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

81 communities near Middletown

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Southport

$400ks - $600ks

Southport, Mashpee, MA

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

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

Great Island

$600ks

Great Island, Plymouth, MA

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

Sawyer's Reach

$400ks - $900ks

Sawyer's Reach, Plymouth, MA

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

Upton Ridge

$400ks - $600ks

Upton Ridge, Upton, MA

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

Brierly Pond Village

$300ks - $400ks

Brierly Pond Village, Millbury, MA

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

Pennington Crossing

$300ks - $600ks

Pennington Crossing, Walpole, MA

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

30 Coppersmith

$700ks

30 Coppersmith, Canton, MA

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

Woodcrest Run

$400ks - $600ks

Woodcrest Run, Sharon, MA

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

Regency at Glen Ellen

$700ks - $900ks

Regency at Glen Ellen, Millis, MA

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

Stonebridge Commons

$500ks

Stonebridge Commons, Hanson, MA

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

The Trails

$500ks - $700ks

The Trails, Hopkinton, MA

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

Woodstone Crossing

$300ks - $400ks

Woodstone Crossing, Weymouth, MA

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

Westbrook Crossing

$400ks - $500ks

Westbrook Crossing, Dedham, MA

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

Bates Quarry

Bates Quarry, Walpole, MA

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

The Seasons at Salisbury

$400ks - $500ks

The Seasons at Salisbury, Holden, MA

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

Brooksmont

$400ks - $600ks

Brooksmont, Holliston, MA

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

Northside Meadows

$600ks - $700ks

Northside Meadows, Framingham, MA

Resale Only | 55+ age-restricted | Built 2017 - 2019 | 60 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

Northwoods at Sudbury

$500ks

Northwoods at Sudbury, Sudbury, MA

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

Want to learn more about 55+ 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

Spring Meadow

$400ks - $500ks

Spring Meadow, Hanover, MA

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

Orchard Hill

$500ks

Orchard Hill, Westborough, MA

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

Wakefield Meadows

$700ks - $800ks

Wakefield Meadows, Wakefield, RI

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

Blue Heron Pond

$500ks

Blue Heron Pond, Lancaster, MA

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

Bailey Brook

$600ks - $700ks

Bailey Brook, Middletown, RI

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

New England Commons

$200ks - $300ks

New England Commons, Webster, MA

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

Southwinds

$600ks - $700ks

Southwinds, South Kingstown, RI

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

5 rating (3 reviews)

Oak Point

$300ks - $400ks

Oak Point, Middleborough, MA

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

Red Mill Village

$400ks - $600ks

Red Mill Village, Norton, MA

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

1 2...3

New The Preserve at Hunters Hill

3047 CLUBHOUSE DR, DIGHTON, MA, 02715, Dighton, MA 02715

$819,900

2 beds

2 baths

1,775 sq ft

House

3047 CLUBHOUSE DR, DIGHTON, MA, 02715

Community: The Preserve at Hunters Hill

New Westbrook Crossing

989 E ST 303, DEDHAM, MA, 02026, Dedham, MA 02026

$749,900

2 beds

2 baths

1,895 sq ft

Condo

989 E ST 303, DEDHAM, MA, 02026

Community: Westbrook Crossing

New WestRidge

7 BARRETTS RD 7, HUDSON, MA, 01749, Hudson, MA 01749

$1,025,000

3 beds

3 baths

2,409 sq ft

Condo

7 BARRETTS RD 7, HUDSON, MA, 01749

Community: WestRidge

New Great Island

8 RED CANOE 8, PLYMOUTH, MA, 02360, Plymouth, MA 02360

$869,000

3 beds

3 baths

2,281 sq ft

Condo

8 RED CANOE 8, PLYMOUTH, MA, 02360

Community: Great Island

New Del Webb Chauncy Lake

4 PETERS FARM WAY 409, WESTBOROUGH, MA, ..., Westborough, MA 01581

$539,900

2 beds

2 baths

1,326 sq ft

Condo

4 PETERS FARM WAY 409, 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

New Southport

7 PAR THREE CT, MASHPEE, MA, 02649, Mashpee, MA 02649

$525,000

2 beds

3 baths

1,685 sq ft

House

7 PAR THREE CT, MASHPEE, MA, 02649

Community: Southport

New Stonebridge Commons

40 STONEBRIDGE DR 40, HANSON, MA, 02341, Hanson, MA 02341

$679,900

2 beds

3 baths

1,800 sq ft

Condo

40 STONEBRIDGE DR 40, HANSON, MA, 02341

Community: Stonebridge Commons

New Del Webb Chauncy Lake

5 PETERS FARM WAY 7405, WESTBOROUGH, MA,..., Westborough, MA 01581

$559,995

2 beds

2 baths

1,166 sq ft

Condo

5 PETERS FARM WAY 7405, WESTBOROUGH, MA,...

Community: Del Webb Chauncy Lake

New Del Webb Chauncy Lake

5305 PETERS FARM WAY 7305, WESTBOROUGH, ..., Westborough, MA 01581

$529,995

2 beds

2 baths

1,166 sq ft

Condo

5305 PETERS FARM WAY 7305, WESTBOROUGH, ...

Community: Del Webb Chauncy Lake

New Pennington Crossing

1102 PENNINGTON DR 1102, WALPOLE, MA, 02..., Walpole, MA 02081

$529,900

1 beds

1 baths

955 sq ft

Condo

1102 PENNINGTON DR 1102, WALPOLE, MA, 02...

Community: Pennington Crossing

New Brierly Pond Village

97 HORNE WAY 97, MILLBURY, MA, 01527, Millbury, MA 01527

$450,000

2 beds

3 baths

1,746 sq ft

Condo

97 HORNE WAY 97, MILLBURY, MA, 01527

Community: Brierly Pond Village

New Southport

126 GREY HAWK DR 697, MASHPEE, MA, 02649, Mashpee, MA 02649

$779,900

2 beds

3 baths

1,620 sq ft

Condo

126 GREY HAWK DR 697, MASHPEE, MA, 02649

Community: Southport

New Southport

12 PGA LN 423, MASHPEE, MA, 02649, Mashpee, MA 02649

$545,000

2 beds

2 baths

1,333 sq ft

Condo

12 PGA LN 423, MASHPEE, MA, 02649

Community: Southport

Stonebridge Commons

31 STONEBRIDGE DR 31, HANSON, MA, 02341, Hanson, MA 02341

$659,000

2 beds

3 baths

2,071 sq ft

Condo

31 STONEBRIDGE DR 31, HANSON, MA, 02341

Community: Stonebridge Commons

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

8 PETERS FARM WAY 113, WESTBOROUGH, MA, ..., Westborough, MA 01581

$639,995

2 beds

2 baths

1,512 sq ft

Condo

8 PETERS FARM WAY 113, 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 103, WESTBOROUGH, MA, ..., Westborough, MA 01581

$414,995

1 beds

2 baths

972 sq ft

Condo

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

Community: Del Webb Chauncy Lake

Sawyer's Reach

35 MARINERS WAY 35, PLYMOUTH, MA, 02360, Plymouth, MA 02360

$929,900

3 beds

3 baths

2,533 sq ft

Condo

35 MARINERS WAY 35, PLYMOUTH, MA, 02360

Community: Sawyer's Reach

Oak Point

$425,900

2 beds

2 baths

1,512 sq ft

House

7012 OAK POINT DR, MIDDLEBORO, MA, 02346

Community: Oak Point

Seton Highlands at The Pinehills

105 SETON HIGHLANDS 105, PLYMOUTH, MA, 0..., Plymouth, MA 02360

$825,000

2 beds

3 baths

2,186 sq ft

Condo

105 SETON HIGHLANDS 105, PLYMOUTH, MA, 0...

Community: Seton Highlands at The Pinehills

Pennington Crossing

2404 PENNINGTON DR 2404, WALPOLE, MA, 02..., Walpole, MA 02081

$559,900

1 beds

1 baths

965 sq ft

Condo

2404 PENNINGTON DR 2404, WALPOLE, MA, 02...

Community: Pennington Crossing

The Pines at Hathaway Pond

31 HATHAWAY POND CIR 31, ROCHESTER, MA, ..., Rochester, MA 02770

$765,000

2 beds

3 baths

2,231 sq ft

Condo

31 HATHAWAY POND CIR 31, ROCHESTER, MA, ...

Community: The Pines at Hathaway Pond

Bates Quarry

16 TIGER TER 29, WALPOLE, MA, 02081, Walpole, MA 02081

$948,159

2 beds

2 baths

2,509 sq ft

Condo

16 TIGER TER 29, WALPOLE, MA, 02081

Community: Bates Quarry

Cindy Certified

12 TIGER TER 28, WALPOLE, MA, 02081, Walpole, MA 02081

$863,659

2 beds

2 baths

1,501 sq ft

126 CLUBHOUSE LN 126, NORTHBRIDGE, MA, 0...

Condo

20 AUDUBON WAY 309, CANTON, MA, 02021

Cindy Certified

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

$659,900

2 baths

1,614 sq ft

Condo

96 AURORA SKY 96, PLYMOUTH, MA, 02360

Woodcrest Run

635 OLD POST RD 109, SHARON, MA, 02067, Sharon, MA 02067

$479,900

2 beds

2 baths

1,056 sq ft

Condo

635 OLD POST RD 109, SHARON, MA, 02067

Community: Woodcrest Run

Woodcrest Run

635 OLD POST RD 110, SHARON, MA, 02067, Sharon, MA 02067

$459,900

1 beds

2 baths

1,056 sq ft

Condo

635 OLD POST RD 110, SHARON, MA, 02067

Community: Woodcrest Run

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

Questions? Call us: (401) 313-4589

Woodcrest Run

635 OLD POST RD 302, SHARON, MA, 02067, Sharon, MA 02067

$489,900

2 beds

2 baths

1,187 sq ft

Condo

635 OLD POST RD 302, SHARON, MA, 02067

Community: Woodcrest Run

Brooksmont

$785,000

2 beds

3 baths

2,360 sq ft

Condo

65 BROOKSMONT DR 15, HOLLISTON, MA, 0174...

Community: Brooksmont

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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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

123 homes near Middletown

2 beds

2 baths

1,775 sq ft

House

2 beds

2 baths

1,895 sq ft

Condo

3 beds

3 baths

2,409 sq ft

Condo

3 beds

3 baths

2,281 sq ft

Condo

2 beds

2 baths

1,326 sq ft

Condo

2 beds

3 baths

1,685 sq ft

House

2 beds

3 baths

1,800 sq ft

Condo

2 beds

2 baths

1,166 sq ft

Condo

2 beds

2 baths

1,166 sq ft

Condo

1 beds

1 baths

955 sq ft

Condo

2 beds

3 baths

1,746 sq ft

Condo

2 beds

3 baths

1,620 sq ft

Condo

2 beds

2 baths

1,333 sq ft

Condo

2 beds

3 baths

2,071 sq ft

Condo

2 beds

3 baths

2,382 sq ft

House

2 beds

2 baths

1,512 sq ft

Condo

1 beds

2 baths

972 sq ft

Condo

3 beds

3 baths

2,533 sq ft

Condo

2 beds

2 baths

1,512 sq ft

House

2 beds