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

80 communities near Middletown

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Bay Ridge

Bay Ridge, Middletown, RI

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

Bailey Brook

Bailey Brook, Middletown, RI

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

5 rating (3 reviews)

Oak Point

Oak Point, Middleborough, MA

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

Southport

Southport, Mashpee, MA

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

Del Webb Chauncy Lake

Del Webb Chauncy Lake, Westborough, MA

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

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Questions? Call us: (401) 313-4589

Great Island

Great Island, Plymouth, MA

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

Regency at Glen Ellen

Regency at Glen Ellen, Millis, MA

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

4 rating (5 reviews)

South Shore Village

South Shore Village, South Kingstown, RI

New and Resale | 55+ age-restricted | Built 2016 - present | 303 homes

The Villages on Mount Hop...

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

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

Sawyer's Reach

Sawyer's Reach, Plymouth, MA

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

Woodstone Crossing

Woodstone Crossing, Weymouth, MA

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

Brierly Pond Village

Brierly Pond Village, Millbury, MA

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

Pennington Crossing

Pennington Crossing, Walpole, MA

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

The Trails

The Trails, Hopkinton, MA

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

Red Mill Village

Red Mill Village, Norton, MA

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

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

Questions? Call us: (401) 313-4589

Villages at Weathervane

Villages at Weathervane, Weymouth, MA

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

Wakefield Meadows

Wakefield Meadows, Wakefield, RI

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

Harmony Place

Harmony Place, Rutland, MA

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

The Preserve at Hunters H...

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

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

Upton Ridge

Upton Ridge, Upton, MA

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

WestRidge

WestRidge, Hudson, MA

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

Angell Brook Village

Angell Brook Village, West Boylston, MA

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

Millwood Preserve

Millwood Preserve, Framingham, MA

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

The Village at Westminste...

The Village at Westminste..., Holden, MA

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

Stonebridge Commons

Stonebridge Commons, Hanson, MA

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

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

Questions? Call us: (401) 313-4589

Seton Highlands at The Pi...

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

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

The Village at Orchard Me...

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

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

Summer Reach

Summer Reach, Plymouth, MA

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

The Villages at Walker Me...

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

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

Orchard Hill

Orchard Hill, Westborough, MA

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

New England Commons

New England Commons, Webster, MA

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

Bates Quarry

Bates Quarry, Walpole, MA

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

The Lanterns at Warren Wo...

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

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

The Village at Auburnvill...

The Village at Auburnvill..., Whitman, MA

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

The Seasons at Salisbury

The Seasons at Salisbury, Holden, MA

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

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

Questions? Call us: (401) 313-4589

The Villages at Crane Mea...

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

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

Adams Farm

Adams Farm, Shrewsbury, MA

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

Southwinds

Southwinds, South Kingstown, RI

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

Bella Vista

Bella Vista, Glocester, RI

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

Regency at Assabet Ridge

Regency at Assabet Ridge, Marlborough, MA

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

23 SEA SPRAY AVE # 563, MASHPEE, MA, 026...

Community: Southport

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

Questions? Call us: (401) 313-4589

The Trails

13 BIRKDALE LN # 13, HOPKINTON, MA, 0174..., Hopkinton, MA 01748

$885,000

2 beds

3 baths

2,277 sq ft

Condo

13 BIRKDALE LN # 13, HOPKINTON, MA, 0174...

Community: The Trails

Southport

15 PEBBLE BEACH AVE # 2005-103, MASHPEE,..., Mashpee, MA 02649

$549,000

2 beds

3 baths

1,685 sq ft

Condo

15 PEBBLE BEACH AVE # 2005-103, MASHPEE,...

Community: Southport

New Great Island

14 PICKET FENCE, PLYMOUTH, MA, 02360, Plymouth, MA 02360

$825,000

3 beds

3 baths

2,555 sq ft

House

14 PICKET FENCE, PLYMOUTH, MA, 02360

Community: Great Island

30 Coppersmith

$610,995

2 beds

2 baths

1,579 sq ft

Condo

30 COPPERSMITH WAY # 107, CANTON, MA, 02...

Community: 30 Coppersmith

Woodstone Crossing

130 TROTTER RD 1309, WEYMOUTH, MA, 02190, Weymouth, MA 02190

$474,900

2 beds

2 baths

1,325 sq ft

Condo

130 TROTTER RD 1309, WEYMOUTH, MA, 02190

Community: Woodstone Crossing

30 Coppersmith

$483,995

1 beds

1 baths

1,027 sq ft

Condo

30 COPPERSMITH WAY # 204, CANTON, MA, 02...

Community: 30 Coppersmith

30 Coppersmith

$581,995

2 beds

2 baths

1,425 sq ft

Condo

30 COPPERSMITH WAY # 409, CANTON, MA, 02...

Community: 30 Coppersmith

Brierly Pond Village

32 HORNE WAY # 32, MILLBURY, MA, 01527, Millbury, MA 01527

$459,500

2 beds

2 baths

1,420 sq ft

Condo

32 HORNE WAY # 32, MILLBURY, MA, 01527

Community: Brierly Pond Village

Forest Glen

100 SPRING HILL DR # 100, UXBRIDGE, MA, ..., Uxbridge, MA 01569

$574,900

2 beds

2 baths

1,694 sq ft

Condo

100 SPRING HILL DR # 100, UXBRIDGE, MA, ...

Community: Forest Glen

New Great Island

16 PICKET FENCE, PLYMOUTH, MA, 02360, Plymouth, MA 02360

$775,000

2 beds

2 baths

2,059 sq ft

House

16 PICKET FENCE, PLYMOUTH, MA, 02360

Community: Great Island

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

Questions? Call us: (401) 313-4589

New The Pines at Hathaway Pond

57 HATHAWAY POND CIR # 57, ROCHESTER, MA..., Rochester, MA 02770

$565,000

1 beds

2 baths

1,500 sq ft

Condo

57 HATHAWAY POND CIR # 57, ROCHESTER, MA...

Community: The Pines at Hathaway Pond

New Oak Point

2602 PHEASANT LN, MIDDLEBORO, MA, 02346, Middleboro, MA 02346

$450,000

3 beds

2 baths

1,802 sq ft

House

2602 PHEASANT LN, MIDDLEBORO, MA, 02346

Community: Oak Point

New Woodstone Crossing

130 TROTTER RD 1211, WEYMOUTH, MA, 02190, Weymouth, MA 02190

$459,000

1 beds

1 baths

1,030 sq ft

Condo

130 TROTTER RD 1211, WEYMOUTH, MA, 02190

Community: Woodstone Crossing

Southport

72 GREY HAWK DR # 670, MASHPEE, MA, 0264..., Mashpee, MA 02649

$649,000

2 beds

3 baths

2,283 sq ft

Condo

72 GREY HAWK DR # 670, MASHPEE, MA, 0264...

Community: Southport

Regency at Glen Ellen

6 GLEN ELLEN BLVD # 6, MILLIS, MA, 02054, Millis, MA 02054

$1,050,000

3 beds

3 baths

2,656 sq ft

Condo

6 GLEN ELLEN BLVD # 6, MILLIS, MA, 02054

Community: Regency at Glen Ellen

The Preserve at Hunters Hill

3075 CLUB HOUSE DR, DIGHTON, MA, 02715, Dighton, MA 02715

$699,000

3 beds

2 baths

2,151 sq ft

House

3075 CLUB HOUSE DR, DIGHTON, MA, 02715

Community: The Preserve at Hunters Hill

New Wolcott Woods

69 WOLCOTT WOODS LN # 69, MILTON, MA, 02..., Milton, MA 02186

$2,099,900

2 beds

3 baths

3,599 sq ft

House

69 WOLCOTT WOODS LN # 69, MILTON, MA, 02...

Community: Wolcott Woods

Great Island

39 WOODSONG, PLYMOUTH, MA, 02360, Plymouth, MA 02360

$999,000

2 beds

3 baths

3,316 sq ft

House

39 WOODSONG, PLYMOUTH, MA, 02360

Community: Great Island

Great Island

27 CROSS WIND, PLYMOUTH, MA, 02360, Plymouth, MA 02360

$750,000

3 beds

3 baths

3,180 sq ft

House

27 CROSS WIND, PLYMOUTH, MA, 02360

Community: Great Island

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+ communities in Middletown? 55places can help!

Questions? Call us: (401) 313-4589

Southport

44 TWIN OAKS DR # 44, MASHPEE, MA, 02649, Mashpee, MA 02649

$534,900

2 beds

2 baths

1,659 sq ft

Condo

44 TWIN OAKS DR # 44, MASHPEE, MA, 02649

Community: Southport

Brooksmont

$639,000

2 beds

2 baths

1,516 sq ft

Condo

104 BROOKSMONT DR # 104, HOLLISTON, MA, ...

Community: Brooksmont

Southport

4 N RIDGE RD # 431, MASHPEE, MA, 02649, Mashpee, MA 02649

$524,900

2 beds

2 baths

1,338 sq ft

Condo

4 N RIDGE RD # 431, MASHPEE, MA, 02649

Community: Southport

Brooksmont

$697,500

2 beds

2 baths

2,431 sq ft

Condo

95 BROOKSMONT DR # 26, HOLLISTON, MA, 01...

Community: Brooksmont

Great Island

22 COTTAGE CV, PLYMOUTH, MA, 02360, Plymouth, MA 02360

$759,000

3 beds

3 baths

2,074 sq ft

House

22 COTTAGE CV, PLYMOUTH, MA, 02360

Community: Great Island

Del Webb Chauncy Lake

4403 PETERS FARM WAY 403, WESTBOROUGH, M..., Westborough, MA 01581

$439,900

1 beds

1 baths

956 sq ft

Condo

4403 PETERS FARM WAY 403, WESTBOROUGH, M...

Community: Del Webb Chauncy Lake

Villages at Weathervane

18 BEN HOGAN LNDG # 18, WEYMOUTH, MA, 02..., Weymouth, MA 02190

$1,300,000

2 beds

4 baths

2,956 sq ft

Condo

18 BEN HOGAN LNDG # 18, WEYMOUTH, MA, 02...

Community: Villages at Weathervane

Del Webb Chauncy Lake

3103 PETERS FARM WAY # 3103, WESTBOROUGH..., Westborough, MA 01581

$386,000

1 beds

1 baths

956 sq ft

Condo

3103 PETERS FARM WAY # 3103, WESTBOROUGH...

Community: Del Webb Chauncy Lake

Southport

181 LEISURE GREEN DR, MASHPEE, MA, 02649, Mashpee, MA 02649

$449,000

2 beds

2 baths

1,338 sq ft

House

181 LEISURE GREEN DR, MASHPEE, MA, 02649

Community: Southport

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

Millwood Preserve

9 HAWK LN # 28, FRAMINGHAM, MA, 01701, Framingham, MA 01701

$1,175,000

2 beds

3 baths

2,306 sq ft

Condo

9 HAWK LN # 28, FRAMINGHAM, MA, 01701

Community: Millwood Preserve

Del Webb Chauncy Lake

11302 PETERS FARM WAY # 11302, WESTBOROU..., Westborough, MA 01581

$359,995

1 beds

1 baths

956 sq ft

Condo

11302 PETERS FARM WAY # 11302, WESTBOROU...

Community: Del Webb Chauncy Lake

Del Webb Chauncy Lake

3112 PETERS FARM WAY # 112, WESTBOROUGH,..., Westborough, MA 01581

$405,000

1 beds

1 baths

1,021 sq ft

Condo

3112 PETERS FARM WAY # 112, WESTBOROUGH,...

Community: Del Webb Chauncy Lake

Great Island

74 CHAMPLAIN CIR, PLYMOUTH, MA, 02360, Plymouth, MA 02360

$745,000

3 beds

3 baths

2,580 sq ft

House

74 CHAMPLAIN CIR, PLYMOUTH, MA, 02360

Community: Great Island

Great Island

21 CROSS WIND, PLYMOUTH, MA, 02360, Plymouth, MA 02360

$749,900

3 beds

3 baths

2,805 sq ft

House

21 CROSS WIND, PLYMOUTH, MA, 02360

Community: Great Island

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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?

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80 communities near Middletown

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

80 communities near Middletown

105 homes near Middletown

2 beds

3 baths

2,485 sq ft

Condo

2 beds

4 baths

3,258 sq ft

Condo

2 beds

2 baths

1,606 sq ft

Condo

2 beds

4 baths

3,503 sq ft

Condo

2 beds

4 baths

2,455 sq ft

Condo

2 beds

3 baths

2,277 sq ft

Condo

2 beds

3 baths

1,685 sq ft

Condo

3 beds

3 baths

2,555 sq ft

House

2 beds

2 baths

1,579 sq ft

Condo

2 beds

2 baths

1,325 sq ft

Condo

1 beds

1 baths

1,027 sq ft

Condo

2 beds

2 baths

1,425 sq ft

Condo

2 beds

2 baths

1,420 sq ft

Condo

2 beds

2 baths

1,694 sq ft

Condo

2 beds

2 baths

2,059 sq ft

House

1 beds

2 baths

1,500 sq ft

Condo

3 beds

2 baths

1,802 sq ft

House

1 beds

1 baths

1,030 sq ft

Condo

2 beds

3 baths

2,283 sq ft

Condo

3 beds