Call us at (401) 313-4589 to learn more about active adult communities in Middletown
Middletown, RI 55+ active adult communities & homes for sale
80 communities near Middletown
80 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
|
55+ age-restricted
|
Built 2006 - present
|
140 homes
$400ks
- $500ks
Harmony Place, Rutland, MA
New Construction
|
55+ age-restricted
|
Built 2023 - present
|
142 homes
$400ks
- $600ks
Southport, Mashpee, MA
New and Resale
|
55+ age-restricted
|
Built 1989 - present
|
730 homes
$700ks
- $900ks
Regency at Glen Ellen, Millis, MA
New Construction
|
55+ age-restricted
|
Built 2017 - present
|
324 homes
Want to learn more about 55+ communities in Middletown?
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$700ks
30 Coppersmith, Canton, MA
New Construction
|
55+ age-restricted
|
Built 2025 - present
|
63 homes
$600ks
- $700ks
Seton Highlands at The Pi..., Plymouth, MA
New and Resale
|
55+ age-restricted
|
Built 2008 - present
|
120 homes
$400ks
- $900ks
Sawyer's Reach, Plymouth, MA
New and Resale
|
55+ age-restricted
|
Built 2017 - present
|
224 homes
$500ks
- $700ks
The Trails, Hopkinton, MA
New Construction
|
55+ age-restricted
|
Built 2017 - present
|
170 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.
5 rating (3 reviews)
![Oak Point]()
$300ks
- $400ks
Oak Point, Middleborough, MA
New and Resale
|
55+ age-restricted
|
Built 1999 - present
|
1,150 homes
Read the Ultimate 55+ Rental Guide
Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
$400ks
- $600ks
Lake Point Village, Lakeville, MA
New Construction
|
55+ age-restricted
|
Built 2020 - present
|
66 homes
$400ks
- $600ks
Woodcrest Run, Sharon, MA
New Construction
|
55+ age-restricted
|
Built 2019 - present
|
25 homes
$500ks
Orchard Hill, Westborough, MA
Resale Only
|
55+ age-restricted
|
Built 2002 - 2010
|
100 homes
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$500ks
- $600ks
Regency at Assabet Ridge, Marlborough, MA
Resale Only
|
55+ age-restricted
|
Built 2010 - 2015
|
69 homes
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$400ks
- $500ks
The Village at Orchard Me..., Shrewsbury, MA
Resale Only
|
55+ age-restricted
|
Built 2002 - 2007
|
114 homes
$500ks
- $700ks
The Elms of Hanover, Hanover, MA
Resale Only
|
55+ age-restricted
|
Built 2003 - 2004
|
51 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
- $800ks
Millwood Preserve, Framingham, MA
New Construction
|
55+ age-restricted
|
Built 2020 - present
|
129 homes
$400ks
- $600ks
Brooksmont, Holliston, MA
Resale Only
|
55+ age-restricted
|
Built 2017 - 2020
|
66 homes
$400ks
- $500ks
Forest Glen, Uxbridge, MA
New Construction
|
55+ age-restricted
|
Built 2018 - present
|
44 homes
Read the Ultimate 55+ Rental Guide
Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
$500ks
- $600ks
Balancing Rock, Holliston, MA
Resale Only
|
55+ age-restricted
|
Built 2006 - 2008
|
49 homes
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$400ks
- $500ks
Westbrook Crossing, Dedham, MA
Resale Only
|
55+ age-restricted
|
Built 2003 - 2004
|
60 homes
$800ks
- $1Ms
Villages at Weathervane, Weymouth, MA
Resale Only
|
55+ age-restricted
|
Built 2003 - 2010
|
149 homes
$200ks
- $300ks
Cranberry Grove, Wareham, MA
Resale Only
|
55+ age-restricted
|
Built 2001 - 2001
|
36 homes
$500ks
Kensington at The Pinehil..., Plymouth, MA
New Construction
|
Age-targeted
|
Built 2017 - present
|
17 homes
Want to learn more about 55+ rental communities in Middletown?
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(401) 313-4589
Download the Ultimate 55+ Homebuying Guide
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$400ks
- $500ks
Arbor Hills, Kingston, MA
Resale Only
|
55+ age-restricted
|
Built 2003 - 2005
|
54 homes
$400ks
- $500ks
Mattapoisett Landing, Mattapoisett, MA
Resale Only
|
55+ age-restricted
|
Built 2012 - 2015
|
27 homes
$600ks
- $700ks
Rockwood Meadows, Upton, MA
New Construction
|
55+ age-restricted
|
Built 2016 - present
|
58 homes
$400ks
- $500ks
Spring Meadow, Hanover, MA
Resale Only
|
55+ age-restricted
|
Built 2004 - 2007
|
39 homes
$300ks
- $500ks
Rockland Glen, Rockland, MA
Resale Only
|
55+ age-restricted
|
Built 2008 - 2015
|
60 homes
Want to learn more about 55+ communities in Middletown?
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Questions? Call us:
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Read the Ultimate 55+ Rental Guide
Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
$600ks
- $700ks
The Villages at Walker Me..., Westborough, MA
Resale Only
|
55+ age-restricted
|
Built 1999 - 2000
|
100 homes
$600ks
- $700ks
Northside Meadows, Framingham, MA
Resale Only
|
55+ age-restricted
|
Built 2017 - 2019
|
60 homes
$900ks
- $1Ms
Seaside at Scituate - The..., Scituate, MA
New Construction
|
55+ age-restricted
|
Built 2019 - present
|
44 homes
$500ks
Northwoods at Sudbury, Sudbury, MA
Resale Only
|
55+ age-restricted
|
Built 1999 - 2019
|
43 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
- $900ks
Wyman Farms, Shrewsbury, MA
New Construction
|
55+ age-restricted
|
Built 2017 - present
|
26 homes
Want to learn more about 55+ rental communities in Middletown?
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$600ks
- $700ks
Rolling Mill, Plymouth, MA
Resale Only
|
55+ age-restricted
|
Built 2018 - 2021
|
46 homes
$300ks
- $400ks
Brierly Pond Village, Millbury, MA
Resale Only
|
55+ age-restricted
|
Built 2003 - 2013
|
199 homes
$900ks
59 North Main, Sherborn, MA
New Construction
|
55+ age-restricted
|
Built 2019 - present
|
12 homes
Want to learn more about 55+ communities in Middletown?
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Questions? Call us:
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$500ks
- $600ks
The Cottages at Lebaron H..., Lakeville, MA
New Construction
|
55+ age-restricted
|
Built 2019 - present
|
32 homes
New
Regency at Assabet Ridge
![13 WILSHIRE WAY 13, MARLBOROUGH, MA, 017..., Marlborough, MA 01752]()
2 beds
|2 baths
|1,584 sq ft
|Condo
13 WILSHIRE WAY 13, MARLBOROUGH, MA, 017...
Community: Regency at Assabet Ridge
MLS 73491917 • Colby Hunter Realty, John Jewett
New
Millwood Preserve
![14 CALLAHAN DR 14, FRAMINGHAM, MA, 01701, Framingham, MA 01701]()
2 beds
|3 baths
|2,454 sq ft
|Condo
14 CALLAHAN DR 14, FRAMINGHAM, MA, 01701
Community: Millwood Preserve
MLS 73491798 • Compass, Bell Property Partners
New
Cranberry Grove
![3 CRANBERRY GROVE WAY C, WAREHAM, MA, 02..., Wareham, MA 02571]()
2 beds
|2 baths
|1,350 sq ft
|Condo
3 CRANBERRY GROVE WAY C, WAREHAM, MA, 02...
Community: Cranberry Grove
MLS 73491457 • Tarantino Real Estate, Phillip Tar...
New
Villages at Weathervane
![6 TEE TIME LN 38, WEYMOUTH, MA, 02190, Weymouth, MA 02190]()
2 beds
|3 baths
|2,030 sq ft
|Condo
6 TEE TIME LN 38, WEYMOUTH, MA, 02190
Community: Villages at Weathervane
MLS 73491140 • Compass, Jeff Alexander
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 73489829 • Mathieu Newton Sotheby's Internati...
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Del Webb Chauncy Lake
![5 PETERS FARM WAY 309, WESTBOROUGH, MA, ..., Westborough, MA 01581]()
2 beds
|2 baths
|1,375 sq ft
|Condo
5 PETERS FARM WAY 309, WESTBOROUGH, MA, ...
Community: Del Webb Chauncy Lake
MLS 73489742 • Pulte Homes of New England, Erin S...
Del Webb Chauncy Lake
![5 PETERS FARM WAY 104, WESTBOROUGH, MA, ..., Westborough, MA 01581]()
1 beds
|1 baths
|972 sq ft
|Condo
5 PETERS FARM WAY 104, WESTBOROUGH, MA, ...
Community: Del Webb Chauncy Lake
MLS 73489727 • Pulte Homes of New England, Erin S...
Great Island
![22 PICKET FENCE, PLYMOUTH, MA, 02360, Plymouth, MA 02360]()
MLS 73489650 • Pinehills Brokerage Services LLC, ...
Arbor Hills
![47 HOLLY CIR 47, KINGSTON, MA, 02364, Kingston, MA 02364]()
MLS 73489433 • Coldwell Banker Realty - Norwell -...
Download the Ultimate 55+ Homebuying Guide
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Del Webb Chauncy Lake
![5 PETERS FARM WAY 5105, WESTBOROUGH, MA,..., Westborough, MA 01581]()
1 beds
|1 baths
|958 sq ft
|Condo
5 PETERS FARM WAY 5105, WESTBOROUGH, MA,...
Community: Del Webb Chauncy Lake
MLS 73489286 • Pulte Homes of New England, Erin S...
Read the Ultimate 55+ Rental Guide
Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
The Trails
![28 WATERVILLE LN 28, HOPKINTON, MA, 0174..., Hopkinton, MA 01748]()
2 beds
|3 baths
|2,510 sq ft
|Condo
28 WATERVILLE LN 28, HOPKINTON, MA, 0174...
Community: The Trails
MLS 73489252 • Realty Executives Boston West, Phi...
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 73489110 • Pulte Homes of New England, Erin S...
Southport
![12 KETTLE LN 31, MASHPEE, MA, 02649, Mashpee, MA 02649]()
MLS 73488797 • Kinlin Grover Compass, Carli Taylo...
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Regency at Glen Ellen
![86 GLEN ELLEN BLVD 86, MILLIS, MA, 02054, Millis, MA 02054]()
3 beds
|3 baths
|3,060 sq ft
|Condo
86 GLEN ELLEN BLVD 86, MILLIS, MA, 02054
Community: Regency at Glen Ellen
MLS 73488324 • Flip and Hold Realty LLC, Christop...
Rockland Glen
![1 VON RHOR DR 1, ROCKLAND, MA, 02370, Rockland, MA 02370]()
2 beds
|4 baths
|1,990 sq ft
|Condo
1 VON RHOR DR 1, ROCKLAND, MA, 02370
Community: Rockland Glen
MLS 73488206 • Lighthouse Realty Group, Inc., Ann...
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Regency at Glen Ellen
![6 JAMESON DR 6, MILLIS, MA, 02054, Millis, MA 02054]()
3 beds
|4 baths
|3,106 sq ft
|Condo
6 JAMESON DR 6, MILLIS, MA, 02054
Community: Regency at Glen Ellen
MLS 73488040 • Concierge Real Estate, LLC, Doris ...
Regency at Assabet Ridge
![25 AVEBURY LN 22, MARLBOROUGH, MA, 01752, Marlborough, MA 01752]()
3 beds
|3 baths
|2,264 sq ft
|Condo
25 AVEBURY LN 22, MARLBOROUGH, MA, 01752
Community: Regency at Assabet Ridge
MLS 73488029 • Barrett Sotheby's International Re...
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 406, PLYMOUTH, MA, 02360, Plymouth, MA 02360]()
2 beds
|2 baths
|1,368 sq ft
|Condo
45 PLAZA WAY 406, PLYMOUTH, MA, 02360
Community: Sawyer's Reach
MLS 73488009 • RE/MAX Platinum, Cindi Ford
Balancing Rock
![20 GLACIER WAY 20, HOLLISTON, MA, 01746, Holliston, MA 01746]()
2 beds
|3 baths
|2,084 sq ft
|Condo
20 GLACIER WAY 20, HOLLISTON, MA, 01746
Community: Balancing Rock
MLS 73487872 • Vesta Real Estate Group, Inc., Ves...
Del Webb Chauncy Lake
![1105 PETERS FARM WAY 105, WESTBOROUGH, M..., Westborough, MA 01581]()
1 beds
|1 baths
|945 sq ft
|Condo
1105 PETERS FARM WAY 105, WESTBOROUGH, M...
Community: Del Webb Chauncy Lake
MLS 73487816 • Mathieu Newton Sotheby's Internati...
Read the Ultimate 55+ Rental Guide
Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
Westbrook Crossing
![989 E ST 402, DEDHAM, MA, 02026, Dedham, MA 02026]()
MLS 73487736 • Donahue Real Estate Co., Mary Elle...
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Regency at Glen Ellen
![8 GLEN ELLEN BLVD 8, MILLIS, MA, 02054, Millis, MA 02054]()
2 beds
|4 baths
|4,247 sq ft
|Condo
8 GLEN ELLEN BLVD 8, MILLIS, MA, 02054
Community: Regency at Glen Ellen
MLS 73487461 • William Raveis R.E. & Home Service...
Southport
![94 PINE HL 94, MASHPEE, MA, 02649, Mashpee, MA 02649]()
MLS 73486928 • Realty ONE Group Suburban Lifestyl...
Del Webb Chauncy Lake
![5 PETERS FARM WAY 305, WESTBOROUGH, MA, ..., Westborough, MA 01581]()
2 beds
|2 baths
|1,175 sq ft
|Condo
5 PETERS FARM WAY 305, WESTBOROUGH, MA, ...
Community: Del Webb Chauncy Lake
MLS 73486054 • Pulte Homes of New England, Erin S...
Northside Meadows
![10 TANGLEWOOD DR 10, FRAMINGHAM, MA, 017..., Framingham, MA 01701]()
2 beds
|3 baths
|2,218 sq ft
|Condo
10 TANGLEWOOD DR 10, FRAMINGHAM, MA, 017...
Community: Northside Meadows
MLS 73485504 • High End Homes Realty Group LLC, J...
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Woodcrest Run
![635 OLD POST RD 210, SHARON, MA, 02067, Sharon, MA 02067]()
2 beds
|2 baths
|1,056 sq ft
|Condo
635 OLD POST RD 210, SHARON, MA, 02067
Community: Woodcrest Run
MLS 73483721 • Coldwell Banker Realty - Westwood,...
Oak Point
![402 BLUEBERRY CIR, MIDDLEBORO, MA, 02346, Middleboro, MA 02346]()
3 beds
|2 baths
|1,568 sq ft
|House
402 BLUEBERRY CIR, MIDDLEBORO, MA, 02346
Community: Oak Point
MLS 73483878 • Conway - Lakeville, Marika Kyranos...
Orchard Hill
![14 BALDWIN CT 14, WESTBOROUGH, MA, 01581, Westborough, MA 01581]()
2 beds
|3 baths
|2,225 sq ft
|Condo
14 BALDWIN CT 14, WESTBOROUGH, MA, 01581
Community: Orchard Hill
MLS 73481699 • Mathieu Newton Sotheby's Internati...
Del Webb Chauncy Lake
![6312 PETERS FARM WAY 6312, WESTBOROUGH, ..., Westborough, MA 01581]()
2 beds
|2 baths
|1,469 sq ft
|Condo
6312 PETERS FARM WAY 6312, WESTBOROUGH, ...
Community: Del Webb Chauncy Lake
MLS 73481383 • Keller Williams Pinnacle MetroWest...
Harmony Place
![10 FIDELITY DR 5, RUTLAND, MA, 01543, Rutland, MA 01543]()
2 beds
|2 baths
|1,582 sq ft
|Condo
10 FIDELITY DR 5, RUTLAND, MA, 01543
Community: Harmony Place
MLS 73481173 • Harbor Classic Realty, Karin Ander...
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Read the Ultimate 55+ Rental Guide
Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
Harmony Place
![12 FIDELITY DR 6, RUTLAND, MA, 01543, Rutland, MA 01543]()
2 beds
|2 baths
|1,582 sq ft
|Condo
12 FIDELITY DR 6, RUTLAND, MA, 01543
Community: Harmony Place
MLS 73481167 • Harbor Classic Realty, Karin Ander...
Del Webb Chauncy Lake
![1 PETERS FARM WAY 411, WESTBOROUGH, MA, ..., Westborough, MA 01581]()
2 beds
|2 baths
|1,326 sq ft
|Condo
1 PETERS FARM WAY 411, WESTBOROUGH, MA, ...
Community: Del Webb Chauncy Lake
MLS 73481034 • Panarelli Properties, Inc., Justin...
Southport
![16 GREY HAWK DR 16, MASHPEE, MA, 02649, Mashpee, MA 02649]()
MLS 73480725 • Sotheby's International Realty, Jo...
Del Webb Chauncy Lake
![1109 PETERS FARM WAY 1109, WESTBOROUGH, ..., Westborough, MA 01581]()
1 beds
|1 baths
|1,030 sq ft
|Condo
1109 PETERS FARM WAY 1109, WESTBOROUGH, ...
Community: Del Webb Chauncy Lake
MLS 73480122 • Oak Realty, Pamela Bathen
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.
Harmony Place
![15 FIDELITY DR 70, RUTLAND, MA, 01543, Rutland, MA 01543]()
2 beds
|2 baths
|1,447 sq ft
|Condo
15 FIDELITY DR 70, RUTLAND, MA, 01543
Community: Harmony Place
MLS 73479872 • Harbor Classic Realty, Karin Ander...
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Harmony Place
![4 FIDELITY DR 2, RUTLAND, MA, 01543, Rutland, MA 01543]()
MLS 73479871 • Harbor Classic Realty, Karin Ander...
The Preserve at Hunters Hill
![R42 CLUBHOUSE DR R42, DIGHTON, MA, 02715, Dighton, MA 02715]()
2 beds
|2 baths
|1,775 sq ft
|House
R42 CLUBHOUSE DR R42, DIGHTON, MA, 02715
Community: The Preserve at Hunters Hill
MLS 73479410 • Long Realty, Patricia Fanning
Regency at Glen Ellen
![124 GLEN ELLEN BLVD 124, MILLIS, MA, 020..., Millis, MA 02054]()
2 beds
|2 baths
|1,797 sq ft
|Condo
124 GLEN ELLEN BLVD 124, MILLIS, MA, 020...
Community: Regency at Glen Ellen
MLS 73478697 • Coldwell Banker Realty - Needham, ...
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Sawyer's Reach
![1 MARINERS WAY 204, PLYMOUTH, MA, 02360, Plymouth, MA 02360]()
1 beds
|2 baths
|1,113 sq ft
|Condo
1 MARINERS WAY 204, PLYMOUTH, MA, 02360
Community: Sawyer's Reach
MLS 73478618 • Engel & Volkers, South Shore, Kim ...
Del Webb Chauncy Lake
![5 PETERS FARM WAY 107, WESTBOROUGH, MA, ..., Westborough, MA 01581]()
2 beds
|2 baths
|1,512 sq ft
|Condo
5 PETERS FARM WAY 107, WESTBOROUGH, MA, ...
Community: Del Webb Chauncy Lake
MLS 73477940 • Pulte Homes of New England, Erin S...
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: Mar 28, 2026.
This application does not include information on all of the properties available for sale at this time.
