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

41 communities near Upton

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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

Harmony Place

$400ks - $500ks

Harmony Place, Rutland, MA

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

Woodcrest Run

$400ks - $600ks

Woodcrest Run, Sharon, MA

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

Upton Ridge

$400ks - $600ks

Upton Ridge, Upton, MA

New Construction | 55+ age-restricted | Built 2019 - present | 139 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 Upton? 55places can help!

Questions? Call us: (508) 603-7097

The Village at Orchard Me...

$400ks - $500ks

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

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

The Trails

$500ks - $700ks

The Trails, Hopkinton, MA

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

Pennington Crossing

$300ks - $600ks

Pennington Crossing, Walpole, MA

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

Regency at Glen Ellen

$700ks - $900ks

Regency at Glen Ellen, Millis, MA

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

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.

Bates Quarry

Bates Quarry, Walpole, MA

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

WestRidge

$700ks

WestRidge, Hudson, MA

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

The Seasons at Salisbury

$400ks - $500ks

The Seasons at Salisbury, Holden, MA

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

Quail Ridge

$600ks - $700ks

Quail Ridge, Acton, MA

Resale Only | 55+ age-restricted | Built 2015 - present | 153 homes

Northwoods at Sudbury

$500ks

Northwoods at Sudbury, Sudbury, MA

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

Orchard Hill

$500ks

Orchard Hill, Westborough, MA

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

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

Questions? Call us: (508) 603-7097

The Village at Westminste...

$400ks - $500ks

The Village at Westminste..., Holden, MA

New and Resale | 55+ age-restricted | Built 2006 - present | 125 homes

Millwood Preserve

$1Ms

Millwood Preserve, Framingham, MA

Resale Only | 55+ age-restricted | Built 2020 - 2024 | 129 homes

Brooksmont

$400ks - $600ks

Brooksmont, Holliston, MA

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

Brookside Village

$700ks

Brookside Village, Walpole, MA

Resale Only | 55+ age-restricted | Built 2018 - 2018 | 30 homes

Enclave at Hudson

$800ks - $1Ms

Enclave at Hudson, Hudson, MA

New Construction | 55+ age-restricted | Built 2021 - present | 64 homes

Village at Silver Hill

$1Ms - $2Ms

Village at Silver Hill, Weston, MA

New Construction | 55+ age-restricted | Built 2021 - present | 8 homes

Bella Vista

$300ks - $400ks

Bella Vista, Glocester, RI

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

Regency at Assabet Ridge

$500ks - $600ks

Regency at Assabet Ridge, Marlborough, MA

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

Angell Brook Village

$300ks

Angell Brook Village, West Boylston, MA

Resale Only | 55+ age-restricted | Built 2005 - 2012 | 132 homes

Pheasant Hill

$300ks - $400ks

Pheasant Hill, Northborough, MA

Resale Only | 55+ age-restricted | Built 2005 - 2006 | 48 homes

New England Commons

$200ks - $300ks

New England Commons, Webster, MA

New and Resale | 55+ age-restricted | Built 2005 - present | 100 homes

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

Questions? Call us: (508) 603-7097

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

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

Forest Glen

$400ks - $500ks

Forest Glen, Uxbridge, MA

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

Trail Ridge at Harvard

$700ks

Trail Ridge at Harvard, Harvard, MA

Resale Only | 55+ age-restricted | Built 2008 - 2023 | 52 homes

Northside Meadows

$600ks - $700ks

Northside Meadows, Framingham, MA

Resale Only | 55+ age-restricted | Built 2017 - 2019 | 60 homes

Garrison Place

$900ks - $1Ms

Garrison Place, Carlisle, MA

Resale Only | 55+ age-restricted | Built 2018 - 2019 | 16 homes

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

Questions? Call us: (508) 603-7097

Wyman Farms

$500ks - $900ks

Wyman Farms, Shrewsbury, MA

New Construction | 55+ age-restricted | Built 2017 - present | 26 homes

59 North Main

$900ks

59 North Main, Sherborn, MA

New Construction | 55+ age-restricted | Built 2019 - present | 12 homes

8 PETERS FARM WAY 106, WESTBOROUGH, MA, ...

Community: Del Webb Chauncy Lake

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

Questions? Call us: (508) 603-7097

Del Webb Chauncy Lake

8 PETERS FARM WAY 108, WESTBOROUGH, MA, ..., Westborough, MA 01581

$549,330

1 beds

2 baths

1,058 sq ft

Condo

8 PETERS FARM WAY 108, WESTBOROUGH, MA, ...

Community: Del Webb Chauncy Lake

Del Webb Chauncy Lake

8 PETERS FARM WAY 105, WESTBOROUGH, MA, ..., Westborough, MA 01581

$499,420

1 beds

2 baths

958 sq ft

Condo

8 PETERS FARM WAY 105, WESTBOROUGH, MA, ...

Community: Del Webb Chauncy Lake

Del Webb Chauncy Lake

1213 CODMAN WAY 1213, WESTBOROUGH, MA, 0..., Westborough, MA 01581

$584,900

2 beds

2 baths

1,512 sq ft

Condo

1213 CODMAN WAY 1213, WESTBOROUGH, MA, 0...

Community: Del Webb Chauncy Lake

Brierly Pond Village

37 HORNE WAY 37, MILLBURY, MA, 01527, Millbury, MA 01527

$479,900

2 beds

3 baths

1,746 sq ft

Condo

37 HORNE WAY 37, MILLBURY, MA, 01527

Community: Brierly Pond Village

The Village at Orchard Meadows

1 APPLE SEED DR 1, SHREWSBURY, MA, 01545, Shrewsbury, MA 01545

$649,900

2 beds

3 baths

1,854 sq ft

Condo

1 APPLE SEED DR 1, SHREWSBURY, MA, 01545

Community: The Village at Orchard Meadows

The Villages at Walker Meadow

14 WESSONVILLE VILLAGE WAY 79, WESTBOROU..., Westborough, MA 01581

$700,000

2 beds

2 baths

2,090 sq ft

Condo

14 WESSONVILLE VILLAGE WAY 79, WESTBOROU...

Community: The Villages at Walker Meadow

The Village at Westminster Place

18 TEA PARTY CIR 18, HOLDEN, MA, 01520, Holden, MA 01520

$649,990

3 beds

3 baths

2,028 sq ft

House

18 TEA PARTY CIR 18, HOLDEN, MA, 01520

Community: The Village at Westminster Place

Del Webb Chauncy Lake

5 PETERS FARM WAY 7409, WESTBOROUGH, MA,..., Westborough, MA 01581

$599,995

2 beds

2 baths

1,375 sq ft

Condo

5 PETERS FARM WAY 7409, WESTBOROUGH, MA,...

Community: Del Webb Chauncy Lake

Bates Quarry

$936,949

2 beds

3 baths

2,301 sq ft

House

4 BATES QUARRY LN 44, WALPOLE, MA, 02081

Community: Bates Quarry

Pennington Crossing

1211 PENNINGTON DR 1211, WALPOLE, MA, 02..., Walpole, MA 02081

$575,000

1 beds

1 baths

1,030 sq ft

Condo

1211 PENNINGTON DR 1211, WALPOLE, MA, 02...

Community: Pennington Crossing

Del Webb Chauncy Lake

8 PETERS FARM WAY 401, WESTBOROUGH, MA, ..., Westborough, MA 01581

$872,440

2 beds

2 baths

1,496 sq ft

Condo

8 PETERS FARM WAY 401, WESTBOROUGH, MA, ...

Community: Del Webb Chauncy Lake

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

Questions? Call us: (508) 603-7097

Regency at Glen Ellen

112 GLEN ELLEN BLVD 112, MILLIS, MA, 020..., Millis, MA 02054

$1,299,950

3 beds

4 baths

4,483 sq ft

Condo

112 GLEN ELLEN BLVD 112, MILLIS, MA, 020...

Community: Regency at Glen Ellen

Cindy Certified

180 U:202 OLD POST RD 202, SHARON, MA, 0..., Sharon, MA 02067

$887,900

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 Upton? 55places can help!

Questions? Call us: (508) 603-7097

Regency at Glen Ellen

43 JAMESON DR 43, MILLIS, MA, 02054, Millis, MA 02054

$1,199,000

3 beds

3 baths

2,873 sq ft

Condo

43 JAMESON DR 43, MILLIS, MA, 02054

Community: Regency at Glen Ellen

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

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

Quail Ridge

20 PARKLAND LN 20, ACTON, MA, 01720, Acton, MA 01720

$925,000

2 beds

2 baths

2,149 sq ft

Condo

20 PARKLAND LN 20, ACTON, MA, 01720

Community: Quail Ridge

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

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

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

Upton Ridge

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

$689,000

2 beds

3 baths

1,950 sq ft

Condo

56 SHANNON WAY 56, UPTON, MA, 01568

Community: Upton Ridge

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

Upton Ridge

204 SAND TRAP CT 204, NORTHBRIDGE, MA, 0..., Northbridge, MA 01534

$625,000

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...

Community: Del Webb Chauncy Lake

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

Questions? Call us: (508) 603-7097

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

7205 PETERS FARM WAY 7205, WESTBOROUGH, ..., Westborough, MA 01581

$489,995

2 beds

2 baths

1,175 sq ft

Condo

7205 PETERS FARM WAY 7205, WESTBOROUGH, ...

Community: Del Webb Chauncy Lake

Frequently Asked Questions

What size 55+ communities are there in Upton?

In Upton, 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 Upton?

The smallest 55+ communities in Upton has 58 homes, the largest has 139 homes, and the average communities consists of 98 homes.

Are there new 55+ homes available in Upton?

Yes, there are new 55+ homes available in Upton. The most recent communities started in Upton include Upton Ridge, Rockwood Meadows. There are also 2 communities in Upton that offer new construction homes, including Upton Ridge, Rockwood Meadows.

Are there gated 55+ communities in Upton?

No, there are no gated 55+ communities in Upton.

How long do listings in 55+ communities in Upton typically stay on the market, and what is the average price of homes for sale?

On average, listings in 55+ communities in Upton stay on the market for around 12 days. The average price of homes for sale in these communities is approximately $729,000, though prices can range widely based on the size, location, and amenities of the communities. For example, homes in Upton Ridge average around $729,000.

Want more information about active adult communities around Upton?

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41 communities

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

41 communities near Upton

56 homes near Upton

2 beds

2 baths

1,056 sq ft

Condo

1 beds

2 baths

1,056 sq ft

Condo

2 beds

2 baths

1,187 sq ft

Condo

2 beds

3 baths

2,360 sq ft

Condo

2 beds

2 baths

1,496 sq ft

Condo

1 beds

2 baths

1,058 sq ft

Condo

1 beds

2 baths

958 sq ft

Condo

2 beds

2 baths

1,512 sq ft

Condo

2 beds

3 baths

1,746 sq ft

Condo

2 beds

3 baths

1,854 sq ft

Condo

2 beds

2 baths

2,090 sq ft

Condo

3 beds

3 baths

2,028 sq ft

House

2 beds

2 baths

1,375 sq ft

Condo

2 beds

3 baths

2,301 sq ft

House

1 beds

1 baths

1,030 sq ft

Condo

2 beds

2 baths

1,496 sq ft

Condo

3 beds

4 baths

4,483 sq ft

Condo

2 beds

3 baths

1,431 sq ft

Condo

2 beds

3 baths

2,601 sq ft

Condo

2 beds