Milton, MA 55+ active adult communities & homes for sale - Page 4

170 communities near Milton

Sort by:

Relevance

Brookedge Village Condomi...

$300ks - $400ks

Brookedge Village Condomi..., South Kingstown, RI

Resale Only | 55+ age-restricted | Built 2007 - 2007 | 28 homes

Brandywyne

$700ks - $800ks

Brandywyne, South Kingstown, RI

Resale Only | 55+ age-restricted | Built 2011 - 2013 | 37 homes

Southwinds

$600ks - $700ks

Southwinds, South Kingstown, RI

Resale Only | 55+ age-restricted | Built 2005 - 2010 | 70 homes

Bailey Brook

$600ks - $700ks

Bailey Brook, Middletown, RI

Resale Only | 55+ age-restricted | Built 2018 - 2024 | 36 homes

English Commons at Topsfi...

$800ks - $900ks

English Commons at Topsfi..., Topsfield, MA

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

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

Questions? Call us: (857) 314-6642

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

Whitestone Village

$400ks - $500ks

Whitestone Village, Groveland, MA

Resale Only | 55+ age-restricted | Built 2002 - 2005 | 100 homes

Red Mill Village

$400ks - $600ks

Red Mill Village, Norton, MA

Resale Only | 55+ age-restricted | Built 2012 - 2014 | 156 homes

5 rating (3 reviews)

Oak Point

$300ks - $400ks

Oak Point, Middleborough, MA

New and Resale | 55+ age-restricted | Built 1999 - present | 1,150 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.

New England Commons

$200ks - $300ks

New England Commons, Webster, MA

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

Villages at Weathervane

$800ks - $1Ms

Villages at Weathervane, Weymouth, MA

Resale Only | 55+ age-restricted | Built 2003 - 2010 | 149 homes

Holliston Woods

$500ks - $700ks

Holliston Woods, Holliston, MA

Resale Only | 55+ age-restricted | Built 2016 - 2018 | 66 homes

Summer Reach

$400ks - $500ks

Summer Reach, Plymouth, MA

Resale Only | 55+ age-restricted | Built 2017 - 2020 | 114 homes

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

Questions? Call us: (857) 314-6642

The Villages at Crane Mea...

$400ks

The Villages at Crane Mea..., Marlborough, MA

Resale Only | 55+ age-restricted | Built 2001 - 2005 | 91 homes

Duxbury Estates

$700ks - $800ks

Duxbury Estates, Duxbury, MA

Resale Only | 55+ age-restricted | Built 2008 - 2013 | 44 homes

Peregrine Woods

$400ks - $600ks

Peregrine Woods, Marshfield, MA

Resale Only | 55+ age-restricted | Built 2002 - 2005 | 32 homes

Tara Woods

$400ks

Tara Woods, Plymouth, MA

Resale Only | 55+ age-restricted | Built 2007 - 2015 | 38 homes

Center Commons

$500ks - $600ks

Center Commons, Pembroke, MA

Resale Only | 55+ age-restricted | Built 2004 - 2009 | 44 homes

Donovan Farm

$500ks - $700ks

Donovan Farm, Norwell, MA

Resale Only | 55+ age-restricted | Built 2001 - 2003 | 40 homes

The Elms of Hanover

$500ks - $700ks

The Elms of Hanover, Hanover, MA

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

Chilton Park Village

$400ks

Chilton Park Village, Plymouth, MA

Resale Only | 55+ age-restricted | Built 2006 - 2015 | 25 homes

Cranberry Grove

$200ks - $300ks

Cranberry Grove, Wareham, MA

Resale Only | 55+ age-restricted | Built 2001 - 2001 | 36 homes

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

Questions? Call us: (857) 314-6642

Kensington at The Pinehil...

$500ks

Kensington at The Pinehil..., Plymouth, MA

New Construction | Age-targeted | Built 2017 - present | 17 homes

Arbor Hills

$400ks - $500ks

Arbor Hills, Kingston, MA

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

Mattapoisett Landing

$400ks - $500ks

Mattapoisett Landing, Mattapoisett, MA

Resale Only | 55+ age-restricted | Built 2012 - 2015 | 27 homes

North Meadow Village

$500ks - $800ks

North Meadow Village, Middleton, MA

Resale Only | 55+ age-restricted | Built 2012 - 2015 | 42 homes

Rockwood Meadows

$600ks - $700ks

Rockwood Meadows, Upton, MA

New Construction | 55+ age-restricted | Built 2016 - present | 58 homes

Rolling Green at Topsfiel...

$600ks - $800ks

Rolling Green at Topsfiel..., Topsfield, MA

Resale Only | 55+ age-restricted | Built 2014 - 2014 | 30 homes

Rockland Glen

$300ks - $500ks

Rockland Glen, Rockland, MA

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

Seaside at Scituate - The...

$900ks - $1Ms

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

New Construction | 55+ age-restricted | Built 2019 - present | 44 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 Milton? 55places can help!

Questions? Call us: (857) 314-6642

Rolling Mill

$600ks - $700ks

Rolling Mill, Plymouth, MA

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

59 North Main

$900ks

59 North Main, Sherborn, MA

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

23 AVEBURY LN 23, MARLBOROUGH, MA, 01752

Community: Regency at Assabet Ridge

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

Questions? Call us: (857) 314-6642

New Upton Ridge

16 LINKSIDE CT 16, NORTHBRIDGE, MA, 0153..., Northbridge, MA 01534

$649,900

2 beds

3 baths

2,030 sq ft

Condo

16 LINKSIDE CT 16, NORTHBRIDGE, MA, 0153...

Community: Upton Ridge

New Willis Brook at Lynnfield

31 FAIRWAY LN 36, LYNNFIELD, MA, 01940, Lynnfield, MA 01940

$1,689,000

2 beds

3 baths

2,442 sq ft

Condo

31 FAIRWAY LN 36, LYNNFIELD, MA, 01940

Community: Willis Brook at Lynnfield

30 Coppersmith

$479,995

1 beds

1 baths

1,129 sq ft

Condo

30 COPPERSMITH WAY 108, CANTON, MA, 0202...

Community: 30 Coppersmith

Woodstone Crossing

70 TROTTER RD 4304, WEYMOUTH, MA, 02190, Weymouth, MA 02190

$459,900

1 beds

1 baths

965 sq ft

Condo

70 TROTTER RD 4304, WEYMOUTH, MA, 02190

Community: Woodstone Crossing

The Preserve at Hunters Hill

3047 CLUBHOUSE DR, DIGHTON, MA, 02715, Dighton, MA 02715

$819,900

2 beds

2 baths

1,775 sq ft

House

3047 CLUBHOUSE DR, DIGHTON, MA, 02715

Community: The Preserve at Hunters Hill

Westbrook Crossing

989 E ST 303, DEDHAM, MA, 02026, Dedham, MA 02026

$749,900

2 beds

2 baths

1,895 sq ft

Condo

989 E ST 303, DEDHAM, MA, 02026

Community: Westbrook Crossing

Martins Landing

230 MARTINS LNDG 111, NORTH READING, MA,..., North Reading, MA 01864

$449,900

1 beds

1 baths

1,030 sq ft

Condo

230 MARTINS LNDG 111, NORTH READING, MA,...

Community: Martins Landing

Martins Landing

320 MARTINS LNDG 501, NORTH READING, MA,..., North Reading, MA 01864

$839,995

2 beds

2 baths

1,586 sq ft

Condo

320 MARTINS LNDG 501, NORTH READING, MA,...

Community: Martins Landing

Great Island

8 RED CANOE 8, PLYMOUTH, MA, 02360, Plymouth, MA 02360

$869,000

3 beds

3 baths

2,281 sq ft

Condo

8 RED CANOE 8, PLYMOUTH, MA, 02360

Community: Great Island

Del Webb Chauncy Lake

4 PETERS FARM WAY 409, WESTBOROUGH, MA, ..., Westborough, MA 01581

$539,900

2 beds

2 baths

1,326 sq ft

Condo

4 PETERS FARM WAY 409, WESTBOROUGH, MA, ...

Community: Del Webb Chauncy Lake

Regency at Emerald Pines

64 PINE TREE DR 64, METHUEN, MA, 01844, Methuen, MA 01844

$785,000

3 beds

3 baths

1,961 sq ft

Condo

64 PINE TREE DR 64, METHUEN, MA, 01844

Community: Regency at Emerald Pines

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

Questions? Call us: (857) 314-6642

Southport

7 PAR THREE CT, MASHPEE, MA, 02649, Mashpee, MA 02649

$525,000

2 beds

3 baths

1,685 sq ft

House

7 PAR THREE CT, MASHPEE, MA, 02649

Community: Southport

Martins Landing

320 MARTINS LNDG 511, NORTH READING, MA,..., North Reading, MA 01864

$669,995

2 beds

2 baths

1,450 sq ft

Condo

320 MARTINS LNDG 511, NORTH READING, MA,...

Community: Martins Landing

Stonebridge Commons

40 STONEBRIDGE DR 40, HANSON, MA, 02341, Hanson, MA 02341

$679,900

2 beds

3 baths

1,800 sq ft

Condo

40 STONEBRIDGE DR 40, HANSON, MA, 02341

Community: Stonebridge Commons

Del Webb Chauncy Lake

5 PETERS FARM WAY 7405, WESTBOROUGH, MA,..., Westborough, MA 01581

$559,995

2 beds

2 baths

1,166 sq ft

Condo

5 PETERS FARM WAY 7405, WESTBOROUGH, MA,...

Community: Del Webb Chauncy Lake

Del Webb Chauncy Lake

5305 PETERS FARM WAY 7305, WESTBOROUGH, ..., Westborough, MA 01581

$529,995

2 beds

2 baths

1,166 sq ft

Condo

5305 PETERS FARM WAY 7305, WESTBOROUGH, ...

Community: Del Webb Chauncy Lake

Martins Landing

320 MARTINS LNDG 310, NORTH READING, MA,..., North Reading, MA 01864

$499,995

1 beds

1 baths

1,129 sq ft

Condo

320 MARTINS LNDG 310, NORTH READING, MA,...

Community: Martins Landing

Pennington Crossing

1102 PENNINGTON DR 1102, WALPOLE, MA, 02..., Walpole, MA 02081

$529,900

1 beds

1 baths

955 sq ft

Condo

1102 PENNINGTON DR 1102, WALPOLE, MA, 02...

Community: Pennington Crossing

Brierly Pond Village

97 HORNE WAY 97, MILLBURY, MA, 01527, Millbury, MA 01527

$450,000

2 beds

3 baths

1,746 sq ft

Condo

97 HORNE WAY 97, MILLBURY, MA, 01527

Community: Brierly Pond Village

The Village at Shepley Hill

138 SAND HILL RD, GROTON, MA, 01450, Groton, MA 01450

$995,000

4 beds

3 baths

2,550 sq ft

House

138 SAND HILL RD, GROTON, MA, 01450

Community: The Village at Shepley Hill

Riverside Woods

2 FRANCIS DR 301, ANDOVER, MA, 01810, Andover, MA 01810

$539,900

2 beds

2 baths

1,490 sq ft

Condo

2 FRANCIS DR 301, ANDOVER, MA, 01810

Community: Riverside Woods

Southport

126 GREY HAWK DR 697, MASHPEE, MA, 02649, Mashpee, MA 02649

$779,900

2 beds

3 baths

1,620 sq ft

Condo

126 GREY HAWK DR 697, MASHPEE, MA, 02649

Community: Southport

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

Questions? Call us: (857) 314-6642

Southport

12 PGA LN 423, MASHPEE, MA, 02649, Mashpee, MA 02649

$545,000

2 beds

2 baths

1,333 sq ft

Condo

12 PGA LN 423, MASHPEE, MA, 02649

Community: Southport

Stone Castle Estates

6 ASHLEY LN 38, METHUEN, MA, 01844, Methuen, MA 01844

$316,648

2 beds

1 baths

1,209 sq ft

Condo

6 ASHLEY LN 38, METHUEN, MA, 01844

Community: Stone Castle Estates

Stonebridge Commons

31 STONEBRIDGE DR 31, HANSON, MA, 02341, Hanson, MA 02341

$659,000

2 beds

3 baths

2,071 sq ft

Condo

31 STONEBRIDGE DR 31, HANSON, MA, 02341

Community: Stonebridge Commons

Great Island

26 CROSS WIND, PLYMOUTH, MA, 02360, Plymouth, MA 02360

$800,000

2 beds

3 baths

2,382 sq ft

House

26 CROSS WIND, PLYMOUTH, MA, 02360

Community: Great Island

Del Webb Chauncy Lake

8 PETERS FARM WAY 113, WESTBOROUGH, MA, ..., Westborough, MA 01581

$639,995

2 beds

2 baths

1,512 sq ft

Condo

8 PETERS FARM WAY 113, WESTBOROUGH, MA, ...

Community: Del Webb Chauncy Lake

Del Webb Chauncy Lake

8 PETERS FARM WAY 103, WESTBOROUGH, MA, ..., Westborough, MA 01581

$414,995

1 beds

2 baths

972 sq ft

Condo

8 PETERS FARM WAY 103, WESTBOROUGH, MA, ...

Community: Del Webb Chauncy Lake

Sawyer's Reach

35 MARINERS WAY 35, PLYMOUTH, MA, 02360, Plymouth, MA 02360

$899,000

3 beds

3 baths

2,533 sq ft

Condo

35 MARINERS WAY 35, PLYMOUTH, MA, 02360

Community: Sawyer's Reach

Oak Point

$425,900

2 beds

2 baths

1,512 sq ft

House

7012 OAK POINT DR, MIDDLEBORO, MA, 02346

Community: Oak Point

Martins Landing

240 MARTINS LNDG 102, NORTH READING, MA,..., North Reading, MA 01864

$449,000

1 beds

1 baths

955 sq ft

Condo

240 MARTINS LNDG 102, NORTH READING, MA,...

Community: Martins Landing

Seton Highlands at The Pinehills

105 SETON HIGHLANDS 105, PLYMOUTH, MA, 0..., Plymouth, MA 02360

$825,000

2 beds

3 baths

2,186 sq ft

Condo

105 SETON HIGHLANDS 105, PLYMOUTH, MA, 0...

Community: Seton Highlands at The Pinehills

Pennington Crossing

2404 PENNINGTON DR 2404, WALPOLE, MA, 02..., Walpole, MA 02081

$559,900

1 beds

1 baths

965 sq ft

Condo

2404 PENNINGTON DR 2404, WALPOLE, MA, 02...

Community: Pennington Crossing

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

Questions? Call us: (857) 314-6642

Bates Quarry

16 TIGER TER 29, WALPOLE, MA, 02081, Walpole, MA 02081

$948,159

2 beds

2 baths

2,509 sq ft

Condo

16 TIGER TER 29, WALPOLE, MA, 02081

Community: Bates Quarry

Cindy Certified

12 TIGER TER 28, WALPOLE, MA, 02081, Walpole, MA 02081

$863,659

2 beds

2 baths

1,501 sq ft

Condo

12 TIGER TER 28, WALPOLE, MA, 02081

Frequently Asked Questions

What size 55+ communities are there in Milton?

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

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

The smallest 55+ community in Milton has 54 homes, the largest has 54 homes, and the average community consists of 54 homes.

Are there new 55+ homes available in Milton?

Yes, there is new 55+ home available in Milton. The most recent community started in Milton include Wolcott Woods. There is also 1 community in Milton that offers new construction homes, including Wolcott Woods.

Are there gated 55+ communities in Milton?

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

Want more information about active adult communities around Milton?

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 optout@55places.com. 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 Milton?

Call us: (857) 314-6642

170 communities

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.
© 2026 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: Sep 17, 2026.
This application does not include information on all of the properties available for sale at this time.

Call Us Call Us

Milton, MA 55+ active adult communities & homes for sale - Page 4

170 communities near Milton

160 homes near Milton

2 beds

3 baths

2,385 sq ft

Condo

2 beds

3 baths

2,290 sq ft

Condo

2 beds

2 baths

1,615 sq ft

Condo

2 beds

3 baths

1,969 sq ft

Condo

4 beds

4 baths

3,561 sq ft

Condo

2 beds

3 baths

2,030 sq ft

Condo

2 beds

3 baths

2,442 sq ft

Condo

1 beds

1 baths

1,129 sq ft

Condo

1 beds

1 baths

965 sq ft

Condo

2 beds

2 baths

1,775 sq ft

House

2 beds

2 baths

1,895 sq ft

Condo

1 beds

1 baths

1,030 sq ft

Condo

2 beds

2 baths

1,586 sq ft

Condo

3 beds

3 baths

2,281 sq ft

Condo

2 beds

2 baths

1,326 sq ft

Condo

3 beds

3 baths

1,961 sq ft

Condo

2 beds

3 baths

1,685 sq ft

House

2 beds

2 baths

1,450 sq ft

Condo

2 beds

3 baths

1,800 sq ft

Condo

2 beds