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

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

Southport

$400ks - $600ks

Southport, Mashpee, MA

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

Harmony Place

$400ks - $500ks

Harmony Place, Rutland, MA

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

30 Coppersmith

$700ks

30 Coppersmith, Canton, MA

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

Regency at Glen Ellen

$700ks - $900ks

Regency at Glen Ellen, Millis, MA

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

Great Island

$600ks

Great Island, Plymouth, MA

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

The Trails

$500ks - $700ks

The Trails, Hopkinton, MA

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

Sawyer's Reach

$400ks - $900ks

Sawyer's Reach, Plymouth, MA

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

The Village at Auburnvill...

$300ks - $400ks

The Village at Auburnvill..., Whitman, MA

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

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

Questions? Call us: (401) 313-4589

Summer Reach

$400ks - $500ks

Summer Reach, Plymouth, MA

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

Regency at Assabet Ridge

$500ks - $600ks

Regency at Assabet Ridge, Marlborough, MA

Resale Only | 55+ age-restricted | Built 2010 - 2015 | 69 homes

Want to learn more about 55+ rental 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

Westbrook Crossing

$400ks - $500ks

Westbrook Crossing, Dedham, MA

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

Brooksmont

$400ks - $600ks

Brooksmont, Holliston, MA

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

Millwood Preserve

$700ks - $800ks

Millwood Preserve, Framingham, MA

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

Lake Point Village

$400ks - $600ks

Lake Point Village, Lakeville, MA

New Construction | 55+ age-restricted | Built 2020 - present | 66 homes

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

Questions? Call us: (401) 313-4589

Brierly Pond Village

$300ks - $400ks

Brierly Pond Village, Millbury, MA

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

Northwoods at Sudbury

$500ks

Northwoods at Sudbury, Sudbury, MA

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

Wyman Farms

$500ks - $900ks

Wyman Farms, Shrewsbury, MA

New Construction | 55+ age-restricted | Built 2017 - present | 26 homes

Cranberry Grove

$200ks - $300ks

Cranberry Grove, Wareham, MA

Resale Only | 55+ age-restricted | Built 2001 - 2001 | 36 homes

Want to learn more about 55+ rental 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

Forest Glen

$400ks - $500ks

Forest Glen, Uxbridge, MA

New Construction | 55+ age-restricted | Built 2018 - present | 44 homes

Pennington Crossing

$300ks - $600ks

Pennington Crossing, Walpole, MA

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

The Villages at Crane Mea...

$400ks

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

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

Pheasant Hill

$300ks - $400ks

Pheasant Hill, Northborough, MA

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

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

Questions? Call us: (401) 313-4589

Holliston Woods

$500ks - $700ks

Holliston Woods, Holliston, MA

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

Angell Brook Village

$300ks

Angell Brook Village, West Boylston, MA

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

Brandywyne

$700ks - $800ks

Brandywyne, South Kingstown, RI

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

Woodstone Crossing

$300ks - $400ks

Woodstone Crossing, Weymouth, MA

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

Adams Farm

$700ks - $800ks

Adams Farm, Shrewsbury, MA

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

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

Questions? Call us: (401) 313-4589

WestRidge

$700ks

WestRidge, Hudson, MA

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

Brookedge Village Condomi...

$300ks - $400ks

Brookedge Village Condomi..., South Kingstown, RI

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

Wakefield Meadows

$700ks - $800ks

Wakefield Meadows, Wakefield, RI

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

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

Questions? Call us: (401) 313-4589

Blue Heron Pond

$500ks

Blue Heron Pond, Lancaster, MA

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

New England Commons

$200ks - $300ks

New England Commons, Webster, MA

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

43 SANDTRAP CIR 43, WEYMOUTH, MA, 02190

Community: Villages at Weathervane

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

New Seton Highlands at The Pinehills

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

$929,000

3 beds

3 baths

2,690 sq ft

Condo

17 ABERDEEN 17, PLYMOUTH, MA, 02360

Community: Seton Highlands at The Pinehills

New Millwood Preserve

11 BAITING BROOK RD 11, FRAMINGHAM, MA, ..., Framingham, MA 01701

$1,275,000

3 beds

3 baths

2,559 sq ft

Condo

11 BAITING BROOK RD 11, FRAMINGHAM, MA, ...

Community: Millwood Preserve

New Pennington Crossing

2301 PENNINGTON DR 2301, WALPOLE, MA, 02..., Walpole, MA 02081

$715,000

2 beds

2 baths

1,490 sq ft

Condo

2301 PENNINGTON DR 2301, WALPOLE, MA, 02...

Community: Pennington Crossing

New Oak Point

3705 PHEASANT LN, MIDDLEBORO, MA, 02346, Middleboro, MA 02346

$425,000

2 beds

2 baths

1,736 sq ft

Mobile Home

3705 PHEASANT LN, MIDDLEBORO, MA, 02346

Community: Oak Point

New Seton Highlands at The Pinehills

73 SETON HIGHLANDS 73, PLYMOUTH, MA, 023..., Plymouth, MA 02360

$825,000

2 beds

4 baths

3,074 sq ft

Condo

73 SETON HIGHLANDS 73, PLYMOUTH, MA, 023...

Community: Seton Highlands at The Pinehills

New Wyman Farms

935 MAIN ST 23, SHREWSBURY, MA, 01545, Shrewsbury, MA 01545

$945,000

2 beds

3 baths

2,435 sq ft

Condo

935 MAIN ST 23, SHREWSBURY, MA, 01545

Community: Wyman Farms

New Great Island

29 FOX HOLW, PLYMOUTH, MA, 02360, Plymouth, MA 02360

$705,000

2 beds

2 baths

2,439 sq ft

House

29 FOX HOLW, PLYMOUTH, MA, 02360

Community: Great Island

New Oak Point

2602 GREEN ST, MIDDLEBORO, MA, 02346, Middleboro, MA 02346

$349,900

2 beds

2 baths

1,680 sq ft

House

2602 GREEN ST, MIDDLEBORO, MA, 02346

Community: Oak Point

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

Questions? Call us: (401) 313-4589

New Summer Reach

14 FOUNDERS WAY 14, PLYMOUTH, MA, 02360, Plymouth, MA 02360

$875,000

3 beds

3 baths

2,181 sq ft

Condo

14 FOUNDERS WAY 14, PLYMOUTH, MA, 02360

Community: Summer Reach

The Village at Auburnville

877 AUBURNVILLE WAY M2, WHITMAN, MA, 023..., Whitman, MA 02382

$524,900

2 beds

2 baths

2,090 sq ft

Condo

877 AUBURNVILLE WAY M2, WHITMAN, MA, 023...

Community: The Village at Auburnville

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

Questions? Call us: (401) 313-4589

Del Webb Chauncy Lake

5 PETERS FARM WAY 312, WESTBOROUGH, MA, ..., Westborough, MA 01581

$724,995

2 beds

2 baths

1,512 sq ft

Condo

5 PETERS FARM WAY 312, WESTBOROUGH, MA, ...

Community: Del Webb Chauncy Lake

Del Webb Chauncy Lake

5 PETERS FARM WAY 109, WESTBOROUGH, MA, ..., Westborough, MA 01581

$474,995

1 beds

1 baths

1,030 sq ft

Condo

5 PETERS FARM WAY 109, WESTBOROUGH, MA, ...

Community: Del Webb Chauncy Lake

Del Webb Chauncy Lake

4403 PETERS FARM WAY 4403, WESTBOROUGH, ..., Westborough, MA 01581

$415,000

1 beds

1 baths

956 sq ft

Condo

4403 PETERS FARM WAY 4403, WESTBOROUGH, ...

Community: Del Webb Chauncy Lake

Angell Brook Village

44 ANGELL BROOK DR 44, WEST BOYLSTON, MA..., West Boylston, MA 01583

$479,000

2 beds

2 baths

1,274 sq ft

Condo

44 ANGELL BROOK DR 44, WEST BOYLSTON, MA...

Community: Angell Brook Village

The Village at Westminster Place

53 TEA PARTY CIR 53, HOLDEN, MA, 01520, Holden, MA 01520

$539,000

2 beds

2 baths

1,258 sq ft

Condo

53 TEA PARTY CIR 53, HOLDEN, MA, 01520

Community: The Village at Westminster Place

Del Webb Chauncy Lake

12308 PETERS FARM WAY 308, WESTBOROUGH, ..., Westborough, MA 01581

$549,900

2 beds

2 baths

1,326 sq ft

Condo

12308 PETERS FARM WAY 308, WESTBOROUGH, ...

Community: Del Webb Chauncy Lake

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

Questions? Call us: (401) 313-4589

Southport

13 PGA LN 424, MASHPEE, MA, 02649, Mashpee, MA 02649

$479,000

2 beds

2 baths

1,338 sq ft

Condo

13 PGA LN 424, MASHPEE, MA, 02649

Community: Southport

Southport

72 PINE HILL BLVD 72, MASHPEE, MA, 02649, Mashpee, MA 02649

$479,900

2 beds

2 baths

1,338 sq ft

House

72 PINE HILL BLVD 72, MASHPEE, MA, 02649

Community: Southport

Orchard Hill

9 BALDWIN CT 9, WESTBOROUGH, MA, 01581, Westborough, MA 01581

$645,000

3 beds

3 baths

2,793 sq ft

Condo

9 BALDWIN CT 9, WESTBOROUGH, MA, 01581

Community: Orchard Hill

Regency at Assabet Ridge

13 WILSHIRE WAY 13, MARLBOROUGH, MA, 017..., Marlborough, MA 01752

$689,000

2 beds

2 baths

1,584 sq ft

Condo

13 WILSHIRE WAY 13, MARLBOROUGH, MA, 017...

Community: Regency at Assabet Ridge

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

Questions? Call us: (401) 313-4589

Cranberry Grove

$419,900

2 beds

2 baths

1,350 sq ft

Condo

3 CRANBERRY GROVE WAY C, WAREHAM, MA, 02...

Community: Cranberry Grove

Del Webb Chauncy Lake

5 PETERS FARM WAY 309, WESTBOROUGH, MA, ..., Westborough, MA 01581

$599,999

2 beds

2 baths

1,375 sq ft

Condo

5 PETERS FARM WAY 309, WESTBOROUGH, MA, ...

Community: Del Webb Chauncy Lake

Del Webb Chauncy Lake

5 PETERS FARM WAY 104, WESTBOROUGH, MA, ..., Westborough, MA 01581

$414,995

1 beds

1 baths

972 sq ft

Condo

5 PETERS FARM WAY 104, WESTBOROUGH, MA, ...

Community: Del Webb Chauncy Lake

Great Island

22 PICKET FENCE, PLYMOUTH, MA, 02360, Plymouth, MA 02360

$949,000

3 beds

3 baths

4,085 sq ft

House

22 PICKET FENCE, PLYMOUTH, MA, 02360

Community: Great Island

The Trails

28 WATERVILLE LN 28, HOPKINTON, MA, 0174..., Hopkinton, MA 01748

$1,069,000

2 beds

3 baths

2,510 sq ft

Condo

28 WATERVILLE LN 28, HOPKINTON, MA, 0174...

Community: The Trails

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

Questions? Call us: (401) 313-4589

30 Coppersmith

$475,995

1 beds

1 baths

1,129 sq ft

Condo

30 COPPERSMITH WAY 108, CANTON, MA, 0202...

Community: 30 Coppersmith

Southport

12 KETTLE LN 31, MASHPEE, MA, 02649, Mashpee, MA 02649

$475,000

2 beds

2 baths

1,606 sq ft

Condo

12 KETTLE LN 31, MASHPEE, MA, 02649

Community: Southport

Regency at Glen Ellen

86 GLEN ELLEN BLVD 86, MILLIS, MA, 02054, Millis, MA 02054

$1,249,900

3 beds

3 baths

3,060 sq ft

Condo

86 GLEN ELLEN BLVD 86, MILLIS, MA, 02054

Community: Regency at Glen Ellen

Balancing Rock

20 GLACIER WAY 20, HOLLISTON, MA, 01746, Holliston, MA 01746

$685,000

2 beds

3 baths

2,084 sq ft

Condo

20 GLACIER WAY 20, HOLLISTON, MA, 01746

Community: Balancing Rock

Del Webb Chauncy Lake

1105 PETERS FARM WAY 105, WESTBOROUGH, M..., Westborough, MA 01581

$389,900

1 beds

1 baths

945 sq ft

Condo

1105 PETERS FARM WAY 105, WESTBOROUGH, M...

Community: Del Webb Chauncy Lake

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

Questions? Call us: (401) 313-4589

Westbrook Crossing

989 E ST 402, DEDHAM, MA, 02026, Dedham, MA 02026

$499,900

1 beds

1 baths

882 sq ft

Condo

989 E ST 402, DEDHAM, MA, 02026

Community: Westbrook Crossing

Regency at Glen Ellen

8 GLEN ELLEN BLVD 8, MILLIS, MA, 02054, Millis, MA 02054

$1,449,000

2 beds

4 baths

4,247 sq ft

Condo

8 GLEN ELLEN BLVD 8, MILLIS, MA, 02054

Community: Regency at Glen Ellen

Southport

94 PINE HL 94, MASHPEE, MA, 02649, Mashpee, MA 02649

$525,000

2 beds

3 baths

1,685 sq ft

Condo

94 PINE HL 94, MASHPEE, MA, 02649

Community: Southport

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 305, WESTBOROUGH, MA, ..., Westborough, MA 01581

$579,999

2 beds

2 baths

1,175 sq ft

Condo

5 PETERS FARM WAY 305, WESTBOROUGH, MA, ...

Community: Del Webb Chauncy Lake

Woodcrest Run

635 OLD POST RD 210, SHARON, MA, 02067, Sharon, MA 02067

$499,900

2 beds

2 baths

1,056 sq ft

Condo

635 OLD POST RD 210, SHARON, MA, 02067

Community: Woodcrest Run

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

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: Apr 11, 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

88 homes near Middletown

1 beds

2 baths

1,616 sq ft

Condo

2 beds

2 baths

1,469 sq ft

Condo

2 beds

2 baths

1,056 sq ft

Condo

2 beds

3 baths

2,029 sq ft

Condo

2 beds

2 baths

1,795 sq ft

Condo

3 beds

3 baths

2,690 sq ft

Condo

3 beds

3 baths

2,559 sq ft

Condo

2 beds

2 baths

1,490 sq ft

Condo

2 beds

2 baths

1,736 sq ft

Mobile Home

2 beds

4 baths

3,074 sq ft

Condo

2 beds

3 baths

2,435 sq ft

Condo

2 beds

2 baths

2,439 sq ft

House

2 beds

2 baths

1,680 sq ft

House

3 beds

3 baths

2,181 sq ft

Condo

2 beds

2 baths

2,090 sq ft

Condo

2 beds

2 baths

1,512 sq ft

Condo

1 beds

1 baths

1,030 sq ft

Condo

1 beds

1 baths

956 sq ft

Condo

2 beds

2 baths

1,274 sq ft

Condo

2 beds