Call us at (857) 314-6642 to learn more about active adult communities in Milton

Milton, MA 55+ active adult communities & homes for sale - Page 2

170 communities near Milton

Sort by:

Relevance

Relevance

The Seasons at Salisbury
$400ks - $500ks
The Seasons at Salisbury, Holden, MA
Resale Only | 55+ age-restricted | Built 2002 - 2006 | 91 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
Summer Reach
$400ks - $500ks
Summer Reach, Plymouth, MA
Resale Only | 55+ age-restricted | Built 2017 - 2020 | 114 homes
Regency at Emerald Pines
$600ks - $900ks
Regency at Emerald Pines, Methuen, MA
Resale Only | 55+ age-restricted | Built 2015 - 2018 | 140 homes
Spring Meadow
$400ks - $500ks
Spring Meadow, Hanover, MA
Resale Only | 55+ age-restricted | Built 2004 - 2007 | 39 homes
Want to learn more about 55+ communities in Milton? 55places can help!
Questions? Call us: (857) 314-6642
Holliston Woods
$500ks - $700ks
Holliston Woods, Holliston, MA
Resale Only | 55+ age-restricted | Built 2016 - 2018 | 66 homes
Rolling Green at Topsfiel...
$600ks - $800ks
Rolling Green at Topsfiel..., Topsfield, MA
Resale Only | 55+ age-restricted | Built 2014 - 2014 | 30 homes
Rockwood Meadows
$600ks - $700ks
Rockwood Meadows, Upton, MA
New Construction | 55+ age-restricted | Built 2016 - present | 58 homes
Red Mill Village
$400ks - $600ks
Red Mill Village, Norton, MA
Resale Only | 55+ age-restricted | Built 2012 - 2014 | 156 homes
Regency at Assabet Ridge
$500ks - $600ks
Regency at Assabet Ridge, Marlborough, MA
Resale Only | 55+ age-restricted | Built 2010 - 2015 | 69 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.
Mattapoisett Landing
$400ks - $500ks
Mattapoisett Landing, Mattapoisett, MA
Resale Only | 55+ age-restricted | Built 2012 - 2015 | 27 homes
Rockland Glen
$300ks - $500ks
Rockland Glen, Rockland, MA
Resale Only | 55+ age-restricted | Built 2008 - 2015 | 60 homes
Arbor Hills
$400ks - $500ks
Arbor Hills, Kingston, MA
Resale Only | 55+ age-restricted | Built 2003 - 2005 | 54 homes
Kensington at The Pinehil...
$500ks
Kensington at The Pinehil..., Plymouth, MA
New Construction | Age-targeted | Built 2017 - present | 17 homes
Villages at Weathervane
$800ks - $1Ms
Villages at Weathervane, Weymouth, MA
Resale Only | 55+ age-restricted | Built 2003 - 2010 | 149 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
Westbrook Crossing
$400ks - $500ks
Westbrook Crossing, Dedham, MA
Resale Only | 55+ age-restricted | Built 2003 - 2004 | 60 homes
Forest Glen
$400ks - $500ks
Forest Glen, Uxbridge, MA
New Construction | 55+ age-restricted | Built 2018 - present | 44 homes
Bigelow Farm
$500ks - $600ks
Bigelow Farm, Northborough, MA
Resale Only | 55+ age-restricted | Built 2006 - 2013 | 41 homes
Lake Point Village
$400ks - $600ks
Lake Point Village, Lakeville, MA
New Construction | 55+ age-restricted | Built 2020 - present | 66 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.
Balancing Rock
$500ks - $600ks
Balancing Rock, Holliston, MA
Resale Only | 55+ age-restricted | Built 2006 - 2008 | 49 homes
Seaside at Scituate - The...
$900ks - $1Ms
Seaside at Scituate - The..., Scituate, MA
New Construction | 55+ age-restricted | Built 2019 - present | 44 homes
Adams Farm
$700ks - $800ks
Adams Farm, Shrewsbury, MA
Resale Only | 55+ age-restricted | Built 2005 - 2013 | 90 homes
Whitestone Village
$400ks - $500ks
Whitestone Village, Groveland, MA
Resale Only | 55+ age-restricted | Built 2002 - 2005 | 100 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
Brooksmont
$400ks - $600ks
Brooksmont, Holliston, MA
Resale Only | 55+ age-restricted | Built 2017 - 2020 | 66 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 Milton? 55places can help!
Questions? Call us: (857) 314-6642
Donovan Farm
$500ks - $700ks
Donovan Farm, Norwell, MA
Resale Only | 55+ age-restricted | Built 2001 - 2003 | 40 homes
The Cottages at Lebaron H...
$500ks - $600ks
The Cottages at Lebaron H..., Lakeville, MA
New Construction | 55+ age-restricted | Built 2019 - present | 32 homes
Center Commons
$500ks - $600ks
Center Commons, Pembroke, MA
Resale Only | 55+ age-restricted | Built 2004 - 2009 | 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.
Blue Heron Pond
$500ks
Blue Heron Pond, Lancaster, MA
Resale Only | 55+ age-restricted | Built 2006 - 2014 | 58 homes
59 North Main
$900ks
59 North Main, Sherborn, MA
New Construction | 55+ age-restricted | Built 2019 - present | 12 homes
Tara Woods
$400ks
Tara Woods, Plymouth, MA
Resale Only | 55+ age-restricted | Built 2007 - 2015 | 38 homes
Peregrine Woods
$400ks - $600ks
Peregrine Woods, Marshfield, MA
Resale Only | 55+ age-restricted | Built 2002 - 2005 | 32 homes
New England Commons
$200ks - $300ks
New England Commons, Webster, MA
New and Resale | 55+ age-restricted | Built 2005 - present | 100 homes
Rolling Mill
$600ks - $700ks
Rolling Mill, Plymouth, MA
Resale Only | 55+ age-restricted | Built 2018 - 2021 | 46 homes
Brookside Village
$700ks
Brookside Village, Walpole, MA
Resale Only | 55+ age-restricted | Built 2018 - 2018 | 30 homes
Wolcott Woods
$1Ms
Wolcott Woods, Milton, MA
New Construction | 55+ age-restricted | Built 2020 - present | 54 homes
Want to learn more about 55+ communities in Milton? 55places can help!
Questions? Call us: (857) 314-6642
Wyman Farms
$500ks - $900ks
Wyman Farms, Shrewsbury, MA
New Construction | 55+ age-restricted | Built 2017 - present | 26 homes
Duxbury Estates
$700ks - $800ks
Duxbury Estates, Duxbury, MA
Resale Only | 55+ age-restricted | Built 2008 - 2013 | 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.
New The Villages at Crane Meadow 7 WHISPERING BRK 7, MARLBOROUGH, MA, 017..., Marlborough, MA 01752
$579,900

2 beds

|

2 baths

|

1,838 sq ft

|

Condo

7 WHISPERING BRK 7, MARLBOROUGH, MA, 017...
New Harmony Place 21 FIDELITY DR 73, RUTLAND, MA, 01543, Rutland, MA 01543
$489,000

2 beds

|

2 baths

|

1,582 sq ft

|

Condo

21 FIDELITY DR 73, RUTLAND, MA, 01543
Community: Harmony Place
New Harmony Place 23 FIDELITY DR 74, RUTLAND, MA, 01543, Rutland, MA 01543
$489,000

2 beds

|

2 baths

|

1,582 sq ft

|

Condo

23 FIDELITY DR 74, RUTLAND, MA, 01543
Community: Harmony Place
New Harmony Place 19 FIDELITY DR 72, RUTLAND, MA, 01543, Rutland, MA 01543
$498,000

2 beds

|

2 baths

|

1,582 sq ft

|

Condo

19 FIDELITY DR 72, RUTLAND, MA, 01543
Community: Harmony Place
New Harmony Place 17 FIDELITY DR 71, RUTLAND, MA, 01543, Rutland, MA 01543
$498,000

2 beds

|

2 baths

|

1,582 sq ft

|

Condo

17 FIDELITY DR 71, RUTLAND, MA, 01543
Community: Harmony Place
Want to learn more about 55+ communities in Milton? 55places can help!
Questions? Call us: (857) 314-6642
New Great Island 12 BELLTREE, PLYMOUTH, MA, 02360, Plymouth, MA 02360
$759,900

2 beds

|

3 baths

|

2,322 sq ft

|

House

12 BELLTREE, PLYMOUTH, MA, 02360
Community: Great Island
New WestRidge 4 HASTINGS RD 4, HUDSON, MA, 01749, Hudson, MA 01749
$610,000

2 beds

|

3 baths

|

1,736 sq ft

|

Condo

4 HASTINGS RD 4, HUDSON, MA, 01749
Community: WestRidge
New 30 Coppersmith 30 COPPERSMITH WAY 501, CANTON, MA, 0202..., Canton, MA 02021
$844,745

2 beds

|

2 baths

|

1,582 sq ft

|

Condo

30 COPPERSMITH WAY 501, CANTON, MA, 0202...
Community: 30 Coppersmith
New Great Island 7 WHITE TRELLIS, PLYMOUTH, MA, 02360, Plymouth, MA 02360
$750,000

2 beds

|

3 baths

|

2,061 sq ft

|

House

7 WHITE TRELLIS, PLYMOUTH, MA, 02360
Community: Great Island
New Great Island 6 CHAMPLAIN CIR, PLYMOUTH, MA, 02360, Plymouth, MA 02360
$659,900

2 beds

|

2 baths

|

1,549 sq ft

|

House

6 CHAMPLAIN CIR, 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.
New The Lanterns at Warren Woods 8 LANTERN WAY 8, ASHLAND, MA, 01721, Ashland, MA 01721
$780,000

2 beds

|

2 baths

|

1,657 sq ft

|

Condo

8 LANTERN WAY 8, ASHLAND, MA, 01721
New Preserve at Emerald Pines 36 PHOEBE ST 36, METHUEN, MA, 01844, Methuen, MA 01844
$914,900

3 beds

|

3 baths

|

2,649 sq ft

|

Condo

36 PHOEBE ST 36, METHUEN, MA, 01844
New Oak Point 408 GREEN ST, MIDDLEBORO, MA, 02346, Middleboro, MA 02346
$389,000

3 beds

|

2 baths

|

1,344 sq ft

|

House

408 GREEN ST, MIDDLEBORO, MA, 02346
Community: Oak Point
New Riverside Woods 2 FRANCIS DR 401, ANDOVER, MA, 01810, Andover, MA 01810
$619,000

2 beds

|

2 baths

|

1,490 sq ft

|

Condo

2 FRANCIS DR 401, ANDOVER, MA, 01810
Community: Riverside Woods
Great Island 6 CLAM PUDDING, PLYMOUTH, MA, 02360, Plymouth, MA 02360
$850,000

3 beds

|

3 baths

|

2,580 sq ft

|

House

6 CLAM PUDDING, PLYMOUTH, MA, 02360
Community: Great Island
Seton Highlands at The Pinehills 24 INVERNESS 24, PLYMOUTH, MA, 02360, Plymouth, MA 02360
$923,000

3 beds

|

3 baths

|

2,719 sq ft

|

Condo

24 INVERNESS 24, PLYMOUTH, MA, 02360
Want to learn more about 55+ communities in Milton? 55places can help!
Questions? Call us: (857) 314-6642
Reading Woods 31 JACOB WAY 31, READING, MA, 01867, Reading, MA 01867
$879,000

3 beds

|

3 baths

|

2,089 sq ft

|

Condo

31 JACOB WAY 31, READING, MA, 01867
Community: Reading Woods
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, ...
Del Webb Chauncy Lake 5 PETERS FARM WAY 410, WESTBOROUGH, MA, ..., Westborough, MA 01581
$594,995

2 beds

|

2 baths

|

1,375 sq ft

|

Condo

5 PETERS FARM WAY 410, WESTBOROUGH, MA, ...
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,...
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 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...
Oak Point 6406 OAK PT, MIDDLEBORO, MA, 02346, Middleboro, MA 02346
$399,000

3 beds

|

2 baths

|

1,456 sq ft

|

House

6406 OAK PT, MIDDLEBORO, MA, 02346
Community: Oak Point
Great Island 5 HIGHBANK TRL, PLYMOUTH, MA, 02360, Plymouth, MA 02360
$691,050

2 beds

|

3 baths

|

2,074 sq ft

|

House

5 HIGHBANK TRL, PLYMOUTH, MA, 02360
Community: Great Island
Stone Castle Estates 4 TILBURY RD 4, METHUEN, MA, 01844, Methuen, MA 01844
$324,424

1 beds

|

2 baths

|

1,128 sq ft

|

Condo

4 TILBURY RD 4, METHUEN, MA, 01844
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
Preserve at Emerald Pines 3 HUMMINGBIRD WAY 3, METHUEN, MA, 01844, Methuen, MA 01844
$879,000

3 beds

|

3 baths

|

2,642 sq ft

|

Condo

3 HUMMINGBIRD WAY 3, METHUEN, MA, 01844
Regency at Glen Ellen 43 JAMESON DR 43, MILLIS, MA, 02054, Millis, MA 02054
$1,299,900

3 beds

|

3 baths

|

2,873 sq ft

|

Condo

43 JAMESON DR 43, MILLIS, MA, 02054
Want to learn more about 55+ communities in Milton? 55places can help!
Questions? Call us: (857) 314-6642
Riverside Woods 2 FRANCIS DR 203, ANDOVER, MA, 01810, Andover, MA 01810
$449,900

1 beds

|

1 baths

|

955 sq ft

|

Condo

2 FRANCIS DR 203, ANDOVER, MA, 01810
Community: Riverside Woods
Regency at Methuen 14 HARTSHORNE WAY 14, METHUEN, MA, 01844, Methuen, MA 01844
$799,900

3 beds

|

3 baths

|

2,407 sq ft

|

Condo

14 HARTSHORNE WAY 14, METHUEN, MA, 01844
Community: Regency at Methuen
Seton Highlands at The Pinehills 17 ABERDEEN 17, PLYMOUTH, MA, 02360, Plymouth, MA 02360
$889,000

3 beds

|

3 baths

|

2,690 sq ft

|

Condo

17 ABERDEEN 17, PLYMOUTH, MA, 02360
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 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...
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...
Preserve at Emerald Pines 53 PHOEBE ST 31, METHUEN, MA, 01844, Methuen, MA 01844
$940,000

2 beds

|

4 baths

|

2,985 sq ft

|

Condo

53 PHOEBE ST 31, METHUEN, MA, 01844
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 Preserve at Hunters Hill 72 CLUB HOUSE DR, DIGHTON, MA, 02715, Dighton, MA 02715
$799,900

2 beds

|

2 baths

|

1,600 sq ft

|

House

72 CLUB HOUSE DR, DIGHTON, MA, 02715
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 Preserve at Hunters Hill 127 CLUBHOUSE DR, DIGHTON, MA, 02715, Dighton, MA 02715
$756,275

2 beds

|

2 baths

|

1,815 sq ft

|

House

127 CLUBHOUSE DR, DIGHTON, MA, 02715
Riverside Woods 1 FRANCIS DR 405, ANDOVER, MA, 01810, Andover, MA 01810
$529,900

2 beds

|

2 baths

|

1,135 sq ft

|

Condo

1 FRANCIS DR 405, ANDOVER, MA, 01810
Community: Riverside Woods
Want to learn more about 55+ communities in Milton? 55places can help!
Questions? Call us: (857) 314-6642
Martins Landing 320 MARTINS LNDG 307, NORTH READING, MA,..., North Reading, MA 01864
$774,995

2 beds

|

2 baths

|

1,579 sq ft

|

Condo

320 MARTINS LNDG 307, NORTH READING, MA,...
Community: Martins Landing
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.

Frequently Asked Questions


Want more information about active adult communities around Milton?

Global - Lead Form - Buyer or Renter
*55places does not provide or maintain community HOA information.
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

Reinmlsx

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: Aug 03, 2026.
This application does not include information on all of the properties available for sale at this time.

Call Us Call Us
Scroll to Top