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

Great Island

$600ks

Great Island, Plymouth, MA

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

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

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

Questions? Call us: (401) 313-4589

30 Coppersmith

$700ks

30 Coppersmith, Canton, MA

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

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

Orchard Hill

$500ks

Orchard Hill, Westborough, MA

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

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

Millwood Preserve

$1Ms

Millwood Preserve, Framingham, MA

Resale Only | 55+ age-restricted | Built 2020 - 2024 | 129 homes

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

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

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

Questions? Call us: (401) 313-4589

The Villages at Crane Mea...

$400ks

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

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

Northside Meadows

$600ks - $700ks

Northside Meadows, Framingham, MA

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

Center Commons

$500ks - $600ks

Center Commons, Pembroke, MA

Resale Only | 55+ age-restricted | Built 2004 - 2009 | 44 homes

Woodcrest Run

$400ks - $600ks

Woodcrest Run, Sharon, MA

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

Rockwood Meadows

$600ks - $700ks

Rockwood Meadows, Upton, MA

New Construction | 55+ age-restricted | Built 2016 - present | 58 homes

Woodstone Crossing

$300ks - $400ks

Woodstone Crossing, Weymouth, MA

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

The Seasons at Salisbury

$400ks - $500ks

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

Spring Meadow

$400ks - $500ks

Spring Meadow, Hanover, MA

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

Chilton Park Village

$400ks

Chilton Park Village, Plymouth, MA

Resale Only | 55+ age-restricted | Built 2006 - 2015 | 25 homes

The Village at Auburnvill...

$300ks - $400ks

The Village at Auburnvill..., Whitman, MA

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

Angell Brook Village

$300ks

Angell Brook Village, West Boylston, MA

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

Summer Reach

$400ks - $500ks

Summer Reach, Plymouth, MA

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

Holliston Woods

$500ks - $700ks

Holliston Woods, Holliston, MA

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

Regency at Assabet Ridge

$500ks - $600ks

Regency at Assabet Ridge, Marlborough, MA

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

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

Adams Farm

$700ks - $800ks

Adams Farm, Shrewsbury, MA

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

1211 PENNINGTON DR 1211, WALPOLE, MA, 02...

Community: Pennington Crossing

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

Questions? Call us: (401) 313-4589

New Del Webb Chauncy Lake

8 PETERS FARM WAY 401, WESTBOROUGH, MA, ..., Westborough, MA 01581

$872,440

2 beds

2 baths

1,496 sq ft

Condo

8 PETERS FARM WAY 401, WESTBOROUGH, MA, ...

Community: Del Webb Chauncy Lake

New Del Webb Chauncy Lake

5 PETERS FARM WAY 404, WESTBOROUGH, MA, ..., Westborough, MA 01581

$489,995

1 beds

1 baths

972 sq ft

Condo

5 PETERS FARM WAY 404, WESTBOROUGH, MA, ...

Community: Del Webb Chauncy Lake

New Center Commons

33 FREEDOM CIR 33, PEMBROKE, MA, 02359, Pembroke, MA 02359

$485,000

2 beds

2 baths

1,452 sq ft

Condo

33 FREEDOM CIR 33, PEMBROKE, MA, 02359

Community: Center Commons

New Southport

7 IRONWOOD PATH 186, MASHPEE, MA, 02649, Mashpee, MA 02649

$564,000

2 beds

3 baths

1,685 sq ft

Condo

7 IRONWOOD PATH 186, MASHPEE, MA, 02649

Community: Southport

New Great Island

9 CANOE LNDG, PLYMOUTH, MA, 02360, Plymouth, MA 02360

$747,000

2 beds

3 baths

2,074 sq ft

House

9 CANOE LNDG, PLYMOUTH, MA, 02360

Community: Great Island

New Great Island

22 CROSS WIND, PLYMOUTH, MA, 02360, Plymouth, MA 02360

$825,000

3 beds

3 baths

2,440 sq ft

House

22 CROSS WIND, PLYMOUTH, MA, 02360

Community: Great Island

New Great Island

6 AUTUMN GLN, PLYMOUTH, MA, 02360, Plymouth, MA 02360

$725,000

2 beds

3 baths

2,061 sq ft

House

6 AUTUMN GLN, PLYMOUTH, MA, 02360

Community: Great Island

Rockwood Meadows

41 ROCKWOOD LN 41, UPTON, MA, 01568, Upton, MA 01568

$779,900

2 beds

2 baths

1,743 sq ft

Condo

41 ROCKWOOD LN 41, UPTON, MA, 01568

Community: Rockwood Meadows

Regency at Glen Ellen

112 GLEN ELLEN BLVD 112, MILLIS, MA, 020..., Millis, MA 02054

$1,299,950

3 beds

4 baths

4,483 sq ft

Condo

112 GLEN ELLEN BLVD 112, MILLIS, MA, 020...

Community: Regency at Glen Ellen

30 Coppersmith

$625,995

1 beds

1 baths

1,027 sq ft

Condo

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

Community: 30 Coppersmith

30 Coppersmith

$827,440

2 beds

2 baths

1,582 sq ft

Condo

30 COPPERSMITH WAY 406, CANTON, MA, 0202...

Community: 30 Coppersmith

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

Questions? Call us: (401) 313-4589

Great Island

66 CLAM PUDDING, PLYMOUTH, MA, 02360, Plymouth, MA 02360

$850,000

3 beds

3 baths

2,555 sq ft

House

66 CLAM PUDDING, PLYMOUTH, MA, 02360

Community: Great Island

The Seasons at Salisbury

148 FIRESIDE LN 148, HOLDEN, MA, 01520, Holden, MA 01520

$700,000

2 beds

3 baths

2,601 sq ft

Condo

148 FIRESIDE LN 148, HOLDEN, MA, 01520

Community: The Seasons at Salisbury

Northside Meadows

11 TOLLAND WAY 11, FRAMINGHAM, MA, 01701, Framingham, MA 01701

$1,195,000

2 beds

3 baths

2,607 sq ft

Condo

11 TOLLAND WAY 11, FRAMINGHAM, MA, 01701

Community: Northside Meadows

Southport

2 MAINSAIL CIR 70, MASHPEE, MA, 02649, Mashpee, MA 02649

$569,000

2 beds

3 baths

1,685 sq ft

Condo

2 MAINSAIL CIR 70, MASHPEE, MA, 02649

Community: Southport

Southport

1 WOODS EDGE LN 191, MASHPEE, MA, 02649, Mashpee, MA 02649

$579,000

2 beds

3 baths

2,542 sq ft

Condo

1 WOODS EDGE LN 191, MASHPEE, MA, 02649

Community: Southport

Southport

26 GREY HAWK DR 647, MASHPEE, MA, 02649, Mashpee, MA 02649

$719,000

2 beds

2 baths

1,952 sq ft

Condo

26 GREY HAWK DR 647, MASHPEE, MA, 02649

Community: Southport

The Villages at Crane Meadow

7 WHISPERING BRK 7, MARLBOROUGH, MA, 017..., Marlborough, MA 01752

$579,900

2 beds

2 baths

1,838 sq ft

Condo

7 WHISPERING BRK 7, MARLBOROUGH, MA, 017...

Community: The Villages at Crane Meadow

Harmony Place

21 FIDELITY DR 73, RUTLAND, MA, 01543, Rutland, MA 01543

$489,000

2 beds

2 baths

1,582 sq ft

Condo

21 FIDELITY DR 73, RUTLAND, MA, 01543

Community: Harmony Place

Harmony Place

23 FIDELITY DR 74, RUTLAND, MA, 01543, Rutland, MA 01543

$489,000

2 beds

2 baths

1,582 sq ft

Condo

23 FIDELITY DR 74, RUTLAND, MA, 01543

Community: Harmony Place

Harmony Place

19 FIDELITY DR 72, RUTLAND, MA, 01543, Rutland, MA 01543

$498,000

2 beds

2 baths

1,582 sq ft

Condo

19 FIDELITY DR 72, RUTLAND, MA, 01543

Community: Harmony Place

Harmony Place

17 FIDELITY DR 71, RUTLAND, MA, 01543, Rutland, MA 01543

$498,000

2 beds

2 baths

1,582 sq ft

Condo

17 FIDELITY DR 71, RUTLAND, MA, 01543

Community: Harmony Place

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

Questions? Call us: (401) 313-4589

Great Island

12 BELLTREE, PLYMOUTH, MA, 02360, Plymouth, MA 02360

$759,900

2 beds

3 baths

2,322 sq ft

House

12 BELLTREE, PLYMOUTH, MA, 02360

Community: Great Island

WestRidge

4 HASTINGS RD 4, HUDSON, MA, 01749, Hudson, MA 01749

$610,000

2 beds

3 baths

1,736 sq ft

Condo

4 HASTINGS RD 4, HUDSON, MA, 01749

Community: WestRidge

Great Island

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

$750,000

2 beds

3 baths

2,061 sq ft

House

7 WHITE TRELLIS, PLYMOUTH, MA, 02360

Community: Great Island

Great Island

6 CHAMPLAIN CIR, PLYMOUTH, MA, 02360, Plymouth, MA 02360

$659,900

2 beds

2 baths

1,549 sq ft

House

6 CHAMPLAIN CIR, PLYMOUTH, MA, 02360

Community: Great Island

Oak Point

408 GREEN ST, MIDDLEBORO, MA, 02346, Middleboro, MA 02346

$379,000

3 beds

2 baths

1,344 sq ft

House

408 GREEN ST, MIDDLEBORO, MA, 02346

Community: Oak Point

Great Island

6 CLAM PUDDING, PLYMOUTH, MA, 02360, Plymouth, MA 02360

$850,000

3 beds

3 baths

2,580 sq ft

House

6 CLAM PUDDING, PLYMOUTH, MA, 02360

Community: Great Island

Seton Highlands at The Pinehills

24 INVERNESS 24, PLYMOUTH, MA, 02360, Plymouth, MA 02360

$923,000

3 beds

3 baths

2,719 sq ft

Condo

24 INVERNESS 24, PLYMOUTH, MA, 02360

Community: Seton Highlands at The Pinehills

Del Webb Chauncy Lake

5 PETERS FARM WAY 411, WESTBOROUGH, MA, ..., Westborough, MA 01581

$649,995

2 beds

2 baths

1,375 sq ft

Condo

5 PETERS FARM WAY 411, WESTBOROUGH, MA, ...

Community: Del Webb Chauncy Lake

Great Island

5 HIGHBANK TRL, PLYMOUTH, MA, 02360, Plymouth, MA 02360

$691,050

2 beds

3 baths

2,074 sq ft

House

5 HIGHBANK TRL, PLYMOUTH, MA, 02360

Community: Great Island

Orchard Hill

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

$600,000

3 beds

3 baths

2,793 sq ft

Condo

9 BALDWIN CT 9, WESTBOROUGH, MA, 01581

Community: Orchard Hill

Regency at Glen Ellen

43 JAMESON DR 43, MILLIS, MA, 02054, Millis, MA 02054

$1,199,000

3 beds

3 baths

2,873 sq ft

Condo

43 JAMESON DR 43, MILLIS, MA, 02054

Community: Regency at Glen Ellen

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

Questions? Call us: (401) 313-4589

Seton Highlands at The Pinehills

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

$889,000

3 beds

3 baths

2,690 sq ft

Condo

17 ABERDEEN 17, PLYMOUTH, MA, 02360

Community: Seton Highlands at The Pinehills

Del Webb Chauncy Lake

2306 TALBOT WAY 2306, WESTBOROUGH, MA, 0..., Westborough, MA 01581

$559,000

2 beds

2 baths

1,469 sq ft

Condo

2306 TALBOT WAY 2306, WESTBOROUGH, MA, 0...

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

95 homes near Middletown

2 beds

2 baths

1,582 sq ft

Condo

2 beds

2 baths

1,375 sq ft

Condo

2 beds

3 baths

2,301 sq ft

House

2 beds

3 baths

2,417 sq ft

Condo

1 beds

1 baths

1,030 sq ft

Condo

2 beds

2 baths

1,496 sq ft

Condo

1 beds

1 baths

972 sq ft

Condo

2 beds

2 baths

1,452 sq ft

Condo

2 beds

3 baths

1,685 sq ft

Condo

2 beds

3 baths

2,074 sq ft

House

3 beds

3 baths

2,440 sq ft

House

2 beds

3 baths

2,061 sq ft

House

2 beds

2 baths

1,743 sq ft

Condo

3 beds

4 baths

4,483 sq ft

Condo

1 beds

1 baths

1,027 sq ft

Condo

2 beds

2 baths

1,582 sq ft

Condo

3 beds

3 baths

2,555 sq ft

House

2 beds

3 baths

2,601 sq ft

Condo

2 beds

3 baths

2,607 sq ft

Condo

2 beds