Call us at (508) 715-6046 to learn more about active adult communities near Middleton
Middleton, MA 55+ active adult communities & homes for sale - Page 4
162 communities near Middleton
111 homes near Middleton
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![Forest Glen]()
$400Ks
- $500Ks
Forest Glen, Uxbridge, MA
New Construction
|
55+ age-restricted
|
Built 2018 - present
|
44 homes
No reviews yet
![Duxbury Estates]()
$500Ks
- $700Ks
Duxbury Estates, Duxbury, MA
Resale Only
|
55+ age-restricted
|
Built 2008 - 2013
|
44 homes
No reviews yet
![King's Landing]()
$300Ks
- $400Ks
King's Landing, Kingston, NH
Resale Only
|
55+ age-restricted
|
Built 2015 - 2017
|
44 homes
No reviews yet
![Northwoods at Sudbury]()
$600Ks
- $1Ms
Northwoods at Sudbury, Sudbury, MA
Resale Only
|
55+ age-restricted
|
Built 1999 - 2019
|
43 homes
No reviews yet
![Pine Creek]()
$300Ks
- $300Ks
Pine Creek, Litchfield, NH
Resale Only
|
55+ age-restricted
|
Built 2007 - 2014
|
42 homes
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No reviews yet
![Webster Woods]()
$300Ks
- $400Ks
Webster Woods, Hooksett, NH
Resale Only
|
55+ age-restricted
|
Built 2005 - 2007
|
41 homes
No reviews yet
![Bigelow Farm]()
$500Ks
- $600Ks
Bigelow Farm, Northborough, MA
Resale Only
|
55+ age-restricted
|
Built 2006 - 2013
|
41 homes
No reviews yet
![Donovan Farm]()
$500Ks
- $700Ks
Donovan Farm, Norwell, MA
Resale Only
|
55+ age-restricted
|
Built 2001 - 2003
|
40 homes
No reviews yet
![Buttrick Village]()
$400Ks
- $500Ks
Buttrick Village, Londonderry, NH
Resale Only
|
55+ age-restricted
|
Built 1997 - 2000
|
40 homes
No reviews yet
![Whispering Winds]()
$300Ks
- $700Ks
Whispering Winds, Windham, NH
Resale Only
|
55+ age-restricted
|
Built 2001 - 2001
|
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.
No reviews yet
![The Villages of Pelham]()
$300Ks
- $400Ks
The Villages of Pelham, Pelham, NH
Resale Only
|
55+ age-restricted
|
Built 2016 - 2018
|
40 homes
No reviews yet
![Thompson's Preserve]()
$500Ks
- $500Ks
Thompson's Preserve, Nashua, NH
Resale Only
|
55+ age-restricted
|
Built 2019 - 2020
|
39 homes
No reviews yet
![Spring Meadow]()
$700Ks
- $700Ks
Spring Meadow, Hanover, MA
Resale Only
|
55+ age-restricted
|
Built 2004 - 2007
|
39 homes
No reviews yet
![Little Mill Woods]()
$300Ks
- $400Ks
Little Mill Woods, Sandown, NH
Resale Only
|
55+ age-restricted
|
Built 2005 - 2012
|
38 homes
No reviews yet
![Stone Sled Farm]()
$500Ks
- $600Ks
Stone Sled Farm, Bow, NH
Resale Only
|
55+ age-restricted
|
Built 2005 - 2013
|
38 homes
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No reviews yet
![Tara Woods]()
$400Ks
- $400Ks
Tara Woods, Plymouth, MA
Resale Only
|
55+ age-restricted
|
Built 2007 - 2015
|
38 homes
No reviews yet
![Parrish Hills]()
$300Ks
- $500Ks
Parrish Hills, Londonderry, NH
Resale Only
|
55+ age-restricted
|
Built 2001 - 2003
|
37 homes
No reviews yet
![Hayden Green]()
$500Ks
- $500Ks
Hayden Green, Nashua, NH
Resale Only
|
55+ age-restricted
|
Built 2013 - 2015
|
37 homes
No reviews yet
![Benjamin Chase Mill]()
$400Ks
- $500Ks
Benjamin Chase Mill, Derry, NH
Resale Only
|
55+ age-restricted
|
Built 2005 - 2015
|
36 homes
No reviews yet
![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.
No reviews yet
![Cranberry Grove]()
$200Ks
- $300Ks
Cranberry Grove, Wareham, MA
Resale Only
|
55+ age-restricted
|
Built 2001 - 2001
|
36 homes
No reviews yet
![Lexington Place]()
$400Ks
- $400Ks
Lexington Place, Hudson, NH
Resale Only
|
55+ age-restricted
|
Built 1999 - 1999
|
34 homes
No reviews yet
![Rowell Estates]()
$300Ks
- $400Ks
Rowell Estates, Kingston, NH
Resale Only
|
55+ age-restricted
|
Built 2004 - 2004
|
33 homes
No reviews yet
![Sugarplum Hill]()
$300Ks
- $400Ks
Sugarplum Hill, Londonderry, NH
Resale Only
|
55+ age-restricted
|
Built 2006 - 2012
|
33 homes
No reviews yet
![Peregrine Woods]()
$400Ks
- $600Ks
Peregrine Woods, Marshfield, MA
Resale Only
|
55+ age-restricted
|
Built 2002 - 2005
|
32 homes
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No reviews yet
![The Cottages at Lebaron H...]()
$500Ks
- $600Ks
The Cottages at Lebaron H..., Lakeville, MA
New Construction
|
55+ age-restricted
|
Built 2019 - present
|
32 homes
No reviews yet
![Rolling Green at Topsfiel...]()
$600Ks
- $800Ks
Rolling Green at Topsfiel..., Topsfield, MA
Resale Only
|
55+ age-restricted
|
Built 2014 - 2014
|
30 homes
No reviews yet
![Brookside Village]()
$700Ks
- $700Ks
Brookside Village, Walpole, MA
Resale Only
|
55+ age-restricted
|
Built 2018 - 2018
|
30 homes
No reviews yet
![Village at Oakwood]()
$600Ks
- $700Ks
Village at Oakwood, Derry, NH
Resale Only
|
55+ age-restricted
|
Built 2019 - 2021
|
30 homes
No reviews yet
![Mattapoisett Landing]()
$400Ks
- $500Ks
Mattapoisett Landing, Mattapoisett, MA
Resale Only
|
55+ age-restricted
|
Built 2012 - 2015
|
27 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.
No reviews yet
![Wyman Farms]()
$500Ks
- $900Ks
Wyman Farms, Shrewsbury, MA
New Construction
|
55+ age-restricted
|
Built 2017 - present
|
26 homes
No reviews yet
![Del Ray Place]()
$700Ks
- $800Ks
Del Ray Place, Windham, NH
New Construction
|
55+ age-restricted
|
Built 2019 - present
|
26 homes
No reviews yet
![The Cottages at Spruce Wo...]()
$400Ks
- $500Ks
The Cottages at Spruce Wo..., Durham, NH
Resale Only
|
55+ age-restricted
|
Built 1999 - 2014
|
25 homes
No reviews yet
![Woodcrest Run]()
$400Ks
- $400Ks
Woodcrest Run, Sharon, MA
New Construction
|
55+ age-restricted
|
Built 2019 - present
|
25 homes
No reviews yet
![Chilton Park Village]()
$400Ks
- $400Ks
Chilton Park Village, Plymouth, MA
Resale Only
|
55+ age-restricted
|
Built 2006 - 2015
|
25 homes
Want to learn more about 55+ communities in Middleton?
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Questions? Call us:
(508) 715-6046
No reviews yet
![Kensington at The Pinehil...]()
$500Ks
- $500Ks
Kensington at The Pinehil..., Plymouth, MA
New Construction
|
Age-targeted
|
Built 2017 - present
|
17 homes
No reviews yet
![Garrison Place]()
$900Ks
- $1Ms
Garrison Place, Carlisle, MA
Resale Only
|
55+ age-restricted
|
Built 2018 - 2019
|
16 homes
No reviews yet
![The Paddock]()
$500Ks
- $600Ks
The Paddock, Salem, NH
Resale Only
|
55+ age-restricted
|
Built 2016 - 2019
|
16 homes
No reviews yet
![Chadwick Place]()
$400Ks
- $500Ks
Chadwick Place, Windham, NH
Resale Only
|
55+ age-restricted
|
Built 2018 - 2020
|
15 homes
No reviews yet
![Eagles Trace]()
$400Ks
- $500Ks
Eagles Trace, Acton, ME
Resale Only
|
55+ age-restricted
|
Built 2005 - 2020
|
14 homes
30 Coppersmith
![30 COPPERSMITH WAY # 204, CANTON, MA, 02..., Canton, MA 02021]()
1 beds
|1 baths
|1,027 sq ft
|Condo
30 COPPERSMITH WAY # 204, CANTON, MA, 02...
Community: 30 Coppersmith
MLS 73441708 • Pulte Homes of New England, Erin S...
30 Coppersmith
![30 COPPERSMITH WAY # 409, CANTON, MA, 02..., Canton, MA 02021]()
2 beds
|2 baths
|1,425 sq ft
|Condo
30 COPPERSMITH WAY # 409, CANTON, MA, 02...
Community: 30 Coppersmith
MLS 73441714 • Pulte Homes of New England, Erin S...
Reading Woods
![62 ABIGAIL WAY UNIT 2007, READING, MA, 0..., Reading, MA 01867]()
1 beds
|1 baths
|930 sq ft
|Condo
62 ABIGAIL WAY UNIT 2007, READING, MA, 0...
Community: Reading Woods
MLS 73407295 • Colonial Manor Realty, Bobbie Bott...
Wolcott Woods
![69 WOLCOTT WOODS LN # 69, MILTON, MA, 02..., Milton, MA 02186]()
2 beds
|3 baths
|3,599 sq ft
|Condo
69 WOLCOTT WOODS LN # 69, MILTON, MA, 02...
Community: Wolcott Woods
MLS 73436524 • Access, Dot Collection
Wolcott Woods
![61 WOLCOTT WOODS LN # 61, MILTON, MA, 02..., Milton, MA 02186]()
2 beds
|3 baths
|2,201 sq ft
|Condo
61 WOLCOTT WOODS LN # 61, MILTON, MA, 02...
Community: Wolcott Woods
MLS 73435597 • LandVest, Inc., Greta Gustafson
Want to learn more about 55+ communities in Middleton?
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New
Village at Silver Hill
![5 PEAKES LN 5, WESTON, MA, 02493, Weston, MA 02493]()
3 beds
|5 baths
|3,161 sq ft
|Condo
5 PEAKES LN 5, WESTON, MA, 02493
Community: Village at Silver Hill
MLS 73446137 • Compass, Donahue Maley and Burns T...
Hatter's Point
![60 MERRIMAC ST 604, AMESBURY, MA, 01913, Amesbury, MA 01913]()
2 beds
|2 baths
|1,265 sq ft
|Condo
60 MERRIMAC ST 604, AMESBURY, MA, 01913
Community: Hatter's Point
MLS 73437505 • Keller Williams Realty Evolution, ...
Great Island
![21 CROSS WIND, PLYMOUTH, MA, 02360, Plymouth, MA 02360]()
MLS 73435722 • Pinehills Brokerage Services LLC, ...
Orchard Hill
![5 BLOSSOM CT # 5, WESTBOROUGH, MA, 01581, Westborough, MA 01581]()
3 beds
|4 baths
|3,373 sq ft
|Condo
5 BLOSSOM CT # 5, WESTBOROUGH, MA, 01581
Community: Orchard Hill
MLS 73437675 • Berkshire Hathaway HomeServices Co...
North Meadow Village
![11 CRANBERRY LN # 11, MIDDLETON, MA, 019..., Middleton, MA 01949]()
2 beds
|3 baths
|2,650 sq ft
|Condo
11 CRANBERRY LN # 11, MIDDLETON, MA, 019...
Community: North Meadow Village
MLS 73443669 • Compass, Nikki Martin Team
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
Pennington Crossing
![2213 PENNINGTON DR # 2213, WALPOLE, MA, ..., Walpole, MA 02081]()
2 beds
|2 baths
|1,490 sq ft
|Condo
2213 PENNINGTON DR # 2213, WALPOLE, MA, ...
Community: Pennington Crossing
MLS 73445916 • Kelley & Rege Properties, Inc., Fr...
Woodstone Crossing
![130 TROTTER RD 1309, WEYMOUTH, MA, 02190, Weymouth, MA 02190]()
2 beds
|2 baths
|1,325 sq ft
|Condo
130 TROTTER RD 1309, WEYMOUTH, MA, 02190
Community: Woodstone Crossing
MLS 73430930 • Keller Williams Realty, Depend on ...
New
30 Coppersmith
![30 COPPERSMITH WAY # 104, CANTON, MA, 02..., Canton, MA 02021]()
1 beds
|1 baths
|1,027 sq ft
|Condo
30 COPPERSMITH WAY # 104, CANTON, MA, 02...
Community: 30 Coppersmith
MLS 73445491 • Pulte Homes of New England, Erin S...
Regency at Glen Ellen
![20 JAMESON DR # 20, MILLIS, MA, 02054, Millis, MA 02054]()
3 beds
|3 baths
|2,581 sq ft
|Condo
20 JAMESON DR # 20, MILLIS, MA, 02054
Community: Regency at Glen Ellen
MLS 73422515 • Coldwell Banker Realty - Needham, ...
Great Island
![22 COTTAGE CV, PLYMOUTH, MA, 02360, Plymouth, MA 02360]()
MLS 73444874 • Engel & Volkers, South Shore, Jenn...
Want to learn more about 55+ communities in Middleton?
55places can help!
Questions? Call us:
(508) 715-6046
The Village at Westminster Place
![8 INDIAN CIR # 8, HOLDEN, MA, 01520, Holden, MA 01520]()
3 beds
|3 baths
|1,998 sq ft
|House
8 INDIAN CIR # 8, HOLDEN, MA, 01520
Community: The Village at Westminster Place
MLS 73444852 • Keller Williams Boston MetroWest, ...
Great Island
![31 FOX HOLW, PLYMOUTH, MA, 02360, Plymouth, MA 02360]()
MLS 73393973 • Compass, Seagate Properties
Sawyer's Reach
![2 MARINERS WAY UNIT 306, PLYMOUTH, MA, 0..., Plymouth, MA 02360]()
2 beds
|2 baths
|1,368 sq ft
|Condo
2 MARINERS WAY UNIT 306, PLYMOUTH, MA, 0...
Community: Sawyer's Reach
MLS 73441511 • Keller Williams Realty, Dennis Mac...
30 Coppersmith
![30 COPPERSMITH WAY # 107, CANTON, MA, 02..., Canton, MA 02021]()
2 beds
|2 baths
|1,579 sq ft
|Condo
30 COPPERSMITH WAY # 107, CANTON, MA, 02...
Community: 30 Coppersmith
MLS 73441720 • Pulte Homes of New England, Erin S...
Great Island
![12 WEATHERVANE, PLYMOUTH, MA, 02360, Plymouth, MA 02360]()
MLS 73432133 • Pinehills Brokerage Services LLC, ...
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 # 101, WESTBOROUGH, MA..., Westborough, MA 01581]()
2 beds
|2 baths
|1,496 sq ft
|Condo
5 PETERS FARM WAY # 101, WESTBOROUGH, MA...
Community: Del Webb Chauncy Lake
MLS 73436336 • Pulte Homes of New England, Erin S...
Brierly Pond Village
![32 HORNE WAY # 32, MILLBURY, MA, 01527, Millbury, MA 01527]()
2 beds
|2 baths
|1,420 sq ft
|Condo
32 HORNE WAY # 32, MILLBURY, MA, 01527
Community: Brierly Pond Village
MLS 73433720 • Lamacchia Realty, Inc, Diane Dabro...
Del Webb Chauncy Lake
![3112 PETERS FARM WAY # 112, WESTBOROUGH,..., Westborough, MA 01581]()
1 beds
|1 baths
|1,021 sq ft
|Condo
3112 PETERS FARM WAY # 112, WESTBOROUGH,...
Community: Del Webb Chauncy Lake
MLS 73441080 • LAER Realty Partners, Debi Malone
Martins Landing
![260 MARTINS LNDG APT 508, NORTH READING,..., North Reading, MA 01864]()
2 beds
|2 baths
|1,340 sq ft
|Condo
260 MARTINS LNDG APT 508, NORTH READING,...
Community: Martins Landing
MLS 73342862 • Lillian Montalto Signature Propert...
The Trails
![71 WESTON LN # 71, HOPKINTON, MA, 01748, Hopkinton, MA 01748]()
2 beds
|4 baths
|3,258 sq ft
|Condo
71 WESTON LN # 71, HOPKINTON, MA, 01748
Community: The Trails
MLS 73444675 • RE/MAX Executive Realty, Erika Ste...
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Oak Point
![1901 PHEASANT LN, MIDDLEBORO, MA, 02346, Middleboro, MA 02346]()
MLS 73442192 • Ron McGann, Inc., Ronald McGann
Del Webb Chauncy Lake
![3102 PETERS FARM WAY # 102, WESTBOROUGH,..., Westborough, MA 01581]()
1 beds
|1 baths
|956 sq ft
|Condo
3102 PETERS FARM WAY # 102, WESTBOROUGH,...
Community: Del Webb Chauncy Lake
MLS 73416001 • Guardian Realty Group, Barton Fink
The Trails
![4 WATERVILLE LN # 4, HOPKINTON, MA, 0174..., Hopkinton, MA 01748]()
2 beds
|3 baths
|2,510 sq ft
|Condo
4 WATERVILLE LN # 4, HOPKINTON, MA, 0174...
Community: The Trails
MLS 73406944 • Realty Executives Boston West, Phi...
Great Island
![4 MILLERS JOIST, PLYMOUTH, MA, 02360, Plymouth, MA 02360]()
MLS 73411665 • Pinehills Brokerage Services LLC, ...
Brooksmont
![95 BROOKSMONT DR # 26, HOLLISTON, MA, 01..., Holliston, MA 01746]()
2 beds
|2 baths
|2,431 sq ft
|Condo
95 BROOKSMONT DR # 26, HOLLISTON, MA, 01...
Community: Brooksmont
MLS 73443624 • Realty Executives Boston West, Kar...
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 Village at Westminster Place
![27 TEA PARTY CIR # 27, HOLDEN, MA, 01520, Holden, MA 01520]()
3 beds
|3 baths
|1,895 sq ft
|Condo
27 TEA PARTY CIR # 27, HOLDEN, MA, 01520
Community: The Village at Westminster Place
MLS 73430095 • BA Property & Lifestyle Advisors, ...
Del Webb Chauncy Lake
![11302 PETERS FARM WAY # 11302, WESTBOROU..., Westborough, MA 01581]()
1 beds
|1 baths
|956 sq ft
|Condo
11302 PETERS FARM WAY # 11302, WESTBOROU...
Community: Del Webb Chauncy Lake
MLS 73443694 • Century 21 Custom Home Realty, Lau...
Whitestone Village
![503 DIANE CIR # 503, GROVELAND, MA, 0183..., Groveland, MA 01834]()
2 beds
|3 baths
|1,830 sq ft
|Condo
503 DIANE CIR # 503, GROVELAND, MA, 0183...
Community: Whitestone Village
MLS 73437320 • Connie Doto Realty Group, Constanc...
Del Webb Chauncy Lake
![11101 PETERS FARM WAY # 101, WESTBOROUGH..., Westborough, MA 01581]()
2 beds
|2 baths
|1,469 sq ft
|Condo
11101 PETERS FARM WAY # 101, WESTBOROUGH...
Community: Del Webb Chauncy Lake
MLS 73438484 • Compass, Dee Kerner
Martins Landing
![300 MARTINS LNDG UNIT 107, NORTH READING..., North Reading, MA 01864]()
2 beds
|2 baths
|1,434 sq ft
|Condo
300 MARTINS LNDG UNIT 107, NORTH READING...
Community: Martins Landing
MLS 73419948 • Better Homes and Gardens Real Esta...
Want to learn more about 55+ communities in Middleton?
55places can help!
Questions? Call us:
(508) 715-6046
Great Island
![74 CHAMPLAIN CIR, PLYMOUTH, MA, 02360, Plymouth, MA 02360]()
3 beds
|3 baths
|2,580 sq ft
|House
74 CHAMPLAIN CIR, PLYMOUTH, MA, 02360
Community: Great Island
MLS 73443148 • Pinehills Brokerage Services LLC, ...
Whitestone Village
![606 ALYSSA DR # 606, GROVELAND, MA, 0183..., Groveland, MA 01834]()
2 beds
|2 baths
|1,306 sq ft
|Condo
606 ALYSSA DR # 606, GROVELAND, MA, 0183...
Community: Whitestone Village
MLS 73435423 • Marc LeBlanc Realty, Marc LeBlanc
Del Webb Chauncy Lake
![3103 PETERS FARM WAY # 3103, WESTBOROUGH..., Westborough, MA 01581]()
1 beds
|1 baths
|956 sq ft
|Condo
3103 PETERS FARM WAY # 3103, WESTBOROUGH...
Community: Del Webb Chauncy Lake
MLS 73415011 • Berkshire Hathaway HomeServices Co...
Great Island
![45 WHITE TRELLIS, PLYMOUTH, MA, 02360, Plymouth, MA 02360]()
3 beds
|3 baths
|2,899 sq ft
|House
45 WHITE TRELLIS, PLYMOUTH, MA, 02360
Community: Great Island
MLS 73443491 • Pinehills Brokerage Services LLC, ...
Regency at Methuen
![42 HOPKINS CIR # 42, METHUEN, MA, 01844, Methuen, MA 01844]()
2 beds
|4 baths
|2,176 sq ft
|Condo
42 HOPKINS CIR # 42, METHUEN, MA, 01844
Community: Regency at Methuen
MLS 73443275 • J. Barrett & Company, Cammy Bille
Frequently Asked Questions
In Middleton, there is 1 small community with less than 500 homes.
The smallest 55+ community in Middleton has 42 homes, the largest has 42 homes, and the average community consists of 42 homes.
No, there are no gated 55+ communities in Middleton.
Want more information about active adult communities around Middleton?
Want to learn more about 55+ communities in Middleton?
162
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near Middleton
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REIN updates its listings on a daily basis. Data last updated: Oct 23, 2025.
This application does not include information on all of the properties available for sale at this time.
