Middletown, RI 55+ active adult communities & homes for sale - Page 2

80 communities near Middletown

Sort by:

Relevance

59 North Main

$900ks

59 North Main, Sherborn, MA

New Construction | 55+ age-restricted | Built 2019 - present | 12 homes

The Cottages at Lebaron H...

$500ks - $600ks

The Cottages at Lebaron H..., Lakeville, MA

New Construction | 55+ age-restricted | Built 2019 - present | 32 homes

Pennington Crossing

$300ks - $600ks

Pennington Crossing, Walpole, MA

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

Upton Ridge

$400ks - $600ks

Upton Ridge, Upton, MA

New Construction | 55+ age-restricted | Built 2019 - present | 139 homes

The Lanterns at Warren Wo...

$500ks - $700ks

The Lanterns at Warren Wo..., Ashland, MA

Resale Only | 55+ age-restricted | Built 2016 - 2020 | 93 homes

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

Questions? Call us: (401) 313-4589

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

Questions? Call us: (401) 313-4589

Millwood Preserve

$700ks - $800ks

Millwood Preserve, Framingham, MA

New Construction | 55+ age-restricted | Built 2020 - present | 129 homes

Brookside Village

$700ks

Brookside Village, Walpole, MA

Resale Only | 55+ age-restricted | Built 2018 - 2018 | 30 homes

Wolcott Woods

$1Ms

Wolcott Woods, Milton, MA

New Construction | 55+ age-restricted | Built 2020 - present | 54 homes

Enclave at Hudson

$800ks - $1Ms

Enclave at Hudson, Hudson, MA

New Construction | 55+ age-restricted | Built 2021 - present | 64 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.

Liberty Woods

$600ks - $700ks

Liberty Woods, Hanson, MA

New Construction | 55+ age-restricted | Built 2023 - present | 56 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.

Village at Silver Hill

$1Ms - $2Ms

Village at Silver Hill, Weston, MA

New Construction | 55+ age-restricted | Built 2021 - present | 8 homes

The Villages on Mount Hop...

$600ks - $1Ms

The Villages on Mount Hop..., Tiverton, RI

New and Resale | 55+ age-restricted | Built 2003 - present | 230 homes

Bay Ridge

$600ks - $800ks

Bay Ridge, Middletown, RI

Resale Only | 55+ age-restricted | Built 2008 - 2014 | 60 homes

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

Questions? Call us: (401) 313-4589

Wakefield Meadows

$700ks - $800ks

Wakefield Meadows, Wakefield, RI

Resale Only | 55+ age-restricted | Built 2009 - 2015 | 142 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

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

Questions? Call us: (401) 313-4589

Bella Vista

$300ks - $400ks

Bella Vista, Glocester, RI

Resale Only | 55+ age-restricted | Built 2015 - 2021 | 70 homes

Brookedge Village Condomi...

$300ks - $400ks

Brookedge Village Condomi..., South Kingstown, RI

Resale Only | 55+ age-restricted | Built 2007 - 2007 | 28 homes

Brandywyne

$700ks - $800ks

Brandywyne, South Kingstown, RI

Resale Only | 55+ age-restricted | Built 2011 - 2013 | 37 homes

Southwinds

$600ks - $700ks

Southwinds, South Kingstown, RI

Resale Only | 55+ age-restricted | Built 2005 - 2010 | 70 homes

Bailey Brook

$600ks - $700ks

Bailey Brook, Middletown, RI

Resale Only | 55+ age-restricted | Built 2018 - 2024 | 36 homes

WestRidge

$700ks

WestRidge, Hudson, MA

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

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

Questions? Call us: (401) 313-4589

Angell Brook Village

$300ks

Angell Brook Village, West Boylston, MA

Resale Only | 55+ age-restricted | Built 2005 - 2012 | 132 homes

Pheasant Hill

$300ks - $400ks

Pheasant Hill, Northborough, MA

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

Stonebridge Commons

$500ks

Stonebridge Commons, Hanson, MA

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

Red Mill Village

$400ks - $600ks

Red Mill Village, Norton, MA

Resale Only | 55+ age-restricted | Built 2012 - 2014 | 156 homes

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

Questions? Call us: (401) 313-4589

The Village at Westminste...

$400ks - $500ks

The Village at Westminste..., Holden, MA

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

New England Commons

$200ks - $300ks

New England Commons, Webster, MA

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

Blue Heron Pond

$500ks

Blue Heron Pond, Lancaster, MA

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

Adams Farm

$700ks - $800ks

Adams Farm, Shrewsbury, MA

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

Westbrook Crossing

$400ks - $500ks

Westbrook Crossing, Dedham, MA

Resale Only | 55+ age-restricted | Built 2003 - 2004 | 60 homes

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

Questions? Call us: (401) 313-4589

Villages at Weathervane

$800ks - $1Ms

Villages at Weathervane, Weymouth, MA

Resale Only | 55+ age-restricted | Built 2003 - 2010 | 149 homes

Woodstone Crossing

$300ks - $400ks

Woodstone Crossing, Weymouth, MA

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

Holliston Woods

$500ks - $700ks

Holliston Woods, Holliston, MA

Resale Only | 55+ age-restricted | Built 2016 - 2018 | 66 homes

Summer Reach

$400ks - $500ks

Summer Reach, Plymouth, MA

Resale Only | 55+ age-restricted | Built 2017 - 2020 | 114 homes

The Villages at Crane Mea...

$400ks

The Villages at Crane Mea..., Marlborough, MA

Resale Only | 55+ age-restricted | Built 2001 - 2005 | 91 homes

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

Questions? Call us: (401) 313-4589

The Village at Auburnvill...

$300ks - $400ks

The Village at Auburnvill..., Whitman, MA

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

The Seasons at Salisbury

$400ks - $500ks

The Seasons at Salisbury, Holden, MA

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

Duxbury Estates

$700ks - $800ks

Duxbury Estates, Duxbury, MA

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

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

Questions? Call us: (401) 313-4589

Peregrine Woods

$400ks - $600ks

Peregrine Woods, Marshfield, MA

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

Tara Woods

$400ks

Tara Woods, Plymouth, MA

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

40 ADAMS FARM RD 40, SHREWSBURY, MA, 015...

Community: Adams Farm

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

Condo

30 COPPERSMITH WAY # 309, CANTON, MA, 02...

Community: 30 Coppersmith

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

Questions? Call us: (401) 313-4589

Brierly Pond Village

100 HORNE WAY # 100, MILLBURY, MA, 01527, Millbury, MA 01527

$509,900

2 beds

3 baths

2,021 sq ft

Condo

100 HORNE WAY # 100, MILLBURY, MA, 01527

Community: Brierly Pond Village

30 Coppersmith

$865,915

2 beds

2 baths

1,582 sq ft

Condo

30 COPPERSMITH WAY 506, CANTON, MA, 0202...

Condo

153 LEISURE GREEN DR # 749, MASHPEE, MA,...

Condo

5 WESSONVILLE VILLAGE WAY 5, WESTBOROUGH...

Community: The Villages at Walker Meadow

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

Questions? Call us: (401) 313-4589

Del Webb Chauncy Lake

1102 PETERS FARM WAY # 1102, WESTBOROUGH..., Westborough, MA 01581

$419,900

1 beds

1 baths

956 sq ft

Condo

1102 PETERS FARM WAY # 1102, WESTBOROUGH...

Community: Del Webb Chauncy Lake

Del Webb Chauncy Lake

5 PETERS FARM WAY 103, WESTBOROUGH, MA, ..., Westborough, MA 01581

$440,485

1 beds

1 baths

972 sq ft

Condo

5 PETERS FARM WAY 103, WESTBOROUGH, MA, ...

Community: Del Webb Chauncy Lake

The Elms of Hanover

18 WINTERBERRY LN # 18, HANOVER, MA, 023..., Hanover, MA 02339

$785,000

2 beds

3 baths

2,258 sq ft

Condo

18 WINTERBERRY LN # 18, HANOVER, MA, 023...

Community: The Elms of Hanover

Harmony Place

20 FIDELITY DR # 10, RUTLAND, MA, 01543, Rutland, MA 01543

$498,000

2 beds

2 baths

1,582 sq ft

Condo

20 FIDELITY DR # 10, RUTLAND, MA, 01543

Community: Harmony Place

Lake Point Village

57 LONG POINT RD 208, LAKEVILLE, MA, 023..., Lakeville, MA 02347

$509,900

2 beds

2 baths

1,453 sq ft

Condo

57 LONG POINT RD 208, LAKEVILLE, MA, 023...

Community: Lake Point Village

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

Questions? Call us: (401) 313-4589

Lake Point Village

57 LONG POINT RD UNIT 104, LAKEVILLE, MA..., Lakeville, MA 02347

$589,000

2 beds

2 baths

1,334 sq ft

Condo

57 LONG POINT RD UNIT 104, LAKEVILLE, MA...

Community: Lake Point Village

Regency at Assabet Ridge

28 BOWOOD LN # 28, MARLBOROUGH, MA, 0175..., Marlborough, MA 01752

$759,900

3 beds

3 baths

2,205 sq ft

Condo

28 BOWOOD LN # 28, MARLBOROUGH, MA, 0175...

Community: Regency at Assabet Ridge

Southport

18 WINDWARD ST # 18, MASHPEE, MA, 02649, Mashpee, MA 02649

$479,900

2 beds

2 baths

1,333 sq ft

Condo

18 WINDWARD ST # 18, MASHPEE, MA, 02649

Community: Southport

Harmony Place

18 FIDELITY DR # 9, RUTLAND, MA, 01543, Rutland, MA 01543

$498,000

2 beds

2 baths

1,582 sq ft

Condo

18 FIDELITY DR # 9, RUTLAND, MA, 01543

Community: Harmony Place

Seton Highlands at The Pinehills

17 ABERDEEN # 17, PLYMOUTH, MA, 02360, Plymouth, MA 02360

$949,000

3 beds

3 baths

2,690 sq ft

Condo

17 ABERDEEN # 17, PLYMOUTH, MA, 02360

Community: Seton Highlands at The Pinehills

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

Questions? Call us: (401) 313-4589

Sawyer's Reach

62 MARINERS WAY UNIT 305, PLYMOUTH, MA, ..., Plymouth, MA 02360

$499,900

1 beds

1 baths

804 sq ft

Condo

62 MARINERS WAY UNIT 305, PLYMOUTH, MA, ...

Community: Sawyer's Reach

Harmony Place

10 FIDELITY DR # 5, RUTLAND, MA, 01543, Rutland, MA 01543

$498,000

2 beds

2 baths

1,582 sq ft

Condo

10 FIDELITY DR # 5, RUTLAND, MA, 01543

Community: Harmony Place

Del Webb Chauncy Lake

2 CODMAN WAY 408, WESTBOROUGH, MA, 01581, Westborough, MA 01581

$589,999

2 beds

2 baths

1,375 sq ft

Condo

2 CODMAN WAY 408, WESTBOROUGH, MA, 01581

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

5 PETERS FARM WAY 5205, WESTBOROUGH, MA,..., Westborough, MA 01581

$576,025

2 beds

2 baths

1,166 sq ft

Condo

5 PETERS FARM WAY 5205, WESTBOROUGH, MA,...

Community: Del Webb Chauncy Lake

Del Webb Chauncy Lake

4203 PETERS FARM WAY # 4203, WESTBOROUGH..., Westborough, MA 01581

$470,000

1 beds

1 baths

945 sq ft

Condo

4203 PETERS FARM WAY # 4203, WESTBOROUGH...

Community: Del Webb Chauncy Lake

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 [email protected]. 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

80 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: Feb 21, 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 - Page 2

80 communities near Middletown

68 homes near Middletown

2 beds

3 baths

2,392 sq ft

Condo

1 beds

2 baths

1,113 sq ft

Condo

2 beds

3 baths

2,671 sq ft

Condo

2 beds

2 baths

1,512 sq ft

Condo

2 beds

3 baths

2,757 sq ft

Condo

2 beds

3 baths

2,144 sq ft

Condo

2 beds

2 baths

1,496 sq ft

Condo

2 beds

2 baths

1,496 sq ft

Condo

2 beds

2 baths

1,370 sq ft

Condo

2 beds

3 baths

4,054 sq ft

Condo

2 beds

2 baths

1,469 sq ft

Condo

2 beds

3 baths

1,659 sq ft

Condo

1 beds

1 baths

1,119 sq ft

Condo

2 beds

3 baths

2,021 sq ft

Condo

2 beds

2 baths

1,582 sq ft

Condo

1 beds

1 baths

1,030 sq ft

Condo

2 beds

2 baths

1,525 sq ft

Condo

2 beds

3 baths

1,871 sq ft

Condo

2 beds

4 baths

2,100 sq ft

Condo

2 beds