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
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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
|
Built 2006 - present
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140 homes
$700ks
30 Coppersmith, Canton, MA
New Construction
|
55+ age-restricted
|
Built 2025 - present
|
63 homes
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$400ks
- $500ks
Harmony Place, Rutland, MA
New Construction
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55+ age-restricted
|
Built 2023 - present
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142 homes
$400ks
- $600ks
Upton Ridge, Upton, MA
New Construction
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55+ age-restricted
|
Built 2019 - present
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139 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
$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
$300ks
- $600ks
Pennington Crossing, Walpole, MA
New Construction
|
55+ age-restricted
|
Built 2018 - present
|
172 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
- $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
$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
$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
$300ks
- $400ks
Brierly Pond Village, Millbury, MA
Resale Only
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55+ age-restricted
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Built 2003 - 2013
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199 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
$500ks
- $700ks
The Trails, Hopkinton, MA
New Construction
|
55+ age-restricted
|
Built 2017 - present
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170 homes
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$700ks
WestRidge, Hudson, MA
Resale Only
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55+ age-restricted
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Built 2009 - 2016
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136 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
$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
Bates Quarry, Walpole, MA
New Construction
|
55+ age-restricted
|
Built 2025 - present
|
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.
$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
- $600ks
Brooksmont, Holliston, MA
Resale Only
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55+ age-restricted
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Built 2017 - 2020
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66 homes
$500ks
Kensington at The Pinehil..., Plymouth, MA
New Construction
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Age-targeted
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Built 2017 - present
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17 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
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
$400ks
- $500ks
The Seasons at Salisbury, Holden, MA
Resale Only
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55+ age-restricted
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Built 2002 - 2006
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91 homes
$500ks
Orchard Hill, Westborough, MA
Resale Only
|
55+ age-restricted
|
Built 2002 - 2010
|
100 homes
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$400ks
- $500ks
Spring Meadow, Hanover, MA
Resale Only
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55+ age-restricted
|
Built 2004 - 2007
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39 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
$400ks
Tara Woods, Plymouth, MA
Resale Only
|
55+ age-restricted
|
Built 2007 - 2015
|
38 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
- $600ks
Peregrine Woods, Marshfield, MA
Resale Only
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55+ age-restricted
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Built 2002 - 2005
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32 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
$700ks
- $800ks
Duxbury Estates, Duxbury, MA
Resale Only
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55+ age-restricted
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Built 2008 - 2013
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44 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
The Villages at Crane Mea..., Marlborough, MA
Resale Only
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55+ age-restricted
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Built 2001 - 2005
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91 homes
$400ks
- $500ks
Summer Reach, Plymouth, MA
Resale Only
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55+ age-restricted
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Built 2017 - 2020
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114 homes
$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
$500ks
- $700ks
Holliston Woods, Holliston, MA
Resale Only
|
55+ age-restricted
|
Built 2016 - 2018
|
66 homes
Want to learn more about 55+ communities in Middletown?
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Questions? Call us:
(401) 313-4589
$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
Westbrook Crossing, Dedham, MA
Resale Only
|
55+ age-restricted
|
Built 2003 - 2004
|
60 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
Seton Highlands at The Pinehills
![105 SETON HIGH LANDS 105, PLYMOUTH, MA, ..., Plymouth, MA 02360]()
2 beds
|3 baths
|2,186 sq ft
|House
105 SETON HIGH LANDS 105, PLYMOUTH, MA, ...
Community: Seton Highlands at The Pinehills
MLS 73571254 • South Shore Sotheby's Internationa... • South Shore Sotheby's International Realty
New
Pennington Crossing
![2404 PENNINGTON DR 2404, WALPOLE, MA, 02..., Walpole, MA 02081]()
1 beds
|1 baths
|965 sq ft
|Condo
2404 PENNINGTON DR 2404, WALPOLE, MA, 02...
Community: Pennington Crossing
MLS 73571224 • Keller Williams Realty, The Varano... • Keller Williams Realty
New
The Pines at Hathaway Pond
![31 HATHAWAY POND CIR 31, ROCHESTER, MA, ..., Rochester, MA 02770]()
2 beds
|3 baths
|2,231 sq ft
|Condo
31 HATHAWAY POND CIR 31, ROCHESTER, MA, ...
Community: The Pines at Hathaway Pond
MLS 73571080 • Coldwell Banker Realty - Marion, M... • Coldwell Banker Realty - Marion
New
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
New
![12 TIGER TER 28, WALPOLE, MA, 02081, Walpole, MA 02081]()
Cindy Certified
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(401) 313-4589
New
![399 NEPONSET 112, CANTON, MA, 02021, Canton, MA 02021]()
Cindy Certified
New
30 Coppersmith
![30 COPPERSMITH WAY 512, CANTON, MA, 0202..., Canton, MA 02021]()
2 beds
|2 baths
|1,582 sq ft
|Condo
30 COPPERSMITH WAY 512, CANTON, MA, 0202...
Community: 30 Coppersmith
MLS 73570978 • Pulte Homes of New England, Erin S... • Pulte Homes of New England
New
30 Coppersmith
![30 COPPERSMITH WAY 509, CANTON, MA, 0202..., Canton, MA 02021]()
2 beds
|2 baths
|1,425 sq ft
|Condo
30 COPPERSMITH WAY 509, CANTON, MA, 0202...
Community: 30 Coppersmith
MLS 73570974 • Pulte Homes of New England, Erin S... • Pulte Homes of New England
New
Southport
![125 LEISURE GREEN DR 167, MASHPEE, MA, 0..., Mashpee, MA 02649]()
2 beds
|2 baths
|1,338 sq ft
|Condo
125 LEISURE GREEN DR 167, MASHPEE, MA, 0...
Community: Southport
MLS 73570571 • Kinlin Grover Compass, Carli Taylo... • Kinlin Grover Compass
New
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 73570388 • Compass, Livingston Group • Compass
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
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
New
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
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
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Cindy Certified
Regency at Glen Ellen
![24 HENRY WAY 24, MILLIS, MA, 02054, Millis, MA 02054]()
2 beds
|3 baths
|2,370 sq ft
|Condo
24 HENRY WAY 24, MILLIS, MA, 02054
Community: Regency at Glen Ellen
MLS 73568986 • Coldwell Banker Realty - Sharon, E... • Coldwell Banker Realty - Sharon
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 73568953 • Compass, Seagate Properties • Compass
Southport
![15 CLASSIC CIR 15, MASHPEE, MA, 02649, Mashpee, MA 02649]()
MLS 73568721 • Dream Home Realty, Marcy L. Fasano • Dream Home 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.
Sawyer's Reach
![1 MARINER’S WAY 207, PLYMOUTH, MA, 023..., Plymouth, MA 02360]()
2 beds
|2 baths
|1,084 sq ft
|Condo
1 MARINER’S WAY 207, PLYMOUTH, MA, 023...
Community: Sawyer's Reach
MLS 73567319 • Gibson Sotheby's International Rea... • Gibson Sotheby's International Realty
Cindy Certified
Woodcrest Run
![635 OLD POST RD 109, SHARON, MA, 02067, Sharon, MA 02067]()
2 beds
|2 baths
|1,056 sq ft
|Condo
635 OLD POST RD 109, SHARON, MA, 02067
Community: Woodcrest Run
MLS 73566337 • Strive Realty, Phillip Gendreau • Strive Realty
Woodcrest Run
![635 OLD POST RD 110, SHARON, MA, 02067, Sharon, MA 02067]()
1 beds
|2 baths
|1,056 sq ft
|Condo
635 OLD POST RD 110, SHARON, MA, 02067
Community: Woodcrest Run
MLS 73566339 • Strive Realty, Phillip Gendreau • Strive Realty
Woodcrest Run
![635 OLD POST RD 302, SHARON, MA, 02067, Sharon, MA 02067]()
2 beds
|2 baths
|1,187 sq ft
|Condo
635 OLD POST RD 302, SHARON, MA, 02067
Community: Woodcrest Run
MLS 73566336 • Strive Realty, Phillip Gendreau • Strive Realty
Brooksmont
![65 BROOKSMONT DR 15, HOLLISTON, MA, 0174..., Holliston, MA 01746]()
2 beds
|3 baths
|2,360 sq ft
|Condo
65 BROOKSMONT DR 15, HOLLISTON, MA, 0174...
Community: Brooksmont
MLS 73566269 • MA Homes, LLC, John Vaillancourt • MA Homes, LLC
Del Webb Chauncy Lake
![8 PETERS FARM WAY 106, WESTBOROUGH, MA, ..., Westborough, MA 01581]()
2 beds
|2 baths
|1,496 sq ft
|Condo
8 PETERS FARM WAY 106, WESTBOROUGH, MA, ...
Community: Del Webb Chauncy Lake
MLS 73566211 • Pulte Homes of New England, Erin S... • Pulte Homes of New England
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Del Webb Chauncy Lake
![8 PETERS FARM WAY 108, WESTBOROUGH, MA, ..., Westborough, MA 01581]()
1 beds
|2 baths
|1,058 sq ft
|Condo
8 PETERS FARM WAY 108, WESTBOROUGH, MA, ...
Community: Del Webb Chauncy Lake
MLS 73566205 • Pulte Homes of New England, Erin S... • Pulte Homes of New England
Del Webb Chauncy Lake
![8 PETERS FARM WAY 105, WESTBOROUGH, MA, ..., Westborough, MA 01581]()
1 beds
|2 baths
|958 sq ft
|Condo
8 PETERS FARM WAY 105, WESTBOROUGH, MA, ...
Community: Del Webb Chauncy Lake
MLS 73566189 • Pulte Homes of New England, Erin S... • Pulte Homes of New England
Cindy Certified
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.
Oak Point
![406 SIMMONS RD, MIDDLEBORO, MA, 02346, Middleboro, MA 02346]()
MLS 73566150 • The Firm, Pamela Vigneau • The Firm
Del Webb Chauncy Lake
![1213 CODMAN WAY 1213, WESTBOROUGH, MA, 0..., Westborough, MA 01581]()
2 beds
|2 baths
|1,512 sq ft
|Condo
1213 CODMAN WAY 1213, WESTBOROUGH, MA, 0...
Community: Del Webb Chauncy Lake
MLS 73565781 • Lamacchia Realty, Inc., Mary G. Wo... • Lamacchia Realty, Inc.
Brierly Pond Village
![37 HORNE WAY 37, MILLBURY, MA, 01527, Millbury, MA 01527]()
2 beds
|3 baths
|1,746 sq ft
|Condo
37 HORNE WAY 37, MILLBURY, MA, 01527
Community: Brierly Pond Village
MLS 73565368 • REMAX Executive Realty, Ron Arpino • REMAX Executive Realty
The Village at Orchard Meadows
![1 APPLE SEED DR 1, SHREWSBURY, MA, 01545, Shrewsbury, MA 01545]()
2 beds
|3 baths
|1,854 sq ft
|Condo
1 APPLE SEED DR 1, SHREWSBURY, MA, 01545
Community: The Village at Orchard Meadows
MLS 73565328 • Lamacchia Realty, Inc., Maribeth M... • Lamacchia Realty, Inc.
Southport
![6 CHADWICK CT 6, MASHPEE, MA, 02649, Mashpee, MA 02649]()
MLS 73565289 • Jack Conway Cape Cod - Sandwich, A... • Jack Conway Cape Cod - Sandwich
The Villages at Walker Meadow
![14 WESSONVILLE VILLAGE WAY 79, WESTBOROU..., Westborough, MA 01581]()
2 beds
|2 baths
|2,090 sq ft
|Condo
14 WESSONVILLE VILLAGE WAY 79, WESTBOROU...
Community: The Villages at Walker Meadow
MLS 73565142 • eXp Realty LLC - Corporate Office,... • eXp Realty LLC - Corporate Office
Southport
![45 GREY HAWK DR 578, MASHPEE, MA, 02649, Mashpee, MA 02649]()
MLS 73564835 • Kinlin Grover Compass, Carli Taylo... • Kinlin Grover Compass
Southport
![51 PORTSIDE DR 51, MASHPEE, MA, 02649, Mashpee, MA 02649]()
MLS 73564384 • Conway - Hanover, Jay Costantino • Conway - Hanover
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The Village at Westminster Place
![18 TEA PARTY CIR 18, HOLDEN, MA, 01520, Holden, MA 01520]()
3 beds
|3 baths
|2,028 sq ft
|House
18 TEA PARTY CIR 18, HOLDEN, MA, 01520
Community: The Village at Westminster Place
MLS 73564128 • Paramount Properties LLC, Barbara ... • Paramount Properties LLC
30 Coppersmith
![30 COPPERSMITH WAY 50701, CANTON, MA, 02..., Canton, MA 02021]()
2 beds
|2 baths
|1,582 sq ft
|Condo
30 COPPERSMITH WAY 50701, CANTON, MA, 02...
Community: 30 Coppersmith
MLS 73563875 • 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.
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?
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REIN updates its listings on a daily basis. Data last updated: Sep 04, 2026.
This application does not include information on all of the properties available for sale at this time.
