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

166 communities near Middleton

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RiverWalk at Bedford
$500ks
RiverWalk at Bedford, Bedford, NH
Resale Only | 55+ age-restricted | Built 2006 - 2006 | 90 homes
Eagles Trace
$400ks - $500ks
Eagles Trace, Acton, ME
Resale Only | 55+ age-restricted | Built 2005 - 2020 | 14 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
Mill Pond Crossing
$300ks - $400ks
Mill Pond Crossing, Brentwood, NH
Resale Only | 55+ age-restricted | Built 2008 - 2013 | 47 homes
Arbor Woods
$400ks - $500ks
Arbor Woods, Dover, NH
Resale Only | 55+ age-restricted | 65 homes
Want to learn more about 55+ communities in Middleton? 55places can help!
Questions? Call us: (508) 715-6046
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Questions? Call us: (508) 715-6046
Souhegan River View Villa...
$400ks - $500ks
Souhegan River View Villa..., Merrimack, NH
Resale Only | 55+ age-restricted | Built 2001 - 2006 | 51 homes
Leddy Fields
$400ks - $600ks
Leddy Fields, Epping, NH
Resale Only | 55+ age-restricted | Built 2005 - 2014 | 50 homes
Lamplighter Estates
$200ks - $300ks
Lamplighter Estates, Kingston, NH
Resale Only | 55+ age-restricted | Built 2001 - 2003 | 50 homes
5 rating (1 reviews) Canberra Village
$400ks - $500ks
Canberra Village, Litchfield, NH
Resale Only | 55+ age-restricted | Built 2004 - 2005 | 49 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.
Cahill Place
$200ks
Cahill Place, Milford, NH
Resale Only | 55+ age-restricted | Built 2006 - 2006 | 49 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.
Beaver Meadow Village
$200ks - $300ks
Beaver Meadow Village, Concord, NH
Resale Only | 55+ age-restricted | Built 1973 - 1974 | 48 homes
Gilcreast Farms
$300ks
Gilcreast Farms, Litchfield, NH
Resale Only | 55+ age-restricted | Built 2003 - 2005 | 47 homes
Prescott Crossing
$400ks
Prescott Crossing, Raymond, NH
Resale Only | 55+ age-restricted | Built 2003 - 2004 | 46 homes
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Questions? Call us: (508) 715-6046
Runnells Landing
$300ks
Runnells Landing, Hollis, NH
Resale Only | 55+ age-restricted | Built 2002 - 2004 | 45 homes
Cohas Landing
$300ks
Cohas Landing, Londonderry, NH
Resale Only | 55+ age-restricted | Built 1991 - 1997 | 44 homes
Want to learn more about 55+ rental communities in Middleton? 55places can help!
Questions? Call us: (508) 715-6046
Braemoor Commons
$300ks - $400ks
Braemoor Commons, Salem, NH
Resale Only | 55+ age-restricted | Built 2014 - 2015 | 44 homes
Pine Creek
$300ks
Pine Creek, Litchfield, NH
Resale Only | 55+ age-restricted | Built 2007 - 2014 | 42 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.
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
Buttrick Village
$400ks - $500ks
Buttrick Village, Londonderry, NH
Resale Only | 55+ age-restricted | Built 1997 - 2000 | 40 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.
The Villages of Pelham
$300ks - $400ks
The Villages of Pelham, Pelham, NH
Resale Only | 55+ age-restricted | Built 2016 - 2018 | 40 homes
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Questions? Call us: (508) 715-6046
Whispering Winds
$300ks - $700ks
Whispering Winds, Windham, NH
Resale Only | 55+ age-restricted | Built 2001 - 2001 | 40 homes
Del Ray Place
$700ks - $800ks
Del Ray Place, Windham, NH
New Construction | 55+ age-restricted | Built 2019 - present | 26 homes
Village at Oakwood
$600ks - $700ks
Village at Oakwood, Derry, NH
Resale Only | 55+ age-restricted | Built 2019 - 2021 | 30 homes
The Nevins
$700ks
The Nevins, Londonderry, NH
Resale Only | 55+ age-restricted | Built 2004 - 2013 | 128 homes
Want to learn more about 55+ rental communities in Middleton? 55places can help!
Questions? Call us: (508) 715-6046
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.
Silver Lake Estates
$700ks - $800ks
Silver Lake Estates, Hollis, NH
Resale Only | 55+ age-restricted | Built 2019 - 2022 | 52 homes
Annandale on The River
$500ks - $600ks
Annandale on The River, Litchfield, NH
Resale Only | 55+ age-restricted | Built 2009 - 2011 | 57 homes
5 rating (1 reviews) Ray Farm
$600ks - $700ks
Ray Farm, Exeter, NH
Resale Only | 55+ age-restricted | Built 2018 - 2023 | 116 homes
Mission Pointe
$500ks
Mission Pointe, Hudson, NH
Resale Only | 62+ age-restricted | Built 2006 - 2011 | 58 homes
The Village at Hollis Dep...
$300ks
The Village at Hollis Dep..., Hollis, NH
Resale Only | 55+ age-restricted | Built 2003 - 2003 | 60 homes
Want to learn more about 55+ communities in Middleton? 55places can help!
Questions? Call us: (508) 715-6046
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.
Blackstone Reserve
$600ks
Blackstone Reserve, Raymond, NH
Resale Only | 55+ age-restricted | Built 2018 - 2022 | 66 homes
Hickory Woods
$400ks - $700ks
Hickory Woods, Londonderry, NH
Resale Only | 55+ age-restricted | Built 2014 - 2016 | 98 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
Hadleigh Woods
$300ks
Hadleigh Woods, Windham, NH
Resale Only | 55+ age-restricted | Built 2003 - 2004 | 62 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.
Bella Vista
$300ks - $400ks
Bella Vista, Glocester, RI
Resale Only | 55+ age-restricted | Built 2015 - 2021 | 70 homes
Want to learn more about 55+ rental communities in Middleton? 55places can help!
Questions? Call us: (508) 715-6046
Sawyer Green
$400ks - $500ks
Sawyer Green, Dover, NH
Resale Only | 55+ age-restricted | Built 2009 - 2013 | 62 homes
Chadwick Place
$400ks - $500ks
Chadwick Place, Windham, NH
Resale Only | 55+ age-restricted | Built 2018 - 2020 | 15 homes
Canterbury Commons
$500ks - $600ks
Canterbury Commons, Epping, NH
New Construction | 55+ age-restricted | Built 2021 - present | 100 homes
Want to learn more about 55+ communities in Middleton? 55places can help!
Questions? Call us: (508) 715-6046
Stone Castle Estates
$200ks - $600ks
Stone Castle Estates, Methuen, MA
Resale Only | 55+ age-restricted | Built 2005 - 2018 | 89 homes
Sugarplum Hill
$300ks - $400ks
Sugarplum Hill, Londonderry, NH
Resale Only | 55+ age-restricted | Built 2006 - 2012 | 33 homes
New 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 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
New Sawyer's Reach 1 MARINERS WAY UNIT 204, PLYMOUTH, MA, 0..., Plymouth, MA 02360
$580,000

1 beds

|

2 baths

|

1,113 sq ft

|

Condo

1 MARINERS WAY UNIT 204, PLYMOUTH, MA, 0...
Community: Sawyer's Reach
Bigelow Farm 6 LYDIAS WAY 6, NORTHBOROUGH, MA, 01532, Northborough, MA 01532
$775,000

2 beds

|

3 baths

|

2,671 sq ft

|

Condo

6 LYDIAS WAY 6, NORTHBOROUGH, MA, 01532
Community: Bigelow Farm
Del Webb Chauncy Lake 5 PETERS FARM WAY 107, WESTBOROUGH, MA, ..., Westborough, MA 01581
$655,995

2 beds

|

2 baths

|

1,512 sq ft

|

Condo

5 PETERS FARM WAY 107, WESTBOROUGH, MA, ...
Want to learn more about 55+ communities in Middleton? 55places can help!
Questions? Call us: (508) 715-6046
Want to learn more about 55+ rental communities in Middleton? 55places can help!
Questions? Call us: (508) 715-6046
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
Martins Landing 320 MARTINS LNDG 2410, NORTH READING, MA..., North Reading, MA 01864
$699,995

2 beds

|

2 baths

|

1,450 sq ft

|

Condo

320 MARTINS LNDG 2410, NORTH READING, MA...
Community: Martins Landing
Adams Farm 40 ADAMS FARM RD 40, SHREWSBURY, MA, 015..., Shrewsbury, MA 01545
$850,000

2 beds

|

3 baths

|

2,757 sq ft

|

Condo

40 ADAMS FARM RD 40, SHREWSBURY, MA, 015...
Community: Adams Farm
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
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 201, WESTBOROUGH, MA, ..., Westborough, MA 01581
$674,995

2 beds

|

2 baths

|

1,496 sq ft

|

Condo

5 PETERS FARM WAY 201, WESTBOROUGH, MA, ...
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.
Del Webb Chauncy Lake 5 PETERS FARM WAY 401, WESTBOROUGH, MA, ..., Westborough, MA 01581
$839,995

2 beds

|

2 baths

|

1,496 sq ft

|

Condo

5 PETERS FARM WAY 401, 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,...
Whitestone Village 901 ALYSSA DR # 901, GROVELAND, MA, 0183..., Groveland, MA 01834
$549,000

2 beds

|

2 baths

|

1,304 sq ft

|

Condo

901 ALYSSA DR # 901, GROVELAND, MA, 0183...
Community: Whitestone Village
Want to learn more about 55+ communities in Middleton? 55places can help!
Questions? Call us: (508) 715-6046
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
Del Webb Chauncy Lake 2306 TALBOT WAY # 2306, WESTBOROUGH, MA,..., Westborough, MA 01581
$599,000

2 beds

|

2 baths

|

1,469 sq ft

|

Condo

2306 TALBOT WAY # 2306, WESTBOROUGH, MA,...
Want to learn more about 55+ rental communities in Middleton? 55places can help!
Questions? Call us: (508) 715-6046
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
Brierly Pond Village 100 HORNE WAY # 100, MILLBURY, MA, 01527, Millbury, MA 01527
$509,900

2 beds

|

3 baths

|

2,021 sq ft

|

Condo

100 HORNE WAY # 100, MILLBURY, MA, 01527
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 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
Del Webb Chauncy Lake 5 PETERS FARM WAY # 111, WESTBOROUGH, MA..., Westborough, MA 01581
$489,995

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
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.
Forest Glen 61 SPRING HILL DR # 61, UXBRIDGE, MA, 01..., Uxbridge, MA 01569
$589,000

2 beds

|

2 baths

|

1,525 sq ft

|

Condo

61 SPRING HILL DR # 61, UXBRIDGE, MA, 01...
Community: Forest Glen
Want to learn more about 55+ communities in Middleton? 55places can help!
Questions? Call us: (508) 715-6046
Sawyer's Reach 44 MARINERS WAY 44, PLYMOUTH, MA, 02360, Plymouth, MA 02360
$795,000

2 beds

|

3 baths

|

1,871 sq ft

|

Condo

44 MARINERS WAY 44, PLYMOUTH, MA, 02360
Community: Sawyer's Reach
Martins Landing 280 MARTINS LNDG 312, NORTH READING, MA,..., North Reading, MA 01864
$625,000

1 beds

|

1 baths

|

1,058 sq ft

|

Condo

280 MARTINS LNDG 312, NORTH READING, MA,...
Community: Martins Landing
Reading Woods 75 AUGUSTUS CT 2003, READING, MA, 01867, Reading, MA 01867
$515,000

1 beds

|

1 baths

|

955 sq ft

|

Condo

75 AUGUSTUS CT 2003, READING, MA, 01867
Community: Reading Woods
Brierly Pond Village 196 HORNE WAY # 196, MILLBURY, MA, 01527, Millbury, MA 01527
$515,000

2 beds

|

4 baths

|

2,100 sq ft

|

Condo

196 HORNE WAY # 196, MILLBURY, MA, 01527
Want to learn more about 55+ rental communities in Middleton? 55places can help!
Questions? Call us: (508) 715-6046
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 Emerald Pines 2 SEQUOIA DR # 2, METHUEN, MA, 01844, Methuen, MA 01844
$799,900

2 beds

|

2 baths

|

1,826 sq ft

|

Condo

2 SEQUOIA DR # 2, METHUEN, MA, 01844
The Trails 6 WATERVILLE LN # 6, HOPKINTON, MA, 0174..., Hopkinton, MA 01748
$1,179,900

2 beds

|

4 baths

|

3,292 sq ft

|

Condo

6 WATERVILLE LN # 6, HOPKINTON, MA, 0174...
Community: The Trails
Brooksmont 59 BROOKSMONT DR # 59, HOLLISTON, MA, 01..., Holliston, MA 01746
$724,900

2 beds

|

3 baths

|

2,360 sq ft

|

Condo

59 BROOKSMONT DR # 59, HOLLISTON, MA, 01...
Community: Brooksmont
Regency at Glen Ellen 13 HATTIE LN 13, MILLIS, MA, 02054, Millis, MA 02054
$920,000

2 beds

|

3 baths

|

2,627 sq ft

|

Condo

13 HATTIE LN 13, MILLIS, MA, 02054
The Villages at Walker Meadow 5 WESSONVILLE VILLAGE WAY 5, WESTBOROUGH..., Westborough, MA 01581
$739,000

2 beds

|

3 baths

|

2,090 sq ft

|

Condo

5 WESSONVILLE VILLAGE WAY 5, WESTBOROUGH...
Want to learn more about 55+ communities in Middleton? 55places can help!
Questions? Call us: (508) 715-6046
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.
Del Webb Chauncy Lake 1102 PETERS FARM WAY # 1102, WESTBOROUGH..., Westborough, MA 01581
$419,900

1 beds

|

1 baths

|

956 sq ft

|

Condo

1102 PETERS FARM WAY # 1102, WESTBOROUGH...
Del Webb Chauncy Lake 5 PETERS FARM WAY 103, WESTBOROUGH, MA, ..., Westborough, MA 01581
$440,485

1 beds

|

1 baths

|

972 sq ft

|

Condo

5 PETERS FARM WAY 103, WESTBOROUGH, MA, ...
Willis Brook at Lynnfield 15 FAIRWAY LN 55, LYNNFIELD, MA, 01940, Lynnfield, MA 01940
$1,819,000

2 beds

|

3 baths

|

2,442 sq ft

|

Condo

15 FAIRWAY LN 55, LYNNFIELD, MA, 01940
The Elms of Hanover 18 WINTERBERRY LN # 18, HANOVER, MA, 023..., Hanover, MA 02339
$785,000

2 beds

|

3 baths

|

2,258 sq ft

|

Condo

18 WINTERBERRY LN # 18, HANOVER, MA, 023...
Community: The Elms of Hanover
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.
Riverside Woods 4 FRANCIS DR 312, ANDOVER, MA, 01810, Andover, MA 01810
$619,900

2 beds

|

2 baths

|

1,500 sq ft

|

Condo

4 FRANCIS DR 312, ANDOVER, MA, 01810
Community: Riverside Woods
Want to learn more about 55+ rental communities in Middleton? 55places can help!
Questions? Call us: (508) 715-6046
Harmony Place 20 FIDELITY DR # 10, RUTLAND, MA, 01543, Rutland, MA 01543
$498,000

2 beds

|

2 baths

|

1,582 sq ft

|

Condo

20 FIDELITY DR # 10, RUTLAND, MA, 01543
Community: Harmony Place
Lake Point Village 57 LONG POINT RD 208, LAKEVILLE, MA, 023..., Lakeville, MA 02347
$509,900

2 beds

|

2 baths

|

1,453 sq ft

|

Condo

57 LONG POINT RD 208, LAKEVILLE, MA, 023...
Community: Lake Point Village
Lake Point Village 57 LONG POINT RD UNIT 104, LAKEVILLE, MA..., Lakeville, MA 02347
$589,000

2 beds

|

2 baths

|

1,334 sq ft

|

Condo

57 LONG POINT RD UNIT 104, LAKEVILLE, MA...
Community: Lake Point Village
Want to learn more about 55+ communities in Middleton? 55places can help!
Questions? Call us: (508) 715-6046
Regency at Assabet Ridge 28 BOWOOD LN # 28, MARLBOROUGH, MA, 0175..., Marlborough, MA 01752
$759,900

3 beds

|

3 baths

|

2,205 sq ft

|

Condo

28 BOWOOD LN # 28, MARLBOROUGH, MA, 0175...
Harmony Place 18 FIDELITY DR # 9, RUTLAND, MA, 01543, Rutland, MA 01543
$498,000

2 beds

|

2 baths

|

1,582 sq ft

|

Condo

18 FIDELITY DR # 9, RUTLAND, MA, 01543
Community: Harmony Place

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