Call us at (401) 313-4589 to learn more about active adult communities near Middletown
Middletown, RI 55+ active adult communities & homes for sale
80 communities near Middletown
114 homes near Middletown
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![Bay Ridge]()
$600Ks
- $800Ks
Bay Ridge, Middletown, RI
Resale Only
|
55+ age-restricted
|
Built 2008 - 2014
|
60 homes
No reviews yet
![Bailey Brook]()
$600Ks
- $700Ks
Bailey Brook, Middletown, RI
Resale Only
|
55+ age-restricted
|
Built 2018 - 2024
|
36 homes
5 rating (3 reviews)
![Oak Point]()
$300Ks
- $400Ks
Oak Point, Middleborough, MA
New and Resale
|
55+ age-restricted
|
Built 1999 - present
|
1,150 homes
No reviews yet
![Southport]()
$400Ks
- $700Ks
Southport, Mashpee, MA
New and Resale
|
55+ age-restricted
|
Built 1989 - present
|
730 homes
No reviews yet
![Del Webb Chauncy Lake]()
$300Ks
- $800Ks
Del Webb Chauncy Lake, Westborough, MA
New Construction
|
55+ age-restricted
|
Built 2018 - present
|
700 homes
Want to learn more about 55+ communities in Middletown?
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Questions? Call us:
(401) 313-4589
No reviews yet
![Great Island]()
$700Ks
- $1Ms
Great Island, Plymouth, MA
Resale Only
|
55+ age-restricted
|
Built 2002 - 2015
|
600 homes
No reviews yet
![Regency at Glen Ellen]()
$800Ks
- $1Ms
Regency at Glen Ellen, Millis, MA
New Construction
|
55+ age-restricted
|
Built 2017 - present
|
324 homes
4 rating (5 reviews)
![South Shore Village]()
$600Ks
- $800Ks
South Shore Village, South Kingstown, RI
New and Resale
|
55+ age-restricted
|
Built 2016 - present
|
303 homes
No reviews yet
![The Villages on Mount Hop...]()
$600Ks
- $1Ms
The Villages on Mount Hop..., Tiverton, RI
New and Resale
|
55+ age-restricted
|
Built 2003 - present
|
230 homes
No reviews yet
![Sawyer's Reach]()
$600Ks
- $600Ks
Sawyer's Reach, Plymouth, MA
New and Resale
|
55+ age-restricted
|
Built 2017 - present
|
224 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
![Woodstone Crossing]()
$500Ks
- $500Ks
Woodstone Crossing, Weymouth, MA
Resale Only
|
Age-targeted
|
Built 2015 - 2019
|
200 homes
No reviews yet
![Brierly Pond Village]()
$400Ks
- $400Ks
Brierly Pond Village, Millbury, MA
Resale Only
|
55+ age-restricted
|
Built 2003 - 2013
|
199 homes
No reviews yet
![Pennington Crossing]()
$500Ks
- $500Ks
Pennington Crossing, Walpole, MA
New Construction
|
55+ age-restricted
|
Built 2018 - present
|
172 homes
No reviews yet
![The Trails]()
$900Ks
- $1Ms
The Trails, Hopkinton, MA
New Construction
|
55+ age-restricted
|
Built 2017 - present
|
170 homes
No reviews yet
![Red Mill Village]()
$500Ks
- $800Ks
Red Mill Village, Norton, MA
Resale Only
|
55+ age-restricted
|
Built 2012 - 2014
|
156 homes
Want to learn more about 55+ communities in Middletown?
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(401) 313-4589
No reviews yet
![Villages at Weathervane]()
$800Ks
- $1Ms
Villages at Weathervane, Weymouth, MA
Resale Only
|
55+ age-restricted
|
Built 2003 - 2010
|
149 homes
No reviews yet
![Harmony Place]()
$400Ks
- $500Ks
Harmony Place, Rutland, MA
New Construction
|
55+ age-restricted
|
Built 2023 - present
|
142 homes
No reviews yet
![Wakefield Meadows]()
$700Ks
- $800Ks
Wakefield Meadows, Wakefield, RI
Resale Only
|
55+ age-restricted
|
Built 2009 - 2015
|
142 homes
No reviews yet
![The Preserve at Hunters H...]()
$600Ks
- $800Ks
The Preserve at Hunters H..., Dighton, MA
New and Resale
|
55+ age-restricted
|
Built 2006 - present
|
140 homes
No reviews yet
![Upton Ridge]()
$600Ks
- $600Ks
Upton Ridge, Upton, MA
New Construction
|
55+ age-restricted
|
Built 2019 - present
|
139 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
![WestRidge]()
$700Ks
- $1Ms
WestRidge, Hudson, MA
Resale Only
|
55+ age-restricted
|
Built 2009 - 2016
|
136 homes
No reviews yet
![Angell Brook Village]()
$400Ks
- $400Ks
Angell Brook Village, West Boylston, MA
Resale Only
|
55+ age-restricted
|
Built 2005 - 2012
|
132 homes
No reviews yet
![Millwood Preserve]()
$1Ms
- $1Ms
Millwood Preserve, Framingham, MA
New Construction
|
55+ age-restricted
|
Built 2020 - present
|
129 homes
No reviews yet
![The Village at Westminste...]()
$400Ks
- $600Ks
The Village at Westminste..., Holden, MA
New and Resale
|
55+ age-restricted
|
Built 2006 - present
|
125 homes
No reviews yet
![Stonebridge Commons]()
$600Ks
- $700Ks
Stonebridge Commons, Hanson, MA
Resale Only
|
55+ age-restricted
|
Built 2007 - 2018
|
121 homes
Want to learn more about 55+ communities in Middletown?
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Questions? Call us:
(401) 313-4589
No reviews yet
![Seton Highlands at The Pi...]()
$700Ks
- $900Ks
Seton Highlands at The Pi..., Plymouth, MA
New and Resale
|
55+ age-restricted
|
Built 2008 - present
|
120 homes
No reviews yet
![Summer Reach]()
$400Ks
- $500Ks
Summer Reach, Plymouth, MA
Resale Only
|
55+ age-restricted
|
Built 2017 - 2020
|
114 homes
No reviews yet
![The Village at Orchard Me...]()
$400Ks
- $500Ks
The Village at Orchard Me..., Shrewsbury, MA
Resale Only
|
55+ age-restricted
|
Built 2002 - 2007
|
114 homes
No reviews yet
![New England Commons]()
$400Ks
- $400Ks
New England Commons, Webster, MA
New and Resale
|
55+ age-restricted
|
Built 2005 - present
|
100 homes
No reviews yet
![Orchard Hill]()
$600Ks
- $600Ks
Orchard Hill, Westborough, MA
Resale Only
|
55+ age-restricted
|
Built 2002 - 2010
|
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.
No reviews yet
![The Villages at Walker Me...]()
$600Ks
- $600Ks
The Villages at Walker Me..., Westborough, MA
Resale Only
|
55+ age-restricted
|
Built 1999 - 2000
|
100 homes
No reviews yet
![Bates Quarry]()
Bates Quarry, Walpole, MA
New Construction
|
55+ age-restricted
|
Built 2025 - present
|
100 homes
No reviews yet
![The Lanterns at Warren Wo...]()
$500Ks
- $700Ks
The Lanterns at Warren Wo..., Ashland, MA
Resale Only
|
55+ age-restricted
|
Built 2016 - 2020
|
93 homes
No reviews yet
![The Village at Auburnvill...]()
$300Ks
- $400Ks
The Village at Auburnvill..., Whitman, MA
Resale Only
|
55+ age-restricted
|
Built 2004 - 2014
|
92 homes
No reviews yet
![The Seasons at Salisbury]()
$600Ks
- $600Ks
The Seasons at Salisbury, Holden, MA
Resale Only
|
55+ age-restricted
|
Built 2002 - 2006
|
91 homes
Want to learn more about 55+ communities in Middletown?
55places can help!
Questions? Call us:
(401) 313-4589
No reviews yet
![The Villages at Crane Mea...]()
$400Ks
- $400Ks
The Villages at Crane Mea..., Marlborough, MA
Resale Only
|
55+ age-restricted
|
Built 2001 - 2005
|
91 homes
No reviews yet
![Adams Farm]()
$800Ks
- $900Ks
Adams Farm, Shrewsbury, MA
Resale Only
|
55+ age-restricted
|
Built 2005 - 2013
|
90 homes
No reviews yet
![Southwinds]()
$600Ks
- $700Ks
Southwinds, South Kingstown, RI
Resale Only
|
55+ age-restricted
|
Built 2005 - 2010
|
70 homes
No reviews yet
![Bella Vista]()
$300Ks
- $400Ks
Bella Vista, Glocester, RI
Resale Only
|
55+ age-restricted
|
Built 2015 - 2021
|
70 homes
No reviews yet
![Regency at Assabet Ridge]()
$500Ks
- $600Ks
Regency at Assabet Ridge, Marlborough, MA
Resale Only
|
55+ age-restricted
|
Built 2010 - 2015
|
69 homes
Great Island
![4 MILLERS JOIST, PLYMOUTH, MA, 02360, Plymouth, MA 02360]()
MLS 73411665 • Pinehills Brokerage Services LLC, ...
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...
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, ...
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, ...
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, ...
Want to learn more about 55+ communities in Middletown?
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Questions? Call us:
(401) 313-4589
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...
Kensington at The Pinehills
![18 BIRMINGHAM, PLYMOUTH, MA, 02360, Plymouth, MA 02360]()
3 beds
|3 baths
|2,369 sq ft
|House
18 BIRMINGHAM, PLYMOUTH, MA, 02360
Community: Kensington at The Pinehills
MLS 73432676 • Coldwell Banker Realty - Plymouth,...
Villages at Weathervane
![18 BEN HOGAN LNDG # 18, WEYMOUTH, MA, 02..., Weymouth, MA 02190]()
2 beds
|4 baths
|2,956 sq ft
|Condo
18 BEN HOGAN LNDG # 18, WEYMOUTH, MA, 02...
Community: Villages at Weathervane
MLS 73442297 • Houston Real Estate, Marci McDonou...
Seton Highlands at The Pinehills
![18 INVERNESS LN # 18, PLYMOUTH, MA, 0236..., Plymouth, MA 02360]()
3 beds
|4 baths
|3,782 sq ft
|Condo
18 INVERNESS LN # 18, PLYMOUTH, MA, 0236...
Community: Seton Highlands at The Pinehills
MLS 73402262 • Coldwell Banker Realty - Plymouth,...
WestRidge
![3 TOWNSEND RD # 3, HUDSON, MA, 01749, Hudson, MA 01749]()
MLS 73438766 • Keller Williams Pinnacle MetroWest...
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 Glen Ellen
![27 RICHARDSON DR # 27, MILLIS, MA, 02054, Millis, MA 02054]()
2 beds
|3 baths
|2,485 sq ft
|Condo
27 RICHARDSON DR # 27, MILLIS, MA, 02054
Community: Regency at Glen Ellen
MLS 73390614 • Redfin Corp., Shelly A. Armstrong
Southport
![2 PGA LN # 2, MASHPEE, MA, 02649, Mashpee, MA 02649]()
MLS 73442847 • Sotheby's International Realty - S...
Great Island
![27 CROSS WIND, PLYMOUTH, MA, 02360, Plymouth, MA 02360]()
MLS 73438468 • Keller Williams Realty Colonial Pa...
Sawyer's Reach
![45 PLAZA WAY UNIT 406, PLYMOUTH, MA, 023..., Plymouth, MA 02360]()
2 beds
|2 baths
|1,368 sq ft
|Condo
45 PLAZA WAY UNIT 406, PLYMOUTH, MA, 023...
Community: Sawyer's Reach
MLS 73426451 • Keller Williams Realty, Dennis Mac...
Seton Highlands at The Pinehills
![9 ABERDEEN # 9, PLYMOUTH, MA, 02360, Plymouth, MA 02360]()
2 beds
|4 baths
|2,987 sq ft
|Condo
9 ABERDEEN # 9, PLYMOUTH, MA, 02360
Community: Seton Highlands at The Pinehills
MLS 73398971 • Compass, Team Suzanne and Company
Want to learn more about 55+ communities in Middletown?
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Questions? Call us:
(401) 313-4589
Southport
![17 CHADWICK CT # 17, MASHPEE, MA, 02649, Mashpee, MA 02649]()
MLS 73395151 • Today Real Estate, Inc., Mari Senn...
Great Island
![24 WEBSTER REACH, PLYMOUTH, MA, 02360, Plymouth, MA 02360]()
3 beds
|3 baths
|2,782 sq ft
|House
24 WEBSTER REACH, PLYMOUTH, MA, 02360
Community: Great Island
MLS 73389479 • Pinehills Brokerage Services LLC, ...
Del Webb Chauncy Lake
![12302 PETERS FARM WAY # 302, WESTBOROUGH..., Westborough, MA 01581]()
1 beds
|1 baths
|956 sq ft
|Condo
12302 PETERS FARM WAY # 302, WESTBOROUGH...
Community: Del Webb Chauncy Lake
MLS 73416795 • Century 21 North East, MG Group
Southport
![80 PINE HILL BLVD # 80, MASHPEE, MA, 026..., Mashpee, MA 02649]()
2 beds
|3 baths
|2,208 sq ft
|Condo
80 PINE HILL BLVD # 80, MASHPEE, MA, 026...
Community: Southport
MLS 73353961 • Keller Williams Realty Boston Sout...
The Preserve at Hunters Hill
![3064 CLUB HOUSE DR, DIGHTON, MA, 02715, Dighton, MA 02715]()
3 beds
|3 baths
|1,928 sq ft
|House
3064 CLUB HOUSE DR, DIGHTON, MA, 02715
Community: The Preserve at Hunters Hill
MLS 73393623 • KAM Realty, Kenneth A Mongeon
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
![3075 CLUB HOUSE DR, DIGHTON, MA, 02715, Dighton, MA 02715]()
3 beds
|2 baths
|2,151 sq ft
|House
3075 CLUB HOUSE DR, DIGHTON, MA, 02715
Community: The Preserve at Hunters Hill
MLS 73430329 • revolv Real Estate, Lynette-Marie ...
Brooksmont
![104 BROOKSMONT DR # 104, HOLLISTON, MA, ..., Holliston, MA 01746]()
2 beds
|2 baths
|1,516 sq ft
|Condo
104 BROOKSMONT DR # 104, HOLLISTON, MA, ...
Community: Brooksmont
MLS 73414911 • Engel & Volkers Wellesley, Cindy L...
Del Webb Chauncy Lake
![2 CODMAN WAY 5401, WESTBOROUGH, MA, 0158..., Westborough, MA 01581]()
2 beds
|2 baths
|1,496 sq ft
|Condo
2 CODMAN WAY 5401, WESTBOROUGH, MA, 0158...
Community: Del Webb Chauncy Lake
MLS 73426688 • Pulte Homes of New England, Erin S...
Del Webb Chauncy Lake
![2 CODMAN WAY 408, WESTBOROUGH, MA, 01581, Westborough, MA 01581]()
2 beds
|2 baths
|1,375 sq ft
|Condo
2 CODMAN WAY 408, WESTBOROUGH, MA, 01581
Community: Del Webb Chauncy Lake
MLS 73433002 • Pulte Homes of New England, Erin S...
Del Webb Chauncy Lake
![5 PETERS FARM WAY # 205, WESTBOROUGH, MA..., Westborough, MA 01581]()
2 beds
|2 baths
|1,166 sq ft
|Condo
5 PETERS FARM WAY # 205, WESTBOROUGH, MA...
Community: Del Webb Chauncy Lake
MLS 73433417 • 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
Southport
![12 KETTLE LN # 31, MASHPEE, MA, 02649, Mashpee, MA 02649]()
MLS 73390536 • Kinlin Grover Compass, Carli Taylo...
Southport
![72 GREY HAWK DR # 670, MASHPEE, MA, 0264..., Mashpee, MA 02649]()
2 beds
|3 baths
|2,283 sq ft
|Condo
72 GREY HAWK DR # 670, MASHPEE, MA, 0264...
Community: Southport
MLS 73436536 • Kinlin Grover Compass, Carli Taylo...
Orchard Hill
![9 BALDWIN CT # 9, WESTBOROUGH, MA, 01581, Westborough, MA 01581]()
3 beds
|3 baths
|2,793 sq ft
|Condo
9 BALDWIN CT # 9, WESTBOROUGH, MA, 01581
Community: Orchard Hill
MLS 73440395 • Mathieu Newton Sotheby's Internati...
Spring Meadow
![116 SPRING MEADOW LN # 116, HANOVER, MA,..., Hanover, MA 02339]()
2 beds
|3 baths
|2,417 sq ft
|Condo
116 SPRING MEADOW LN # 116, HANOVER, MA,...
Community: Spring Meadow
MLS 73386182 • Berkshire Hathaway HomeServices E...
Seton Highlands at The Pinehills
![105 SETON HIGHLANDS # 105, PLYMOUTH, MA,..., Plymouth, MA 02360]()
2 beds
|3 baths
|2,186 sq ft
|Condo
105 SETON HIGHLANDS # 105, PLYMOUTH, MA,...
Community: Seton Highlands at The Pinehills
MLS 73323375 • South Shore Sotheby's Internationa...
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
![3049 CLUBHOUSE DR 77, DIGHTON, MA, 02715, Dighton, MA 02715]()
2 beds
|2 baths
|2,024 sq ft
|House
3049 CLUBHOUSE DR 77, DIGHTON, MA, 02715
Community: The Preserve at Hunters Hill
MLS 73429691 • Long Realty, Patricia Fanning
Southport
![18 EXECUTIVE DR, MASHPEE, MA, 02649, Mashpee, MA 02649]()
MLS 73439676 • Sotheby's International Realty, Ja...
Regency at Glen Ellen
![1 JAMESON DR # 1, MILLIS, MA, 02054, Millis, MA 02054]()
2 beds
|2 baths
|1,875 sq ft
|Condo
1 JAMESON DR # 1, MILLIS, MA, 02054
Community: Regency at Glen Ellen
MLS 73422509 • Coldwell Banker Realty - Needham, ...
Seton Highlands at The Pinehills
![17 ABERDEEN # 17, PLYMOUTH, MA, 02360, Plymouth, MA 02360]()
3 beds
|3 baths
|2,690 sq ft
|Condo
17 ABERDEEN # 17, PLYMOUTH, MA, 02360
Community: Seton Highlands at The Pinehills
MLS 73437805 • Pinehills Brokerage Services LLC, ...
The Villages at Walker Meadow
![9 SHAKER WAY # 9, WESTBOROUGH, MA, 01581, Westborough, MA 01581]()
2 beds
|2 baths
|2,090 sq ft
|Condo
9 SHAKER WAY # 9, WESTBOROUGH, MA, 01581
Community: The Villages at Walker Meadow
MLS 73429776 • Mathieu Newton Sotheby's Internati...
Want to learn more about 55+ communities in Middletown?
55places can help!
Questions? Call us:
(401) 313-4589
Del Webb Chauncy Lake
![12208 PETERS FARM WAY # 12208, WESTBOROU..., Westborough, MA 01581]()
1 beds
|1 baths
|1,021 sq ft
|Condo
12208 PETERS FARM WAY # 12208, WESTBOROU...
Community: Del Webb Chauncy Lake
MLS 73428524 • ERA Key Realty Services- Fram, Mic...
Southport
![8 CHIPPERS LN # 390, MASHPEE, MA, 02649, Mashpee, MA 02649]()
MLS 73436733 • Kinlin Grover Compass, Carli Taylo...
Great Island
![39 WOODSONG, PLYMOUTH, MA, 02360, Plymouth, MA 02360]()
MLS 73435623 • Pinehills Brokerage Services LLC, ...
Regency at Glen Ellen
![6 GLEN ELLEN BLVD # 6, MILLIS, MA, 02054, Millis, MA 02054]()
3 beds
|3 baths
|2,656 sq ft
|Condo
6 GLEN ELLEN BLVD # 6, MILLIS, MA, 02054
Community: Regency at Glen Ellen
MLS 73437375 • Vesta Real Estate Group, Inc., Ves...
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
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?
114
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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.
