baths

|

2,598 sq ft

|

Condo

8 LYDIA'S WAY 8, NORTHBOROUGH, MA, 01532
Community: Bigelow Farm
Del Webb Chauncy Lake 5 PETERS FARM WAY 405, WESTBOROUGH, MA, ..., Westborough, MA 01581
$624,995

2 beds

|

2 baths

|

1,166 sq ft

|

Condo

5 PETERS FARM WAY 405, WESTBOROUGH, 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.
Del Webb Chauncy Lake 5 PETERS FARM WAY 7207, WESTBOROUGH, MA,..., Westborough, MA 01581
$706,855

2 beds

|

2 baths

|

1,512 sq ft

|

Condo

5 PETERS FARM WAY 7207, WESTBOROUGH, MA,...
Martins Landing 220 MARTINS LNDG 107, NORTH READING, MA,..., North Reading, MA 01864
$639,900

2 beds

|

2 baths

|

1,496 sq ft

|

Condo

220 MARTINS LNDG 107, NORTH READING, MA,...
Community: Martins Landing
Woodstone Crossing 130 TROTTER RD 1212, WEYMOUTH, MA, 02190, Weymouth, MA 02190
$440,000

1 beds

|

1 baths

|

1,020 sq ft

|

Condo

130 TROTTER RD 1212, WEYMOUTH, MA, 02190
Community: Woodstone Crossing
The Village at Westminster Place 4 KING PHILIP TRL 601, HOLDEN, MA, 01520, Holden, MA 01520
$519,900

2 beds

|

2 baths

|

1,435 sq ft

|

Condo

4 KING PHILIP TRL 601, HOLDEN, MA, 01520
Del Webb Chauncy Lake 5 PETERS FARM WAY 407, WESTBOROUGH, MA, ..., Westborough, MA 01581
$799,995

2 beds

|

2 baths

|

1,512 sq ft

|

Condo

5 PETERS FARM WAY 407, WESTBOROUGH, MA, ...
Del Webb Chauncy Lake 11 PETERS FARM WAY 409, WESTBOROUGH, MA,..., Westborough, MA 01581
$525,000

2 beds

|

2 baths

|

1,326 sq ft

|

Condo

11 PETERS FARM WAY 409, WESTBOROUGH, MA,...
Want to learn more about 55+ communities in Middleton? 55places can help!
Questions? Call us: (508) 715-6046
Brierly Pond Village 6 ASHTON LN 6, MILLBURY, MA, 01527, Millbury, MA 01527
$524,900

2 beds

|

4 baths

|

2,256 sq ft

|

Condo

6 ASHTON LN 6, MILLBURY, MA, 01527
Regency at Glen Ellen 65 GLEN ELLEN BLVD 65, MILLIS, MA, 02054, Millis, MA 02054
$885,000

2 beds

|

3 baths

|

2,408 sq ft

|

Condo

65 GLEN ELLEN BLVD 65, MILLIS, MA, 02054
Preserve at Emerald Pines 15 CARDINAL RD 15, METHUEN, MA, 01844, Methuen, MA 01844
$899,900

3 beds

|

3 baths

|

2,407 sq ft

|

Condo

15 CARDINAL RD 15, METHUEN, MA, 01844
Whitestone Village 1305 ALYSSA DR 1305, GROVELAND, MA, 0183..., Groveland, MA 01834
$549,900

2 beds

|

3 baths

|

1,829 sq ft

|

Condo

1305 ALYSSA DR 1305, GROVELAND, MA, 0183...
Community: Whitestone Village
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 3080 CLUB HOUSE DR, DIGHTON, MA, 02715, Dighton, MA 02715
$629,000

2 beds

|

2 baths

|

1,420 sq ft

|

House

3080 CLUB HOUSE DR, DIGHTON, MA, 02715
Garrison Place 16 GARRISON WAY 16, CARLISLE, MA, 01741, Carlisle, MA 01741
$1,250,000

2 beds

|

4 baths

|

3,230 sq ft

|

House

16 GARRISON WAY 16, CARLISLE, MA, 01741
Community: Garrison Place
Great Island 2 MADISON REACH, PLYMOUTH, MA, 02360, Plymouth, MA 02360
$939,000

3 beds

|

3 baths

|

3,500 sq ft

|

House

2 MADISON REACH, PLYMOUTH, MA, 02360
Community: Great Island
Millwood Preserve 11 BAITING BROOK RD 11, FRAMINGHAM, MA, ..., Framingham, MA 01701
$1,275,000

2 beds

|

3 baths

|

2,559 sq ft

|

Condo

11 BAITING BROOK RD 11, FRAMINGHAM, MA, ...
Community: Millwood Preserve
Bigelow Farm 29 LYDIAS WAY 29, NORTHBOROUGH, MA, 0153..., Northborough, MA 01532
$875,000

2 beds

|

3 baths

|

2,656 sq ft

|

Condo

29 LYDIAS WAY 29, NORTHBOROUGH, MA, 0153...
Community: Bigelow Farm
Del Webb Chauncy Lake 1 CODMAN WAY 312, WESTBOROUGH, MA, 01581, Westborough, MA 01581
$624,900

2 beds

|

2 baths

|

1,510 sq ft

|

Condo

1 CODMAN WAY 312, WESTBOROUGH, MA, 01581
Regency at Methuen 67 SHERWOOD DR 67, METHUEN, MA, 01844, Methuen, MA 01844
$799,900

3 beds

|

3 baths

|

2,488 sq ft

|

Condo

67 SHERWOOD DR 67, METHUEN, MA, 01844
Community: Regency at Methuen
Want to learn more about 55+ communities in Middleton? 55places can help!
Questions? Call us: (508) 715-6046
Regency at Methuen 2 HOPKINS CIR 2, METHUEN, MA, 01844, Methuen, MA 01844
$659,900

2 beds

|

2 baths

|

1,415 sq ft

|

Condo

2 HOPKINS CIR 2, METHUEN, MA, 01844
Community: Regency at Methuen
Great Island 23 WOODSONG, PLYMOUTH, MA, 02360, Plymouth, MA 02360
$949,000

2 beds

|

2 baths

|

2,096 sq ft

|

House

23 WOODSONG, PLYMOUTH, MA, 02360
Community: Great Island
Seton Highlands at The Pinehills 18 ABERDEEN 18, PLYMOUTH, MA, 02360, Plymouth, MA 02360
$875,000

2 beds

|

3 baths

|

4,054 sq ft

|

Condo

18 ABERDEEN 18, PLYMOUTH, MA, 02360
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.
WestRidge 15 HASTINGS RD 15, HUDSON, MA, 01749, Hudson, MA 01749
$650,000

2 beds

|

3 baths

|

1,934 sq ft

|

Condo

15 HASTINGS RD 15, HUDSON, MA, 01749
Community: WestRidge
Del Webb Chauncy Lake 5 PETERS FARM WAY 308, WESTBOROUGH, MA, ..., Westborough, MA 01581
$639,995

2 beds

|

2 baths

|

1,375 sq ft

|

Condo

5 PETERS FARM WAY 308, WESTBOROUGH, MA, ...
Del Webb Chauncy Lake 5 PETERS FARM WAY 304, WESTBOROUGH, MA, ..., Westborough, MA 01581
$454,995

1 beds

|

1 baths

|

972 sq ft

|

Condo

5 PETERS FARM WAY 304, WESTBOROUGH, MA, ...
Angell Brook Village 14 ANGELL BROOK DR 14, WEST BOYLSTON, MA..., West Boylston, MA 01583
$619,900

3 beds

|

3 baths

|

1,962 sq ft

|

Condo

14 ANGELL BROOK DR 14, WEST BOYLSTON, MA...
Great Island 51 CHAMPLAIN CIR, PLYMOUTH, MA, 02360, Plymouth, MA 02360
$795,000

3 beds

|

3 baths

|

2,822 sq ft

|

House

51 CHAMPLAIN CIR, PLYMOUTH, MA, 02360
Community: Great Island
Westbrook Crossing 989 E ST 310, DEDHAM, MA, 02026, Dedham, MA 02026
$499,000

2 beds

|

2 baths

|

1,164 sq ft

|

Condo

989 E ST 310, DEDHAM, MA, 02026
Community: Westbrook Crossing
Martins Landing 300 MARTINS LNDG 103, NORTH READING, MA,..., North Reading, MA 01864
$525,000

1 beds

|

1 baths

|

1,027 sq ft

|

Condo

300 MARTINS LNDG 103, NORTH READING, MA,...
Community: Martins Landing
Martins Landing 320 MARTINS LNDG 311, NORTH READING, MA,..., North Reading, MA 01864
$614,995

1 beds

|

1 baths

|

1,115 sq ft

|

Condo

320 MARTINS LNDG 311, NORTH READING, MA,...
Community: Martins Landing
Want to learn more about 55+ communities in Middleton? 55places can help!
Questions? Call us: (508) 715-6046
Martins Landing 320 MARTINS LNDG 508, NORTH READING, MA,..., North Reading, MA 01864
$779,995

2 beds

|

2 baths

|

1,450 sq ft

|

Condo

320 MARTINS LNDG 508, NORTH READING, MA,...
Community: Martins Landing
Great Island 7 MADISON REACH, PLYMOUTH, MA, 02360, Plymouth, MA 02360
$729,000

2 beds

|

3 baths

|

2,074 sq ft

|

House

7 MADISON REACH, 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.

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