Middleton, MA 55+ active adult communities & homes for sale - Page 3

162 communities near Middleton

Sort by:

Relevance

30 Coppersmith

$400Ks - $800Ks

30 Coppersmith, Canton, MA

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

Hadleigh Woods

$300Ks

Hadleigh Woods, Windham, NH

Resale Only | 55+ age-restricted | Built 2003 - 2004 | 62 homes

Sawyer Green

$400Ks - $500Ks

Sawyer Green, Dover, NH

Resale Only | 55+ age-restricted | Built 2009 - 2013 | 62 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

Rockland Glen

$300Ks - $500Ks

Rockland Glen, Rockland, MA

Resale Only | 55+ age-restricted | Built 2008 - 2015 | 60 homes

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

Questions? Call us: (508) 715-6046

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

The Village at Hollis Dep...

$300Ks

The Village at Hollis Dep..., Hollis, NH

Resale Only | 55+ age-restricted | Built 2003 - 2003 | 60 homes

Mission Pointe

$500Ks

Mission Pointe, Hudson, NH

Resale Only | 62+ age-restricted | Built 2006 - 2011 | 58 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

Annandale on The River

$500Ks - $600Ks

Annandale on The River, Litchfield, NH

Resale Only | 55+ age-restricted | Built 2009 - 2011 | 57 homes

Liberty Woods

$600Ks - $700Ks

Liberty Woods, Hanson, MA

New Construction | 55+ age-restricted | Built 2023 - present | 56 homes

Rollins Hill

$500Ks - $700Ks

Rollins Hill, Stratham, NH

Resale Only | 55+ age-restricted | Built 2017 - 2021 | 55 homes

Wolcott Woods

$1Ms - $2Ms

Wolcott Woods, Milton, MA

New Construction | 55+ age-restricted | Built 2020 - present | 54 homes

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

Questions? Call us: (508) 715-6046

Arbor Hills

$400Ks - $500Ks

Arbor Hills, Kingston, MA

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

Trail Ridge at Harvard

$700Ks

Trail Ridge at Harvard, Harvard, MA

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

Silver Lake Estates

$700Ks - $800Ks

Silver Lake Estates, Hollis, NH

Resale Only | 55+ age-restricted | Built 2019 - 2022 | 52 homes

Souhegan River View Villa...

$400Ks - $500Ks

Souhegan River View Villa..., Merrimack, NH

Resale Only | 55+ age-restricted | Built 2001 - 2006 | 51 homes

The Elms of Hanover

$500Ks - $700Ks

The Elms of Hanover, Hanover, MA

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

Leddy Fields

$400Ks - $600Ks

Leddy Fields, Epping, NH

Resale Only | 55+ age-restricted | Built 2005 - 2014 | 50 homes

Lamplighter Estates

$200Ks - $300Ks

Lamplighter Estates, Kingston, NH

Resale Only | 55+ age-restricted | Built 2001 - 2003 | 50 homes

5 rating (1 reviews)

Canberra Village

$400Ks - $500Ks

Canberra Village, Litchfield, NH

Resale Only | 55+ age-restricted | Built 2004 - 2005 | 49 homes

Cahill Place

$200Ks

Cahill Place, Milford, NH

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

Balancing Rock

$500Ks - $600Ks

Balancing Rock, Holliston, MA

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

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

Questions? Call us: (508) 715-6046

English Commons at Topsfi...

$800Ks - $900Ks

English Commons at Topsfi..., Topsfield, MA

Resale Only | 55+ age-restricted | Built 2010 - 2014 | 49 homes

Pheasant Hill

$300Ks - $400Ks

Pheasant Hill, Northborough, MA

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

Beaver Meadow Village

$200Ks - $300Ks

Beaver Meadow Village, Concord, NH

Resale Only | 55+ age-restricted | Built 1973 - 1974 | 48 homes

Gilcreast Farms

$300Ks

Gilcreast Farms, Litchfield, NH

Resale Only | 55+ age-restricted | Built 2003 - 2005 | 47 homes

Mill Pond Crossing

$300Ks - $400Ks

Mill Pond Crossing, Brentwood, NH

Resale Only | 55+ age-restricted | Built 2008 - 2013 | 47 homes

Prescott Crossing

$400Ks

Prescott Crossing, Raymond, NH

Resale Only | 55+ age-restricted | Built 2003 - 2004 | 46 homes

Stone Bridge Estates of S...

$600Ks

Stone Bridge Estates of S..., Salem, NH

Resale Only | 55+ age-restricted | Built 2015 - 2020 | 46 homes

Fairway View Village

$500Ks - $600Ks

Fairway View Village, Wells, ME

New Construction | 55+ age-restricted | Built 2021 - present | 46 homes

Rolling Mill

$600Ks - $700Ks

Rolling Mill, Plymouth, MA

Resale Only | 55+ age-restricted | Built 2018 - 2021 | 46 homes

Runnells Landing

$300Ks

Runnells Landing, Hollis, NH

Resale Only | 55+ age-restricted | Built 2002 - 2004 | 45 homes

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

Questions? Call us: (508) 715-6046

Harvest Village

$300Ks - $400Ks

Harvest Village, Londonderry, NH

Resale Only | 55+ age-restricted | Built 1995 - 1999 | 45 homes

King's Landing

$300Ks - $400Ks

King's Landing, Kingston, NH

Resale Only | 55+ age-restricted | Built 2015 - 2017 | 44 homes

Cohas Landing

$300Ks

Cohas Landing, Londonderry, NH

Resale Only | 55+ age-restricted | Built 1991 - 1997 | 44 homes

Braemoor Commons

$300Ks - $400Ks

Braemoor Commons, Salem, NH

Resale Only | 55+ age-restricted | Built 2014 - 2015 | 44 homes

Seaside at Scituate - The...

$900Ks - $1Ms

Seaside at Scituate - The..., Scituate, MA

New Construction | 55+ age-restricted | Built 2019 - present | 44 homes

1 2 3 4...5

30 Coppersmith

$581,995

2 beds

2 baths

1,425 sq ft

Condo

30 COPPERSMITH WAY # 409, CANTON, MA, 02...

Community: 30 Coppersmith

Riverside Woods

4 FRANCIS DR 207, ANDOVER, MA, 01810, Andover, MA 01810

$620,000

2 beds

2 baths

1,490 sq ft

Condo

4 FRANCIS DR 207, ANDOVER, MA, 01810

Community: Riverside Woods

New 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...

Community: Del Webb Chauncy Lake

Wolcott Woods

$1,999,900

2 beds

3 baths

3,599 sq ft

Condo

69 WOLCOTT WOODS LN # 69, MILTON, MA, 02...

Community: Wolcott Woods

Riverside Woods

4 FRANCIS DR 105, ANDOVER, MA, 01810, Andover, MA 01810

$449,900

1 beds

1 baths

945 sq ft

Condo

4 FRANCIS DR 105, ANDOVER, MA, 01810

Community: Riverside Woods

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

Questions? Call us: (508) 715-6046

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

Seton Highlands at The Pinehills

9 ABERDEEN # 9, PLYMOUTH, MA, 02360, Plymouth, MA 02360

$799,000

2 beds

4 baths

2,987 sq ft

Condo

9 ABERDEEN # 9, PLYMOUTH, MA, 02360

Community: Seton Highlands at The Pinehills

Riverside Woods

2 FRANCIS DR 412, ANDOVER, MA, 01810, Andover, MA 01810

$624,900

2 beds

2 baths

1,490 sq ft

Condo

2 FRANCIS DR 412, ANDOVER, MA, 01810

Community: Riverside Woods

Woodstone Crossing

130 TROTTER RD 1211, WEYMOUTH, MA, 02190, Weymouth, MA 02190

$459,000

1 beds

1 baths

1,030 sq ft

Condo

130 TROTTER RD 1211, WEYMOUTH, MA, 02190

Community: Woodstone Crossing

New Whitestone Village

603 ALYSSA DR # 603, GROVELAND, MA, 0183..., Groveland, MA 01834

$549,900

2 beds

3 baths

2,426 sq ft

Condo

603 ALYSSA DR # 603, GROVELAND, MA, 0183...

Community: Whitestone Village

New Martins Landing

200 MARTINS LNDG APT 102, NORTH READING,..., North Reading, MA 01864

$538,000

1 beds

1 baths

955 sq ft

Condo

200 MARTINS LNDG APT 102, NORTH READING,...

Community: Martins Landing

Regency at Methuen

42 HOPKINS CIR # 42, METHUEN, MA, 01844, Methuen, MA 01844

$849,900

2 beds

4 baths

3,085 sq ft

Condo

42 HOPKINS CIR # 42, METHUEN, MA, 01844

Community: Regency at Methuen

New The Preserve at Hunters Hill

RR33 CLUB HOUSE DR RR33, DIGHTON, MA, 02..., Dighton, MA 02715

$719,900

2 beds

2 baths

1,928 sq ft

House

RR33 CLUB HOUSE DR RR33, DIGHTON, MA, 02...

Community: The Preserve at Hunters Hill

New 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

Community: Del Webb Chauncy Lake

New Oak Point

503 HASTINGS RD, MIDDLEBORO, MA, 02346, Middleboro, MA 02346

$395,000

2 beds

2 baths

1,620 sq ft

House

503 HASTINGS RD, MIDDLEBORO, MA, 02346

Community: Oak Point

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

Questions? Call us: (508) 715-6046

New 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

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...

Community: The Preserve at Hunters Hill

New Martins Landing

320 MARTINS LNDG APT 406, NORTH READING,..., North Reading, MA 01864

$903,920

2 beds

2 baths

1,586 sq ft

Condo

320 MARTINS LNDG APT 406, NORTH READING,...

Community: Martins Landing

New Martins Landing

320 MARTINS LNDG APT 311, NORTH READING,..., North Reading, MA 01864

$599,985

1 beds

1 baths

1,115 sq ft

Condo

320 MARTINS LNDG APT 311, NORTH READING,...

Community: Martins Landing

New Martins Landing

320 MARTINS LNDG 107, NORTH READING, MA,..., North Reading, MA 01864

$702,115

2 beds

2 baths

1,579 sq ft

Condo

320 MARTINS LNDG 107, NORTH READING, MA,...

Community: Martins Landing

New Martins Landing

320 MARTINS LNDG APT 210, NORTH READING,..., North Reading, MA 01864

$600,620

1 beds

1 baths

1,129 sq ft

Condo

320 MARTINS LNDG APT 210, NORTH READING,...

Community: Martins Landing

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

Community: Regency at Glen Ellen

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

Community: The Villages at Walker Meadow

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

Community: The Village at Westminster Place

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

Community: Brierly Pond Village

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

Questions? Call us: (508) 715-6046

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

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...

Community: Del Webb Chauncy Lake

Hatter's Point

60 MERRIMAC ST 604, AMESBURY, MA, 01913, Amesbury, MA 01913

$695,000

2 beds

2 baths

1,265 sq ft

Condo

60 MERRIMAC ST 604, AMESBURY, MA, 01913

Community: Hatter's Point

Martins Landing

220 MARTINS LNDG APT 309, NORTH READING,..., North Reading, MA 01864

$640,000

2 beds

2 baths

1,335 sq ft

Condo

220 MARTINS LNDG APT 309, NORTH READING,...

Community: Martins Landing

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

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

Community: Del Webb Chauncy Lake

Great Island

74 CHAMPLAIN CIR, PLYMOUTH, MA, 02360, Plymouth, MA 02360

$745,000

3 beds

3 baths

2,580 sq ft

House

74 CHAMPLAIN CIR, PLYMOUTH, MA, 02360

Community: Great Island

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

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

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

Questions? Call us: (508) 715-6046

Sawyer's Reach

2 MARINERS WAY UNIT 306, PLYMOUTH, MA, 0..., Plymouth, MA 02360

$650,000

2 beds

2 baths

1,368 sq ft

Condo

2 MARINERS WAY UNIT 306, PLYMOUTH, MA, 0...

Community: Sawyer's Reach

The Trails

30 WATERVILLE LN # 30, HOPKINTON, MA, 01..., Hopkinton, MA 01748

$1,129,000

2 beds

3 baths

2,510 sq ft

Condo

30 WATERVILLE LN # 30, HOPKINTON, MA, 01...

Community: The Trails

The Preserve at Hunters Hill

3057 CLUB HOUSE DR, DIGHTON, MA, 02715, Dighton, MA 02715

$739,900

2 beds

2 baths

2,044 sq ft

House

3057 CLUB HOUSE DR, DIGHTON, MA, 02715

Community: The Preserve at Hunters Hill

Orchard Hill

5 BLOSSOM CT # 5, WESTBOROUGH, MA, 01581, Westborough, MA 01581

$690,000

3 beds

4 baths

3,373 sq ft

Condo

5 BLOSSOM CT # 5, WESTBOROUGH, MA, 01581

Community: Orchard Hill

Brierly Pond Village

192 HORNE WAY # 192, MILLBURY, MA, 01527, Millbury, MA 01527

$475,000

2 beds

3 baths

1,746 sq ft

Condo

192 HORNE WAY # 192, MILLBURY, MA, 01527

Community: Brierly Pond Village

1 2…3

Frequently Asked Questions

What size 55+ communities are there in Middleton?

In Middleton, there is 1 small community with less than 500 homes.

How many homes are there in the smallest, largest, and average 55+ communities in Middleton?

The smallest 55+ community in Middleton has 42 homes, the largest has 42 homes, and the average community consists of 42 homes.

Are there gated 55+ communities in Middleton?

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

Want more information about active adult communities around Middleton?

Global - Lead Form - Buyer or Renter

First Name

Last Name

Phone/Mobile

Text

I'm looking to:

Rent

Buy

*55places does not provide or maintain community HOA information.

Yes, I want to subscribe to email updates from 55places.com, including newsletters, community announcements, and more.

I agree to receive SMS messages to connect me with a local expert.

By requesting more information, you agree that 55places may call, text, or email you about your inquiry, which may be made with automated means (including recorded voice messages, SMS, or text messages). You understand that your consent is not a prerequisite for buying, selling or renting a property. You may revoke your consent at any time by contacting [email protected]. Message/data rates may apply. You also agree to 55places.com’s Privacy Policy and Terms of Use.

Want to learn more about 55+ communities in Middleton?

Call us: (508) 715-6046

162 communities near Middleton

Remove Boundaries ×

Map Satellite

The listings data displayed on this medium comes in part from the Real Estate Information Network Inc. (REIN) and has been authorized by participating listing Broker Members of REIN for display. REIN's listings are based upon Data submitted by its Broker Members, and REIN therefore makes no representation or warranty regarding the accuracy of the Data. All users of REIN's listings database should confirm the accuracy of the listing information directly with the listing agent.
© 2025 REIN. REIN's listings Data and information is protected under federal copyright laws. Federal law prohibits, among other acts, the unauthorized copying or alteration of, or preparation of derivative works from, all or any part of copyrighted materials, including certain compilations of Data and information. COPYRIGHT VIOLATORS MAY BE SUBJECT TO SEVERE FINES AND PENALTIES UNDER FEDERAL LAW.
REIN updates its listings on a daily basis. Data last updated: Dec 08, 2025.
This application does not include information on all of the properties available for sale at this time.

Call Us Call Us

Middleton, MA 55+ active adult communities & homes for sale - Page 3

162 communities near Middleton

96 homes near Middleton

2 beds

2 baths

1,425 sq ft

Condo

2 beds

2 baths

1,490 sq ft

Condo

1 beds

1 baths

1,021 sq ft

Condo

2 beds

3 baths

3,599 sq ft

Condo

1 beds

1 baths

945 sq ft

Condo

2 beds

2 baths

1,600 sq ft

House

2 beds

4 baths

2,987 sq ft

Condo

2 beds

2 baths

1,490 sq ft

Condo

1 beds

1 baths

1,030 sq ft

Condo

2 beds

3 baths

2,426 sq ft

Condo

1 beds

1 baths

955 sq ft

Condo

2 beds

4 baths

3,085 sq ft

Condo

2 beds

2 baths

1,928 sq ft

House

1 beds

1 baths

972 sq ft

Condo

2 beds

2 baths

1,620 sq ft

House

3 beds

2 baths

1,344 sq ft

House

2 beds

2 baths

1,775 sq ft

House

2 beds

2 baths

1,586 sq ft

Condo

1 beds

1 baths

1,115 sq ft

Condo

2 beds