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

80 communities near Middletown

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Bay Ridge
$600Ks - $800Ks
Bay Ridge, Middletown, RI
Resale Only | 55+ age-restricted | Built 2008 - 2014 | 60 homes
Bailey Brook
$600Ks - $700Ks
Bailey Brook, Middletown, RI
Resale Only | 55+ age-restricted | Built 2018 - 2024 | 36 homes
5 rating (3 reviews) Oak Point
$300Ks
Oak Point, Middleborough, MA
New and Resale | 55+ age-restricted | Built 1999 - present | 1,150 homes
Southport
$400Ks - $700Ks
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
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (401) 313-4589
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Questions? Call us: (401) 313-4589
Great Island
$700Ks - $800Ks
Great Island, Plymouth, MA
Resale Only | 55+ age-restricted | Built 2002 - 2015 | 600 homes
Regency at Glen Ellen
$1Ms
Regency at Glen Ellen, Millis, MA
New Construction | 55+ age-restricted | Built 2017 - present | 324 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
The Villages on Mount Hop...
$600Ks - $1Ms
The Villages on Mount Hop..., Tiverton, RI
New and Resale | 55+ age-restricted | Built 2003 - present | 230 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.
Sawyer's Reach
$400Ks - $600Ks
Sawyer's Reach, Plymouth, MA
New and Resale | 55+ age-restricted | Built 2017 - present | 224 homes
Read the Ultimate 55+ Rental Guide Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
Woodstone Crossing
$400Ks
Woodstone Crossing, Weymouth, MA
Resale Only | Age-targeted | Built 2015 - 2019 | 200 homes
Brierly Pond Village
$400Ks
Brierly Pond Village, Millbury, MA
Resale Only | 55+ age-restricted | Built 2003 - 2013 | 199 homes
Pennington Crossing
$500Ks
Pennington Crossing, Walpole, MA
New Construction | 55+ age-restricted | Built 2018 - present | 172 homes
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Questions? Call us: (401) 313-4589
The Trails
$900Ks - $1Ms
The Trails, Hopkinton, MA
New Construction | 55+ age-restricted | Built 2017 - present | 170 homes
Red Mill Village
$500Ks - $800Ks
Red Mill Village, Norton, MA
Resale Only | 55+ age-restricted | Built 2012 - 2014 | 156 homes
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Questions? Call us: (401) 313-4589
Villages at Weathervane
$800Ks - $1Ms
Villages at Weathervane, Weymouth, MA
Resale Only | 55+ age-restricted | Built 2003 - 2010 | 149 homes
Harmony Place
$400Ks - $500Ks
Harmony Place, Rutland, MA
New Construction | 55+ age-restricted | Built 2023 - present | 142 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.
Wakefield Meadows
$700Ks - $800Ks
Wakefield Meadows, Wakefield, RI
Resale Only | 55+ age-restricted | Built 2009 - 2015 | 142 homes
The Preserve at Hunters H...
$700Ks - $800Ks
The Preserve at Hunters H..., Dighton, MA
New and Resale | 55+ age-restricted | Built 2006 - present | 140 homes
Upton Ridge
$600Ks
Upton Ridge, Upton, MA
New Construction | 55+ age-restricted | Built 2019 - present | 139 homes
Read the Ultimate 55+ Rental Guide Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
WestRidge
$700Ks - $1Ms
WestRidge, Hudson, MA
Resale Only | 55+ age-restricted | Built 2009 - 2016 | 136 homes
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Angell Brook Village
$400Ks
Angell Brook Village, West Boylston, MA
Resale Only | 55+ age-restricted | Built 2005 - 2012 | 132 homes
Millwood Preserve
$1Ms
Millwood Preserve, Framingham, MA
New Construction | 55+ age-restricted | Built 2020 - present | 129 homes
The Village at Westminste...
$500Ks - $600Ks
The Village at Westminste..., Holden, MA
New and Resale | 55+ age-restricted | Built 2006 - present | 125 homes
Stonebridge Commons
$600Ks - $700Ks
Stonebridge Commons, Hanson, MA
Resale Only | 55+ age-restricted | Built 2007 - 2018 | 121 homes
Want to learn more about 55+ rental communities in Middletown? 55places can help!
Questions? Call us: (401) 313-4589
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.
Seton Highlands at The Pi...
$800Ks - $900Ks
Seton Highlands at The Pi..., Plymouth, MA
New and Resale | 55+ age-restricted | Built 2008 - present | 120 homes
Summer Reach
$400Ks - $500Ks
Summer Reach, Plymouth, MA
Resale Only | 55+ age-restricted | Built 2017 - 2020 | 114 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
New England Commons
$400Ks
New England Commons, Webster, MA
New and Resale | 55+ age-restricted | Built 2005 - present | 100 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
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (401) 313-4589
Read the Ultimate 55+ Rental Guide Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
Orchard Hill
$600Ks
Orchard Hill, Westborough, MA
Resale Only | 55+ age-restricted | Built 2002 - 2010 | 100 homes
Bates Quarry
Bates Quarry, Walpole, MA
New Construction | 55+ age-restricted | Built 2025 - present | 100 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
The Village at Auburnvill...
$300Ks - $400Ks
The Village at Auburnvill..., Whitman, MA
Resale Only | 55+ age-restricted | Built 2004 - 2014 | 92 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.
The Seasons at Salisbury
$600Ks
The Seasons at Salisbury, Holden, MA
Resale Only | 55+ age-restricted | Built 2002 - 2006 | 91 homes
Want to learn more about 55+ rental 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
Adams Farm
$800Ks - $900Ks
Adams Farm, Shrewsbury, MA
Resale Only | 55+ age-restricted | Built 2005 - 2013 | 90 homes
Bella Vista
$300Ks - $400Ks
Bella Vista, Glocester, RI
Resale Only | 55+ age-restricted | Built 2015 - 2021 | 70 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
Regency at Assabet Ridge
$500Ks - $600Ks
Regency at Assabet Ridge, Marlborough, MA
Resale Only | 55+ age-restricted | Built 2010 - 2015 | 69 homes
1...2
Southport 1 UPLAND CIR # 1, MASHPEE, MA, 02649, Mashpee, MA 02649
$485,000

2 beds

|

2 baths

|

1,333 sq ft

|

Condo

1 UPLAND CIR # 1, MASHPEE, MA, 02649
Community: Southport
30 Coppersmith 30 COPPERSMITH WAY # 408, CANTON, MA, 02..., Canton, MA 02021
$622,995

2 beds

|

2 baths

|

1,425 sq ft

|

Condo

30 COPPERSMITH WAY # 408, CANTON, MA, 02...
Community: 30 Coppersmith
Harmony Place 132 FIDELITY DR # 61, RUTLAND, MA, 01543, Rutland, MA 01543
$539,000

2 beds

|

2 baths

|

2,149 sq ft

|

Condo

132 FIDELITY DR # 61, RUTLAND, MA, 01543
Community: Harmony Place
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 210 FIDELITY DR 84, RUTLAND, MA, 01543, Rutland, MA 01543
$498,000

2 beds

|

2 baths

|

1,582 sq ft

|

Condo

210 FIDELITY DR 84, RUTLAND, MA, 01543
Community: Harmony Place
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (401) 313-4589
Want to learn more about 55+ rental communities in Middletown? 55places can help!
Questions? Call us: (401) 313-4589
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
Harmony Place 12 FIDELITY DR # 6, RUTLAND, MA, 01543, Rutland, MA 01543
$498,000

2 beds

|

2 baths

|

1,582 sq ft

|

Condo

12 FIDELITY DR # 6, RUTLAND, MA, 01543
Community: Harmony Place
Seton Highlands at The Pinehills 105 SETON HIGHLANDS # 105, PLYMOUTH, MA,..., Plymouth, MA 02360
$849,000

2 beds

|

3 baths

|

2,186 sq ft

|

Condo

105 SETON HIGHLANDS # 105, PLYMOUTH, MA,...
Southport 20 TWIN OAKS DR # 20, MASHPEE, MA, 02649, Mashpee, MA 02649
$524,900

2 beds

|

2 baths

|

1,491 sq ft

|

Condo

20 TWIN OAKS DR # 20, MASHPEE, MA, 02649
Community: Southport
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.
Southport 10 KETTLE LN # 10, MASHPEE, MA, 02649, Mashpee, MA 02649
$535,000

2 beds

|

3 baths

|

1,685 sq ft

|

Condo

10 KETTLE LN # 10, MASHPEE, MA, 02649
Community: Southport
Read the Ultimate 55+ Rental Guide Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
Del Webb Chauncy Lake 11101 PETERS FARM WAY # 101, WESTBOROUGH..., Westborough, MA 01581
$599,000

2 beds

|

2 baths

|

1,469 sq ft

|

Condo

11101 PETERS FARM WAY # 101, WESTBOROUGH...
Southport 15 PEBBLE BEACH AVE # 2005-103, MASHPEE,..., Mashpee, MA 02649
$549,000

2 beds

|

3 baths

|

1,685 sq ft

|

Condo

15 PEBBLE BEACH AVE # 2005-103, MASHPEE,...
Community: Southport
The Trails 14 WATERVILLE LN # 14, HOPKINTON, MA, 01..., Hopkinton, MA 01748
$989,000

2 beds

|

3 baths

|

2,274 sq ft

|

Condo

14 WATERVILLE LN # 14, HOPKINTON, MA, 01...
Community: The Trails
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (401) 313-4589
Southport 80 PINE HILL BLVD # 80, MASHPEE, MA, 026..., Mashpee, MA 02649
$599,000

2 beds

|

3 baths

|

2,208 sq ft

|

Condo

80 PINE HILL BLVD # 80, MASHPEE, MA, 026...
Community: Southport
The Preserve at Hunters Hill 3051 CLUBHOUSE DR 78, DIGHTON, MA, 02715, Dighton, MA 02715
$829,225

2 beds

|

2 baths

|

2,266 sq ft

|

House

3051 CLUBHOUSE DR 78, DIGHTON, MA, 02715
Want to learn more about 55+ rental communities in Middletown? 55places can help!
Questions? Call us: (401) 313-4589
The Villages at Walker Meadow 9 SHAKER WAY # 9, WESTBOROUGH, MA, 01581, Westborough, MA 01581
$700,000

2 beds

|

2 baths

|

2,090 sq ft

|

Condo

9 SHAKER WAY # 9, WESTBOROUGH, MA, 01581
New Great Island 25 GREAT POINTE, PLYMOUTH, MA, 02360, Plymouth, MA 02360
$839,000

3 beds

|

3 baths

|

2,822 sq ft

|

House

25 GREAT POINTE, PLYMOUTH, MA, 02360
Community: Great Island
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.
New Enclave at Hudson 16 BARNES BLVD # 16, HUDSON, MA, 01749, Hudson, MA 01749
$1,299,000

2 beds

|

4 baths

|

3,731 sq ft

|

Condo

16 BARNES BLVD # 16, HUDSON, MA, 01749
Community: Enclave at Hudson
Regency at Glen Ellen 86 GLEN ELLEN BLVD # 86, MILLIS, MA, 020..., Millis, MA 02054
$1,299,900

3 beds

|

3 baths

|

3,060 sq ft

|

Condo

86 GLEN ELLEN BLVD # 86, MILLIS, MA, 020...
The Village at Westminster Place 27 TEA PARTY CIR # 27, HOLDEN, MA, 01520, Holden, MA 01520
$579,900

3 beds

|

3 baths

|

1,895 sq ft

|

House

27 TEA PARTY CIR # 27, HOLDEN, MA, 01520
Read the Ultimate 55+ Rental Guide Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
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
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (401) 313-4589
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...
Del Webb Chauncy Lake 2 TALBOT WAY 2103, WESTBOROUGH, MA, 0158..., Westborough, MA 01581
$395,000

1 beds

|

1 baths

|

956 sq ft

|

Condo

2 TALBOT WAY 2103, WESTBOROUGH, MA, 0158...
Del Webb Chauncy Lake 2 CODMAN WAY 104, WESTBOROUGH, MA, 01581, Westborough, MA 01581
$389,999

1 beds

|

1 baths

|

972 sq ft

|

Condo

2 CODMAN WAY 104, WESTBOROUGH, MA, 01581
Stonebridge Commons 26 STONEBRIDGE DR # 26, HANSON, MA, 0234..., Hanson, MA 02341
$710,000

3 beds

|

3 baths

|

2,158 sq ft

|

Condo

26 STONEBRIDGE DR # 26, HANSON, MA, 0234...
Community: Stonebridge Commons
Want to learn more about 55+ rental communities in Middletown? 55places can help!
Questions? Call us: (401) 313-4589
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.
Oak Point 2602 GREEN ST, MIDDLEBORO, MA, 02346, Middleboro, MA 02346
$349,900

2 beds

|

2 baths

|

1,680 sq ft

|

House

2602 GREEN ST, MIDDLEBORO, MA, 02346
Community: Oak Point
Harmony Place 212 FIDELITY DR 83, RUTLAND, MA, 01543, Rutland, MA 01543
$498,000

2 beds

|

2 baths

|

1,582 sq ft

|

Condo

212 FIDELITY DR 83, RUTLAND, MA, 01543
Community: Harmony Place
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
Sawyer's Reach 1 MARINERS WAY UNIT 309, PLYMOUTH, MA, 0..., Plymouth, MA 02360
$635,000

2 beds

|

2 baths

|

1,308 sq ft

|

Condo

1 MARINERS WAY UNIT 309, PLYMOUTH, MA, 0...
Community: Sawyer's Reach
Oak Point 3402 ISLAND DR, MIDDLEBORO, MA, 02346, Middleboro, MA 02346
$349,900

3 beds

|

2 baths

|

1,344 sq ft

|

House

3402 ISLAND 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
Read the Ultimate 55+ Rental Guide Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
Southport 4 N RIDGE RD # 431, MASHPEE, MA, 02649, Mashpee, MA 02649
$524,900

2 beds

|

2 baths

|

1,338 sq ft

|

Condo

4 N RIDGE RD # 431, MASHPEE, MA, 02649
Community: Southport
The Preserve at Hunters Hill 3057 CLUB HOUSE DR MODEL, DIGHTON, MA, 0..., Dighton, MA 02715
$739,900

2 beds

|

2 baths

|

2,044 sq ft

|

House

3057 CLUB HOUSE DR MODEL, DIGHTON, MA, 0...
The Preserve at Hunters Hill RR74 CLUB HOUSE DR RR74, DIGHTON, MA, 02..., Dighton, MA 02715
$769,900

2 beds

|

2 baths

|

2,216 sq ft

|

House

RR74 CLUB HOUSE DR RR74, DIGHTON, MA, 02...
The Preserve at Hunters Hill G1 CLUB HOUSE DR G1, DIGHTON, MA, 02715, Dighton, MA 02715
$729,900

2 beds

|

2 baths

|

1,928 sq ft

|

House

G1 CLUB HOUSE DR G1, DIGHTON, MA, 02715
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.
The Preserve at Hunters Hill RR76 CLUBHOUSE DR RR76, DIGHTON, MA, 027..., Dighton, MA 02715
$789,900

2 beds

|

2 baths

|

2,700 sq ft

|

House

RR76 CLUBHOUSE DR RR76, DIGHTON, MA, 027...
Want to learn more about 55+ rental communities in Middletown? 55places can help!
Questions? Call us: (401) 313-4589
Del Webb Chauncy Lake 5 PETERS FARM WAY # 207, WESTBOROUGH, MA..., Westborough, MA 01581
$671,025

2 beds

|

2 baths

|

1,512 sq ft

|

Condo

5 PETERS FARM WAY # 207, WESTBOROUGH, MA...
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
Del Webb Chauncy Lake 5 PETERS FARM WAY # 101, WESTBOROUGH, MA..., Westborough, MA 01581
$650,535

2 beds

|

2 baths

|

1,496 sq ft

|

Condo

5 PETERS FARM WAY # 101, WESTBOROUGH, MA...
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 # 112, WESTBOROUGH, MA..., Westborough, MA 01581
$480,978

1 beds

|

1 baths

|

1,058 sq ft

|

Condo

5 PETERS FARM WAY # 112, WESTBOROUGH, MA...
Del Webb Chauncy Lake 5 PETERS FARM WAY # 105, WESTBOROUGH, MA..., Westborough, MA 01581
$430,975

1 beds

|

1 baths

|

958 sq ft

|

Condo

5 PETERS FARM WAY # 105, WESTBOROUGH, MA...

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