Call us at (401) 313-4589 to learn more about active adult communities in Middletown
Middletown, RI 55+ active adult communities & homes for sale - Page 2
81 communities near Middletown
100 homes near Middletown
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$400ks
- $600ks
Del Webb Chauncy Lake, Westborough, MA
New Construction
|
55+ age-restricted
|
Built 2018 - present
|
700 homes
$400ks
- $500ks
The Preserve at Hunters H..., Dighton, MA
New and Resale
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55+ age-restricted
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Built 2006 - present
|
140 homes
$400ks
- $600ks
Southport, Mashpee, MA
New and Resale
|
55+ age-restricted
|
Built 1989 - present
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730 homes
$400ks
- $900ks
Sawyer's Reach, Plymouth, MA
New and Resale
|
55+ age-restricted
|
Built 2017 - present
|
224 homes
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$700ks
30 Coppersmith, Canton, MA
New Construction
|
55+ age-restricted
|
Built 2025 - present
|
63 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
5 rating (3 reviews)
![Oak Point]()
$300ks
- $400ks
Oak Point, Middleborough, MA
New and Resale
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55+ age-restricted
|
Built 1999 - present
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1,150 homes
$500ks
- $700ks
The Trails, Hopkinton, MA
New Construction
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55+ age-restricted
|
Built 2017 - present
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170 homes
$400ks
- $600ks
Upton Ridge, Upton, MA
New Construction
|
55+ age-restricted
|
Built 2019 - present
|
139 homes
Download the Ultimate 55+ Homebuying Guide
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$600ks
- $700ks
Seton Highlands at The Pi..., Plymouth, MA
New and Resale
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55+ age-restricted
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Built 2008 - present
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120 homes
$400ks
- $500ks
Harmony Place, Rutland, MA
New Construction
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55+ age-restricted
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Built 2023 - present
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142 homes
$300ks
- $400ks
Brierly Pond Village, Millbury, MA
Resale Only
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55+ age-restricted
|
Built 2003 - 2013
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199 homes
$300ks
- $600ks
Pennington Crossing, Walpole, MA
New Construction
|
55+ age-restricted
|
Built 2018 - present
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172 homes
$500ks
Orchard Hill, Westborough, MA
Resale Only
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55+ age-restricted
|
Built 2002 - 2010
|
100 homes
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$300ks
- $500ks
The Pines at Hathaway Pon..., Rochester, MA
Resale Only
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55+ age-restricted
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Built 2006 - 2014
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61 homes
$900ks
- $1Ms
Seaside at Scituate - The..., Scituate, MA
New Construction
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55+ age-restricted
|
Built 2019 - present
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44 homes
$300ks
- $400ks
The Village at Auburnvill..., Whitman, MA
Resale Only
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55+ age-restricted
|
Built 2004 - 2014
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92 homes
$300ks
- $400ks
Woodstone Crossing, Weymouth, MA
Resale Only
|
Age-targeted
|
Built 2015 - 2019
|
200 homes
Download the Ultimate 55+ Homebuying Guide
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$700ks
- $800ks
Millwood Preserve, Framingham, MA
New Construction
|
55+ age-restricted
|
Built 2020 - present
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129 homes
$600ks
- $700ks
The Villages at Walker Me..., Westborough, MA
Resale Only
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55+ age-restricted
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Built 1999 - 2000
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100 homes
$500ks
Northwoods at Sudbury, Sudbury, MA
Resale Only
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55+ age-restricted
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Built 1999 - 2019
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43 homes
$500ks
Stonebridge Commons, Hanson, MA
Resale Only
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55+ age-restricted
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Built 2007 - 2018
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121 homes
$400ks
Chilton Park Village, Plymouth, MA
Resale Only
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55+ age-restricted
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Built 2006 - 2015
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25 homes
$500ks
- $600ks
Bigelow Farm, Northborough, MA
Resale Only
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55+ age-restricted
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Built 2006 - 2013
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41 homes
$400ks
- $600ks
Woodcrest Run, Sharon, MA
New Construction
|
55+ age-restricted
|
Built 2019 - present
|
25 homes
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(401) 313-4589
$500ks
- $700ks
The Elms of Hanover, Hanover, MA
Resale Only
|
55+ age-restricted
|
Built 2003 - 2004
|
51 homes
$500ks
- $700ks
Donovan Farm, Norwell, MA
Resale Only
|
55+ age-restricted
|
Built 2001 - 2003
|
40 homes
$500ks
- $600ks
Center Commons, Pembroke, MA
Resale Only
|
55+ age-restricted
|
Built 2004 - 2009
|
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.
$600ks
- $700ks
Bailey Brook, Middletown, RI
Resale Only
|
55+ age-restricted
|
Built 2018 - 2024
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36 homes
$400ks
- $600ks
Peregrine Woods, Marshfield, MA
Resale Only
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55+ age-restricted
|
Built 2002 - 2005
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32 homes
$700ks
- $800ks
Duxbury Estates, Duxbury, MA
Resale Only
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55+ age-restricted
|
Built 2008 - 2013
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44 homes
$900ks
- $1Ms
Hawthorn Preserve, Braintree, MA
New Construction
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55+ age-restricted
|
Built 2025 - present
|
51 homes
$600ks
- $700ks
Southwinds, South Kingstown, RI
Resale Only
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55+ age-restricted
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Built 2005 - 2010
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70 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
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(401) 313-4589
$400ks
- $500ks
Summer Reach, Plymouth, MA
Resale Only
|
55+ age-restricted
|
Built 2017 - 2020
|
114 homes
$600ks
- $700ks
Rolling Mill, Plymouth, MA
Resale Only
|
55+ age-restricted
|
Built 2018 - 2021
|
46 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.
Del Webb Chauncy Lake
![5 PETERS FARM WAY 7104, WESTBOROUGH, MA,..., Westborough, MA 01581]()
1 beds
|1 baths
|972 sq ft
|Condo
5 PETERS FARM WAY 7104, WESTBOROUGH, MA,...
Community: Del Webb Chauncy Lake
MLS 73539608 • Pulte Homes of New England, Erin S... • Pulte Homes of New England
Great Island
![22 PICKET FENCE, PLYMOUTH, MA, 02360, Plymouth, MA 02360]()
MLS 73539322 • Pinehills Brokerage Services LLC, ... • Pinehills Brokerage Services LLC
Great Island
![9 MADISON REACH, PLYMOUTH, MA, 02360, Plymouth, MA 02360]()
MLS 73537994 • Keller Williams Realty Colonial Pa... • Keller Williams Realty Colonial Partners
Bigelow Farm
![14 LYDIAS WAY 14, NORTHBOROUGH, MA, 0153..., Northborough, MA 01532]()
2 beds
|3 baths
|2,691 sq ft
|Condo
14 LYDIAS WAY 14, NORTHBOROUGH, MA, 0153...
Community: Bigelow Farm
MLS 73537648 • Keller Williams Pinnacle MetroWest... • Keller Williams Pinnacle MetroWest
The Village at Auburnville
![877 AUBURNVILLE WAY K6, WHITMAN, MA, 023..., Whitman, MA 02382]()
2 beds
|2 baths
|2,103 sq ft
|Condo
877 AUBURNVILLE WAY K6, WHITMAN, MA, 023...
Community: The Village at Auburnville
MLS 73535803 • Lamacchia Realty, Inc., Gregory Mu... • Lamacchia Realty, Inc.
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Del Webb Chauncy Lake
![5 PETERS FARM WAY 7106, WESTBOROUGH, MA,..., Westborough, MA 01581]()
2 beds
|2 baths
|1,512 sq ft
|Condo
5 PETERS FARM WAY 7106, WESTBOROUGH, MA,...
Community: Del Webb Chauncy Lake
MLS 73535133 • Pulte Homes of New England, Erin S... • Pulte Homes of New England
The Village at Auburnville
![877 AUBURNVILLE WAY A3, WHITMAN, MA, 023..., Whitman, MA 02382]()
2 beds
|3 baths
|2,103 sq ft
|Condo
877 AUBURNVILLE WAY A3, WHITMAN, MA, 023...
Community: The Village at Auburnville
MLS 73533487 • William Raveis R.E. & Home Service... • William Raveis R.E. & Home Services
Woodcrest Run
![635 OLD POST RD 2-303, SHARON, MA, 02067, Sharon, MA 02067]()
2 beds
|3 baths
|2,400 sq ft
|Condo
635 OLD POST RD 2-303, SHARON, MA, 02067
Community: Woodcrest Run
MLS 73533117 • Hammond Residential Real Estate, W... • Hammond Residential Real Estate
Del Webb Chauncy Lake
![5 PETERS FARM WAY 7305, WESTBOROUGH, MA,..., Westborough, MA 01581]()
2 beds
|2 baths
|1,175 sq ft
|Condo
5 PETERS FARM WAY 7305, WESTBOROUGH, MA,...
Community: Del Webb Chauncy Lake
MLS 73531811 • Pulte Homes of New England, Erin S... • Pulte Homes of New England
30 Coppersmith
![30 COPPERSMITH WAY 410, CANTON, MA, 0202..., Canton, MA 02021]()
2 beds
|2 baths
|1,425 sq ft
|Condo
30 COPPERSMITH WAY 410, CANTON, MA, 0202...
Community: 30 Coppersmith
MLS 73531643 • Pulte Homes of New England, Erin S... • Pulte Homes of New England
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.
Southport
![1 SANDVIEW TER 1, MASHPEE, MA, 02649, Mashpee, MA 02649]()
MLS 73531561 • Compass, Cynthia Crawford • Compass
Del Webb Chauncy Lake
![2 CODMAN WAY 2203, WESTBOROUGH, MA, 0158..., Westborough, MA 01581]()
1 beds
|1 baths
|972 sq ft
|Condo
2 CODMAN WAY 2203, WESTBOROUGH, MA, 0158...
Community: Del Webb Chauncy Lake
MLS 73531474 • Keller Williams Elite, Lisa Pazol • Keller Williams Elite
The Village at Orchard Meadows
![4 APPLE SEED DR 4, SHREWSBURY, MA, 01545, Shrewsbury, MA 01545]()
2 beds
|3 baths
|1,854 sq ft
|Condo
4 APPLE SEED DR 4, SHREWSBURY, MA, 01545
Community: The Village at Orchard Meadows
MLS 73530647 • Andrew J. Abu Inc., REALTORS®, Li... • Andrew J. Abu Inc., REALTORS®
Oak Point
![5604 OAK POINT DR, MIDDLEBORO, MA, 02346, Middleboro, MA 02346]()
3 beds
|2 baths
|1,612 sq ft
|House
5604 OAK POINT DR, MIDDLEBORO, MA, 02346
Community: Oak Point
MLS 73530629 • The Firm, Fern Langella • The Firm
Millwood Preserve
![32 HAWK LN 48, FRAMINGHAM, MA, 01701, Framingham, MA 01701]()
2 beds
|3 baths
|2,306 sq ft
|Condo
32 HAWK LN 48, FRAMINGHAM, MA, 01701
Community: Millwood Preserve
MLS 73529206 • Andrew J. Abu Inc., REALTORS®, An... • Andrew J. Abu Inc., REALTORS®
30 Coppersmith
![50 COPPERSMITH WAY 302, CANTON, MA, 0202..., Canton, MA 02021]()
2 beds
|2 baths
|1,561 sq ft
|Condo
50 COPPERSMITH WAY 302, CANTON, MA, 0202...
Community: 30 Coppersmith
MLS 73528497 • Options 153, Mullen & Partners, Sa... • Options 153, Mullen & Partners
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Pennington Crossing
![2305 PENNINGTON DR 305, WALPOLE, MA, 020..., Walpole, MA 02081]()
2 beds
|2 baths
|1,140 sq ft
|Condo
2305 PENNINGTON DR 305, WALPOLE, MA, 020...
Community: Pennington Crossing
MLS 73528426 • Berkshire Hathaway HomeServices Co... • Berkshire Hathaway HomeServices Commonwealth Real Estate
Seton Highlands at The Pinehills
![25 SETON HIGHLANDS 25, PLYMOUTH, MA, 023..., Plymouth, MA 02360]()
2 beds
|3 baths
|2,321 sq ft
|Condo
25 SETON HIGHLANDS 25, PLYMOUTH, MA, 023...
Community: Seton Highlands at The Pinehills
MLS 73527807 • Pinehills Brokerage Services LLC, ... • Pinehills Brokerage Services LLC
Del Webb Chauncy Lake
![5 PETERS FARM WAY 408, WESTBOROUGH, MA, ..., Westborough, MA 01581]()
2 beds
|2 baths
|1,375 sq ft
|Condo
5 PETERS FARM WAY 408, WESTBOROUGH, MA, ...
Community: Del Webb Chauncy Lake
MLS 73527623 • Pulte Homes of New England, Erin S... • Pulte Homes of New England
Sawyer's Reach
![45 PLAZA WAY 208, PLYMOUTH, MA, 02360, Plymouth, MA 02360]()
2 beds
|2 baths
|1,368 sq ft
|Condo
45 PLAZA WAY 208, PLYMOUTH, MA, 02360
Community: Sawyer's Reach
MLS 73526552 • Coldwell Banker Realty - Plymouth,... • Coldwell Banker Realty - Plymouth
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
![3405 PETERS FARM WAY 3405, WESTBOROUGH, ..., Westborough, MA 01581]()
2 beds
|2 baths
|1,121 sq ft
|Condo
3405 PETERS FARM WAY 3405, WESTBOROUGH, ...
Community: Del Webb Chauncy Lake
MLS 73526545 • RE/MAX Prof Associates, Pierre Bou... • RE/MAX Prof Associates
Del Webb Chauncy Lake
![3103 PETERS FARM WAY 103, WESTBOROUGH, M..., Westborough, MA 01581]()
1 beds
|1 baths
|956 sq ft
|Condo
3103 PETERS FARM WAY 103, WESTBOROUGH, M...
Community: Del Webb Chauncy Lake
MLS 73526470 • Keller Williams Pinnacle MetroWest... • Keller Williams Pinnacle MetroWest
Sawyer's Reach
![27 MARINERS WAY 27, PLYMOUTH, MA, 02360, Plymouth, MA 02360]()
2 beds
|3 baths
|2,626 sq ft
|House
27 MARINERS WAY 27, PLYMOUTH, MA, 02360
Community: Sawyer's Reach
MLS 73526294 • Keller Williams Realty, Dennis Mac... • Keller Williams Realty
The Village at Orchard Meadows
![70 ORCHARD MEADOW DR 70, SHREWSBURY, MA,..., Shrewsbury, MA 01545]()
2 beds
|3 baths
|1,896 sq ft
|Condo
70 ORCHARD MEADOW DR 70, SHREWSBURY, MA,...
Community: The Village at Orchard Meadows
MLS 73526186 • ERA Key Realty Services, Laura Heb... • ERA Key Realty Services
Chilton Park Village
![3 HARBORLIGHT CIR 3, PLYMOUTH, MA, 02360, Plymouth, MA 02360]()
2 beds
|3 baths
|2,228 sq ft
|Condo
3 HARBORLIGHT CIR 3, PLYMOUTH, MA, 02360
Community: Chilton Park Village
MLS 73526140 • eXp Realty LLC, Nathan Meyer • eXp Realty LLC
Del Webb Chauncy Lake
![4311 PETERS FARM WAY 311, WESTBOROUGH, M..., Westborough, MA 01581]()
2 beds
|2 baths
|1,326 sq ft
|Condo
4311 PETERS FARM WAY 311, WESTBOROUGH, M...
Community: Del Webb Chauncy Lake
MLS 73525921 • ERA Key Realty Services- Fram, Rob... • ERA Key Realty Services- Fram
Woodstone Crossing
![70 TROTTER RD 312, WEYMOUTH, MA, 02190, Weymouth, MA 02190]()
3 beds
|2 baths
|1,475 sq ft
|Condo
70 TROTTER RD 312, WEYMOUTH, MA, 02190
Community: Woodstone Crossing
MLS 73525695 • William Raveis R.E. & Home Service... • William Raveis R.E. & Home Services
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(401) 313-4589
Southport
![21 ROLLING GREEN LN 140, MASHPEE, MA, 02..., Mashpee, MA 02649]()
2 beds
|3 baths
|1,685 sq ft
|Condo
21 ROLLING GREEN LN 140, MASHPEE, MA, 02...
Community: Southport
MLS 73525607 • Kinlin Grover Compass, Carli Taylo... • Kinlin Grover Compass
Upton Ridge
![87 SHANNON WAY 86, UPTON, MA, 01568, Upton, MA 01568]()
MLS 73524427 • Keller Williams Realty, Shane Brad... • Keller Williams Realty
The Preserve at Hunters Hill
![3085 HUNTERS HILL DR 3085, DIGHTON, MA, ..., Dighton, MA 02715]()
2 beds
|2 baths
|1,973 sq ft
|House
3085 HUNTERS HILL DR 3085, DIGHTON, MA, ...
Community: The Preserve at Hunters Hill
MLS 73524358 • Lamacchia Realty, Inc., Nicole Ver... • Lamacchia Realty, Inc.
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
![12101 PETERS FARM WAY 12101, WESTBOROUGH..., Westborough, MA 01712]()
2 beds
|2 baths
|1,459 sq ft
|Condo
12101 PETERS FARM WAY 12101, WESTBOROUGH...
Community: Del Webb Chauncy Lake
MLS 73523938 • Spangler SELECT, Kathleen Spangler • Spangler SELECT
Del Webb Chauncy Lake
![11 PETERS FARM WAY 310, WESTBOROUGH, MA,..., Westborough, MA 01581]()
2 beds
|2 baths
|1,326 sq ft
|Condo
11 PETERS FARM WAY 310, WESTBOROUGH, MA,...
Community: Del Webb Chauncy Lake
MLS 73522908 • Panarelli Properties, Inc., Justin... • Panarelli Properties, Inc.
Brierly Pond Village
![6 ASHTON LN 6, MILLBURY, MA, 01527, Millbury, MA 01527]()
2 beds
|4 baths
|2,256 sq ft
|Condo
6 ASHTON LN 6, MILLBURY, MA, 01527
Community: Brierly Pond Village
MLS 73519853 • Lamacchia Realty, Inc., Donna Duca • Lamacchia Realty, Inc.
WestRidge
![15 HASTINGS RD 15, HUDSON, MA, 01749, Hudson, MA 01749]()
MLS 73515846 • ERA Key Realty Services - Distinct... • ERA Key Realty Services - Distinctive Group
30 Coppersmith
![30 COPPERSMITH WAY 304, CANTON, MA, 0202..., Canton, MA 02021]()
1 beds
|1 baths
|1,027 sq ft
|Condo
30 COPPERSMITH WAY 304, CANTON, MA, 0202...
Community: 30 Coppersmith
MLS 73511239 • Pulte Homes of New England, Erin S... • Pulte Homes of New England
30 Coppersmith
![30 COPPERSMITH WAY 507, CANTON, MA, 0202..., Canton, MA 02021]()
2 beds
|2 baths
|1,582 sq ft
|Condo
30 COPPERSMITH WAY 507, CANTON, MA, 0202...
Community: 30 Coppersmith
MLS 73511235 • Pulte Homes of New England, Erin S... • Pulte Homes of New England
Seton Highlands at The Pinehills
![105 SETON HIGHLANDS 105, PLYMOUTH, MA, 0..., Plymouth, MA 02360]()
2 beds
|3 baths
|2,186 sq ft
|House
105 SETON HIGHLANDS 105, PLYMOUTH, MA, 0...
Community: Seton Highlands at The Pinehills
MLS 73510534 • South Shore Sotheby's Internationa... • South Shore Sotheby's International Realty
Oak Point
![6802 OAK POINT DR, MIDDLEBORO, MA, 02346, Middleboro, MA 02346]()
2 beds
|2 baths
|1,674 sq ft
|House
6802 OAK POINT DR, MIDDLEBORO, MA, 02346
Community: Oak Point
MLS 73510435 • The Firm - Duxbury, Marni Migliacc... • The Firm - Duxbury
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Southport
![118 GREY HAWK DR 118, MASHPEE, MA, 02649, Mashpee, MA 02649]()
2 beds
|2 baths
|1,416 sq ft
|Condo
118 GREY HAWK DR 118, MASHPEE, MA, 02649
Community: Southport
MLS 73508052 • Compass, Cynthia Crawford • Compass
Del Webb Chauncy Lake
![4204 PETERS FARM WAY 204, WESTBOROUGH, M..., Westborough, MA 01581]()
1 beds
|1 baths
|956 sq ft
|Condo
4204 PETERS FARM WAY 204, WESTBOROUGH, M...
Community: Del Webb Chauncy Lake
MLS 73503550 • ERA Key Realty Services - Distinct... • ERA Key Realty Services - Distinctive Group
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.
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?
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REIN updates its listings on a daily basis. Data last updated: Jul 18, 2026.
This application does not include information on all of the properties available for sale at this time.
