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

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

Southport

$400ks - $600ks

Southport, Mashpee, MA

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

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

Upton Ridge

$400ks - $600ks

Upton Ridge, Upton, MA

New Construction | 55+ age-restricted | Built 2019 - present | 139 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 Village at Orchard Me...

$400ks - $500ks

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

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

Orchard Hill

$500ks

Orchard Hill, Westborough, MA

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

Brierly Pond Village

$300ks - $400ks

Brierly Pond Village, Millbury, MA

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

Harmony Place

$400ks - $500ks

Harmony Place, Rutland, MA

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

WestRidge

$700ks

WestRidge, Hudson, MA

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

Woodstone Crossing

$300ks - $400ks

Woodstone Crossing, Weymouth, MA

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

Stonebridge Commons

$500ks

Stonebridge Commons, Hanson, MA

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

Millwood Preserve

$700ks - $800ks

Millwood Preserve, Framingham, MA

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

Pennington Crossing

$300ks - $600ks

Pennington Crossing, Walpole, MA

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

Woodcrest Run

$400ks - $600ks

Woodcrest Run, Sharon, MA

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

Northwoods at Sudbury

$500ks

Northwoods at Sudbury, Sudbury, MA

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

Chilton Park Village

$400ks

Chilton Park Village, Plymouth, MA

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

The Lanterns at Warren Wo...

$500ks - $700ks

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

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

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

Questions? Call us: (401) 313-4589

Adams Farm

$700ks - $800ks

Adams Farm, Shrewsbury, MA

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

Brandywyne

$700ks - $800ks

Brandywyne, South Kingstown, RI

Resale Only | 55+ age-restricted | Built 2011 - 2013 | 37 homes

Blue Heron Pond

$500ks

Blue Heron Pond, Lancaster, MA

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

Hawthorn Preserve

$900ks - $1Ms

Hawthorn Preserve, Braintree, MA

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

Brookedge Village Condomi...

$300ks - $400ks

Brookedge Village Condomi..., South Kingstown, RI

Resale Only | 55+ age-restricted | Built 2007 - 2007 | 28 homes

Wakefield Meadows

$700ks - $800ks

Wakefield Meadows, Wakefield, RI

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

Red Mill Village

$400ks - $600ks

Red Mill Village, Norton, MA

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

Bates Quarry

Bates Quarry, Walpole, MA

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

Tara Woods

$400ks

Tara Woods, Plymouth, MA

Resale Only | 55+ age-restricted | Built 2007 - 2015 | 38 homes

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

Questions? Call us: (401) 313-4589

Bella Vista

$300ks - $400ks

Bella Vista, Glocester, RI

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

Peregrine Woods

$400ks - $600ks

Peregrine Woods, Marshfield, MA

Resale Only | 55+ age-restricted | Built 2002 - 2005 | 32 homes

1 2...3

New 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

New 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

New The Lanterns at Warren Woods

8 LANTERN WAY 8, ASHLAND, MA, 01721, Ashland, MA 01721

$780,000

2 beds

2 baths

1,657 sq ft

Condo

8 LANTERN WAY 8, ASHLAND, MA, 01721

Community: The Lanterns at Warren Woods

New Oak Point

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

$389,000

3 beds

2 baths

1,344 sq ft

House

408 GREEN ST, MIDDLEBORO, MA, 02346

Community: Oak Point

New 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

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

Questions? Call us: (401) 313-4589

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

$654,995

2 beds

2 baths

1,375 sq ft

Condo

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

Community: Del Webb Chauncy Lake

Del Webb Chauncy Lake

5 PETERS FARM WAY 410, WESTBOROUGH, MA, ..., Westborough, MA 01581

$594,995

2 beds

2 baths

1,375 sq ft

Condo

5 PETERS FARM WAY 410, WESTBOROUGH, MA, ...

Community: Del Webb Chauncy Lake

Del Webb Chauncy Lake

5 PETERS FARM WAY 7303, WESTBOROUGH, MA,..., Westborough, MA 01581

$429,995

1 beds

1 baths

972 sq ft

Condo

5 PETERS FARM WAY 7303, WESTBOROUGH, MA,...

Community: Del Webb Chauncy Lake

Del Webb Chauncy Lake

5312 PETERS FARM WAY 312, WESTBOROUGH, M..., Westborough, MA 01581

$699,995

2 beds

2 baths

1,512 sq ft

Condo

5312 PETERS FARM WAY 312, WESTBOROUGH, M...

Community: Del Webb Chauncy Lake

Oak Point

6406 OAK PT, MIDDLEBORO, MA, 02346, Middleboro, MA 02346

$399,000

3 beds

2 baths

1,456 sq ft

House

6406 OAK PT, MIDDLEBORO, MA, 02346

Community: Oak Point

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

$1,299,900

3 beds

3 baths

2,873 sq ft

Condo

43 JAMESON DR 43, MILLIS, MA, 02054

Community: Regency at Glen Ellen

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

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

Questions? Call us: (401) 313-4589

Angell Brook Village

10 ANGELL BROOK DR 10, WEST BOYLSTON, MA..., West Boylston, MA 01583

$540,000

3 beds

2 baths

2,228 sq ft

Condo

10 ANGELL BROOK DR 10, WEST BOYLSTON, MA...

Community: Angell Brook Village

Millwood Preserve

5 BAITING BROOK RD 5, FRAMINGHAM, MA, 01..., Framingham, MA 01701

$1,429,000

2 beds

4 baths

3,396 sq ft

Condo

5 BAITING BROOK RD 5, FRAMINGHAM, MA, 01...

Community: Millwood Preserve

The Preserve at Hunters Hill

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

$799,900

2 beds

2 baths

1,600 sq ft

House

72 CLUB HOUSE DR, DIGHTON, MA, 02715

Community: The Preserve at Hunters Hill

The Preserve at Hunters Hill

127 CLUBHOUSE DR, DIGHTON, MA, 02715, Dighton, MA 02715

$756,275

2 beds

2 baths

1,815 sq ft

House

127 CLUBHOUSE DR, DIGHTON, MA, 02715

Community: The Preserve at Hunters Hill

The Village at Orchard Meadows

79 ORCHARD MEADOWS DR 79, SHREWSBURY, MA..., Shrewsbury, MA 01545

$534,900

2 beds

2 baths

1,370 sq ft

Condo

79 ORCHARD MEADOWS DR 79, SHREWSBURY, MA...

Community: The Village at Orchard Meadows

Oak Point

307 BLUEBERRY CIR, MIDDLEBORO, MA, 02346, Middleboro, MA 02346

$450,000

3 beds

2 baths

1,700 sq ft

House

307 BLUEBERRY CIR, MIDDLEBORO, MA, 02346

Community: Oak Point

The Pines at Hathaway Pond

14 HATHAWAY POND CIR 14, ROCHESTER, MA, ..., Rochester, MA 02770

$685,000

2 beds

3 baths

1,776 sq ft

Condo

14 HATHAWAY POND CIR 14, ROCHESTER, MA, ...

Community: The Pines at Hathaway Pond

WestRidge

68 HASTINGS RD 68, HUDSON, MA, 01749, Hudson, MA 01749

$835,000

3 beds

3 baths

2,264 sq ft

Condo

68 HASTINGS RD 68, HUDSON, MA, 01749

Community: WestRidge

Southport

14 STONY BROOK DR 516, MASHPEE, MA, 0264..., Mashpee, MA 02649

$699,000

2 beds

3 baths

1,792 sq ft

Condo

14 STONY BROOK DR 516, MASHPEE, MA, 0264...

Community: Southport

Pennington Crossing

4402 PENNINGTON DR 4402, WALPOLE, MA, 02..., Walpole, MA 02081

$799,900

2 beds

2 baths

1,339 sq ft

Condo

4402 PENNINGTON DR 4402, WALPOLE, MA, 02...

Community: Pennington Crossing

The Trails

21 BIRKDALE LN 21, HOPKINTON, MA, 01748, Hopkinton, MA 01748

$999,000

2 beds

4 baths

3,610 sq ft

Condo

21 BIRKDALE LN 21, HOPKINTON, MA, 01748

Community: The Trails

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

Questions? Call us: (401) 313-4589

Northwoods at Sudbury

10 NORTHWOOD DR 301, SUDBURY, MA, 01776, Sudbury, MA 01776

$649,000

1 beds

2 baths

1,668 sq ft

Condo

10 NORTHWOOD DR 301, SUDBURY, MA, 01776

Community: Northwoods at Sudbury

Sawyer's Reach

62 MARINERS WAY 210, PLYMOUTH, MA, 02360, Plymouth, MA 02360

$504,900

1 beds

2 baths

910 sq ft

Condo

62 MARINERS WAY 210, PLYMOUTH, MA, 02360

Community: Sawyer's Reach

Great Island

23 WOODSONG, PLYMOUTH, MA, 02360, Plymouth, MA 02360

$949,000

2 beds

2 baths

2,096 sq ft

House

23 WOODSONG, PLYMOUTH, MA, 02360

Community: Great Island

Great Island

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

$725,000

2 beds

3 baths

2,061 sq ft

House

7 MADISON REACH, PLYMOUTH, MA, 02360

Community: Great Island

Great Island

28 CROSS WIND, PLYMOUTH, MA, 02360, Plymouth, MA 02360

$745,000

2 beds

3 baths

2,061 sq ft

House

28 CROSS WIND, PLYMOUTH, MA, 02360

Community: Great Island

Great Island

28 COTTAGE CV, PLYMOUTH, MA, 02360, Plymouth, MA 02360

$929,000

2 beds

3 baths

3,276 sq ft

House

28 COTTAGE CV, PLYMOUTH, MA, 02360

Community: Great Island

Upton Ridge

56 SHANNON WAY 56, UPTON, MA, 01568, Upton, MA 01568

$709,000

2 beds

3 baths

1,950 sq ft

Condo

56 SHANNON WAY 56, UPTON, MA, 01568

Community: Upton Ridge

Southport

68 LEISURE GREEN DR 68, MASHPEE, MA, 026..., Mashpee, MA 02649

$779,900

2 beds

3 baths

1,620 sq ft

House

68 LEISURE GREEN DR 68, MASHPEE, MA, 026...

Community: Southport

Seton Highlands at The Pinehills

26 ABERDEEN 26, PLYMOUTH, MA, 02360, Plymouth, MA 02360

$1,065,000

3 beds

5 baths

3,680 sq ft

Condo

26 ABERDEEN 26, PLYMOUTH, MA, 02360

Community: Seton Highlands at The Pinehills

Southport

18 BONWOOD DR 402, MASHPEE, MA, 02649, Mashpee, MA 02649

$599,000

2 beds

4 baths

2,527 sq ft

Condo

18 BONWOOD DR 402, MASHPEE, MA, 02649

Community: Southport

Great Island

39 COTTAGE CV, PLYMOUTH, MA, 02360, Plymouth, MA 02360

$759,000

2 beds

3 baths

2,427 sq ft

House

39 COTTAGE CV, PLYMOUTH, MA, 02360

Community: Great Island

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

Questions? Call us: (401) 313-4589

Orchard Hill

19 IMPERIAL CT 19, WESTBOROUGH, MA, 0158..., Westborough, MA 01581

$597,500

2 beds

3 baths

2,183 sq ft

Condo

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

Community: Orchard Hill

Stonebridge Commons

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

$675,000

2 beds

3 baths

2,071 sq ft

Condo

31 STONEBRIDGE DR 31, HANSON, MA, 02341

Community: Stonebridge Commons

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

91 homes near Middletown

2 beds

3 baths

2,061 sq ft

House

2 beds

2 baths

1,549 sq ft

House

2 beds

2 baths

1,657 sq ft

Condo

3 beds

2 baths

1,344 sq ft

House

3 beds

3 baths

2,580 sq ft

House

3 beds

3 baths

2,719 sq ft

Condo

2 beds

2 baths

1,375 sq ft

Condo

2 beds

2 baths

1,375 sq ft

Condo

1 beds

1 baths

972 sq ft

Condo

2 beds

2 baths

1,512 sq ft

Condo

3 beds

2 baths

1,456 sq ft

House

2 beds

3 baths

2,074 sq ft

House

3 beds

3 baths

2,793 sq ft

Condo

3 beds

3 baths

2,873 sq ft

Condo

3 beds

3 baths

2,690 sq ft

Condo

2 beds

2 baths

1,469 sq ft

Condo

3 beds

2 baths

2,228 sq ft

Condo

2 beds

4 baths

3,396 sq ft

Condo

2 beds

2 baths

1,600 sq ft

House

2 beds