Call us at (401) 313-4589 to learn more about active adult communities near Middletown
Middletown, RI 55+ active adult communities & homes for sale - Page 2
80 communities near Middletown
114 homes near Middletown
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![Holliston Woods]()
$500Ks
- $700Ks
Holliston Woods, Holliston, MA
Resale Only
|
55+ age-restricted
|
Built 2016 - 2018
|
66 homes
No reviews yet
![Lake Point Village]()
$400Ks
- $400Ks
Lake Point Village, Lakeville, MA
New Construction
|
55+ age-restricted
|
Built 2020 - present
|
66 homes
No reviews yet
![Brooksmont]()
$600Ks
- $700Ks
Brooksmont, Holliston, MA
Resale Only
|
55+ age-restricted
|
Built 2017 - 2020
|
66 homes
No reviews yet
![Enclave at Hudson]()
$800Ks
- $1Ms
Enclave at Hudson, Hudson, MA
New Construction
|
55+ age-restricted
|
Built 2021 - present
|
64 homes
No reviews yet
![30 Coppersmith]()
$400Ks
- $600Ks
30 Coppersmith, Canton, MA
New Construction
|
55+ age-restricted
|
Built 2025 - present
|
63 homes
Want to learn more about 55+ communities in Middletown?
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Questions? Call us:
(401) 313-4589
No reviews yet
![The Pines at Hathaway Pon...]()
$300Ks
- $500Ks
The Pines at Hathaway Pon..., Rochester, MA
Resale Only
|
55+ age-restricted
|
Built 2006 - 2014
|
61 homes
No reviews yet
![Westbrook Crossing]()
$400Ks
- $500Ks
Westbrook Crossing, Dedham, MA
Resale Only
|
55+ age-restricted
|
Built 2003 - 2004
|
60 homes
No reviews yet
![Northside Meadows]()
$600Ks
- $700Ks
Northside Meadows, Framingham, MA
Resale Only
|
55+ age-restricted
|
Built 2017 - 2019
|
60 homes
No reviews yet
![Rockland Glen]()
$300Ks
- $500Ks
Rockland Glen, Rockland, MA
Resale Only
|
55+ age-restricted
|
Built 2008 - 2015
|
60 homes
No reviews yet
![Rockwood Meadows]()
$600Ks
- $700Ks
Rockwood Meadows, Upton, MA
New Construction
|
55+ age-restricted
|
Built 2016 - present
|
58 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
![Blue Heron Pond]()
$400Ks
- $500Ks
Blue Heron Pond, Lancaster, MA
Resale Only
|
55+ age-restricted
|
Built 2006 - 2014
|
58 homes
No reviews yet
![Liberty Woods]()
$600Ks
- $700Ks
Liberty Woods, Hanson, MA
New Construction
|
55+ age-restricted
|
Built 2023 - present
|
56 homes
No reviews yet
![Wolcott Woods]()
$1Ms
- $2Ms
Wolcott Woods, Milton, MA
New Construction
|
55+ age-restricted
|
Built 2020 - present
|
54 homes
No reviews yet
![Arbor Hills]()
$400Ks
- $500Ks
Arbor Hills, Kingston, MA
Resale Only
|
55+ age-restricted
|
Built 2003 - 2005
|
54 homes
No reviews yet
![The Elms of Hanover]()
$500Ks
- $700Ks
The Elms of Hanover, Hanover, MA
Resale Only
|
55+ age-restricted
|
Built 2003 - 2004
|
51 homes
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No reviews yet
![Balancing Rock]()
$500Ks
- $600Ks
Balancing Rock, Holliston, MA
Resale Only
|
55+ age-restricted
|
Built 2006 - 2008
|
49 homes
No reviews yet
![Pheasant Hill]()
$300Ks
- $400Ks
Pheasant Hill, Northborough, MA
Resale Only
|
55+ age-restricted
|
Built 2005 - 2006
|
48 homes
No reviews yet
![Rolling Mill]()
$600Ks
- $700Ks
Rolling Mill, Plymouth, MA
Resale Only
|
55+ age-restricted
|
Built 2018 - 2021
|
46 homes
No reviews yet
![Forest Glen]()
$400Ks
- $500Ks
Forest Glen, Uxbridge, MA
New Construction
|
55+ age-restricted
|
Built 2018 - present
|
44 homes
No reviews yet
![Seaside at Scituate - The...]()
$900Ks
- $1Ms
Seaside at Scituate - The..., Scituate, MA
New Construction
|
55+ age-restricted
|
Built 2019 - present
|
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.
No reviews yet
![Duxbury Estates]()
$500Ks
- $700Ks
Duxbury Estates, Duxbury, MA
Resale Only
|
55+ age-restricted
|
Built 2008 - 2013
|
44 homes
No reviews yet
![Center Commons]()
$500Ks
- $600Ks
Center Commons, Pembroke, MA
Resale Only
|
55+ age-restricted
|
Built 2004 - 2009
|
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
![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
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Questions? Call us:
(401) 313-4589
No reviews yet
![Spring Meadow]()
$700Ks
- $700Ks
Spring Meadow, Hanover, MA
Resale Only
|
55+ age-restricted
|
Built 2004 - 2007
|
39 homes
No reviews yet
![Tara Woods]()
$400Ks
- $400Ks
Tara Woods, Plymouth, MA
Resale Only
|
55+ age-restricted
|
Built 2007 - 2015
|
38 homes
No reviews yet
![Brandywyne]()
$700Ks
- $800Ks
Brandywyne, South Kingstown, RI
Resale Only
|
55+ age-restricted
|
Built 2011 - 2013
|
37 homes
No reviews yet
![Cranberry Grove]()
$200Ks
- $300Ks
Cranberry Grove, Wareham, MA
Resale Only
|
55+ age-restricted
|
Built 2001 - 2001
|
36 homes
No reviews yet
![Peregrine Woods]()
$400Ks
- $600Ks
Peregrine Woods, Marshfield, MA
Resale Only
|
55+ age-restricted
|
Built 2002 - 2005
|
32 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 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
![Brookside Village]()
$700Ks
- $700Ks
Brookside Village, Walpole, MA
Resale Only
|
55+ age-restricted
|
Built 2018 - 2018
|
30 homes
No reviews yet
![Brookedge Village Condomi...]()
$300Ks
- $400Ks
Brookedge Village Condomi..., South Kingstown, RI
Resale Only
|
55+ age-restricted
|
Built 2007 - 2007
|
28 homes
No reviews yet
![Mattapoisett Landing]()
$400Ks
- $500Ks
Mattapoisett Landing, Mattapoisett, MA
Resale Only
|
55+ age-restricted
|
Built 2012 - 2015
|
27 homes
No reviews yet
![Wyman Farms]()
$500Ks
- $900Ks
Wyman Farms, Shrewsbury, MA
New Construction
|
55+ age-restricted
|
Built 2017 - present
|
26 homes
Want to learn more about 55+ communities in Middletown?
55places can help!
Questions? Call us:
(401) 313-4589
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
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
![59 North Main]()
$900Ks
- $900Ks
59 North Main, Sherborn, MA
New Construction
|
55+ age-restricted
|
Built 2019 - present
|
12 homes
No reviews yet
![Village at Silver Hill]()
$1Ms
- $1Ms
Village at Silver Hill, Weston, MA
New Construction
|
55+ age-restricted
|
Built 2021 - present
|
8 homes
Southport
![116 GREY HAWK DR # 116, MASHPEE, MA, 026..., Mashpee, MA 02649]()
2 beds
|2 baths
|1,864 sq ft
|Condo
116 GREY HAWK DR # 116, MASHPEE, MA, 026...
Community: Southport
MLS 73434139 • Compass, Livia Freitas Monteforte
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...
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...
Oak Point
![2602 GREEN ST, MIDDLEBORO, MA, 02346, Middleboro, MA 02346]()
MLS 73422842 • Conway - Bridgewater, Stephen Damo...
Southport
![23 SEA SPRAY AVE # 563, MASHPEE, MA, 026..., Mashpee, MA 02649]()
2 beds
|4 baths
|2,455 sq ft
|Condo
23 SEA SPRAY AVE # 563, MASHPEE, MA, 026...
Community: Southport
MLS 73439922 • Kinlin Grover Compass, Carli Taylo...
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Questions? Call us:
(401) 313-4589
Millwood Preserve
![11 EAGLE LN 105, FRAMINGHAM, MA, 01701, Framingham, MA 01701]()
2 beds
|4 baths
|3,503 sq ft
|Condo
11 EAGLE LN 105, FRAMINGHAM, MA, 01701
Community: Millwood Preserve
MLS 73440251 • Andrew J. Abu Inc., REALTORS®, Li...
The Village at Westminster Place
![2 EXPLORERS WAY # 2, HOLDEN, MA, 01520, Holden, MA 01520]()
2 beds
|2 baths
|1,661 sq ft
|Condo
2 EXPLORERS WAY # 2, HOLDEN, MA, 01520
Community: The Village at Westminster Place
MLS 73437136 • RE/MAX Partners, David Stead
New
Del Webb Chauncy Lake
![4403 PETERS FARM WAY 403, WESTBOROUGH, M..., Westborough, MA 01581]()
1 beds
|1 baths
|956 sq ft
|Condo
4403 PETERS FARM WAY 403, WESTBOROUGH, M...
Community: Del Webb Chauncy Lake
MLS 73446787 • Boucher Real Estate, Inc., Duane B...
New
30 Coppersmith
![30 COPPERSMITH WAY # 505, CANTON, MA, 02..., Canton, MA 02021]()
2 beds
|2 baths
|1,270 sq ft
|Condo
30 COPPERSMITH WAY # 505, CANTON, MA, 02...
Community: 30 Coppersmith
MLS 73446678 • Pulte Homes of New England, Erin S...
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...
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
![26 STONEBRIDGE DR # 26, HANSON, MA, 0234..., Hanson, MA 02341]()
3 beds
|3 baths
|2,158 sq ft
|Condo
26 STONEBRIDGE DR # 26, HANSON, MA, 0234...
Community: Stonebridge Commons
MLS 73408460 • Coldwell Banker Realty - Marion, M...
Southport
![44 TWIN OAKS DR # 44, MASHPEE, MA, 02649, Mashpee, MA 02649]()
2 beds
|2 baths
|1,659 sq ft
|Condo
44 TWIN OAKS DR # 44, MASHPEE, MA, 02649
Community: Southport
MLS 73367775 • Berkshire Hathaway HomeServices Ro...
New
The Village at Auburnville
![877 AUBURNVILLE WAY D4, WHITMAN, MA, 023..., Whitman, MA 02382]()
2 beds
|2 baths
|2,090 sq ft
|Condo
877 AUBURNVILLE WAY D4, WHITMAN, MA, 023...
Community: The Village at Auburnville
MLS 73446263 • Redfin Corp., Sue Shiels
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...
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...
Want to learn more about 55+ communities in Middletown?
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Questions? Call us:
(401) 313-4589
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, ...
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
New
Duxbury Estates
![6 CARRIAGE LN # 6, DUXBURY, MA, 02332, Duxbury, MA 02332]()
2 beds
|2 baths
|1,525 sq ft
|Condo
6 CARRIAGE LN # 6, DUXBURY, MA, 02332
Community: Duxbury Estates
MLS 73443620 • Waterfront Realty Group, Barbara R...
Southport
![4 N RIDGE RD # 431, MASHPEE, MA, 02649, Mashpee, MA 02649]()
MLS 73302091 • Harriet Dugan Realty, Robert B. Du...
Great Island
![21 CROSS WIND, PLYMOUTH, MA, 02360, Plymouth, MA 02360]()
MLS 73435722 • 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.
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...
Southport
![14 SANDVIEW TER # 14, MASHPEE, MA, 02649, Mashpee, MA 02649]()
2 beds
|2 baths
|1,338 sq ft
|Condo
14 SANDVIEW TER # 14, MASHPEE, MA, 02649
Community: Southport
MLS 73421494 • Cape and Islands Realty Advisors I...
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...
Southport
![1 UPLAND CIR # 1, MASHPEE, MA, 02649, Mashpee, MA 02649]()
MLS 73429760 • William Raveis R.E. & Home Service...
Want to learn more about 55+ communities in Middletown?
55places can help!
Questions? Call us:
(401) 313-4589
Great Island
![31 FOX HOLW, PLYMOUTH, MA, 02360, Plymouth, MA 02360]()
MLS 73393973 • Compass, Seagate Properties
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...
Southport
![181 LEISURE GREEN DR, MASHPEE, MA, 02649, Mashpee, MA 02649]()
2 beds
|2 baths
|1,338 sq ft
|House
181 LEISURE GREEN DR, MASHPEE, MA, 02649
Community: Southport
MLS 73432442 • LandVest, Inc., Woods Hole, Martha...
Southport
![20 TWIN OAKS DR # 20, MASHPEE, MA, 02649, Mashpee, MA 02649]()
2 beds
|2 baths
|1,491 sq ft
|Condo
20 TWIN OAKS DR # 20, MASHPEE, MA, 02649
Community: Southport
MLS 73428763 • Keller Williams Realty, Jamie Rega...
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 # 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 # 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...
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...
Great Island
![12 WEATHERVANE, PLYMOUTH, MA, 02360, Plymouth, MA 02360]()
MLS 73432133 • Pinehills Brokerage Services LLC, ...
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...
Want to learn more about 55+ communities in Middletown?
55places can help!
Questions? Call us:
(401) 313-4589
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
Southport
![15 PEBBLE BEACH AVE # 2005-103, MASHPEE,..., Mashpee, MA 02649]()
2 beds
|3 baths
|1,685 sq ft
|Condo
15 PEBBLE BEACH AVE # 2005-103, MASHPEE,...
Community: Southport
MLS 73389783 • eXp Realty, J. Gary Bostwick
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...
Frequently Asked Questions
In Middletown, there are no large communities, no medium communities, and 2 small communities with less than 500 homes.
The smallest 55+ communities in Middletown has 36 homes, the largest has 60 homes, and the average communities consists of 48 homes.
Yes, there is gated 55+ communities in Middletown. Approximately 50.0% of 55+ communities in the area are gated. For instance, Bay Ridge is a gated communities with 60 homes.
Want more information about active adult communities around Middletown?
Want to learn more about 55+ communities in Middletown?
80
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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.
