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Middletown, RI 55+ active adult communities & homes for sale - Page 2

80 communities near Middletown

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Holliston Woods
$500Ks - $700Ks
Holliston Woods, Holliston, MA
Resale Only | 55+ age-restricted | Built 2016 - 2018 | 66 homes
Brooksmont
$600Ks - $700Ks
Brooksmont, Holliston, MA
Resale Only | 55+ age-restricted | Built 2017 - 2020 | 66 homes
Lake Point Village
$400Ks
Lake Point Village, Lakeville, MA
New Construction | 55+ age-restricted | Built 2020 - present | 66 homes
Enclave at Hudson
$800Ks - $1Ms
Enclave at Hudson, Hudson, MA
New Construction | 55+ age-restricted | Built 2021 - present | 64 homes
30 Coppersmith
$400Ks - $800Ks
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
The Pines at Hathaway Pon...
$300Ks - $500Ks
The Pines at Hathaway Pon..., Rochester, MA
Resale Only | 55+ age-restricted | Built 2006 - 2014 | 61 homes
Rockland Glen
$300Ks - $500Ks
Rockland Glen, Rockland, MA
Resale Only | 55+ age-restricted | Built 2008 - 2015 | 60 homes
Westbrook Crossing
$400Ks - $500Ks
Westbrook Crossing, Dedham, MA
Resale Only | 55+ age-restricted | Built 2003 - 2004 | 60 homes
Northside Meadows
$600Ks - $700Ks
Northside Meadows, Framingham, MA
Resale Only | 55+ age-restricted | Built 2017 - 2019 | 60 homes
Blue Heron Pond
$400Ks - $500Ks
Blue Heron Pond, Lancaster, MA
Resale Only | 55+ age-restricted | Built 2006 - 2014 | 58 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.
Rockwood Meadows
$600Ks - $700Ks
Rockwood Meadows, Upton, MA
New Construction | 55+ age-restricted | Built 2016 - present | 58 homes
Liberty Woods
$600Ks - $700Ks
Liberty Woods, Hanson, MA
New Construction | 55+ age-restricted | Built 2023 - present | 56 homes
Wolcott Woods
$1Ms - $2Ms
Wolcott Woods, Milton, MA
New Construction | 55+ age-restricted | Built 2020 - present | 54 homes
Arbor Hills
$400Ks - $500Ks
Arbor Hills, Kingston, MA
Resale Only | 55+ age-restricted | Built 2003 - 2005 | 54 homes
The Elms of Hanover
$500Ks - $700Ks
The Elms of Hanover, Hanover, MA
Resale Only | 55+ age-restricted | Built 2003 - 2004 | 51 homes
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (401) 313-4589
Balancing Rock
$500Ks - $600Ks
Balancing Rock, Holliston, MA
Resale Only | 55+ age-restricted | Built 2006 - 2008 | 49 homes
Pheasant Hill
$300Ks - $400Ks
Pheasant Hill, Northborough, MA
Resale Only | 55+ age-restricted | Built 2005 - 2006 | 48 homes
Rolling Mill
$600Ks - $700Ks
Rolling Mill, Plymouth, MA
Resale Only | 55+ age-restricted | Built 2018 - 2021 | 46 homes
Seaside at Scituate - The...
$900Ks - $1Ms
Seaside at Scituate - The..., Scituate, MA
New Construction | 55+ age-restricted | Built 2019 - present | 44 homes
Forest Glen
$400Ks - $500Ks
Forest Glen, Uxbridge, MA
New Construction | 55+ age-restricted | Built 2018 - present | 44 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.
Duxbury Estates
$500Ks - $700Ks
Duxbury Estates, Duxbury, MA
Resale Only | 55+ age-restricted | Built 2008 - 2013 | 44 homes
Center Commons
$500Ks - $600Ks
Center Commons, Pembroke, MA
Resale Only | 55+ age-restricted | Built 2004 - 2009 | 44 homes
Northwoods at Sudbury
$600Ks - $1Ms
Northwoods at Sudbury, Sudbury, MA
Resale Only | 55+ age-restricted | Built 1999 - 2019 | 43 homes
Bigelow Farm
$500Ks - $600Ks
Bigelow Farm, Northborough, MA
Resale Only | 55+ age-restricted | Built 2006 - 2013 | 41 homes
Donovan Farm
$500Ks - $700Ks
Donovan Farm, Norwell, MA
Resale Only | 55+ age-restricted | Built 2001 - 2003 | 40 homes
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (401) 313-4589
Spring Meadow
$700Ks
Spring Meadow, Hanover, MA
Resale Only | 55+ age-restricted | Built 2004 - 2007 | 39 homes
Tara Woods
$400Ks
Tara Woods, Plymouth, MA
Resale Only | 55+ age-restricted | Built 2007 - 2015 | 38 homes
Brandywyne
$700Ks - $800Ks
Brandywyne, South Kingstown, RI
Resale Only | 55+ age-restricted | Built 2011 - 2013 | 37 homes
Cranberry Grove
$200Ks - $300Ks
Cranberry Grove, Wareham, MA
Resale Only | 55+ age-restricted | Built 2001 - 2001 | 36 homes
Peregrine Woods
$400Ks - $600Ks
Peregrine Woods, Marshfield, MA
Resale Only | 55+ age-restricted | Built 2002 - 2005 | 32 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 Cottages at Lebaron H...
$500Ks - $600Ks
The Cottages at Lebaron H..., Lakeville, MA
New Construction | 55+ age-restricted | Built 2019 - present | 32 homes
Brookside Village
$700Ks
Brookside Village, Walpole, MA
Resale Only | 55+ age-restricted | Built 2018 - 2018 | 30 homes
Brookedge Village Condomi...
$300Ks - $400Ks
Brookedge Village Condomi..., South Kingstown, RI
Resale Only | 55+ age-restricted | Built 2007 - 2007 | 28 homes
Mattapoisett Landing
$400Ks - $500Ks
Mattapoisett Landing, Mattapoisett, MA
Resale Only | 55+ age-restricted | Built 2012 - 2015 | 27 homes
Wyman Farms
$500Ks - $900Ks
Wyman Farms, Shrewsbury, MA
New Construction | 55+ age-restricted | Built 2017 - present | 26 homes
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (401) 313-4589
Woodcrest Run
$400Ks
Woodcrest Run, Sharon, MA
New Construction | 55+ age-restricted | Built 2019 - present | 25 homes
Chilton Park Village
$400Ks
Chilton Park Village, Plymouth, MA
Resale Only | 55+ age-restricted | Built 2006 - 2015 | 25 homes
Kensington at The Pinehil...
$500Ks
Kensington at The Pinehil..., Plymouth, MA
New Construction | Age-targeted | Built 2017 - present | 17 homes
59 North Main
$900Ks
59 North Main, Sherborn, MA
New Construction | 55+ age-restricted | Built 2019 - present | 12 homes
Village at Silver Hill
$1Ms
Village at Silver Hill, Weston, MA
New Construction | 55+ age-restricted | Built 2021 - present | 8 homes
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
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
Woodstone Crossing 130 TROTTER RD 1309, WEYMOUTH, MA, 02190, Weymouth, MA 02190
$474,900

2 beds

|

2 baths

|

1,325 sq ft

|

Condo

130 TROTTER RD 1309, WEYMOUTH, MA, 02190
Community: Woodstone Crossing
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

|

Condo

27 TEA PARTY CIR # 27, HOLDEN, MA, 01520
The Preserve at Hunters Hill 3035 CLUBHOUSE DR 3, DIGHTON, MA, 02715, Dighton, MA 02715
$749,900

2 beds

|

2 baths

|

1,928 sq ft

|

House

3035 CLUBHOUSE DR 3, DIGHTON, MA, 02715
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (401) 313-4589
The Preserve at Hunters Hill 3035 CLUBHOUSE DR 2, DIGHTON, MA, 02715, Dighton, MA 02715
$749,900

2 beds

|

2 baths

|

1,928 sq ft

|

House

3035 CLUBHOUSE DR 2, DIGHTON, MA, 02715
The Preserve at Hunters Hill 3035 CLUBHOUSE DR, DIGHTON, MA, 02715, Dighton, MA 02715
$709,900

2 beds

|

2 baths

|

1,775 sq ft

|

House

3035 CLUBHOUSE DR, DIGHTON, MA, 02715
The Preserve at Hunters Hill 3035 CLUBHOUSE DR 4, DIGHTON, MA, 02715, Dighton, MA 02715
$709,900

2 beds

|

2 baths

|

1,775 sq ft

|

House

3035 CLUBHOUSE DR 4, DIGHTON, MA, 02715
The Preserve at Hunters Hill 3035 CLUBHOUSE DR 1, DIGHTON, MA, 02715, Dighton, MA 02715
$709,900

2 beds

|

2 baths

|

1,775 sq ft

|

House

3035 CLUBHOUSE DR 1, DIGHTON, MA, 02715
Great Island 38 GREAT POINTE, PLYMOUTH, MA, 02360, Plymouth, MA 02360
$939,000

3 beds

|

3 baths

|

3,579 sq ft

|

House

38 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.
Great Island 25 FOX HOLW, PLYMOUTH, MA, 02360, Plymouth, MA 02360
$699,000

2 beds

|

2 baths

|

1,529 sq ft

|

House

25 FOX HOLW, PLYMOUTH, MA, 02360
Community: Great Island
Del Webb Chauncy Lake 5 PETERS FARM WAY # 112, WESTBOROUGH, MA..., Westborough, MA 01581
$463,995

1 beds

|

1 baths

|

1,058 sq ft

|

Condo

5 PETERS FARM WAY # 112, WESTBOROUGH, MA...
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
The Preserve at Hunters Hill 3064 CLUB HOUSE DR, DIGHTON, MA, 02715, Dighton, MA 02715
$639,900

3 beds

|

3 baths

|

1,928 sq ft

|

House

3064 CLUB HOUSE DR, DIGHTON, MA, 02715
Oak Point 2612 OAK POINT DR, MIDDLEBORO, MA, 02346, Middleboro, MA 02346
$374,900

3 beds

|

2 baths

|

1,456 sq ft

|

House

2612 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
Southport 181 LEISURE GREEN DR # 181, MASHPEE, MA,..., Mashpee, MA 02649
$449,000

2 beds

|

2 baths

|

1,338 sq ft

|

Condo

181 LEISURE GREEN DR # 181, MASHPEE, MA,...
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
Regency at Glen Ellen 18 LANSING WAY # 18, MILLIS, MA, 02054, Millis, MA 02054
$799,000

2 beds

|

3 baths

|

2,306 sq ft

|

Condo

18 LANSING WAY # 18, MILLIS, MA, 02054
Great Island 16 PICKET FENCE, PLYMOUTH, MA, 02360, Plymouth, MA 02360
$775,000

2 beds

|

2 baths

|

2,059 sq ft

|

House

16 PICKET FENCE, PLYMOUTH, MA, 02360
Community: Great Island
Oak Point 3402 ISLAND DR, MIDDLEBORO, MA, 02346, Middleboro, MA 02346
$369,000

3 beds

|

2 baths

|

1,344 sq ft

|

House

3402 ISLAND DR, MIDDLEBORO, MA, 02346
Community: Oak Point
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 Villages at Crane Meadow 11 WHISPERING BROOK RD # 55, MARLBOROUGH..., Marlborough, MA 01752
$569,900

2 beds

|

3 baths

|

1,830 sq ft

|

Condo

11 WHISPERING BROOK RD # 55, MARLBOROUGH...
Southport 23 SEA SPRAY AVE # 563, MASHPEE, MA, 026..., Mashpee, MA 02649
$769,900

2 beds

|

4 baths

|

2,455 sq ft

|

Condo

23 SEA SPRAY AVE # 563, MASHPEE, MA, 026...
Community: Southport
The Preserve at Hunters Hill 3035 CLUBHOUSE DR 7, DIGHTON, MA, 02715, Dighton, MA 02715
$779,900

2 beds

|

2 baths

|

2,216 sq ft

|

House

3035 CLUBHOUSE DR 7, DIGHTON, MA, 02715
The Preserve at Hunters Hill 3035 CLUBHOUSE DR 5, DIGHTON, MA, 02715, Dighton, MA 02715
$759,900

2 beds

|

2 baths

|

2,097 sq ft

|

House

3035 CLUBHOUSE DR 5, DIGHTON, MA, 02715
The Preserve at Hunters Hill 3035 CLUBHOUSE DR 6, DIGHTON, MA, 02715, Dighton, MA 02715
$759,900

2 beds

|

2 baths

|

2,097 sq ft

|

House

3035 CLUBHOUSE DR 6, DIGHTON, MA, 02715
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (401) 313-4589
Del Webb Chauncy Lake 2 TALBOT WAY 2208, WESTBOROUGH, MA, 0158..., Westborough, MA 01581
$390,000

1 beds

|

1 baths

|

1,021 sq ft

|

Condo

2 TALBOT WAY 2208, WESTBOROUGH, MA, 0158...
30 Coppersmith 30 COPPERSMITH WAY # 107, CANTON, MA, 02..., Canton, MA 02021
$610,995

2 beds

|

2 baths

|

1,582 sq ft

|

Condo

30 COPPERSMITH WAY # 107, CANTON, MA, 02...
Community: 30 Coppersmith
Oak Point 3905 PHEASANT LN, MIDDLEBORO, MA, 02346, Middleboro, MA 02346
$415,000

2 beds

|

2 baths

|

1,600 sq ft

|

House

3905 PHEASANT LN, MIDDLEBORO, MA, 02346
Community: Oak Point
Southport 18 EXECUTIVE DR, MASHPEE, MA, 02649, Mashpee, MA 02649
$450,000

2 beds

|

2 baths

|

1,338 sq ft

|

House

18 EXECUTIVE DR, MASHPEE, MA, 02649
Community: Southport
30 Coppersmith 50 COPPERSMITH WAY UNIT 211, CANTON, MA,..., Canton, MA 02021
$899,000

2 beds

|

2 baths

|

1,831 sq ft

|

Condo

50 COPPERSMITH WAY UNIT 211, CANTON, MA,...
Community: 30 Coppersmith
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.
Center Commons 29 LIBERTY DR # 29, PEMBROKE, MA, 02359, Pembroke, MA 02359
$629,900

2 beds

|

3 baths

|

1,966 sq ft

|

Condo

29 LIBERTY DR # 29, PEMBROKE, MA, 02359
Community: Center Commons
Del Webb Chauncy Lake 2 CODMAN WAY 402, WESTBOROUGH, MA, 01581, Westborough, MA 01581
$424,999

1 beds

|

1 baths

|

972 sq ft

|

Condo

2 CODMAN WAY 402, WESTBOROUGH, MA, 01581
The Preserve at Hunters Hill 3055 CLUB HOUSE DR # 80, DIGHTON, MA, 02..., Dighton, MA 02715
$743,175

2 beds

|

2 baths

|

1,775 sq ft

|

House

3055 CLUB HOUSE DR # 80, DIGHTON, MA, 02...
Regency at Glen Ellen 6 GLEN ELLEN BLVD # 6, MILLIS, MA, 02054, Millis, MA 02054
$1,050,000

3 beds

|

3 baths

|

2,656 sq ft

|

Condo

6 GLEN ELLEN BLVD # 6, MILLIS, MA, 02054
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
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (401) 313-4589
Brierly Pond Village 32 HORNE WAY # 32, MILLBURY, MA, 01527, Millbury, MA 01527
$449,900

2 beds

|

2 baths

|

1,420 sq ft

|

Condo

32 HORNE WAY # 32, MILLBURY, MA, 01527
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...
Great Island 19 RED LEAF, PLYMOUTH, MA, 02360, Plymouth, MA 02360
$755,000

2 beds

|

2 baths

|

1,534 sq ft

|

House

19 RED LEAF, PLYMOUTH, MA, 02360
Community: Great Island
Del Webb Chauncy Lake 2 CODMAN WAY 104, WESTBOROUGH, MA, 01581, Westborough, MA 01581
$374,999

1 beds

|

1 baths

|

972 sq ft

|

Condo

2 CODMAN WAY 104, WESTBOROUGH, MA, 01581
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
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80 communities near Middletown
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