Call us at (401) 313-4589 to learn more about active adult communities in Middletown
Middletown, RI 55+ active adult communities & homes for sale
81 communities near Middletown
118 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
- $600ks
Southport, Mashpee, MA
New and Resale
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55+ age-restricted
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Built 1989 - present
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730 homes
$600ks
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
$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
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140 homes
$300ks
- $400ks
Brierly Pond Village, Millbury, MA
Resale Only
|
55+ age-restricted
|
Built 2003 - 2013
|
199 homes
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$400ks
- $500ks
Harmony Place, Rutland, MA
New Construction
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55+ age-restricted
|
Built 2023 - present
|
142 homes
$400ks
- $600ks
Upton Ridge, Upton, MA
New Construction
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55+ age-restricted
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Built 2019 - present
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139 homes
$400ks
- $900ks
Sawyer's Reach, Plymouth, MA
New and Resale
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55+ age-restricted
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Built 2017 - present
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224 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
$400ks
- $600ks
Woodcrest Run, Sharon, MA
New Construction
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55+ age-restricted
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Built 2019 - present
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25 homes
Download the Ultimate 55+ Homebuying Guide
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$300ks
- $600ks
Pennington Crossing, Walpole, MA
New Construction
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55+ age-restricted
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Built 2018 - present
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172 homes
$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
$700ks
30 Coppersmith, Canton, MA
New Construction
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55+ age-restricted
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Built 2025 - present
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63 homes
$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
$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
$700ks
- $900ks
Regency at Glen Ellen, Millis, MA
New Construction
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55+ age-restricted
|
Built 2017 - present
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324 homes
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$500ks
- $700ks
The Trails, Hopkinton, MA
New Construction
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55+ age-restricted
|
Built 2017 - present
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170 homes
$300ks
- $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
Westbrook Crossing, Dedham, MA
Resale Only
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55+ age-restricted
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Built 2003 - 2004
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60 homes
$400ks
- $500ks
The Seasons at Salisbury, Holden, MA
Resale Only
|
55+ age-restricted
|
Built 2002 - 2006
|
91 homes
Download the Ultimate 55+ Homebuying Guide
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Bates Quarry, Walpole, MA
New Construction
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55+ age-restricted
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Built 2025 - present
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100 homes
$400ks
- $500ks
The Village at Westminste..., Holden, MA
New and Resale
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55+ age-restricted
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Built 2006 - present
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125 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
$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
$600ks
- $700ks
Northside Meadows, Framingham, MA
Resale Only
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55+ age-restricted
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Built 2017 - 2019
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60 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
|
55+ age-restricted
|
Built 1999 - 2019
|
43 homes
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(401) 313-4589
$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
$500ks
- $600ks
Regency at Assabet Ridge, Marlborough, MA
Resale Only
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55+ age-restricted
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Built 2010 - 2015
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69 homes
$400ks
- $500ks
Spring Meadow, Hanover, MA
Resale Only
|
55+ age-restricted
|
Built 2004 - 2007
|
39 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.
$500ks
Orchard Hill, Westborough, MA
Resale Only
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55+ age-restricted
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Built 2002 - 2010
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100 homes
$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
$700ks
- $800ks
Adams Farm, Shrewsbury, MA
Resale Only
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55+ age-restricted
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Built 2005 - 2013
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90 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
$500ks
Blue Heron Pond, Lancaster, MA
Resale Only
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55+ age-restricted
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Built 2006 - 2014
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58 homes
$200ks
- $300ks
New England Commons, Webster, MA
New and Resale
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55+ age-restricted
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Built 2005 - present
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100 homes
$600ks
- $700ks
Bailey Brook, Middletown, RI
Resale Only
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55+ age-restricted
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Built 2018 - 2024
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36 homes
$700ks
- $800ks
Wakefield Meadows, Wakefield, RI
Resale Only
|
55+ age-restricted
|
Built 2009 - 2015
|
142 homes
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$400ks
- $600ks
Red Mill Village, Norton, MA
Resale Only
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55+ age-restricted
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Built 2012 - 2014
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156 homes
$600ks
- $700ks
Southwinds, South Kingstown, RI
Resale Only
|
55+ age-restricted
|
Built 2005 - 2010
|
70 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.
New
Del Webb Chauncy Lake
![8310 PETERS FARM WAY 310, WESTBOROUGH, M..., Westborough, MA 01581]()
2 beds
|2 baths
|1,375 sq ft
|Condo
8310 PETERS FARM WAY 310, WESTBOROUGH, M...
Community: Del Webb Chauncy Lake
MLS 73582700 • Pulte Homes of New England, Erin S... • Pulte Homes of New England
New
The Village at Westminster Place
![9 SETTLERS LN 583, HOLDEN, MA, 01520, Holden, MA 01520]()
3 beds
|3 baths
|1,877 sq ft
|House
9 SETTLERS LN 583, HOLDEN, MA, 01520
Community: The Village at Westminster Place
MLS 73582679 • eXp Realty LLC, Christine L. Najem • eXp Realty LLC
New
Great Island
![28 CROSS WIND, PLYMOUTH, MA, 02360, Plymouth, MA 02360]()
MLS 73582634 • Coldwell Banker Realty - Plymouth,... • Coldwell Banker Realty - Plymouth
New
Regency at Glen Ellen
![29 HENRY WAY 29, MILLIS, MA, 02054, Millis, MA 02054]()
2 beds
|3 baths
|2,432 sq ft
|Condo
29 HENRY WAY 29, MILLIS, MA, 02054
Community: Regency at Glen Ellen
MLS 73582026 • Rutledge Properties, Christine Law... • Rutledge Properties
New
Great Island
![12 MAPLEWOOD, PLYMOUTH, MA, 02360, Plymouth, MA 02360]()
MLS 73581951 • Pinehills Brokerage Services LLC, ... • Pinehills Brokerage Services LLC
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New
The Village at Orchard Meadows
![4 BLOSSOM TREE DR 4, SHREWSBURY, MA, 015..., Shrewsbury, MA 01545]()
2 beds
|2 baths
|1,580 sq ft
|Condo
4 BLOSSOM TREE DR 4, SHREWSBURY, MA, 015...
Community: The Village at Orchard Meadows
MLS 73581232 • Lamacchia Realty, Inc., Maribeth M... • Lamacchia Realty, Inc.
Brierly Pond Village
![22 HORNE WAY 22, MILLBURY, MA, 01527, Millbury, MA 01527]()
2 beds
|2 baths
|1,746 sq ft
|Condo
22 HORNE WAY 22, MILLBURY, MA, 01527
Community: Brierly Pond Village
MLS 73580213 • L & M Realty, Daniel G. Smachetti • L & M Realty
Great Island
![67 SOUTHWARD TRL, PLYMOUTH, MA, 02360, Plymouth, MA 02360]()
3 beds
|4 baths
|3,768 sq ft
|House
67 SOUTHWARD TRL, PLYMOUTH, MA, 02360
Community: Great Island
MLS 73580150 • Engel & Volkers, South Shore, Mary... • Engel & Volkers, South Shore
Harmony Place
![136 FIDELITY DR 6, RUTLAND, MA, 01543, Rutland, MA 01543]()
2 beds
|2 baths
|1,582 sq ft
|Condo
136 FIDELITY DR 6, RUTLAND, MA, 01543
Community: Harmony Place
MLS 73580035 • Harbor Classic Realty, Karin Ander... • Harbor Classic Realty
Oak Point
![412 GREEN ST, MIDDLEBORO, MA, 02346, Middleboro, MA 02346]()
3 beds
|2 baths
|1,670 sq ft
|Mobile Home
412 GREEN ST, MIDDLEBORO, MA, 02346
Community: Oak Point
MLS 73579900 • Djust Realty, Carl Djusberg • Djust Realty
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.
Rockland Glen
![23 NORTHFIELD DR 23, ROCKLAND, MA, 02370, Rockland, MA 02370]()
2 beds
|3 baths
|1,770 sq ft
|Condo
23 NORTHFIELD DR 23, ROCKLAND, MA, 02370
Community: Rockland Glen
MLS 73579549 • RF Boston Realty Group, Richard Kn... • RF Boston Realty Group
The Lanterns at Warren Woods
![20 FERN XING 20, ASHLAND, MA, 01721, Ashland, MA 01721]()
2 beds
|3 baths
|2,290 sq ft
|Condo
20 FERN XING 20, ASHLAND, MA, 01721
Community: The Lanterns at Warren Woods
MLS 73578086 • Gibson Sotheby's International Rea... • Gibson Sotheby's International Realty
The Pines at Hathaway Pond
![38 HATHAWAY POND CIR 38, ROCHESTER, MA, ..., Rochester, MA 02770]()
2 beds
|3 baths
|1,969 sq ft
|Condo
38 HATHAWAY POND CIR 38, ROCHESTER, MA, ...
Community: The Pines at Hathaway Pond
MLS 73576476 • New Year Realty, Edmund Wong • New Year Realty
Regency at Assabet Ridge
![23 AVEBURY LN 23, MARLBOROUGH, MA, 01752, Marlborough, MA 01752]()
4 beds
|4 baths
|3,561 sq ft
|Condo
23 AVEBURY LN 23, MARLBOROUGH, MA, 01752
Community: Regency at Assabet Ridge
MLS 73576699 • eXp Realty LLC, Rachael Peterson • eXp Realty LLC
Upton Ridge
![16 LINKSIDE CT 16, NORTHBRIDGE, MA, 0153..., Northbridge, MA 01534]()
2 beds
|3 baths
|2,030 sq ft
|Condo
16 LINKSIDE CT 16, NORTHBRIDGE, MA, 0153...
Community: Upton Ridge
MLS 73570500 • ERA Key Realty Services- Milf, Kim... • ERA Key Realty Services- Milf
30 Coppersmith
![30 COPPERSMITH WAY 108, CANTON, MA, 0202..., Canton, MA 02021]()
1 beds
|1 baths
|1,129 sq ft
|Condo
30 COPPERSMITH WAY 108, CANTON, MA, 0202...
Community: 30 Coppersmith
MLS 73576045 • Pulte Homes of New England, Erin S... • Pulte Homes of New England
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(401) 313-4589
Woodstone Crossing
![70 TROTTER RD 4304, WEYMOUTH, MA, 02190, Weymouth, MA 02190]()
1 beds
|1 baths
|965 sq ft
|Condo
70 TROTTER RD 4304, WEYMOUTH, MA, 02190
Community: Woodstone Crossing
MLS 73575992 • Coldwell Banker Realty - Westwood,... • Coldwell Banker Realty - Westwood
The Preserve at Hunters Hill
![3047 CLUBHOUSE DR, DIGHTON, MA, 02715, Dighton, MA 02715]()
2 beds
|2 baths
|1,775 sq ft
|House
3047 CLUBHOUSE DR, DIGHTON, MA, 02715
Community: The Preserve at Hunters Hill
MLS 73575815 • Long Realty, Patricia Fanning • Long Realty
Westbrook Crossing
![989 E ST 303, DEDHAM, MA, 02026, Dedham, MA 02026]()
2 beds
|2 baths
|1,895 sq ft
|Condo
989 E ST 303, DEDHAM, MA, 02026
Community: Westbrook Crossing
MLS 73575432 • RE/MAX Distinct Advantage, The Jow... • RE/MAX Distinct Advantage
Del Webb Chauncy Lake
![4 PETERS FARM WAY 409, WESTBOROUGH, MA, ..., Westborough, MA 01581]()
2 beds
|2 baths
|1,326 sq ft
|Condo
4 PETERS FARM WAY 409, WESTBOROUGH, MA, ...
Community: Del Webb Chauncy Lake
MLS 73575237 • ERA Key Realty Services- Fram, Rob... • ERA Key Realty Services- Fram
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
![7 PAR THREE CT, MASHPEE, MA, 02649, Mashpee, MA 02649]()
MLS 73574754 • William Raveis R.E. & Home Service... • William Raveis R.E. & Home Services
Stonebridge Commons
![40 STONEBRIDGE DR 40, HANSON, MA, 02341, Hanson, MA 02341]()
2 beds
|3 baths
|1,800 sq ft
|Condo
40 STONEBRIDGE DR 40, HANSON, MA, 02341
Community: Stonebridge Commons
MLS 73574423 • William Raveis R.E. & Home Service... • William Raveis R.E. & Home Services
Del Webb Chauncy Lake
![5 PETERS FARM WAY 7405, WESTBOROUGH, MA,..., Westborough, MA 01581]()
2 beds
|2 baths
|1,166 sq ft
|Condo
5 PETERS FARM WAY 7405, WESTBOROUGH, MA,...
Community: Del Webb Chauncy Lake
MLS 73574409 • Pulte Homes of New England, Erin S... • Pulte Homes of New England
Pennington Crossing
![1102 PENNINGTON DR 1102, WALPOLE, MA, 02..., Walpole, MA 02081]()
1 beds
|1 baths
|955 sq ft
|Condo
1102 PENNINGTON DR 1102, WALPOLE, MA, 02...
Community: Pennington Crossing
MLS 73574324 • Gelineau & Associates, R.E., Glenn... • Gelineau & Associates, R.E.
Brierly Pond Village
![97 HORNE WAY 97, MILLBURY, MA, 01527, Millbury, MA 01527]()
2 beds
|3 baths
|1,746 sq ft
|Condo
97 HORNE WAY 97, MILLBURY, MA, 01527
Community: Brierly Pond Village
MLS 73574309 • Lamacchia Realty, Inc., Colleen Cr... • Lamacchia Realty, Inc.
Southport
![126 GREY HAWK DR 697, MASHPEE, MA, 02649, Mashpee, MA 02649]()
2 beds
|3 baths
|1,620 sq ft
|Condo
126 GREY HAWK DR 697, MASHPEE, MA, 02649
Community: Southport
MLS 73573597 • Cape Coastal Sotheby's Internation... • Cape Coastal Sotheby's International Realty
Stonebridge Commons
![31 STONEBRIDGE DR 31, HANSON, MA, 02341, Hanson, MA 02341]()
2 beds
|3 baths
|2,071 sq ft
|Condo
31 STONEBRIDGE DR 31, HANSON, MA, 02341
Community: Stonebridge Commons
MLS 73572593 • Keller Williams Realty Colonial Pa... • Keller Williams Realty Colonial Partners
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Great Island
![26 CROSS WIND, PLYMOUTH, MA, 02360, Plymouth, MA 02360]()
MLS 73572237 • Pinehills Brokerage Services LLC, ... • Pinehills Brokerage Services LLC
Del Webb Chauncy Lake
![8113 PETERS FARM WAY 113, WESTBOROUGH, M..., Westborough, MA 01581]()
2 beds
|2 baths
|1,512 sq ft
|Condo
8113 PETERS FARM WAY 113, WESTBOROUGH, M...
Community: Del Webb Chauncy Lake
MLS 73572089 • Pulte Homes of New England, Erin S... • Pulte Homes of New England
Del Webb Chauncy Lake
![8103 PETERS FARM WAY 103, WESTBOROUGH, M..., Westborough, MA 01581]()
1 beds
|2 baths
|972 sq ft
|Condo
8103 PETERS FARM WAY 103, WESTBOROUGH, M...
Community: Del Webb Chauncy Lake
MLS 73572083 • 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.
Sawyer's Reach
![35 MARINERS WAY 35, PLYMOUTH, MA, 02360, Plymouth, MA 02360]()
3 beds
|3 baths
|2,533 sq ft
|Condo
35 MARINERS WAY 35, PLYMOUTH, MA, 02360
Community: Sawyer's Reach
MLS 73571547 • Century 21 Tassinari & Assoc., Ada... • Century 21 Tassinari & Assoc.
Seton Highlands at The Pinehills
![105 SETON HIGHLANDS 105, PLYMOUTH, MA, 0..., Plymouth, MA 02360]()
2 beds
|3 baths
|2,186 sq ft
|Condo
105 SETON HIGHLANDS 105, PLYMOUTH, MA, 0...
Community: Seton Highlands at The Pinehills
MLS 73571255 • South Shore Sotheby's Internationa... • South Shore Sotheby's International Realty
Bates Quarry
![16 TIGER TER 29, WALPOLE, MA, 02081, Walpole, MA 02081]()
MLS 73571022 • Pulte Homes of New England, Erin S... • Pulte Homes of New England
Cindy Certified
Upton Ridge
![126 CLUBHOUSE LN 126, NORTHBRIDGE, MA, 0..., Northbridge, MA 01534]()
3 beds
|3 baths
|2,130 sq ft
|Condo
126 CLUBHOUSE LN 126, NORTHBRIDGE, MA, 0...
Community: Upton Ridge
MLS 73570037 • McCormick Properties, Bill McCormi... • McCormick Properties
The Trails
![30 WATERVILLE LN 30, HOPKINTON, MA, 0174..., Hopkinton, MA 01748]()
2 beds
|3 baths
|2,510 sq ft
|Condo
30 WATERVILLE LN 30, HOPKINTON, MA, 0174...
Community: The Trails
MLS 73569915 • Realty Executives Boston West, Phi... • Realty Executives Boston West
The Pines at Hathaway Pond
![20 HATHAWAY POND CIR 20, ROCHESTER, MA, ..., Rochester, MA 02770]()
2 beds
|3 baths
|1,968 sq ft
|Condo
20 HATHAWAY POND CIR 20, ROCHESTER, MA, ...
Community: The Pines at Hathaway Pond
MLS 73569509 • Conway - Mattapoisett, Joanne Meck... • Conway - Mattapoisett
Cindy Certified
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Cindy Certified
Seton Highlands at The Pinehills
![15 ABERDEEN 15, PLYMOUTH, MA, 02360, Plymouth, MA 02360]()
3 beds
|4 baths
|3,703 sq ft
|Condo
15 ABERDEEN 15, PLYMOUTH, MA, 02360
Community: Seton Highlands at The Pinehills
MLS 73569328 • Pinehills Brokerage Services LLC, ... • 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.
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: Sep 28, 2026.
This application does not include information on all of the properties available for sale at this time.
