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

68 homes 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

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

Harmony Place

$400ks - $500ks

Harmony Place, Rutland, MA

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

30 Coppersmith

$700ks

30 Coppersmith, Canton, MA

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

The Trails

$500ks - $700ks

The Trails, Hopkinton, MA

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

Regency at Glen Ellen

$700ks - $900ks

Regency at Glen Ellen, Millis, MA

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

Lake Point Village

$400ks - $600ks

Lake Point Village, Lakeville, MA

New Construction | 55+ age-restricted | Built 2020 - present | 66 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

Bates Quarry

Bates Quarry, Walpole, MA

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

Great Island

$600ks

Great Island, Plymouth, MA

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

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

Questions? Call us: (401) 313-4589

Brierly Pond Village

$300ks - $400ks

Brierly Pond Village, Millbury, MA

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

Rockwood Meadows

$600ks - $700ks

Rockwood Meadows, Upton, MA

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

Bigelow Farm

$500ks - $600ks

Bigelow Farm, Northborough, MA

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

Brooksmont

$400ks - $600ks

Brooksmont, Holliston, MA

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

Forest Glen

$400ks - $500ks

Forest Glen, Uxbridge, MA

New Construction | 55+ age-restricted | Built 2018 - present | 44 homes

Regency at Assabet Ridge

$500ks - $600ks

Regency at Assabet Ridge, Marlborough, MA

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

Holliston Woods

$500ks - $700ks

Holliston Woods, Holliston, MA

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

Summer Reach

$400ks - $500ks

Summer Reach, Plymouth, MA

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

The Villages at Crane Mea...

$400ks

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

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

The Village at Auburnvill...

$300ks - $400ks

The Village at Auburnvill..., Whitman, MA

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

The Seasons at Salisbury

$400ks - $500ks

The Seasons at Salisbury, Holden, MA

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

Duxbury Estates

$700ks - $800ks

Duxbury Estates, Duxbury, MA

Resale Only | 55+ age-restricted | Built 2008 - 2013 | 44 homes

Peregrine Woods

$400ks - $600ks

Peregrine Woods, Marshfield, MA

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

Tara Woods

$400ks

Tara Woods, Plymouth, MA

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

Center Commons

$500ks - $600ks

Center Commons, Pembroke, MA

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

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

Questions? Call us: (401) 313-4589

Donovan Farm

$500ks - $700ks

Donovan Farm, Norwell, MA

Resale Only | 55+ age-restricted | Built 2001 - 2003 | 40 homes

The Elms of Hanover

$500ks - $700ks

The Elms of Hanover, Hanover, MA

Resale Only | 55+ age-restricted | Built 2003 - 2004 | 51 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

Balancing Rock

$500ks - $600ks

Balancing Rock, Holliston, MA

Resale Only | 55+ age-restricted | Built 2006 - 2008 | 49 homes

Chilton Park Village

$400ks

Chilton Park Village, Plymouth, MA

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

Cranberry Grove

$200ks - $300ks

Cranberry Grove, Wareham, MA

Resale Only | 55+ age-restricted | Built 2001 - 2001 | 36 homes

Kensington at The Pinehil...

$500ks

Kensington at The Pinehil..., Plymouth, MA

New Construction | Age-targeted | Built 2017 - present | 17 homes

Arbor Hills

$400ks - $500ks

Arbor Hills, Kingston, MA

Resale Only | 55+ age-restricted | Built 2003 - 2005 | 54 homes

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

Questions? Call us: (401) 313-4589

Mattapoisett Landing

$400ks - $500ks

Mattapoisett Landing, Mattapoisett, MA

Resale Only | 55+ age-restricted | Built 2012 - 2015 | 27 homes

Orchard Hill

$500ks

Orchard Hill, Westborough, MA

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

40 ADAMS FARM RD 40, SHREWSBURY, MA, 015...

Condo

30 COPPERSMITH WAY # 309, CANTON, MA, 02...

Condo

153 LEISURE GREEN DR # 749, MASHPEE, MA,...

Community: Southport

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

Questions? Call us: (401) 313-4589

Southport

50 PINE HILL BLVD # 46, MASHPEE, MA, 026..., Mashpee, MA 02649

$479,000

2 beds

2 baths

1,338 sq ft

Condo

50 PINE HILL BLVD # 46, MASHPEE, MA, 026...

Community: Southport

Brooksmont

$724,900

2 beds

3 baths

2,360 sq ft

Condo

59 BROOKSMONT DR # 59, HOLLISTON, MA, 01...

Community: Brooksmont

Regency at Glen Ellen

13 HATTIE LN 13, MILLIS, MA, 02054, Millis, MA 02054

$920,000

2 beds

3 baths

2,627 sq ft

Condo

13 HATTIE LN 13, MILLIS, MA, 02054

Community: Regency at Glen Ellen

The Villages at Walker Meadow

5 WESSONVILLE VILLAGE WAY 5, WESTBOROUGH..., Westborough, MA 01581

$739,000

2 beds

3 baths

2,090 sq ft

Condo

5 WESSONVILLE VILLAGE WAY 5, WESTBOROUGH...

Community: The Villages at Walker Meadow

Del Webb Chauncy Lake

1102 PETERS FARM WAY # 1102, WESTBOROUGH..., Westborough, MA 01581

$419,900

1 beds

1 baths

956 sq ft

Condo

1102 PETERS FARM WAY # 1102, WESTBOROUGH...

Community: Del Webb Chauncy Lake

Del Webb Chauncy Lake

5 PETERS FARM WAY 103, WESTBOROUGH, MA, ..., Westborough, MA 01581

$440,485

1 beds

1 baths

972 sq ft

Condo

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

Community: Del Webb Chauncy Lake

The Elms of Hanover

18 WINTERBERRY LN # 18, HANOVER, MA, 023..., Hanover, MA 02339

$785,000

2 beds

3 baths

2,258 sq ft

Condo

18 WINTERBERRY LN # 18, HANOVER, MA, 023...

Community: The Elms of Hanover

Harmony Place

20 FIDELITY DR # 10, RUTLAND, MA, 01543, Rutland, MA 01543

$498,000

2 beds

2 baths

1,582 sq ft

Condo

20 FIDELITY DR # 10, RUTLAND, MA, 01543

Community: Harmony Place

Lake Point Village

57 LONG POINT RD 208, LAKEVILLE, MA, 023..., Lakeville, MA 02347

$509,900

2 beds

2 baths

1,453 sq ft

Condo

57 LONG POINT RD 208, LAKEVILLE, MA, 023...

Community: Lake Point Village

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

Questions? Call us: (401) 313-4589

Lake Point Village

57 LONG POINT RD UNIT 104, LAKEVILLE, MA..., Lakeville, MA 02347

$589,000

2 beds

2 baths

1,334 sq ft

Condo

57 LONG POINT RD UNIT 104, LAKEVILLE, MA...

Community: Lake Point Village

Regency at Assabet Ridge

28 BOWOOD LN # 28, MARLBOROUGH, MA, 0175..., Marlborough, MA 01752

$759,900

3 beds

3 baths

2,205 sq ft

Condo

28 BOWOOD LN # 28, MARLBOROUGH, MA, 0175...

Community: Regency at Assabet Ridge

Southport

18 WINDWARD ST # 18, MASHPEE, MA, 02649, Mashpee, MA 02649

$479,900

2 beds

2 baths

1,333 sq ft

Condo

18 WINDWARD ST # 18, MASHPEE, MA, 02649

Community: Southport

Harmony Place

18 FIDELITY DR # 9, RUTLAND, MA, 01543, Rutland, MA 01543

$498,000

2 beds

2 baths

1,582 sq ft

Condo

18 FIDELITY DR # 9, RUTLAND, MA, 01543

Community: Harmony Place

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

Sawyer's Reach

62 MARINERS WAY UNIT 305, PLYMOUTH, MA, ..., Plymouth, MA 02360

$499,900

1 beds

1 baths

804 sq ft

Condo

62 MARINERS WAY UNIT 305, PLYMOUTH, MA, ...

Community: Sawyer's Reach

Harmony Place

10 FIDELITY DR # 5, RUTLAND, MA, 01543, Rutland, MA 01543

$498,000

2 beds

2 baths

1,582 sq ft

Condo

10 FIDELITY DR # 5, RUTLAND, MA, 01543

Community: Harmony Place

Del Webb Chauncy Lake

2 CODMAN WAY 408, WESTBOROUGH, MA, 01581, Westborough, MA 01581

$589,999

2 beds

2 baths

1,375 sq ft

Condo

2 CODMAN WAY 408, WESTBOROUGH, MA, 01581

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

5 PETERS FARM WAY 5205, WESTBOROUGH, MA,..., Westborough, MA 01581

$576,025

2 beds

2 baths

1,166 sq ft

Condo

5 PETERS FARM WAY 5205, WESTBOROUGH, MA,...

Community: Del Webb Chauncy Lake

Del Webb Chauncy Lake

4203 PETERS FARM WAY # 4203, WESTBOROUGH..., Westborough, MA 01581

$470,000

1 beds

1 baths

945 sq ft

Condo

4203 PETERS FARM WAY # 4203, WESTBOROUGH...

Community: Del Webb Chauncy Lake

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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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55+ homes for sale in Tiverton

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68 homes

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

80 communities near Middletown

68 homes near Middletown

2 beds

3 baths

2,392 sq ft

Condo

1 beds

2 baths

1,113 sq ft

Condo

2 beds

3 baths

2,671 sq ft

Condo

2 beds

2 baths

1,512 sq ft

Condo

2 beds

3 baths

2,757 sq ft

Condo

2 beds

3 baths

2,144 sq ft

Condo

2 beds

2 baths

1,496 sq ft

Condo

2 beds

2 baths

1,496 sq ft

Condo

2 beds

2 baths

1,370 sq ft

Condo

2 beds

3 baths

4,054 sq ft

Condo

2 beds

2 baths

1,469 sq ft

Condo

2 beds

3 baths

1,659 sq ft

Condo

1 beds

1 baths

1,119 sq ft

Condo

2 beds

3 baths

2,021 sq ft

Condo

2 beds

2 baths

1,582 sq ft

Condo

1 beds

1 baths

1,030 sq ft

Condo

2 beds

2 baths

1,525 sq ft

Condo

2 beds

3 baths

1,871 sq ft

Condo

2 beds

4 baths

2,100 sq ft

Condo

2 beds