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
99 homes near Middletown
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$600Ks
- $800Ks
Bay Ridge, Middletown, RI
Resale Only
|
55+ age-restricted
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Built 2008 - 2014
|
60 homes
$600Ks
- $700Ks
Bailey Brook, Middletown, RI
Resale Only
|
55+ age-restricted
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Built 2018 - 2024
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36 homes
5 rating (3 reviews)
![Oak Point]()
$300Ks
- $400Ks
Oak Point, Middleborough, MA
New and Resale
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55+ age-restricted
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Built 1999 - present
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1,150 homes
$400Ks
- $700Ks
Southport, Mashpee, MA
New and Resale
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55+ age-restricted
|
Built 1989 - present
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730 homes
$300Ks
- $800Ks
Del Webb Chauncy Lake, Westborough, MA
New Construction
|
55+ age-restricted
|
Built 2018 - present
|
700 homes
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$700Ks
- $800Ks
Great Island, Plymouth, MA
Resale Only
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55+ age-restricted
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Built 2002 - 2015
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600 homes
$800Ks
- $1Ms
Regency at Glen Ellen, Millis, MA
New Construction
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55+ age-restricted
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Built 2017 - present
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324 homes
4 rating (5 reviews)
![South Shore Village]()
$600Ks
- $800Ks
South Shore Village, South Kingstown, RI
New and Resale
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55+ age-restricted
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Built 2016 - present
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303 homes
$600Ks
- $1Ms
The Villages on Mount Hop..., Tiverton, RI
New and Resale
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55+ age-restricted
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Built 2003 - present
|
230 homes
$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.
$400Ks
- $400Ks
Woodstone Crossing, Weymouth, MA
Resale Only
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Age-targeted
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Built 2015 - 2019
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200 homes
$400Ks
- $500Ks
Brierly Pond Village, Millbury, MA
Resale Only
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55+ age-restricted
|
Built 2003 - 2013
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199 homes
$500Ks
- $500Ks
Pennington Crossing, Walpole, MA
New Construction
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55+ age-restricted
|
Built 2018 - present
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172 homes
$800Ks
- $1Ms
The Trails, Hopkinton, MA
New Construction
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55+ age-restricted
|
Built 2017 - present
|
170 homes
$500Ks
- $800Ks
Red Mill Village, Norton, MA
Resale Only
|
55+ age-restricted
|
Built 2012 - 2014
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156 homes
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$800Ks
- $1Ms
Villages at Weathervane, Weymouth, MA
Resale Only
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55+ age-restricted
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Built 2003 - 2010
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149 homes
$400Ks
- $500Ks
Harmony Place, Rutland, MA
New Construction
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55+ age-restricted
|
Built 2023 - present
|
142 homes
$700Ks
- $800Ks
Wakefield Meadows, Wakefield, RI
Resale Only
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55+ age-restricted
|
Built 2009 - 2015
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142 homes
$600Ks
- $800Ks
The Preserve at Hunters H..., Dighton, MA
New and Resale
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55+ age-restricted
|
Built 2006 - present
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140 homes
$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.
$700Ks
- $1Ms
WestRidge, Hudson, MA
Resale Only
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55+ age-restricted
|
Built 2009 - 2016
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136 homes
$400Ks
- $400Ks
Angell Brook Village, West Boylston, MA
Resale Only
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55+ age-restricted
|
Built 2005 - 2012
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132 homes
$1Ms
- $1Ms
Millwood Preserve, Framingham, MA
New Construction
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55+ age-restricted
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Built 2020 - present
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129 homes
$500Ks
- $600Ks
The Village at Westminste..., Holden, MA
New and Resale
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55+ age-restricted
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Built 2006 - present
|
125 homes
$600Ks
- $700Ks
Stonebridge Commons, Hanson, MA
Resale Only
|
55+ age-restricted
|
Built 2007 - 2018
|
121 homes
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(401) 313-4589
$700Ks
- $900Ks
Seton Highlands at The Pi..., Plymouth, MA
New and Resale
|
55+ age-restricted
|
Built 2008 - present
|
120 homes
$400Ks
- $500Ks
Summer Reach, Plymouth, MA
Resale Only
|
55+ age-restricted
|
Built 2017 - 2020
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114 homes
$400Ks
- $500Ks
The Village at Orchard Me..., Shrewsbury, MA
Resale Only
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55+ age-restricted
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Built 2002 - 2007
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114 homes
$600Ks
- $700Ks
The Villages at Walker Me..., Westborough, MA
Resale Only
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55+ age-restricted
|
Built 1999 - 2000
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100 homes
$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.
$400Ks
- $400Ks
New England Commons, Webster, MA
New and Resale
|
55+ age-restricted
|
Built 2005 - present
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100 homes
$500Ks
- $700Ks
The Lanterns at Warren Wo..., Ashland, MA
Resale Only
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55+ age-restricted
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Built 2016 - 2020
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93 homes
$300Ks
- $400Ks
The Village at Auburnvill..., Whitman, MA
Resale Only
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55+ age-restricted
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Built 2004 - 2014
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92 homes
$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?
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Questions? Call us:
(401) 313-4589
$400Ks
- $400Ks
The Villages at Crane Mea..., Marlborough, MA
Resale Only
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55+ age-restricted
|
Built 2001 - 2005
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91 homes
$800Ks
- $900Ks
Adams Farm, Shrewsbury, MA
Resale Only
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55+ age-restricted
|
Built 2005 - 2013
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90 homes
$600Ks
- $700Ks
Southwinds, South Kingstown, RI
Resale Only
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55+ age-restricted
|
Built 2005 - 2010
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70 homes
$300Ks
- $400Ks
Bella Vista, Glocester, RI
Resale Only
|
55+ age-restricted
|
Built 2015 - 2021
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70 homes
Southport
![37 PINE HILL BLVD # 30, MASHPEE, MA, 026..., Mashpee, MA 02649]()
2 beds
|2 baths
|1,338 sq ft
|Condo
37 PINE HILL BLVD # 30, MASHPEE, MA, 026...
Community: Southport
MLS 73396871 • Kinlin Grover Compass, Carli Taylo...
The Preserve at Hunters Hill
![3035 CLUBHOUSE DR 8, DIGHTON, MA, 02715, Dighton, MA 02715]()
2 beds
|2 baths
|2,216 sq ft
|House
3035 CLUBHOUSE DR 8, DIGHTON, MA, 02715
Community: The Preserve at Hunters Hill
MLS 73256663 • Long Realty, Patricia Fanning
The Preserve at Hunters Hill
![3035 CLUBHOUSE DR 6, DIGHTON, MA, 02715, Dighton, MA 02715]()
2 beds
|2 baths
|2,097 sq ft
|House
3035 CLUBHOUSE DR 6, DIGHTON, MA, 02715
Community: The Preserve at Hunters Hill
MLS 73256656 • Long Realty, Patricia Fanning
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
Southport
![1 UPLAND CIR # 1, MASHPEE, MA, 02649, Mashpee, MA 02649]()
MLS 73429760 • William Raveis R.E. & Home Service...
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Great Island
![31 FOX HOLW, PLYMOUTH, MA, 02360, Plymouth, MA 02360]()
MLS 73393973 • Compass, Seagate Properties
The Trails
![13 BIRKDALE LN # 13, HOPKINTON, MA, 0174..., Hopkinton, MA 01748]()
2 beds
|3 baths
|2,277 sq ft
|Condo
13 BIRKDALE LN # 13, HOPKINTON, MA, 0174...
Community: The Trails
MLS 73430544 • Keller Williams Elite, Sue Sindoni
The Preserve at Hunters Hill
![3035 CLUBHOUSE DR 1, DIGHTON, MA, 02715, Dighton, MA 02715]()
2 beds
|2 baths
|1,775 sq ft
|House
3035 CLUBHOUSE DR 1, DIGHTON, MA, 02715
Community: The Preserve at Hunters Hill
MLS 73256626 • Long Realty, Patricia Fanning
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
New
Brierly Pond Village
![92 HORNE WAY # 92, MILLBURY, MA, 01527, Millbury, MA 01527]()
2 beds
|2 baths
|1,420 sq ft
|Condo
92 HORNE WAY # 92, MILLBURY, MA, 01527
Community: Brierly Pond Village
MLS 73454040 • RE/MAX Partners, Stephanie McNamar...
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.
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...
Southport
![17 CHADWICK CT # 17, MASHPEE, MA, 02649, Mashpee, MA 02649]()
MLS 73395151 • Today Real Estate, Inc., Mari Senn...
New
Red Mill Village
![31 OWEN RD # 31, NORTON, MA, 02766, Norton, MA 02766]()
2 beds
|3 baths
|2,000 sq ft
|Condo
31 OWEN RD # 31, NORTON, MA, 02766
Community: Red Mill Village
MLS 73453830 • Gibson Sotheby's International Rea...
Oak Point
![2612 OAK POINT DR, MIDDLEBORO, MA, 02346, Middleboro, MA 02346]()
3 beds
|2 baths
|1,456 sq ft
|House
2612 OAK POINT DR, MIDDLEBORO, MA, 02346
Community: Oak Point
MLS 73452946 • Diamond Realty, Peter Veneto
The Village at Westminster Place
![27 TEA PARTY CIR # 27, HOLDEN, MA, 01520, Holden, MA 01520]()
3 beds
|3 baths
|1,895 sq ft
|House
27 TEA PARTY CIR # 27, HOLDEN, MA, 01520
Community: The Village at Westminster Place
MLS 73430027 • BA Property & Lifestyle Advisors, ...
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The Pines at Hathaway Pond
![57 HATHAWAY POND CIR # 57, ROCHESTER, MA..., Rochester, MA 02770]()
1 beds
|2 baths
|1,500 sq ft
|Condo
57 HATHAWAY POND CIR # 57, ROCHESTER, MA...
Community: The Pines at Hathaway Pond
MLS 73451670 • Compass, Cherie Poirier
The Villages at Walker Meadow
![3 DOVER WAY # 3, WESTBOROUGH, MA, 01581, Westborough, MA 01581]()
2 beds
|2 baths
|1,874 sq ft
|Condo
3 DOVER WAY # 3, WESTBOROUGH, MA, 01581
Community: The Villages at Walker Meadow
MLS 73452352 • Mathieu Newton Sotheby's Internati...
The Preserve at Hunters Hill
![3035 CLUBHOUSE DR 3, DIGHTON, MA, 02715, Dighton, MA 02715]()
2 beds
|2 baths
|1,928 sq ft
|House
3035 CLUBHOUSE DR 3, DIGHTON, MA, 02715
Community: The Preserve at Hunters Hill
MLS 73256641 • Long Realty, Patricia Fanning
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...
Westbrook Crossing
![989 EAST ST 107, DEDHAM, MA, 02026, Dedham, MA 02026]()
1 beds
|1 baths
|882 sq ft
|Condo
989 EAST ST 107, DEDHAM, MA, 02026
Community: Westbrook Crossing
MLS 73434932 • Coldwell Banker Realty - Belmont, ...
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.
Great Island
![39 WOODSONG, PLYMOUTH, MA, 02360, Plymouth, MA 02360]()
MLS 73435623 • Pinehills Brokerage Services LLC, ...
New
30 Coppersmith
![30 COPPERSMITH WAY # 113, CANTON, MA, 02..., Canton, MA 02021]()
2 beds
|2 baths
|1,582 sq ft
|Condo
30 COPPERSMITH WAY # 113, CANTON, MA, 02...
Community: 30 Coppersmith
MLS 73453325 • Pulte Homes of New England, Erin S...
Del Webb Chauncy Lake
![2 CODMAN WAY 411, WESTBOROUGH, MA, 01581, Westborough, MA 01581]()
2 beds
|2 baths
|1,375 sq ft
|Condo
2 CODMAN WAY 411, WESTBOROUGH, MA, 01581
Community: Del Webb Chauncy Lake
MLS 73452782 • Pulte Homes of New England, Erin S...
Regency at Glen Ellen
![18 LANSING WAY # 18, MILLIS, MA, 02054, Millis, MA 02054]()
2 beds
|3 baths
|2,306 sq ft
|Condo
18 LANSING WAY # 18, MILLIS, MA, 02054
Community: Regency at Glen Ellen
MLS 73424107 • Berkshire Hathaway HomeServices Co...
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...
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30 Coppersmith
![30 COPPERSMITH WAY # 107, CANTON, MA, 02..., Canton, MA 02021]()
2 beds
|2 baths
|1,582 sq ft
|Condo
30 COPPERSMITH WAY # 107, CANTON, MA, 02...
Community: 30 Coppersmith
MLS 73441720 • Pulte Homes of New England, Erin S...
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...
Pennington Crossing
![4403 PENNINGTON DR # 4403, WALPOLE, MA, ..., Walpole, MA 02081]()
2 beds
|2 baths
|1,520 sq ft
|Condo
4403 PENNINGTON DR # 4403, WALPOLE, MA, ...
Community: Pennington Crossing
MLS 73452401 • Berkshire Hathaway HomeServices Co...
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...
Regency at Assabet Ridge
![13 WILSHIRE WAY # 13, MARLBOROUGH, MA, 0..., Marlborough, MA 01752]()
2 beds
|2 baths
|1,584 sq ft
|Condo
13 WILSHIRE WAY # 13, MARLBOROUGH, MA, 0...
Community: Regency at Assabet Ridge
MLS 73424705 • Colby Hunter Realty, John Jewett
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.
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...
Del Webb Chauncy Lake
![5 PETERS FARM WAY # 412, WESTBOROUGH, MA..., Westborough, MA 01581]()
2 beds
|2 baths
|1,512 sq ft
|Condo
5 PETERS FARM WAY # 412, WESTBOROUGH, MA...
Community: Del Webb Chauncy Lake
MLS 73436343 • Pulte Homes of New England, Erin S...
The Preserve at Hunters Hill
![3035 CLUBHOUSE DR 4, DIGHTON, MA, 02715, Dighton, MA 02715]()
2 beds
|2 baths
|1,775 sq ft
|House
3035 CLUBHOUSE DR 4, DIGHTON, MA, 02715
Community: The Preserve at Hunters Hill
MLS 73256645 • Long Realty, Patricia Fanning
Forest Glen
![100 SPRING HILL DR # 100, UXBRIDGE, MA, ..., Uxbridge, MA 01569]()
2 beds
|2 baths
|1,694 sq ft
|Condo
100 SPRING HILL DR # 100, UXBRIDGE, MA, ...
Community: Forest Glen
MLS 73449018 • Keller Williams Elite, Anthony Rug...
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
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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 ...
Oak Point
![2602 PHEASANT LN, MIDDLEBORO, MA, 02346, Middleboro, MA 02346]()
MLS 73451128 • The Real Estate Collaborative, San...
Great Island
![14 PICKET FENCE, PLYMOUTH, MA, 02360, Plymouth, MA 02360]()
MLS 73451083 • Pinehills Brokerage Services LLC, ...
Great Island
![16 PICKET FENCE, PLYMOUTH, MA, 02360, Plymouth, MA 02360]()
MLS 73451088 • Pinehills Brokerage Services LLC, ...
Wolcott Woods
![69 WOLCOTT WOODS LN # 69, MILTON, MA, 02..., Milton, MA 02186]()
2 beds
|3 baths
|3,599 sq ft
|House
69 WOLCOTT WOODS LN # 69, MILTON, MA, 02...
Community: Wolcott Woods
MLS 73451114 • 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?
80
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© 2025 REIN. REIN's listings Data and information is protected under federal copyright laws. Federal law prohibits, among other acts, the unauthorized copying or alteration of, or preparation of derivative works from, all or any part of copyrighted materials, including certain compilations of Data and information. COPYRIGHT VIOLATORS MAY BE SUBJECT TO SEVERE FINES AND PENALTIES UNDER FEDERAL LAW.
REIN updates its listings on a daily basis. Data last updated: Nov 14, 2025.
This application does not include information on all of the properties available for sale at this time.
