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Middleton, MA 55+ active adult communities & homes for sale - Page 2

167 communities near Middleton

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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
Willis Brook at Lynnfield
$1Ms
Willis Brook at Lynnfield, Lynnfield, MA
New Construction | 55+ age-restricted | Built 2026 - present | 100 homes
Hawthorn Preserve
$900ks - $1Ms
Hawthorn Preserve, Braintree, MA
New Construction | 55+ age-restricted | Built 2025 - present | 51 homes
The Cliffs at Evergreen
$700ks - $600ks
The Cliffs at Evergreen, Auburn, NH
New Construction | 55+ age-restricted | Built 2022 - present | 79 homes
Want to learn more about 55+ communities in Middleton? 55places can help!
Questions? Call us: (508) 715-6046
The Village at Cider Hill
$400ks - $500ks
The Village at Cider Hill, Old Orchard Beach, ME
Resale Only | 55+ age-restricted | Built 2003 - 2007 | 176 homes
5 rating (1 reviews) The Village at Great Broo...
$500ks - $700ks
The Village at Great Broo..., Eliot, ME
Resale Only | 55+ age-restricted | Built 2016 - 2023 | 90 homes
Eagles Trace
$400ks - $500ks
Eagles Trace, Acton, ME
Resale Only | 55+ age-restricted | Built 2005 - 2020 | 14 homes
Fairway View Village
$500ks - $600ks
Fairway View Village, Wells, ME
New Construction | 55+ age-restricted | Built 2021 - present | 46 homes
The Villages at Hobbs Pon...
$600ks - $800ks
The Villages at Hobbs Pon..., Wells, ME
Resale Only | 55+ age-restricted | Built 2019 - 2023 | 120 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.
RiverWalk at Bedford
$500ks
RiverWalk at Bedford, Bedford, NH
Resale Only | 55+ age-restricted | Built 2006 - 2006 | 90 homes
Brook Ridge
$400ks
Brook Ridge, Hooksett, NH
Resale Only | 55+ age-restricted | Built 2004 - present | 91 homes
Black Rocks Village
$300ks
Black Rocks Village, Fremont, NH
Resale Only | 55+ age-restricted | Built 2013 - 2016 | 112 homes
Berry Hill Estates
$600ks - $700ks
Berry Hill Estates, Hooksett, NH
Resale Only | 55+ age-restricted | Built 2009 - 2022 | 107 homes
King's Landing
$300ks - $400ks
King's Landing, Kingston, NH
Resale Only | 55+ age-restricted | Built 2015 - 2017 | 44 homes
The Villages at Three Pon...
$500ks - $700ks
The Villages at Three Pon..., Brentwood, NH
Resale Only | 55+ age-restricted | Built 2019 - 2023 | 68 homes
Want to learn more about 55+ communities in Middleton? 55places can help!
Questions? Call us: (508) 715-6046
Blackstone Reserve
$600ks
Blackstone Reserve, Raymond, NH
Resale Only | 55+ age-restricted | Built 2018 - 2022 | 66 homes
5 rating (1 reviews) Ray Farm
$600ks - $700ks
Ray Farm, Exeter, NH
Resale Only | 55+ age-restricted | Built 2018 - 2023 | 116 homes
Village at Oakwood
$600ks - $700ks
Village at Oakwood, Derry, NH
Resale Only | 55+ age-restricted | Built 2019 - 2021 | 30 homes
Arbor Woods
$400ks - $500ks
Arbor Woods, Dover, NH
Resale Only | 55+ age-restricted | 65 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.
Hampton Meadows
$700ks - $900ks
Hampton Meadows, Hampton, NH
Resale Only | 55+ age-restricted | Built 1998 - 2002 | 116 homes
The Mews of Bedford
$500ks
The Mews of Bedford, Bedford, NH
Resale Only | 55+ age-restricted | Built 1999 - 2002 | 108 homes
Sherwood Glen
$400ks - $500ks
Sherwood Glen, Raymond, NH
Resale Only | 55+ age-restricted | Built 2005 - 2010 | 82 homes
The Vineyards
$500ks - $600ks
The Vineyards, Stratham, NH
Resale Only | 55+ age-restricted | Built 2002 - 2007 | 77 homes
Bramber Green
$900ks
Bramber Green, Greenland, NH
Resale Only | 55+ age-restricted | Built 2016 - 2017 | 73 homes
Clearwater Estates
$300ks - $400ks
Clearwater Estates, Raymond, NH
Resale Only | 55+ age-restricted | Built 2005 - 2019 | 64 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 Middleton? 55places can help!
Questions? Call us: (508) 715-6046
Mill Pond Crossing
$300ks - $400ks
Mill Pond Crossing, Brentwood, NH
Resale Only | 55+ age-restricted | Built 2008 - 2013 | 47 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
Leddy Fields
$400ks - $600ks
Leddy Fields, Epping, NH
Resale Only | 55+ age-restricted | Built 2005 - 2014 | 50 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.
Lamplighter Estates
$200ks - $300ks
Lamplighter Estates, Kingston, NH
Resale Only | 55+ age-restricted | Built 2001 - 2003 | 50 homes
Beaver Meadow Village
$200ks - $300ks
Beaver Meadow Village, Concord, NH
Resale Only | 55+ age-restricted | Built 1973 - 1974 | 48 homes
Prescott Crossing
$400ks
Prescott Crossing, Raymond, NH
Resale Only | 55+ age-restricted | Built 2003 - 2004 | 46 homes
Cohas Landing
$300ks
Cohas Landing, Londonderry, NH
Resale Only | 55+ age-restricted | Built 1991 - 1997 | 44 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
Benjamin Chase Mill
$400ks - $500ks
Benjamin Chase Mill, Derry, NH
Resale Only | 55+ age-restricted | Built 2005 - 2015 | 36 homes
Stone Sled Farm
$500ks - $600ks
Stone Sled Farm, Bow, NH
Resale Only | 55+ age-restricted | Built 2005 - 2013 | 38 homes
Want to learn more about 55+ communities in Middleton? 55places can help!
Questions? Call us: (508) 715-6046
Little Mill Woods
$300ks - $400ks
Little Mill Woods, Sandown, NH
Resale Only | 55+ age-restricted | Built 2005 - 2012 | 38 homes
Country Hills
$600ks
Country Hills, East Kingston, NH
Resale Only | 55+ age-restricted | Built 2005 - 2005 | 36 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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