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

81 communities near Middletown

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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

Great Island

$600ks

Great Island, Plymouth, MA

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

Sawyer's Reach

$400ks - $900ks

Sawyer's Reach, Plymouth, MA

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

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

Questions? Call us: (401) 313-4589

Upton Ridge

$400ks - $600ks

Upton Ridge, Upton, MA

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

Harmony Place

$400ks - $500ks

Harmony Place, Rutland, MA

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

Brierly Pond Village

$300ks - $400ks

Brierly Pond Village, Millbury, MA

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

30 Coppersmith

$700ks

30 Coppersmith, Canton, MA

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

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

The Pines at Hathaway Pon...

$300ks - $500ks

The Pines at Hathaway Pon..., Rochester, MA

Resale Only | 55+ age-restricted | Built 2006 - 2014 | 61 homes

The Village at Auburnvill...

$300ks - $400ks

The Village at Auburnvill..., Whitman, MA

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

Regency at Glen Ellen

$700ks - $900ks

Regency at Glen Ellen, Millis, MA

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

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

Questions? Call us: (401) 313-4589

Woodcrest Run

$400ks - $600ks

Woodcrest Run, Sharon, MA

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

The Village at Westminste...

$400ks - $500ks

The Village at Westminste..., Holden, MA

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

Enclave at Hudson

$800ks - $1Ms

Enclave at Hudson, Hudson, MA

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

Regency at Assabet Ridge

$500ks - $600ks

Regency at Assabet Ridge, Marlborough, MA

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

Bates Quarry

Bates Quarry, Walpole, MA

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

Northwoods at Sudbury

$500ks

Northwoods at Sudbury, Sudbury, MA

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

Spring Meadow

$400ks - $500ks

Spring Meadow, Hanover, MA

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

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

Questions? Call us: (401) 313-4589

The Seasons at Salisbury

$400ks - $500ks

The Seasons at Salisbury, Holden, MA

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

Bigelow Farm

$500ks - $600ks

Bigelow Farm, Northborough, MA

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

WestRidge

$700ks

WestRidge, Hudson, MA

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

Orchard Hill

$500ks

Orchard Hill, Westborough, MA

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

Northside Meadows

$600ks - $700ks

Northside Meadows, Framingham, MA

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

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

Questions? Call us: (401) 313-4589

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

1 2...3

New Sawyer's Reach

62 MARINERS WAY 312, PLYMOUTH, MA, 02360, Plymouth, MA 02360

$685,000

2 beds

2 baths

1,457 sq ft

Condo

62 MARINERS WAY 312, PLYMOUTH, MA, 02360

Community: Sawyer's Reach

New The Village at Auburnville

877 AUBURNVILLE WAY N3, WHITMAN, MA, 023..., Whitman, MA 02382

$499,000

2 beds

2 baths

2,090 sq ft

Condo

877 AUBURNVILLE WAY N3, WHITMAN, MA, 023...

Community: The Village at Auburnville

New

Cindy Certified

20 AUDUBON WAY 109, CANTON, MA, 02021, Canton, MA 02021

$734,900

2 beds

3 baths

1,421 sq ft

Condo

20 AUDUBON WAY 109, CANTON, MA, 02021

New Upton Ridge

87 SHANNON WAY 1, UPTON, MA, 01568, Upton, MA 01568

$669,900

2 beds

3 baths

1,950 sq ft

Condo

87 SHANNON WAY 1, UPTON, MA, 01568

Community: Upton Ridge

New WestRidge

29 HASTINGS 29, HUDSON, MA, 01749, Hudson, MA 01749

$799,000

3 beds

3 baths

2,264 sq ft

Condo

29 HASTINGS 29, HUDSON, MA, 01749

Community: WestRidge

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

Questions? Call us: (401) 313-4589

New Oak Point

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

$459,900

3 beds

2 baths

1,750 sq ft

House

5006 OAK POINT DR, MIDDLEBORO, MA, 02346

Community: Oak Point

New Great Island

7 MADISON REACH, PLYMOUTH, MA, 02360, Plymouth, MA 02360

$685,000

2 beds

3 baths

2,061 sq ft

House

7 MADISON REACH, PLYMOUTH, MA, 02360

Community: Great Island

New Great Island

15 MINT SPRIG, PLYMOUTH, MA, 02360, Plymouth, MA 02360

$979,000

3 beds

4 baths

4,417 sq ft

House

15 MINT SPRIG, PLYMOUTH, MA, 02360

Community: Great Island

Great Island

14 HORIZON, PLYMOUTH, MA, 02360, Plymouth, MA 02360

$795,000

2 beds

2 baths

2,267 sq ft

House

14 HORIZON, PLYMOUTH, MA, 02360

Community: Great Island

WestRidge

33 HASTINGS 33, HUDSON, MA, 01749, Hudson, MA 01749

$599,999

2 beds

3 baths

1,758 sq ft

Condo

33 HASTINGS 33, HUDSON, MA, 01749

Community: WestRidge

Arbor Hills

46 HOLLY CIR 46, KINGSTON, MA, 02364, Kingston, MA 02364

$699,900

2 beds

3 baths

2,137 sq ft

Condo

46 HOLLY CIR 46, KINGSTON, MA, 02364

Community: Arbor Hills

The Pines at Hathaway Pond

39 HATHAWAY POND CIR 39, ROCHESTER, MA, ..., Rochester, MA 02770

$739,900

2 beds

3 baths

2,004 sq ft

Condo

39 HATHAWAY POND CIR 39, ROCHESTER, MA, ...

Community: The Pines at Hathaway Pond

Great Island

10 GREAT POINTE, PLYMOUTH, MA, 02360, Plymouth, MA 02360

$785,000

2 beds

2 baths

2,048 sq ft

House

10 GREAT POINTE, PLYMOUTH, MA, 02360

Community: Great Island

Enclave at Hudson

38 BARNES BLVD 23, HUDSON, MA, 01749, Hudson, MA 01749

$1,125,000

2 beds

3 baths

2,544 sq ft

Condo

38 BARNES BLVD 23, HUDSON, MA, 01749

Community: Enclave at Hudson

Bigelow Farm

5 LYDIA'S WAY 5, NORTHBOROUGH, MA, 01532, Northborough, MA 01532

$799,900

2 beds

3 baths

2,556 sq ft

Condo

5 LYDIA'S WAY 5, NORTHBOROUGH, MA, 01532

Community: Bigelow Farm

Oak Point

$399,900

3 beds

2 baths

1,344 sq ft

House

701 OAK POINT DR, MIDDLEBORO, MA, 02346

Community: Oak Point

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

Questions? Call us: (401) 313-4589

The Village at Auburnville

877 AUBURNVILLE WAY C2, WHITMAN, MA, 023..., Whitman, MA 02382

$525,000

2 beds

2 baths

2,090 sq ft

Condo

877 AUBURNVILLE WAY C2, WHITMAN, MA, 023...

Community: The Village at Auburnville

Del Webb Chauncy Lake

3 PETERS FARM WAY 107, WESTBOROUGH, MA, ..., Westborough, MA 01581

$560,000

2 beds

2 baths

1,469 sq ft

Condo

3 PETERS FARM WAY 107, WESTBOROUGH, MA, ...

Community: Del Webb Chauncy Lake

Great Island

11 SADDLEBACK, PLYMOUTH, MA, 02360, Plymouth, MA 02360

$1,175,000

2 beds

3 baths

3,463 sq ft

House

11 SADDLEBACK, PLYMOUTH, MA, 02360

Community: Great Island

The Trails

38 WESTON LN 38, HOPKINTON, MA, 01748, Hopkinton, MA 01748

$999,900

2 beds

3 baths

2,274 sq ft

Condo

38 WESTON LN 38, HOPKINTON, MA, 01748

Community: The Trails

Sawyer's Reach

45 PLAZA WAY 204, PLYMOUTH, MA, 02360, Plymouth, MA 02360

$565,000

1 beds

2 baths

1,113 sq ft

Condo

45 PLAZA WAY 204, PLYMOUTH, MA, 02360

Community: Sawyer's Reach

Great Island

7 WHITE TRELLIS, PLYMOUTH, MA, 02360, Plymouth, MA 02360

$719,900

2 beds

3 baths

2,061 sq ft

House

7 WHITE TRELLIS, PLYMOUTH, MA, 02360

Community: Great Island

The Trails

10 WATERVILLE LN 10, HOPKINTON, MA, 0174..., Hopkinton, MA 01748

$999,900

2 beds

3 baths

2,274 sq ft

Condo

10 WATERVILLE LN 10, HOPKINTON, MA, 0174...

Community: The Trails

Del Webb Chauncy Lake

8310 PETERS FARM WAY 310, WESTBOROUGH, M..., Westborough, MA 01581

$564,995

2 beds

2 baths

1,375 sq ft

Condo

8310 PETERS FARM WAY 310, WESTBOROUGH, M...

Community: Del Webb Chauncy Lake

Great Island

12 MAPLEWOOD, PLYMOUTH, MA, 02360, Plymouth, MA 02360

$720,000

2 beds

2 baths

1,548 sq ft

House

12 MAPLEWOOD, PLYMOUTH, MA, 02360

Community: Great Island

The Village at Westminster Place

9 SETTLERS LN 583, HOLDEN, MA, 01520, Holden, MA 01520

$649,000

3 beds

3 baths

1,877 sq ft

Condo

9 SETTLERS LN 583, HOLDEN, MA, 01520

Community: The Village at Westminster Place

The Village at Orchard Meadows

4 BLOSSOM TREE DR 4, SHREWSBURY, MA, 015..., Shrewsbury, MA 01545

$599,900

2 beds

2 baths

1,580 sq ft

Condo

4 BLOSSOM TREE DR 4, SHREWSBURY, MA, 015...

Community: The Village at Orchard Meadows

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

Questions? Call us: (401) 313-4589

Brierly Pond Village

22 HORNE WAY 22, MILLBURY, MA, 01527, Millbury, MA 01527

$459,900

2 beds

2 baths

1,746 sq ft

Condo

22 HORNE WAY 22, MILLBURY, MA, 01527

Community: Brierly Pond Village

The Lanterns at Warren Woods

20 FERN XING 20, ASHLAND, MA, 01721, Ashland, MA 01721

$850,000

2 beds

3 baths

2,290 sq ft

Condo

20 FERN XING 20, ASHLAND, MA, 01721

Community: The Lanterns at Warren Woods

The Pines at Hathaway Pond

38 HATHAWAY POND CIR 38, ROCHESTER, MA, ..., Rochester, MA 02770

$699,999

2 beds

3 baths

1,969 sq ft

Condo

38 HATHAWAY POND CIR 38, ROCHESTER, MA, ...

Community: The Pines at Hathaway Pond

Regency at Assabet Ridge

23 AVEBURY LN 23, MARLBOROUGH, MA, 01752, Marlborough, MA 01752

$800,000

4 beds

4 baths

3,561 sq ft

Condo

23 AVEBURY LN 23, MARLBOROUGH, MA, 01752

Community: Regency at Assabet Ridge

Upton Ridge

16 LINKSIDE CT 16, NORTHBRIDGE, MA, 0153..., Northbridge, MA 01534

$649,900

2 beds

3 baths

2,030 sq ft

Condo

16 LINKSIDE CT 16, NORTHBRIDGE, MA, 0153...

Community: Upton Ridge

30 Coppersmith

$458,995

1 beds

1 baths

1,129 sq ft

Condo

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

Community: 30 Coppersmith

Woodstone Crossing

70 TROTTER RD 4304, WEYMOUTH, MA, 02190, Weymouth, MA 02190

$449,900

1 beds

1 baths

965 sq ft

Condo

70 TROTTER RD 4304, WEYMOUTH, MA, 02190

Community: Woodstone Crossing

The Preserve at Hunters Hill

3047 CLUB HOUSE DR, DIGHTON, MA, 02715, Dighton, MA 02715

$819,900

2 beds

2 baths

1,775 sq ft

House

3047 CLUB HOUSE DR, DIGHTON, MA, 02715

Community: The Preserve at Hunters Hill

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

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

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

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

Questions? Call us: (401) 313-4589

Stonebridge Commons

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

$649,900

2 beds

3 baths

1,800 sq ft

Condo

40 STONEBRIDGE DR 40, HANSON, MA, 02341

Community: Stonebridge Commons

Del Webb Chauncy Lake

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

$539,995

2 beds

2 baths

1,166 sq ft

Condo

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

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?

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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

119 homes near Middletown

2 beds

2 baths

1,457 sq ft

Condo

2 beds

2 baths

2,090 sq ft

Condo

2 beds

3 baths

1,421 sq ft

Condo

2 beds

3 baths

1,950 sq ft

Condo

3 beds

3 baths

2,264 sq ft

Condo

3 beds

2 baths

1,750 sq ft

House

2 beds

3 baths

2,061 sq ft

House

3 beds

4 baths

4,417 sq ft

House

2 beds

2 baths

2,267 sq ft

House

2 beds

3 baths

1,758 sq ft

Condo

2 beds

3 baths

2,137 sq ft

Condo

2 beds

3 baths

2,004 sq ft

Condo

2 beds

2 baths

2,048 sq ft

House

2 beds

3 baths

2,544 sq ft

Condo

2 beds

3 baths

2,556 sq ft

Condo

3 beds

2 baths

1,344 sq ft

House

2 beds

2 baths

2,090 sq ft

Condo

2 beds

2 baths

1,469 sq ft

Condo

2 beds

3 baths

3,463 sq ft

House

2 beds