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Westborough, MA 55+ active adult communities & homes for sale

25 communities near Westborough

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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
Upton Ridge
$400ks - $600ks
Upton Ridge, Upton, MA
New Construction | 55+ age-restricted | Built 2019 - present | 139 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
Brierly Pond Village
$300ks - $400ks
Brierly Pond Village, Millbury, MA
Resale Only | 55+ age-restricted | Built 2003 - 2013 | 199 homes
Want to learn more about 55+ communities in Westborough? 55places can help!
Questions? Call us: (774) 512-3099
WestRidge
$700ks
WestRidge, Hudson, MA
Resale Only | 55+ age-restricted | Built 2009 - 2016 | 136 homes
Orchard Hill
$500ks
Orchard Hill, Westborough, MA
Resale Only | 55+ age-restricted | Built 2002 - 2010 | 100 homes
Millwood Preserve
$700ks - $800ks
Millwood Preserve, Framingham, MA
New Construction | 55+ age-restricted | Built 2020 - present | 129 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
Angell Brook Village
$300ks
Angell Brook Village, West Boylston, MA
Resale Only | 55+ age-restricted | Built 2005 - 2012 | 132 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.
Northside Meadows
$600ks - $700ks
Northside Meadows, Framingham, MA
Resale Only | 55+ age-restricted | Built 2017 - 2019 | 60 homes
Wyman Farms
$500ks - $900ks
Wyman Farms, Shrewsbury, MA
New Construction | 55+ age-restricted | Built 2017 - present | 26 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
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
Enclave at Hudson
$800ks - $1Ms
Enclave at Hudson, Hudson, MA
New Construction | 55+ age-restricted | Built 2021 - present | 64 homes
Want to learn more about 55+ communities in Westborough? 55places can help!
Questions? Call us: (774) 512-3099
Regency at Assabet Ridge
$500ks - $600ks
Regency at Assabet Ridge, Marlborough, MA
Resale Only | 55+ age-restricted | Built 2010 - 2015 | 69 homes
Pheasant Hill
$300ks - $400ks
Pheasant Hill, Northborough, MA
Resale Only | 55+ age-restricted | Built 2005 - 2006 | 48 homes
Blue Heron Pond
$500ks
Blue Heron Pond, Lancaster, MA
Resale Only | 55+ age-restricted | Built 2006 - 2014 | 58 homes
Adams Farm
$700ks - $800ks
Adams Farm, Shrewsbury, MA
Resale Only | 55+ age-restricted | Built 2005 - 2013 | 90 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.
Holliston Woods
$500ks - $700ks
Holliston Woods, Holliston, MA
Resale Only | 55+ age-restricted | Built 2016 - 2018 | 66 homes
The Villages at Crane Mea...
$400ks
The Villages at Crane Mea..., Marlborough, MA
Resale Only | 55+ age-restricted | Built 2001 - 2005 | 91 homes
Balancing Rock
$500ks - $600ks
Balancing Rock, Holliston, MA
Resale Only | 55+ age-restricted | Built 2006 - 2008 | 49 homes
Bigelow Farm
$500ks - $600ks
Bigelow Farm, Northborough, MA
Resale Only | 55+ age-restricted | Built 2006 - 2013 | 41 homes
Rockwood Meadows
$600ks - $700ks
Rockwood Meadows, Upton, MA
New Construction | 55+ age-restricted | Built 2016 - present | 58 homes
New 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, ...
New Del Webb Chauncy Lake 5 PETERS FARM WAY 410, WESTBOROUGH, MA, ..., Westborough, MA 01581
$599,995

2 beds

|

2 baths

|

1,375 sq ft

|

Condo

5 PETERS FARM WAY 410, WESTBOROUGH, MA, ...
New 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,...
New 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...
New 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
Want to learn more about 55+ communities in Westborough? 55places can help!
Questions? Call us: (774) 512-3099
New Upton Ridge 213 SAND TRAP CT 213, NORTHBRIDGE, MA, 0..., Northbridge, MA 01534
$699,999

2 beds

|

3 baths

|

2,410 sq ft

|

Condo

213 SAND TRAP CT 213, NORTHBRIDGE, MA, 0...
Community: Upton Ridge
New 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...
New 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...
New 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 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...
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.
WestRidge 68 HASTINGS RD 68, HUDSON, MA, 01749, Hudson, MA 01749
$850,000

3 beds

|

3 baths

|

2,264 sq ft

|

Condo

68 HASTINGS RD 68, HUDSON, MA, 01749
Community: WestRidge
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
Brierly Pond Village 26 HORNE WAY 26, MILLBURY, MA, 01527, Millbury, MA 01527
$546,000

2 beds

|

3 baths

|

1,968 sq ft

|

Condo

26 HORNE WAY 26, MILLBURY, MA, 01527
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
Del Webb Chauncy Lake 5 PETERS FARM WAY 302, WESTBOROUGH, MA, ..., Westborough, MA 01581
$414,995

1 beds

|

1 baths

|

972 sq ft

|

Condo

5 PETERS FARM WAY 302, WESTBOROUGH, MA, ...
Del Webb Chauncy Lake 6305 PETERS FARM WAY 6305, WESTBOROUGH, ..., Westborough, MA 01581
$474,999

2 beds

|

2 baths

|

1,166 sq ft

|

Condo

6305 PETERS FARM WAY 6305, WESTBOROUGH, ...
Want to learn more about 55+ communities in Westborough? 55places can help!
Questions? Call us: (774) 512-3099
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
Brierly Pond Village 168 HORNE WAY 168, MILLBURY, MA, 01527, Millbury, MA 01527
$475,000

2 beds

|

3 baths

|

1,735 sq ft

|

Condo

168 HORNE WAY 168, MILLBURY, MA, 01527
Upton Ridge 204 SAND TRAP CT 204, NORTHBRIDGE, MA, 0..., Northbridge, MA 01534
$650,000

3 beds

|

3 baths

|

2,170 sq ft

|

Condo

204 SAND TRAP CT 204, NORTHBRIDGE, MA, 0...
Community: Upton Ridge
Del Webb Chauncy Lake 3202 PETERS FARM WAY 202, WESTBOROUGH, M..., Westborough, MA 01581
$440,000

1 beds

|

1 baths

|

956 sq ft

|

Condo

3202 PETERS FARM WAY 202, WESTBOROUGH, M...
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 Village at Orchard Meadows 19 CORTLAND GROVE DR 19, SHREWSBURY, MA,..., Shrewsbury, MA 01545
$534,900

2 beds

|

2 baths

|

1,370 sq ft

|

Condo

19 CORTLAND GROVE DR 19, SHREWSBURY, MA,...
The Trails 9 WATERVILLE LN 9, HOPKINTON, MA, 01748, Hopkinton, MA 01748
$999,900

2 beds

|

3 baths

|

2,274 sq ft

|

Condo

9 WATERVILLE LN 9, HOPKINTON, MA, 01748
Community: The Trails
Del Webb Chauncy Lake 5205 PETERS FARM WAY 7205, WESTBOROUGH, ..., Westborough, MA 01581
$499,995

2 beds

|

2 baths

|

1,175 sq ft

|

Condo

5205 PETERS FARM WAY 7205, WESTBOROUGH, ...
Bigelow Farm 14 LYDIAS WAY 14, NORTHBOROUGH, MA, 0153..., Northborough, MA 01532
$799,000

2 beds

|

3 baths

|

2,691 sq ft

|

Condo

14 LYDIAS WAY 14, NORTHBOROUGH, MA, 0153...
Community: Bigelow Farm
Del Webb Chauncy Lake 5 PETERS FARM WAY 7106, WESTBOROUGH, MA,..., Westborough, MA 01581
$619,995

2 beds

|

2 baths

|

1,512 sq ft

|

Condo

5 PETERS FARM WAY 7106, WESTBOROUGH, MA,...
Del Webb Chauncy Lake 5 PETERS FARM WAY 7305, WESTBOROUGH, MA,..., Westborough, MA 01581
$549,995

2 beds

|

2 baths

|

1,175 sq ft

|

Condo

5 PETERS FARM WAY 7305, WESTBOROUGH, MA,...
Del Webb Chauncy Lake 2 CODMAN WAY 2203, WESTBOROUGH, MA, 0158..., Westborough, MA 01581
$400,000

1 beds

|

1 baths

|

972 sq ft

|

Condo

2 CODMAN WAY 2203, WESTBOROUGH, MA, 0158...
Want to learn more about 55+ communities in Westborough? 55places can help!
Questions? Call us: (774) 512-3099
The Village at Orchard Meadows 4 APPLE SEED DR 4, SHREWSBURY, MA, 01545, Shrewsbury, MA 01545
$609,000

2 beds

|

3 baths

|

1,854 sq ft

|

Condo

4 APPLE SEED DR 4, SHREWSBURY, MA, 01545
Millwood Preserve 32 HAWK LN 48, FRAMINGHAM, MA, 01701, Framingham, MA 01701
$1,225,000

2 beds

|

3 baths

|

2,306 sq ft

|

Condo

32 HAWK LN 48, FRAMINGHAM, MA, 01701
Community: Millwood Preserve
Del Webb Chauncy Lake 3405 PETERS FARM WAY 3405, WESTBOROUGH, ..., Westborough, MA 01581
$529,500

2 beds

|

2 baths

|

1,121 sq ft

|

Condo

3405 PETERS FARM WAY 3405, WESTBOROUGH, ...
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.
Del Webb Chauncy Lake 3103 PETERS FARM WAY 103, WESTBOROUGH, M..., Westborough, MA 01581
$385,000

1 beds

|

1 baths

|

956 sq ft

|

Condo

3103 PETERS FARM WAY 103, WESTBOROUGH, M...
The Village at Orchard Meadows 70 ORCHARD MEADOW DR 70, SHREWSBURY, MA,..., Shrewsbury, MA 01545
$649,000

2 beds

|

3 baths

|

1,896 sq ft

|

Condo

70 ORCHARD MEADOW DR 70, SHREWSBURY, MA,...
Del Webb Chauncy Lake 4311 PETERS FARM WAY 311, WESTBOROUGH, M..., Westborough, MA 01581
$559,000

2 beds

|

2 baths

|

1,326 sq ft

|

Condo

4311 PETERS FARM WAY 311, WESTBOROUGH, M...
Upton Ridge 87 SHANNON WAY 86, UPTON, MA, 01568, Upton, MA 01568
$699,900

2 beds

|

3 baths

|

1,930 sq ft

|

Condo

87 SHANNON WAY 86, UPTON, MA, 01568
Community: Upton Ridge
Del Webb Chauncy Lake 12101 PETERS FARM WAY 12101, WESTBOROUGH..., Westborough, MA 01712
$579,000

2 beds

|

2 baths

|

1,459 sq ft

|

Condo

12101 PETERS FARM WAY 12101, WESTBOROUGH...
Del Webb Chauncy Lake 11 PETERS FARM WAY 310, WESTBOROUGH, MA,..., Westborough, MA 01581
$560,000

2 beds

|

2 baths

|

1,326 sq ft

|

Condo

11 PETERS FARM WAY 310, WESTBOROUGH, MA,...
Brierly Pond Village 6 ASHTON LN 6, MILLBURY, MA, 01527, Millbury, MA 01527
$524,900

2 beds

|

4 baths

|

2,256 sq ft

|

Condo

6 ASHTON LN 6, MILLBURY, MA, 01527
WestRidge 15 HASTINGS RD 15, HUDSON, MA, 01749, Hudson, MA 01749
$624,900

2 beds

|

3 baths

|

1,934 sq ft

|

Condo

15 HASTINGS RD 15, HUDSON, MA, 01749
Community: WestRidge
Want to learn more about 55+ communities in Westborough? 55places can help!
Questions? Call us: (774) 512-3099
Del Webb Chauncy Lake 4204 PETERS FARM WAY 204, WESTBOROUGH, M..., Westborough, MA 01581
$430,000

1 beds

|

1 baths

|

956 sq ft

|

Condo

4204 PETERS FARM WAY 204, WESTBOROUGH, M...
The Villages at Walker Meadow 3 QUAKER WAY 40, WESTBOROUGH, MA, 01581, Westborough, MA 01581
$599,900

2 beds

|

2 baths

|

1,876 sq ft

|

Condo

3 QUAKER WAY 40, WESTBOROUGH, MA, 01581
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.

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