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

81 communities near Middletown

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Great Island

$600ks

Great Island, Plymouth, MA

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

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

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

Upton Ridge

$400ks - $600ks

Upton Ridge, Upton, MA

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

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

Questions? Call us: (401) 313-4589

Harmony Place

$400ks - $500ks

Harmony Place, Rutland, MA

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

Sawyer's Reach

$400ks - $900ks

Sawyer's Reach, Plymouth, MA

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

30 Coppersmith

$700ks

30 Coppersmith, Canton, MA

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

5 rating (3 reviews)

Oak Point

$300ks - $400ks

Oak Point, Middleborough, MA

New and Resale | 55+ age-restricted | Built 1999 - present | 1,150 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.

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

Woodstone Crossing

$300ks - $400ks

Woodstone Crossing, Weymouth, MA

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

The Village at Auburnvill...

$300ks - $400ks

The Village at Auburnvill..., Whitman, MA

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

Orchard Hill

$500ks

Orchard Hill, Westborough, MA

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

Want to learn more about 55+ 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

Brierly Pond Village

$300ks - $400ks

Brierly Pond Village, Millbury, MA

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

Woodcrest Run

$400ks - $600ks

Woodcrest Run, Sharon, MA

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

The Villages at Walker Me...

$600ks - $700ks

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

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

Westbrook Crossing

$400ks - $500ks

Westbrook Crossing, Dedham, MA

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

Enclave at Hudson

$800ks - $1Ms

Enclave at Hudson, Hudson, MA

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

Bates Quarry

Bates Quarry, Walpole, MA

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

Angell Brook Village

$300ks

Angell Brook Village, West Boylston, MA

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

The Seasons at Salisbury

$400ks - $500ks

The Seasons at Salisbury, Holden, MA

Resale Only | 55+ age-restricted | Built 2002 - 2006 | 91 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+ communities in Middletown? 55places can help!

Questions? Call us: (401) 313-4589

Bigelow Farm

$500ks - $600ks

Bigelow Farm, Northborough, MA

Resale Only | 55+ age-restricted | Built 2006 - 2013 | 41 homes

Rockland Glen

$300ks - $500ks

Rockland Glen, Rockland, MA

Resale Only | 55+ age-restricted | Built 2008 - 2015 | 60 homes

Northwoods at Sudbury

$500ks

Northwoods at Sudbury, Sudbury, MA

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

Brooksmont

$400ks - $600ks

Brooksmont, Holliston, MA

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

Villages at Weathervane

$800ks - $1Ms

Villages at Weathervane, Weymouth, MA

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

Adams Farm

$700ks - $800ks

Adams Farm, Shrewsbury, MA

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

Blue Heron Pond

$500ks

Blue Heron Pond, Lancaster, MA

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

Hawthorn Preserve

$900ks - $1Ms

Hawthorn Preserve, Braintree, MA

New Construction | 55+ age-restricted | Built 2025 - present | 51 homes

New England Commons

$200ks - $300ks

New England Commons, Webster, MA

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

The Village at Westminste...

$400ks - $500ks

The Village at Westminste..., Holden, MA

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

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

Questions? Call us: (401) 313-4589

Bailey Brook

$600ks - $700ks

Bailey Brook, Middletown, RI

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

Wakefield Meadows

$700ks - $800ks

Wakefield Meadows, Wakefield, RI

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

1 2...3

New Great Island

25 CANOE LNDG, PLYMOUTH, MA, 02360, Plymouth, MA 02360

$850,000

2 beds

3 baths

2,306 sq ft

House

25 CANOE LNDG, PLYMOUTH, MA, 02360

Community: Great Island

New Oak Point

5006 OAK POINT DR, MIDDLEBORO, MA, 02346, Middleboro, MA 02346

$434,000

3 beds

2 baths

1,568 sq ft

House

5006 OAK POINT DR, MIDDLEBORO, MA, 02346

Community: Oak Point

New Oak Point

602 WAVERLY RD, MIDDLEBORO, MA, 02346, Middleboro, MA 02346

$449,000

3 beds

2 baths

1,462 sq ft

House

602 WAVERLY RD, MIDDLEBORO, MA, 02346

Community: Oak Point

New Del Webb Chauncy Lake

12101 PETERS FARM WAY 12101, WESTBOROUGH..., Westborough, MA 01712

$574,444

2 beds

2 baths

1,459 sq ft

Condo

12101 PETERS FARM WAY 12101, WESTBOROUGH...

Community: Del Webb Chauncy Lake

New The Villages at Walker Meadow

4 WESSONVILLE VILLAGE WAY 4, WESTBOROUGH..., Westborough, MA 01581

$750,000

2 beds

2 baths

2,090 sq ft

Condo

4 WESSONVILLE VILLAGE WAY 4, WESTBOROUGH...

Community: The Villages at Walker Meadow

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

Questions? Call us: (401) 313-4589

New 30 Coppersmith

30 COPPERSMITH WAY 502, CANTON, MA, 0202..., Canton, MA 02021

$544,995

1 beds

1 baths

1,027 sq ft

Condo

30 COPPERSMITH WAY 502, CANTON, MA, 0202...

Community: 30 Coppersmith

New 30 Coppersmith

30 COPPERSMITH WAY 306, CANTON, MA, 0202..., Canton, MA 02021

$689,995

2 beds

2 baths

1,582 sq ft

Condo

30 COPPERSMITH WAY 306, CANTON, MA, 0202...

Community: 30 Coppersmith

New

Cindy Certified

150 LIZOTTE DR 311, MARLBOROUGH, MA, 017..., Marlborough, MA 01752

$503,305

2 beds

3 baths

1,425 sq ft

Condo

150 LIZOTTE DR 311, MARLBOROUGH, MA, 017...

New Del Webb Chauncy Lake

11 PETERS FARM WAY 310, WESTBOROUGH, MA,..., Westborough, MA 01581

$499,900

2 beds

2 baths

1,326 sq ft

Condo

11 PETERS FARM WAY 310, WESTBOROUGH, MA,...

Community: Del Webb Chauncy Lake

New

Cindy Certified

6 MUIRFIELD 6, PLYMOUTH, MA, 02360, Plymouth, MA 02360

$869,000

3 baths

1,582 sq ft

Condo

150 LIZOTTE DR 312, MARLBOROUGH, MA, 017...

Red Mill Village

30 CODDING RD 30, NORTON, MA, 02766, Norton, MA 02766

$925,000

3 beds

3 baths

2,387 sq ft

Condo

30 CODDING RD 30, NORTON, MA, 02766

Community: Red Mill Village

Condo

19 IMPERIAL CT 19, WESTBOROUGH, MA, 0158...

Community: Orchard Hill

Oak Point

5111 PHEASANT, MIDDLEBORO, MA, 02346, Middleboro, MA 02346

$459,900

2 beds

2 baths

1,674 sq ft

House

5111 PHEASANT, MIDDLEBORO, MA, 02346

Community: Oak Point

Woodstone Crossing

70 TROTTER RD 203, WEYMOUTH, MA, 02190, Weymouth, MA 02190

$445,000

1 beds

1 baths

955 sq ft

Condo

70 TROTTER RD 203, WEYMOUTH, MA, 02190

Community: Woodstone Crossing

Great Island

37 WEATHERVANE, PLYMOUTH, MA, 02360, Plymouth, MA 02360

$725,000

2 beds

2 baths

1,548 sq ft

House

37 WEATHERVANE, PLYMOUTH, MA, 02360

Community: Great Island

Great Island

26 CROSS WIND, PLYMOUTH, MA, 02360, Plymouth, MA 02360

$800,000

2 beds

3 baths

2,382 sq ft

House

26 CROSS WIND, PLYMOUTH, MA, 02360

Community: Great Island

Del Webb Chauncy Lake

4206 PETERS FARM WAY 206, WESTBOROUGH, M..., Westborough, MA 01581

$539,000

2 beds

2 baths

1,469 sq ft

Condo

4206 PETERS FARM WAY 206, WESTBOROUGH, M...

Community: Del Webb Chauncy Lake

Cindy Certified

150 LIZOTTE DR 201, MARLBOROUGH, MA, 017..., Marlborough, MA 01752

$516,995

2 beds

3 baths

1,582 sq ft

Condo

150 LIZOTTE DR 201, MARLBOROUGH, MA, 017...

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

Questions? Call us: (401) 313-4589

Great Island

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

$900,000

3 beds

4 baths

4,085 sq ft

House

22 PICKET FENCE, PLYMOUTH, MA, 02360

Community: Great Island

Del Webb Chauncy Lake

8 PETERS FARM WAY 307, WESTBOROUGH, MA, ..., Westborough, MA 01581

$663,995

2 beds

2 baths

1,512 sq ft

Condo

8 PETERS FARM WAY 307, WESTBOROUGH, MA, ...

Community: Del Webb Chauncy Lake

Southport

10 CHIPPERS LN 10, MASHPEE, MA, 02649, Mashpee, MA 02649

$625,000

2 beds

3 baths

2,007 sq ft

Condo

10 CHIPPERS LN 10, MASHPEE, MA, 02649

Community: Southport

Orchard Hill

5 GILMORE FARM RD 5, WESTBOROUGH, MA, 01..., Westborough, MA 01581

$608,000

2 beds

3 baths

2,183 sq ft

Condo

5 GILMORE FARM RD 5, WESTBOROUGH, MA, 01...

Community: Orchard Hill

Rockland Glen

4 MIDFIELD DR 4, ROCKLAND, MA, 02370, Rockland, MA 02370

$699,900

2 beds

3 baths

2,857 sq ft

Condo

4 MIDFIELD DR 4, ROCKLAND, MA, 02370

Community: Rockland Glen

Westbrook Crossing

989 E ST 115, DEDHAM, MA, 02026, Dedham, MA 02026

$530,000

2 beds

2 baths

1,485 sq ft

Condo

989 E ST 115, DEDHAM, MA, 02026

Community: Westbrook Crossing

The Preserve at Hunters Hill

65 CLUB HOUSE DR, DIGHTON, MA, 02715, Dighton, MA 02715

$739,900

2 beds

2 baths

1,775 sq ft

House

65 CLUB HOUSE DR, DIGHTON, MA, 02715

Community: The Preserve at Hunters Hill

Seton Highlands at The Pinehills

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

$895,000

3 beds

4 baths

3,703 sq ft

Condo

15 ABERDEEN 15, PLYMOUTH, MA, 02360

Community: Seton Highlands at The Pinehills

Angell Brook Village

138 ANGELL BROOK DR 138, WEST BOYLSTON, ..., West Boylston, MA 01583

$505,900

2 beds

2 baths

1,404 sq ft

Condo

138 ANGELL BROOK DR 138, WEST BOYLSTON, ...

Community: Angell Brook Village

Del Webb Chauncy Lake

8 PETERS FARM WAY 102, WESTBOROUGH, MA, ..., Westborough, MA 01581

$414,995

1 beds

2 baths

972 sq ft

Condo

8 PETERS FARM WAY 102, WESTBOROUGH, MA, ...

Community: Del Webb Chauncy Lake

Cindy Certified

150 LIZOTTE DR 107, MARLBOROUGH, MA, 017..., Marlborough, MA 01752

$487,095

2 beds

3 baths

1,586 sq ft

Condo

150 LIZOTTE DR 107, MARLBOROUGH, MA, 017...

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

Questions? Call us: (401) 313-4589

Upton Ridge

72 SHANNON WAY 72, UPTON, MA, 01568, Upton, MA 01568

$699,000

2 beds

3 baths

2,875 sq ft

Condo

72 SHANNON WAY 72, UPTON, MA, 01568

Community: Upton Ridge

30 Coppersmith

$589,995

2 beds

2 baths

1,425 sq ft

Condo

30 COPPERSMITH WAY 411, CANTON, MA, 0202...

Community: 30 Coppersmith

Frequently Asked Questions

What size 55+ communities are there in Middletown?

Of the 2 55+ communities in Middletown, 2 are for sale and none are rentals. By size, 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?

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55+ communities in Tiverton

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81 communities

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

81 communities near Middletown

126 homes near Middletown

2 beds

3 baths

2,306 sq ft

House

3 beds

2 baths

1,568 sq ft

House

3 beds

2 baths

1,462 sq ft

House

2 beds

2 baths

1,459 sq ft

Condo

2 beds

2 baths

2,090 sq ft

Condo

1 beds

1 baths

1,027 sq ft

Condo

2 beds

2 baths

1,582 sq ft

Condo

2 beds

3 baths

1,425 sq ft

Condo

2 beds

2 baths

1,326 sq ft

Condo

2 beds

2 baths

2,296 sq ft

Condo

2 beds

3 baths

2,447 sq ft

House

1 beds

1 baths

804 sq ft

Condo

1 beds

1 baths

965 sq ft

Condo

2 beds

2 baths

1,496 sq ft

Condo

2 beds

3 baths

1,582 sq ft

Condo

3 beds

3 baths

2,387 sq ft

Condo

2 beds

3 baths

1,421 sq ft

Condo

2 beds

3 baths

1,421 sq ft

Condo

2 beds

3 baths

1,471 sq ft

Condo

2 beds