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

101 homes near Milton

Sort by:

Relevance

Martins Landing

$400ks - $700ks

Martins Landing, North Reading, MA

New Construction | 55+ age-restricted | Built 2018 - present | 450 homes

Del Webb Chauncy Lake

$400ks - $600ks

Del Webb Chauncy Lake, Westborough, MA

New Construction | 55+ age-restricted | Built 2018 - present | 700 homes

The Preserve at Hunters H...

$400ks - $500ks

The Preserve at Hunters H..., Dighton, MA

New and Resale | 55+ age-restricted | Built 2006 - present | 140 homes

Southport

$400ks - $600ks

Southport, Mashpee, MA

New and Resale | 55+ age-restricted | Built 1989 - present | 730 homes

Harmony Place

$400ks - $500ks

Harmony Place, Rutland, MA

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

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

Questions? Call us: (857) 314-6642

Sawyer's Reach

$400ks - $900ks

Sawyer's Reach, Plymouth, MA

New and Resale | 55+ age-restricted | Built 2017 - present | 224 homes

30 Coppersmith

$700ks

30 Coppersmith, Canton, MA

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

Riverside Woods

$400ks - $600ks

Riverside Woods, Andover, MA

Resale Only | 55+ age-restricted | Built 2017 - present | 200 homes

The Trails

$500ks - $700ks

The Trails, Hopkinton, MA

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

Seton Highlands at The Pi...

$600ks - $700ks

Seton Highlands at The Pi..., Plymouth, MA

New and Resale | 55+ age-restricted | Built 2008 - present | 120 homes

Regency at Glen Ellen

$700ks - $900ks

Regency at Glen Ellen, Millis, MA

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

Orchard Hill

$500ks

Orchard Hill, Westborough, MA

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

Bates Quarry

Bates Quarry, Walpole, MA

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

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

Questions? Call us: (857) 314-6642

Lake Point Village

$400ks - $600ks

Lake Point Village, Lakeville, MA

New Construction | 55+ age-restricted | Built 2020 - present | 66 homes

Willis Brook at Lynnfield

$1Ms

Willis Brook at Lynnfield, Lynnfield, MA

New Construction | 55+ age-restricted | Built 2026 - present | 100 homes

Woodcrest Run

$400ks - $600ks

Woodcrest Run, Sharon, MA

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

Preserve at Emerald Pines

$800ks

Preserve at Emerald Pines, Methuen, MA

Resale Only | 55+ age-restricted | Built 2017 - 2024 | 192 homes

Forest Glen

$400ks - $500ks

Forest Glen, Uxbridge, MA

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

5 rating (3 reviews)

Oak Point

$300ks - $400ks

Oak Point, Middleborough, MA

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

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

Questions? Call us: (857) 314-6642

The Village at Orchard Me...

$400ks - $500ks

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

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

Great Island

$600ks

Great Island, Plymouth, MA

Resale Only | 55+ age-restricted | Built 2002 - 2015 | 600 homes

4 rating (2 reviews)

Regency at Methuen

$500ks - $600ks

Regency at Methuen, Methuen, MA

Resale Only | 55+ age-restricted | Built 2011 - 2015 | 240 homes

Chadwick Place

$400ks - $500ks

Chadwick Place, Windham, NH

Resale Only | 55+ age-restricted | Built 2018 - 2020 | 15 homes

Parker Village

$400ks

Parker Village, Merrimack, NH

Resale Only | 55+ age-restricted | Built 2003 - 2008 | 76 homes

Stage Crossing

$400ks - $500ks

Stage Crossing, Litchfield, NH

Resale Only | 55+ age-restricted | Built 2005 - 2008 | 76 homes

The Villages at Three Pon...

$500ks - $700ks

The Villages at Three Pon..., Brentwood, NH

Resale Only | 55+ age-restricted | Built 2019 - 2023 | 68 homes

Colliston Yard

$400ks - $500ks

Colliston Yard, Nashua, NH

Resale Only | 55+ age-restricted | Built 2005 - 2006 | 75 homes

Bramber Green

$900ks

Bramber Green, Greenland, NH

Resale Only | 55+ age-restricted | Built 2016 - 2017 | 73 homes

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

Questions? Call us: (857) 314-6642

The Nevins

$700ks

The Nevins, Londonderry, NH

Resale Only | 55+ age-restricted | Built 2004 - 2013 | 128 homes

The Vineyards

$500ks - $600ks

The Vineyards, Stratham, NH

Resale Only | 55+ age-restricted | Built 2002 - 2007 | 77 homes

Summerfield of Amherst

$600ks

Summerfield of Amherst, Amherst, NH

Resale Only | 55+ age-restricted | Built 2005 - 2008 | 77 homes

Cross Farm

$700ks - $800ks

Cross Farm, Londonderry, NH

Resale Only | 55+ age-restricted | Built 2018 - 2024 | 189 homes

Sherwood Glen

$400ks - $500ks

Sherwood Glen, Raymond, NH

Resale Only | 55+ age-restricted | Built 2005 - 2010 | 82 homes

Ledgewood of Milford

$400ks

Ledgewood of Milford, Milford, NH

Resale Only | 55+ age-restricted | Built 2003 - 2004 | 98 homes

The Paddock

$500ks - $600ks

The Paddock, Salem, NH

Resale Only | 55+ age-restricted | Built 2016 - 2019 | 16 homes

Hickory Woods

$400ks - $700ks

Hickory Woods, Londonderry, NH

Resale Only | 55+ age-restricted | Built 2014 - 2016 | 98 homes

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

Questions? Call us: (857) 314-6642

Brook Ridge

$400ks

Brook Ridge, Hooksett, NH

Resale Only | 55+ age-restricted | Built 2004 - present | 91 homes

Oak Ridge Estates

$500ks - $600ks

Oak Ridge Estates, Hudson, NH

Resale Only | 55+ age-restricted | Built 2012 - 2015 | 101 homes

11101 PETERS FARM WAY # 101, WESTBOROUGH...

Community: Del Webb Chauncy Lake

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

Questions? Call us: (857) 314-6642

Regency at Glen Ellen

6 GLEN ELLEN BLVD 6, MILLIS, MA, 02054, Millis, MA 02054

$999,999

3 beds

3 baths

2,656 sq ft

Condo

6 GLEN ELLEN BLVD 6, MILLIS, MA, 02054

Community: Regency at Glen Ellen

Southport

1 UPLAND CIR 1, MASHPEE, MA, 02649, Mashpee, MA 02649

$485,000

2 beds

2 baths

1,333 sq ft

Condo

1 UPLAND CIR 1, MASHPEE, MA, 02649

Community: Southport

The Preserve at Hunters Hill

3051 CLUBHOUSE DR 78, DIGHTON, MA, 02715, Dighton, MA 02715

$829,225

2 beds

2 baths

2,266 sq ft

House

3051 CLUBHOUSE DR 78, DIGHTON, MA, 02715

Community: The Preserve at Hunters Hill

Southport

15 PEBBLE BCH 2005-103, MASHPEE, MA, 026..., Mashpee, MA 02649

$549,000

2 beds

3 baths

1,685 sq ft

Condo

15 PEBBLE BCH 2005-103, MASHPEE, MA, 026...

Community: Southport

The Preserve at Hunters Hill

3057 CLUB HOUSE DR MODEL, DIGHTON, MA, 0..., Dighton, MA 02715

$739,900

2 beds

2 baths

2,044 sq ft

House

3057 CLUB HOUSE DR MODEL, DIGHTON, MA, 0...

Community: The Preserve at Hunters Hill

Southport

80 PINE HILL BLVD # 80, MASHPEE, MA, 026..., Mashpee, MA 02649

$569,000

2 beds

3 baths

2,208 sq ft

Condo

80 PINE HILL BLVD # 80, MASHPEE, MA, 026...

Community: Southport

Martins Landing

260 MARTINS LNDG 508, NORTH READING, MA,..., North Reading, MA 01864

$649,900

2 beds

2 baths

1,340 sq ft

Condo

260 MARTINS LNDG 508, NORTH READING, MA,...

Community: Martins Landing

Seton Highlands at The Pinehills

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

$849,000

2 beds

3 baths

2,186 sq ft

Condo

105 SETON HIGHLANDS # 105, PLYMOUTH, MA,...

House

G1 CLUBHOUSE DR G1, DIGHTON, MA, 02715

Community: The Preserve at Hunters Hill

1 2 3

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.

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

On average, listings in 55+ community in Milton stay on the market for around 4 days. The average price of homes for sale in this community is approximately $1,675,000, though prices can range widely based on the size, location, and amenities of the community. For example, homes in Wolcott Woods average around $1,675,000.

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 [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 Milton?

Call us: (857) 314-6642

101 homes

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: Mar 05, 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 3

169 communities near Milton

101 homes near Milton

2 beds

3 baths

1,832 sq ft

Condo

1 beds

1 baths

956 sq ft

Condo

2 beds

4 baths

2,455 sq ft

Condo

2 beds

2 baths

1,338 sq ft

Condo

2 beds

2 baths

1,469 sq ft

Condo

3 beds

3 baths

2,656 sq ft

Condo

2 beds

2 baths

1,333 sq ft

Condo

2 beds

2 baths

2,266 sq ft

House

2 beds

3 baths

1,685 sq ft

Condo

2 beds

2 baths

2,044 sq ft

House

2 beds

3 baths

2,208 sq ft

Condo

2 beds

2 baths

1,340 sq ft

Condo

2 beds

3 baths

2,186 sq ft

Condo

2 beds

2 baths

1,775 sq ft

House

2 beds

2 baths

1,899 sq ft

House

2 beds

2 baths

1,928 sq ft

House

2 beds

2 baths

2,097 sq ft

House

2 beds

3 baths

2,216 sq ft

House

2 beds

2 baths

1,775 sq ft

House

2 beds