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

111 homes near Middleton

Sort by:

Relevance

No reviews yet

North Meadow Village

$500Ks - $800Ks

North Meadow Village, Middleton, MA

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

No reviews yet

Del Webb Chauncy Lake

$300Ks - $800Ks

Del Webb Chauncy Lake, Westborough, MA

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

No reviews yet

Great Island

$700Ks - $1Ms

Great Island, Plymouth, MA

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

No reviews yet

Martins Landing

$400Ks - $800Ks

Martins Landing, North Reading, MA

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

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

Questions? Call us: (508) 715-6046

No reviews yet

Reading Woods

$500Ks - $600Ks

Reading Woods, Reading, MA

Resale Only | 55+ age-restricted | Built 2011 - 2016 | 424 homes

No reviews yet

Regency at Glen Ellen

$800Ks - $1Ms

Regency at Glen Ellen, Millis, MA

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

4 rating (2 reviews)

Regency at Methuen

$800Ks - $800Ks

Regency at Methuen, Methuen, MA

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

No reviews yet

Sawyer's Reach

$600Ks - $600Ks

Sawyer's Reach, Plymouth, MA

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

No reviews yet

Woodstone Crossing

$500Ks - $500Ks

Woodstone Crossing, Weymouth, MA

Resale Only | Age-targeted | Built 2015 - 2019 | 200 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.

No reviews yet

Riverside Woods

$400Ks - $600Ks

Riverside Woods, Andover, MA

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

No reviews yet

Brierly Pond Village

$400Ks - $400Ks

Brierly Pond Village, Millbury, MA

Resale Only | 55+ age-restricted | Built 2003 - 2013 | 199 homes

No reviews yet

Preserve at Emerald Pines

$800Ks - $1Ms

Preserve at Emerald Pines, Methuen, MA

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

No reviews yet

Cross Farm

$700Ks - $800Ks

Cross Farm, Londonderry, NH

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

No reviews yet

The Village at Cider Hill

$400Ks - $500Ks

The Village at Cider Hill, Old Orchard Beach, ME

Resale Only | 55+ age-restricted | Built 2003 - 2007 | 176 homes

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

Questions? Call us: (508) 715-6046

No reviews yet

Pennington Crossing

$500Ks - $500Ks

Pennington Crossing, Walpole, MA

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

No reviews yet

The Trails

$900Ks - $1Ms

The Trails, Hopkinton, MA

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

No reviews yet

Red Mill Village

$500Ks - $800Ks

Red Mill Village, Norton, MA

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

No reviews yet

Quail Ridge

$800Ks - $800Ks

Quail Ridge, Acton, MA

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

No reviews yet

Villages at Weathervane

$800Ks - $1Ms

Villages at Weathervane, Weymouth, MA

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

No reviews yet

Harmony Place

$400Ks - $500Ks

Harmony Place, Rutland, MA

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

No reviews yet

Regency at Emerald Pines

$800Ks - $800Ks

Regency at Emerald Pines, Methuen, MA

Resale Only | 55+ age-restricted | Built 2015 - 2018 | 140 homes

No reviews yet

The Preserve at Hunters H...

$600Ks - $800Ks

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

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

No reviews yet

Upton Ridge

$600Ks - $600Ks

Upton Ridge, Upton, MA

New Construction | 55+ age-restricted | Built 2019 - present | 139 homes

No reviews yet

WestRidge

$700Ks - $1Ms

WestRidge, Hudson, MA

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

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

Questions? Call us: (508) 715-6046

No reviews yet

Angell Brook Village

$400Ks - $400Ks

Angell Brook Village, West Boylston, MA

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

No reviews yet

Millwood Preserve

$1Ms - $1Ms

Millwood Preserve, Framingham, MA

New Construction | 55+ age-restricted | Built 2020 - present | 129 homes

No reviews yet

The Nevins

$700Ks - $700Ks

The Nevins, Londonderry, NH

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

No reviews yet

The Village at Westminste...

$400Ks - $600Ks

The Village at Westminste..., Holden, MA

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

No reviews yet

Stonebridge Commons

$600Ks - $700Ks

Stonebridge Commons, Hanson, MA

Resale Only | 55+ age-restricted | Built 2007 - 2018 | 121 homes

No reviews yet

Seton Highlands at The Pi...

$700Ks - $900Ks

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

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

No reviews yet

The Villages at Hobbs Pon...

$600Ks - $800Ks

The Villages at Hobbs Pon..., Wells, ME

Resale Only | 55+ age-restricted | Built 2019 - 2023 | 120 homes

No reviews yet

The Club at Meadowbrook

$300Ks

The Club at Meadowbrook, Salem, NH

Resale Only | 55+ age-restricted | Built 2005 - 2005 | 117 homes

5 rating (1 reviews)

Ray Farm

$600Ks - $700Ks

Ray Farm, Exeter, NH

Resale Only | 55+ age-restricted | Built 2018 - 2023 | 116 homes

No reviews yet

Hampton Meadows

$700Ks - $900Ks

Hampton Meadows, Hampton, NH

Resale Only | 55+ age-restricted | Built 1998 - 2002 | 116 homes

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

Questions? Call us: (508) 715-6046

No reviews yet

Summer Reach

$400Ks - $500Ks

Summer Reach, Plymouth, MA

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

No reviews yet

The Village at Orchard Me...

$400Ks - $500Ks

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

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

No reviews yet

Sargent Woods

$500Ks - $500Ks

Sargent Woods, Newton, NH

Resale Only | 55+ age-restricted | Built 2008 - 2014 | 113 homes

No reviews yet

Black Rocks Village

$300Ks - $300Ks

Black Rocks Village, Fremont, NH

Resale Only | 55+ age-restricted | Built 2013 - 2016 | 112 homes

No reviews yet

The Mews of Bedford

$500Ks - $500Ks

The Mews of Bedford, Bedford, NH

Resale Only | 55+ age-restricted | Built 1999 - 2002 | 108 homes

1 2 3 4...5

Kensington at The Pinehills

18 BIRMINGHAM, PLYMOUTH, MA, 02360, Plymouth, MA 02360

$825,000

3 beds

3 baths

2,369 sq ft

House

18 BIRMINGHAM, PLYMOUTH, MA, 02360

Community: Kensington at The Pinehills

Villages at Weathervane

18 BEN HOGAN LNDG # 18, WEYMOUTH, MA, 02..., Weymouth, MA 02190

$1,400,000

2 beds

4 baths

2,956 sq ft

Condo

18 BEN HOGAN LNDG # 18, WEYMOUTH, MA, 02...

Community: Villages at Weathervane

Seton Highlands at The Pinehills

18 INVERNESS LN # 18, PLYMOUTH, MA, 0236..., Plymouth, MA 02360

$875,000

3 beds

4 baths

3,782 sq ft

Condo

18 INVERNESS LN # 18, PLYMOUTH, MA, 0236...

Community: Seton Highlands at The Pinehills

WestRidge

3 TOWNSEND RD # 3, HUDSON, MA, 01749, Hudson, MA 01749

$650,000

2 beds

3 baths

1,928 sq ft

Condo

3 TOWNSEND RD # 3, HUDSON, MA, 01749

Community: WestRidge

Martins Landing

320 MARTINS LNDG APT 110, NORTH READING,..., North Reading, MA 01864

$565,400

1 beds

1 baths

1,129 sq ft

Condo

320 MARTINS LNDG APT 110, NORTH READING,...

Community: Martins Landing

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

Questions? Call us: (508) 715-6046

Martins Landing

320 MARTINS LNDG # 2307, NORTH READING, ..., North Reading, MA 01864

$799,310

2 beds

2 baths

1,579 sq ft

Condo

320 MARTINS LNDG # 2307, NORTH READING, ...

Community: Martins Landing

Martins Landing

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

$883,920

2 beds

2 baths

1,586 sq ft

Condo

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

Community: Martins Landing

Martins Landing

320 MARTINS LNDG APT 302, NORTH READING,..., North Reading, MA 01864

$506,375

1 beds

1 baths

1,027 sq ft

Condo

320 MARTINS LNDG APT 302, NORTH READING,...

Community: Martins Landing

Regency at Glen Ellen

27 RICHARDSON DR # 27, MILLIS, MA, 02054, Millis, MA 02054

$974,900

2 beds

3 baths

2,485 sq ft

Condo

27 RICHARDSON DR # 27, MILLIS, MA, 02054

Community: Regency at Glen Ellen

Great Island

27 CROSS WIND, PLYMOUTH, MA, 02360, Plymouth, MA 02360

$750,000

3 beds

3 baths

3,180 sq ft

House

27 CROSS WIND, PLYMOUTH, MA, 02360

Community: Great Island

Sawyer's Reach

45 PLAZA WAY UNIT 406, PLYMOUTH, MA, 023..., Plymouth, MA 02360

$600,000

2 beds

2 baths

1,368 sq ft

Condo

45 PLAZA WAY UNIT 406, PLYMOUTH, MA, 023...

Community: Sawyer's Reach

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

Great Island

24 WEBSTER REACH, PLYMOUTH, MA, 02360, Plymouth, MA 02360

$739,000

3 beds

3 baths

2,782 sq ft

House

24 WEBSTER REACH, PLYMOUTH, MA, 02360

Community: Great Island

Del Webb Chauncy Lake

12302 PETERS FARM WAY # 302, WESTBOROUGH..., Westborough, MA 01581

$379,999

1 beds

1 baths

956 sq ft

Condo

12302 PETERS FARM WAY # 302, WESTBOROUGH...

Community: Del Webb Chauncy Lake

Martins Landing

320 MARTINS LNDG # 2410, NORTH READING, ..., North Reading, MA 01864

$706,665

2 beds

2 baths

1,450 sq ft

Condo

320 MARTINS LNDG # 2410, NORTH READING, ...

Community: Martins Landing

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

Questions? Call us: (508) 715-6046

The Preserve at Hunters Hill

3064 CLUB HOUSE DR, DIGHTON, MA, 02715, Dighton, MA 02715

$649,900

3 beds

3 baths

1,928 sq ft

House

3064 CLUB HOUSE DR, DIGHTON, MA, 02715

Community: The Preserve at Hunters Hill

Stonebridge Commons

26 STONEBRIDGE DR # 26, HANSON, MA, 0234..., Hanson, MA 02341

$725,000

3 beds

3 baths

2,158 sq ft

Condo

26 STONEBRIDGE DR # 26, HANSON, MA, 0234...

Community: Stonebridge Commons

The Preserve at Hunters Hill

3075 CLUB HOUSE DR, DIGHTON, MA, 02715, Dighton, MA 02715

$749,999

3 beds

2 baths

2,151 sq ft

House

3075 CLUB HOUSE DR, DIGHTON, MA, 02715

Community: The Preserve at Hunters Hill

Del Webb Chauncy Lake

5 PETERS FARM WAY # 205, WESTBOROUGH, MA..., Westborough, MA 01581

$545,995

2 beds

2 baths

1,166 sq ft

Condo

5 PETERS FARM WAY # 205, WESTBOROUGH, MA...

Community: Del Webb Chauncy Lake

Oak Point

2602 GREEN ST, MIDDLEBORO, MA, 02346, Middleboro, MA 02346

$359,900

2 beds

2 baths

1,680 sq ft

House

2602 GREEN ST, MIDDLEBORO, MA, 02346

Community: Oak Point

Del Webb Chauncy Lake

2 CODMAN WAY 5401, WESTBOROUGH, MA, 0158..., Westborough, MA 01581

$749,995

2 beds

2 baths

1,496 sq ft

Condo

2 CODMAN WAY 5401, WESTBOROUGH, MA, 0158...

Community: Del Webb Chauncy Lake

Martins Landing

260 MARTINS LNDG APT 103, NORTH READING,..., North Reading, MA 01864

$499,000

1 beds

1 baths

940 sq ft

Condo

260 MARTINS LNDG APT 103, NORTH READING,...

Community: Martins Landing

Del Webb Chauncy Lake

2 CODMAN WAY 408, WESTBOROUGH, MA, 01581, Westborough, MA 01581

$639,999

2 beds

2 baths

1,375 sq ft

Condo

2 CODMAN WAY 408, WESTBOROUGH, MA, 01581

Community: Del Webb Chauncy Lake

Brooksmont

$639,000

2 beds

2 baths

1,516 sq ft

Condo

104 BROOKSMONT DR # 104, HOLLISTON, MA, ...

Community: Brooksmont

Martins Landing

240 MARTINS LNDG APT 201, NORTH READING,..., North Reading, MA 01864

$664,900

2 beds

2 baths

1,490 sq ft

Condo

240 MARTINS LNDG APT 201, NORTH READING,...

Community: Martins Landing

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

Questions? Call us: (508) 715-6046

Orchard Hill

9 BALDWIN CT # 9, WESTBOROUGH, MA, 01581, Westborough, MA 01581

$650,000

3 beds

3 baths

2,793 sq ft

Condo

9 BALDWIN CT # 9, WESTBOROUGH, MA, 01581

Community: Orchard Hill

Spring Meadow

$724,900

2 beds

3 baths

2,417 sq ft

Condo

116 SPRING MEADOW LN # 116, HANOVER, MA,...

Community: Spring Meadow

Millwood Preserve

11 EAGLE LN 105, FRAMINGHAM, MA, 01701, Framingham, MA 01701

$1,375,000

2 beds

4 baths

3,503 sq ft

Condo

11 EAGLE LN 105, FRAMINGHAM, MA, 01701

Community: Millwood Preserve

The Village at Westminster Place

2 EXPLORERS WAY # 2, HOLDEN, MA, 01520, Holden, MA 01520

$499,900

2 beds

2 baths

1,661 sq ft

Condo

2 EXPLORERS WAY # 2, HOLDEN, MA, 01520

Community: The Village at Westminster Place

Seton Highlands at The Pinehills

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

$859,999

2 beds

3 baths

2,186 sq ft

Condo

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

Community: Seton Highlands at The Pinehills

The Preserve at Hunters Hill

3049 CLUBHOUSE DR 77, DIGHTON, MA, 02715, Dighton, MA 02715

$803,000

2 beds

2 baths

2,024 sq ft

House

3049 CLUBHOUSE DR 77, DIGHTON, MA, 02715

Community: The Preserve at Hunters Hill

Riverside Woods

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

$464,900

1 beds

1 baths

945 sq ft

Condo

4 FRANCIS DR 105, ANDOVER, MA, 01810

Community: Riverside Woods

Del Webb Chauncy Lake

12208 PETERS FARM WAY # 12208, WESTBOROU..., Westborough, MA 01581

$439,000

1 beds

1 baths

1,021 sq ft

Condo

12208 PETERS FARM WAY # 12208, WESTBOROU...

Community: Del Webb Chauncy Lake

The Villages at Walker Meadow

9 SHAKER WAY # 9, WESTBOROUGH, MA, 01581, Westborough, MA 01581

$750,000

2 beds

2 baths

2,090 sq ft

Condo

9 SHAKER WAY # 9, WESTBOROUGH, MA, 01581

Community: The Villages at Walker Meadow

Seton Highlands at The Pinehills

17 ABERDEEN # 17, PLYMOUTH, MA, 02360, Plymouth, MA 02360

$975,000

3 beds

3 baths

2,690 sq ft

Condo

17 ABERDEEN # 17, PLYMOUTH, MA, 02360

Community: Seton Highlands at The Pinehills

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

Questions? Call us: (508) 715-6046

Riverside Woods

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

$629,900

2 beds

2 baths

1,490 sq ft

Condo

2 FRANCIS DR 412, ANDOVER, MA, 01810

Community: Riverside Woods

Regency at Glen Ellen

1 JAMESON DR # 1, MILLIS, MA, 02054, Millis, MA 02054

$1,170,000

2 beds

2 baths

1,875 sq ft

Condo

1 JAMESON DR # 1, MILLIS, MA, 02054

Community: Regency at Glen Ellen

Great Island

39 WOODSONG, PLYMOUTH, MA, 02360, Plymouth, MA 02360

$1,050,000

2 beds

3 baths

3,316 sq ft

House

39 WOODSONG, PLYMOUTH, MA, 02360

Community: Great Island

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

Del Webb Chauncy Lake

5 PETERS FARM WAY # 412, WESTBOROUGH, MA..., Westborough, MA 01581

$813,995

2 beds

2 baths

1,512 sq ft

Condo

5 PETERS FARM WAY # 412, WESTBOROUGH, MA...

Community: Del Webb Chauncy Lake

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

111 homes 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: Oct 23, 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

162 communities near Middleton

111 homes near Middleton

3 beds

3 baths

2,369 sq ft

House

2 beds

4 baths

2,956 sq ft

Condo

3 beds

4 baths

3,782 sq ft

Condo

2 beds

3 baths

1,928 sq ft

Condo

1 beds

1 baths

1,129 sq ft

Condo

2 beds

2 baths

1,579 sq ft

Condo

2 beds

2 baths

1,586 sq ft

Condo

1 beds

1 baths

1,027 sq ft

Condo

2 beds

3 baths

2,485 sq ft

Condo

3 beds

3 baths

3,180 sq ft

House

2 beds

2 baths

1,368 sq ft

Condo

2 beds

4 baths

2,987 sq ft

Condo

3 beds

3 baths

2,782 sq ft

House

1 beds

1 baths

956 sq ft

Condo

2 beds

2 baths

1,450 sq ft

Condo

3 beds

3 baths

1,928 sq ft

House

3 beds

3 baths

2,158 sq ft

Condo

3 beds

2 baths

2,151 sq ft

House

2 beds

2 baths

1,166 sq ft

Condo

2 beds