Middletown, RI 55+ active adult communities & homes for sale

81 communities near Middletown

Sort by:

Relevance

Del Webb Chauncy Lake

$400ks - $600ks

Del Webb Chauncy Lake, Westborough, MA

New Construction | 55+ age-restricted | Built 2018 - present | 700 homes

Southport

$400ks - $600ks

Southport, Mashpee, MA

New and Resale | 55+ age-restricted | Built 1989 - present | 730 homes

Great Island

$600ks

Great Island, Plymouth, MA

Resale Only | 55+ age-restricted | Built 2002 - 2015 | 600 homes

The Preserve at Hunters H...

$400ks - $500ks

The Preserve at Hunters H..., Dighton, MA

New and Resale | 55+ age-restricted | Built 2006 - present | 140 homes

Harmony Place

$400ks - $500ks

Harmony Place, Rutland, MA

New Construction | 55+ age-restricted | Built 2023 - present | 142 homes

Want to learn more about 55+ communities in Middletown? 55places can help!

Questions? Call us: (401) 313-4589

30 Coppersmith

$700ks

30 Coppersmith, Canton, MA

New Construction | 55+ age-restricted | Built 2025 - present | 63 homes

Seton Highlands at The Pi...

$600ks - $700ks

Seton Highlands at The Pi..., Plymouth, MA

New and Resale | 55+ age-restricted | Built 2008 - present | 120 homes

Woodcrest Run

$400ks - $600ks

Woodcrest Run, Sharon, MA

New Construction | 55+ age-restricted | Built 2019 - present | 25 homes

Regency at Glen Ellen

$700ks - $900ks

Regency at Glen Ellen, Millis, MA

New Construction | 55+ age-restricted | Built 2017 - present | 324 homes

Upton Ridge

$400ks - $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.

Sawyer's Reach

$400ks - $900ks

Sawyer's Reach, Plymouth, MA

New and Resale | 55+ age-restricted | Built 2017 - present | 224 homes

The Village at Orchard Me...

$400ks - $500ks

The Village at Orchard Me..., Shrewsbury, MA

Resale Only | 55+ age-restricted | Built 2002 - 2007 | 114 homes

Brierly Pond Village

$300ks - $400ks

Brierly Pond Village, Millbury, MA

Resale Only | 55+ age-restricted | Built 2003 - 2013 | 199 homes

Pennington Crossing

$300ks - $600ks

Pennington Crossing, Walpole, MA

New Construction | 55+ age-restricted | Built 2018 - present | 172 homes

The Trails

$500ks - $700ks

The Trails, Hopkinton, MA

New Construction | 55+ age-restricted | Built 2017 - present | 170 homes

The Pines at Hathaway Pon...

$300ks - $500ks

The Pines at Hathaway Pon..., Rochester, MA

Resale Only | 55+ age-restricted | Built 2006 - 2014 | 61 homes

Want to learn more about 55+ communities in Middletown? 55places can help!

Questions? Call us: (401) 313-4589

Orchard Hill

$500ks

Orchard Hill, Westborough, MA

Resale Only | 55+ age-restricted | Built 2002 - 2010 | 100 homes

The Village at Auburnvill...

$300ks - $400ks

The Village at Auburnvill..., Whitman, MA

Resale Only | 55+ age-restricted | Built 2004 - 2014 | 92 homes

Millwood Preserve

$1Ms

Millwood Preserve, Framingham, MA

Resale Only | 55+ age-restricted | Built 2020 - 2024 | 129 homes

WestRidge

$700ks

WestRidge, Hudson, MA

Resale Only | 55+ age-restricted | Built 2009 - 2016 | 136 homes

Brooksmont

$400ks - $600ks

Brooksmont, Holliston, MA

Resale Only | 55+ age-restricted | Built 2017 - 2020 | 66 homes

The Seasons at Salisbury

$400ks - $500ks

The Seasons at Salisbury, Holden, MA

Resale Only | 55+ age-restricted | Built 2002 - 2006 | 91 homes

Bates Quarry

Bates Quarry, Walpole, MA

New Construction | 55+ age-restricted | Built 2025 - present | 100 homes

Stonebridge Commons

$500ks

Stonebridge Commons, Hanson, MA

Resale Only | 55+ age-restricted | Built 2007 - 2018 | 121 homes

Northwoods at Sudbury

$500ks

Northwoods at Sudbury, Sudbury, MA

Resale Only | 55+ age-restricted | Built 1999 - 2019 | 43 homes

Woodstone Crossing

$300ks - $400ks

Woodstone Crossing, Weymouth, MA

Resale Only | Age-targeted | Built 2015 - 2019 | 200 homes

Chilton Park Village

$400ks

Chilton Park Village, Plymouth, MA

Resale Only | 55+ age-restricted | Built 2006 - 2015 | 25 homes

Want to learn more about 55+ communities in Middletown? 55places can help!

Questions? Call us: (401) 313-4589

The Villages at Walker Me...

$600ks - $700ks

The Villages at Walker Me..., Westborough, MA

Resale Only | 55+ age-restricted | Built 1999 - 2000 | 100 homes

Spring Meadow

$400ks - $500ks

Spring Meadow, Hanover, MA

Resale Only | 55+ age-restricted | Built 2004 - 2007 | 39 homes

The Elms of Hanover

$500ks - $700ks

The Elms of Hanover, Hanover, MA

Resale Only | 55+ age-restricted | Built 2003 - 2004 | 51 homes

Donovan Farm

$500ks - $700ks

Donovan Farm, Norwell, MA

Resale Only | 55+ age-restricted | Built 2001 - 2003 | 40 homes

Center Commons

$500ks - $600ks

Center Commons, Pembroke, MA

Resale Only | 55+ age-restricted | Built 2004 - 2009 | 44 homes

Adams Farm

$700ks - $800ks

Adams Farm, Shrewsbury, MA

Resale Only | 55+ age-restricted | Built 2005 - 2013 | 90 homes

Tara Woods

$400ks

Tara Woods, Plymouth, MA

Resale Only | 55+ age-restricted | Built 2007 - 2015 | 38 homes

Peregrine Woods

$400ks - $600ks

Peregrine Woods, Marshfield, MA

Resale Only | 55+ age-restricted | Built 2002 - 2005 | 32 homes

Blue Heron Pond

$500ks

Blue Heron Pond, Lancaster, MA

Resale Only | 55+ age-restricted | Built 2006 - 2014 | 58 homes

Duxbury Estates

$700ks - $800ks

Duxbury Estates, Duxbury, MA

Resale Only | 55+ age-restricted | Built 2008 - 2013 | 44 homes

New England Commons

$200ks - $300ks

New England Commons, Webster, MA

New and Resale | 55+ age-restricted | Built 2005 - present | 100 homes

Want to learn more about 55+ communities in Middletown? 55places can help!

Questions? Call us: (401) 313-4589

Pheasant Hill

$300ks - $400ks

Pheasant Hill, Northborough, MA

Resale Only | 55+ age-restricted | Built 2005 - 2006 | 48 homes

The Village at Westminste...

$400ks - $500ks

The Village at Westminste..., Holden, MA

New and Resale | 55+ age-restricted | Built 2006 - present | 125 homes

1 2...3

New The Pines at Hathaway Pond

20 HATHAWAY POND CIR 20, ROCHESTER, MA, ..., Rochester, MA 02770

$749,000

2 beds

3 baths

1,968 sq ft

Condo

20 HATHAWAY POND CIR 20, ROCHESTER, MA, ...

Community: The Pines at Hathaway Pond

New

Cindy Certified

20 AUDUBON WAY 309, CANTON, MA, 02021, Canton, MA 02021

$784,900

2 beds

3 baths

1,421 sq ft

Condo

20 AUDUBON WAY 309, CANTON, MA, 02021

New

Cindy Certified

20 AUDUBON WAY U 102, CANTON, MA, 02021, Canton, MA 02021

$659,900

2 beds

3 baths

1,440 sq ft

Condo

20 AUDUBON WAY U 102, CANTON, MA, 02021

New Seton Highlands at The Pinehills

15 ABERDEEN 15, PLYMOUTH, MA, 02360, Plymouth, MA 02360

$900,000

3 beds

4 baths

3,703 sq ft

Condo

15 ABERDEEN 15, PLYMOUTH, MA, 02360

Community: Seton Highlands at The Pinehills

New

Cindy Certified

399 NEPONSET 213, CANTON, MA, 02021, Canton, MA 02021

$755,945

2 beds

2 baths

1,058 sq ft

Condo

8 PETERS FARM WAY 108, WESTBOROUGH, MA, ...

Community: Del Webb Chauncy Lake

Want to learn more about 55+ communities in Middletown? 55places can help!

Questions? Call us: (401) 313-4589

Del Webb Chauncy Lake

8 PETERS FARM WAY 105, WESTBOROUGH, MA, ..., Westborough, MA 01581

$499,420

1 beds

2 baths

958 sq ft

Condo

8 PETERS FARM WAY 105, WESTBOROUGH, MA, ...

Community: Del Webb Chauncy Lake

Cindy Certified

9 DORSET LN 9, PLYMOUTH, MA, 02360, Plymouth, MA 02360

$769,000

3 baths

2,028 sq ft

House

18 TEA PARTY CIR 18, HOLDEN, MA, 01520

Community: The Village at Westminster Place

Want to learn more about 55+ communities in Middletown? 55places can help!

Questions? Call us: (401) 313-4589

30 Coppersmith

$817,325

2 beds

2 baths

1,582 sq ft

Condo

30 COPPERSMITH WAY 50701, CANTON, MA, 02...

Community: 30 Coppersmith

Bates Quarry

$936,949

2 beds

3 baths

2,301 sq ft

House

4 BATES QUARRY LN 44, WALPOLE, MA, 02081

Community: Bates Quarry

Spring Meadow

$750,000

2 beds

3 baths

2,417 sq ft

Condo

152 SPRING MEADOW LN 152, HANOVER, MA, 0...

Community: Spring Meadow

Pennington Crossing

1211 PENNINGTON DR 1211, WALPOLE, MA, 02..., Walpole, MA 02081

$575,000

1 beds

1 baths

1,030 sq ft

Condo

1211 PENNINGTON DR 1211, WALPOLE, MA, 02...

Community: Pennington Crossing

Center Commons

33 FREEDOM CIR 33, PEMBROKE, MA, 02359, Pembroke, MA 02359

$485,000

2 beds

2 baths

1,452 sq ft

Condo

33 FREEDOM CIR 33, PEMBROKE, MA, 02359

Community: Center Commons

Southport

7 IRONWOOD PATH 186, MASHPEE, MA, 02649, Mashpee, MA 02649

$564,000

2 beds

3 baths

1,685 sq ft

Condo

7 IRONWOOD PATH 186, MASHPEE, MA, 02649

Community: Southport

Great Island

9 CANOE LNDG, PLYMOUTH, MA, 02360, Plymouth, MA 02360

$735,000

2 beds

3 baths

2,074 sq ft

House

9 CANOE LNDG, PLYMOUTH, MA, 02360

Community: Great Island

Great Island

22 CROSS WIND, PLYMOUTH, MA, 02360, Plymouth, MA 02360

$825,000

3 beds

3 baths

2,440 sq ft

House

22 CROSS WIND, PLYMOUTH, MA, 02360

Community: Great Island

Great Island

6 AUTUMN GLN, PLYMOUTH, MA, 02360, Plymouth, MA 02360

$725,000

2 beds

3 baths

2,061 sq ft

House

6 AUTUMN GLN, PLYMOUTH, MA, 02360

Community: Great Island

Regency at Glen Ellen

112 GLEN ELLEN BLVD 112, MILLIS, MA, 020..., Millis, MA 02054

$1,299,950

3 beds

4 baths

4,483 sq ft

Condo

112 GLEN ELLEN BLVD 112, MILLIS, MA, 020...

Community: Regency at Glen Ellen

Cindy Certified

399 NEPONSET 409, CANTON, MA, 02021, Canton, MA 02021

$705,855

2 beds

2 baths

1,425 sq ft

Condo

399 NEPONSET 409, CANTON, MA, 02021

Want to learn more about 55+ communities in Middletown? 55places can help!

Questions? Call us: (401) 313-4589

Cindy Certified

180 U:202 OLD POST RD 202, SHARON, MA, 0..., Sharon, MA 02067

$887,900

2 beds

3 baths

1,431 sq ft

Condo

180 U:202 OLD POST RD 202, SHARON, MA, 0...

Cindy Certified

134 COURT ST 2, PLYMOUTH, MA, 02360, Plymouth, MA 02360

$999,000

2 beds

2 baths

1,744 sq ft

Condo

134 COURT ST 2, PLYMOUTH, MA, 02360

Frequently Asked Questions

What size 55+ communities are there in Middletown?

In Middletown, there are no large communities, no medium communities, and 2 small communities with less than 500 homes.

How many homes are there in the smallest, largest, and average 55+ communities in Middletown?

The smallest 55+ communities in Middletown has 36 homes, the largest has 60 homes, and the average communities consists of 48 homes.

Are there gated 55+ communities in Middletown?

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?

Global - Lead Form - Buyer or Renter

First Name

Last Name

Phone/Mobile

Text

I'm looking to:

Rent

Buy

*55places does not provide or maintain community HOA information.

Yes, I want to subscribe to email updates from 55places.com, including newsletters, community announcements, and more.

I agree to receive SMS messages to connect me with a local expert.

By requesting more information, you agree that 55places may call, text, or email you about your inquiry, which may be made with automated means (including recorded voice messages, SMS, or text messages). You understand that your consent is not a prerequisite for buying, selling or renting a property. You may revoke your consent at any time by contacting optout@55places.com. Message/data rates may apply. You also agree to 55places.com’s Privacy Policy and Terms of Use.

55+ communities in Tiverton

Want to learn more about 55+ communities in Middletown?

Call us: (401) 313-4589

81 communities

Remove Boundaries ×

Map Satellite

The listings data displayed on this medium comes in part from the Real Estate Information Network Inc. (REIN) and has been authorized by participating listing Broker Members of REIN for display. REIN's listings are based upon Data submitted by its Broker Members, and REIN therefore makes no representation or warranty regarding the accuracy of the Data. All users of REIN's listings database should confirm the accuracy of the listing information directly with the listing agent.
© 2026 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: Aug 29, 2026.
This application does not include information on all of the properties available for sale at this time.

Call Us Call Us

Middletown, RI 55+ active adult communities & homes for sale

81 communities near Middletown

112 homes near Middletown

2 beds

3 baths

1,968 sq ft

Condo

2 beds

3 baths

1,421 sq ft

Condo

2 beds

3 baths

1,440 sq ft

Condo

3 beds

4 baths

3,703 sq ft

Condo

2 beds

2 baths

1,582 sq ft

Condo

2 beds

3 baths

2,370 sq ft

Condo

2 beds

3 baths

2,321 sq ft

Condo

2 beds

2 baths

1,333 sq ft

Condo

2 beds

2 baths

1,084 sq ft

Condo

2 beds

2 baths

1,614 sq ft

Condo

2 beds

2 baths

1,056 sq ft

Condo

1 beds

2 baths

1,056 sq ft

Condo

2 beds

2 baths

1,187 sq ft

Condo

2 beds

3 baths

2,360 sq ft

Condo

2 beds

2 baths

1,496 sq ft

Condo

1 beds

2 baths

1,058 sq ft

Condo

1 beds

2 baths

958 sq ft

Condo

2 beds

2 baths

1,786 sq ft

Condo

3 beds

2 baths

1,416 sq ft

House

2 beds