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

166 communities near Middleton

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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

Harmony Place

$400ks - $500ks

Harmony Place, Rutland, MA

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

Regency at Glen Ellen

$700ks - $900ks

Regency at Glen Ellen, Millis, MA

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

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

Questions? Call us: (508) 715-6046

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

Questions? Call us: (508) 715-6046

30 Coppersmith

$700ks

30 Coppersmith, Canton, MA

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

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 Assabet Ridge

$500ks - $600ks

Regency at Assabet Ridge, Marlborough, MA

Resale Only | 55+ age-restricted | Built 2010 - 2015 | 69 homes

Riverside Woods

$400ks - $600ks

Riverside Woods, Andover, MA

Resale Only | 55+ age-restricted | Built 2017 - present | 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.

The Trails

$500ks - $700ks

The Trails, Hopkinton, MA

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

Read the Ultimate 55+ Rental Guide Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.

Preserve at Emerald Pines

$800ks

Preserve at Emerald Pines, Methuen, MA

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

Sawyer's Reach

$400ks - $900ks

Sawyer's Reach, Plymouth, MA

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

Willis Brook at Lynnfield

$1Ms

Willis Brook at Lynnfield, Lynnfield, MA

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

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

Questions? Call us: (508) 715-6046

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

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

Questions? Call us: (508) 715-6046

5 rating (3 reviews)

Oak Point

$300ks - $400ks

Oak Point, Middleborough, MA

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

Regency at Emerald Pines

$600ks - $900ks

Regency at Emerald Pines, Methuen, MA

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

Westbrook Crossing

$400ks - $500ks

Westbrook Crossing, Dedham, MA

Resale Only | 55+ age-restricted | Built 2003 - 2004 | 60 homes

Quail Ridge

$600ks - $700ks

Quail Ridge, Acton, MA

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

Reading Woods

$400ks - $600ks

Reading Woods, Reading, MA

Resale Only | 55+ age-restricted | Built 2011 - 2016 | 424 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 Middleton? 55places can help!

Questions? Call us: (508) 715-6046

The Village at Auburnvill...

$300ks - $400ks

The Village at Auburnvill..., Whitman, MA

Resale Only | 55+ age-restricted | Built 2004 - 2014 | 92 homes

Cranberry Grove

$200ks - $300ks

Cranberry Grove, Wareham, MA

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

North Meadow Village

$500ks - $800ks

North Meadow Village, Middleton, MA

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

Orchard Hill

$500ks

Orchard Hill, Westborough, MA

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

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

Questions? Call us: (508) 715-6046

Forest Glen

$400ks - $500ks

Forest Glen, Uxbridge, MA

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

Woodcrest Run

$400ks - $600ks

Woodcrest Run, Sharon, MA

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

Brooksmont

$400ks - $600ks

Brooksmont, Holliston, MA

Resale Only | 55+ age-restricted | Built 2017 - 2020 | 66 homes

Lake Point Village

$400ks - $600ks

Lake Point Village, Lakeville, MA

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

Angell Brook Village

$300ks

Angell Brook Village, West Boylston, MA

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

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

Questions? Call us: (508) 715-6046

The Village at Westminste...

$400ks - $500ks

The Village at Westminste..., Holden, MA

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

The Village at Orchard Me...

$400ks - $500ks

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

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

Bates Quarry

Bates Quarry, Walpole, MA

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

The Village at Northridge

$500ks - $600ks

The Village at Northridge, North Reading, MA

Resale Only | 55+ age-restricted | 56 homes

The Village at Shepley Hi...

$900ks

The Village at Shepley Hi..., Groton, MA

New and Resale | 55+ age-restricted | Built 2023 - present | 26 homes

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

Questions? Call us: (508) 715-6046

Blackberry Hill Village

$400ks - $500ks

Blackberry Hill Village, Berwick, ME

New and Resale | 55+ age-restricted | Built 2023 - present | 77 homes

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

5 rating (1 reviews)

The Village at Great Broo...

$500ks - $700ks

The Village at Great Broo..., Eliot, ME

Resale Only | 55+ age-restricted | Built 2016 - 2023 | 90 homes

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

Questions? Call us: (508) 715-6046

Eagles Trace

$400ks - $500ks

Eagles Trace, Acton, ME

Resale Only | 55+ age-restricted | Built 2005 - 2020 | 14 homes

Fairway View Village

$500ks - $600ks

Fairway View Village, Wells, ME

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

877 AUBURNVILLE WAY M2, WHITMAN, MA, 023...

Community: The Village at Auburnville

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

Questions? Call us: (508) 715-6046

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

Questions? Call us: (508) 715-6046

Del Webb Chauncy Lake

5 PETERS FARM WAY 312, WESTBOROUGH, MA, ..., Westborough, MA 01581

$724,995

2 beds

2 baths

1,512 sq ft

Condo

5 PETERS FARM WAY 312, WESTBOROUGH, MA, ...

Community: Del Webb Chauncy Lake

Del Webb Chauncy Lake

5 PETERS FARM WAY 109, WESTBOROUGH, MA, ..., Westborough, MA 01581

$474,995

1 beds

1 baths

1,030 sq ft

Condo

5 PETERS FARM WAY 109, WESTBOROUGH, MA, ...

Community: Del Webb Chauncy Lake

Del Webb Chauncy Lake

4403 PETERS FARM WAY 4403, WESTBOROUGH, ..., Westborough, MA 01581

$415,000

1 beds

1 baths

956 sq ft

Condo

4403 PETERS FARM WAY 4403, WESTBOROUGH, ...

Community: Del Webb Chauncy Lake

Angell Brook Village

44 ANGELL BROOK DR 44, WEST BOYLSTON, MA..., West Boylston, MA 01583

$479,000

2 beds

2 baths

1,274 sq ft

Condo

44 ANGELL BROOK DR 44, WEST BOYLSTON, MA...

Community: Angell Brook Village

The Village at Westminster Place

53 TEA PARTY CIR 53, HOLDEN, MA, 01520, Holden, MA 01520

$539,000

2 beds

2 baths

1,258 sq ft

Condo

53 TEA PARTY CIR 53, HOLDEN, MA, 01520

Community: The Village at Westminster Place

Del Webb Chauncy Lake

12308 PETERS FARM WAY 308, WESTBOROUGH, ..., Westborough, MA 01581

$549,900

2 beds

2 baths

1,326 sq ft

Condo

12308 PETERS FARM WAY 308, WESTBOROUGH, ...

Community: Del Webb Chauncy Lake

Reading Woods

7 AUGUSTUS CT 1013, READING, MA, 01867, Reading, MA 01867

$699,900

2 beds

2 baths

1,475 sq ft

Condo

7 AUGUSTUS CT 1013, READING, MA, 01867

Community: Reading Woods

Martins Landing

220 MARTINS LNDG 403, NORTH READING, MA,..., North Reading, MA 01864

$529,900

1 beds

1 baths

965 sq ft

Condo

220 MARTINS LNDG 403, NORTH READING, MA,...

Community: Martins Landing

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

Questions? Call us: (508) 715-6046

Martins Landing

280 MARTINS 306, NORTH READING, MA, 0186..., North Reading, MA 01864

$794,999

2 beds

2 baths

1,496 sq ft

Condo

280 MARTINS 306, NORTH READING, MA, 0186...

Community: Martins Landing

Orchard Hill

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

$645,000

3 beds

3 baths

2,793 sq ft

Condo

9 BALDWIN CT 9, WESTBOROUGH, MA, 01581

Community: Orchard Hill

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

Questions? Call us: (508) 715-6046

Quail Ridge

35 GREENSIDE LN 35, ACTON, MA, 01720, Acton, MA 01720

$945,000

2 beds

3 baths

2,956 sq ft

House

35 GREENSIDE LN 35, ACTON, MA, 01720

Community: Quail Ridge

Riverside Woods

6 OVERLOOK DR 403, ANDOVER, MA, 01810, Andover, MA 01810

$661,000

2 beds

2 baths

1,495 sq ft

Condo

6 OVERLOOK DR 403, ANDOVER, MA, 01810

Community: Riverside Woods

Regency at Assabet Ridge

13 WILSHIRE WAY 13, MARLBOROUGH, MA, 017..., Marlborough, MA 01752

$689,000

2 beds

2 baths

1,584 sq ft

Condo

13 WILSHIRE WAY 13, MARLBOROUGH, MA, 017...

Community: Regency at Assabet Ridge

Millwood Preserve

14 CALLAHAN DR 14, FRAMINGHAM, MA, 01701, Framingham, MA 01701

$1,215,000

2 beds

3 baths

2,454 sq ft

Condo

14 CALLAHAN DR 14, FRAMINGHAM, MA, 01701

Community: Millwood Preserve

Cranberry Grove

$419,900

2 beds

2 baths

1,350 sq ft

Condo

3 CRANBERRY GROVE WAY C, WAREHAM, MA, 02...

Community: Cranberry Grove

Martins Landing

320 MARTINS LNDG 108, NORTH READING, MA,..., North Reading, MA 01864

$550,000

1 beds

1 baths

1,129 sq ft

Condo

320 MARTINS LNDG 108, NORTH READING, MA,...

Community: Martins Landing

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

Questions? Call us: (508) 715-6046

Villages at Weathervane

6 TEE TIME LN 38, WEYMOUTH, MA, 02190, Weymouth, MA 02190

$1,185,000

2 beds

3 baths

2,030 sq ft

Condo

6 TEE TIME LN 38, WEYMOUTH, MA, 02190

Community: Villages at Weathervane

Martins Landing

250-402 MARTIN'S LNDG 402, NORTH READING..., North Reading, MA 01864

$404,900

1 beds

1 baths

1,027 sq ft

Condo

250-402 MARTIN'S LNDG 402, NORTH READING...

Community: Martins Landing

Del Webb Chauncy Lake

5 PETERS FARM WAY 309, WESTBOROUGH, MA, ..., Westborough, MA 01581

$599,999

2 beds

2 baths

1,375 sq ft

Condo

5 PETERS FARM WAY 309, WESTBOROUGH, MA, ...

Community: Del Webb Chauncy Lake

Del Webb Chauncy Lake

5 PETERS FARM WAY 104, WESTBOROUGH, MA, ..., Westborough, MA 01581

$414,995

1 beds

1 baths

972 sq ft

Condo

5 PETERS FARM WAY 104, WESTBOROUGH, MA, ...

Community: Del Webb Chauncy Lake

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

Questions? Call us: (508) 715-6046

Great Island

22 PICKET FENCE, PLYMOUTH, MA, 02360, Plymouth, MA 02360

$949,000

3 beds

3 baths

4,085 sq ft

House

22 PICKET FENCE, PLYMOUTH, MA, 02360

Community: Great Island

The Trails

28 WATERVILLE LN 28, HOPKINTON, MA, 0174..., Hopkinton, MA 01748

$1,069,000

2 beds

3 baths

2,510 sq ft

Condo

28 WATERVILLE LN 28, HOPKINTON, MA, 0174...

Community: The Trails

Preserve at Emerald Pines

125 PHOEBE ST 125, METHUEN, MA, 01844, Methuen, MA 01844

$859,900

3 beds

3 baths

2,319 sq ft

Condo

125 PHOEBE ST 125, METHUEN, MA, 01844

Community: Preserve at Emerald Pines

30 Coppersmith

$475,995

1 beds

1 baths

1,129 sq ft

Condo

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

Community: 30 Coppersmith

Martins Landing

230 MARTINS LNDG 209, NORTH READING, MA,..., North Reading, MA 01864

$499,000

1 beds

1 baths

1,030 sq ft

Condo

230 MARTINS LNDG 209, NORTH READING, MA,...

Condo

20 GLACIER WAY 20, HOLLISTON, MA, 01746

Community: Balancing Rock

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

Questions? Call us: (508) 715-6046

Del Webb Chauncy Lake

1105 PETERS FARM WAY 105, WESTBOROUGH, M..., Westborough, MA 01581

$389,900

1 beds

1 baths

945 sq ft

Condo

1105 PETERS FARM WAY 105, WESTBOROUGH, M...

Community: Del Webb Chauncy Lake

Westbrook Crossing

989 E ST 402, DEDHAM, MA, 02026, Dedham, MA 02026

$499,900

1 beds

1 baths

882 sq ft

Condo

989 E ST 402, DEDHAM, MA, 02026

Community: Westbrook Crossing

Regency at Glen Ellen

8 GLEN ELLEN BLVD 8, MILLIS, MA, 02054, Millis, MA 02054

$1,449,000

2 beds

4 baths

4,247 sq ft

Condo

8 GLEN ELLEN BLVD 8, MILLIS, MA, 02054

Community: Regency at Glen Ellen

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

Questions? Call us: (508) 715-6046

Preserve at Emerald Pines

127 PHOEBE 127, METHUEN, MA, 01844, Methuen, MA 01844

$885,000

2 beds

3 baths

2,294 sq ft

Condo

127 PHOEBE 127, METHUEN, MA, 01844

Community: Preserve at Emerald Pines

Del Webb Chauncy Lake

5 PETERS FARM WAY 305, WESTBOROUGH, MA, ..., Westborough, MA 01581

$579,999

2 beds

2 baths

1,175 sq ft

Condo

5 PETERS FARM WAY 305, WESTBOROUGH, MA, ...

Community: Del Webb Chauncy Lake

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.

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166 communities

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

166 communities near Middleton

101 homes near Middleton

2 beds

2 baths

1,579 sq ft

Condo

2 beds

2 baths

1,335 sq ft

Condo

2 beds

2 baths

1,680 sq ft

House

3 beds

3 baths

2,181 sq ft

Condo

2 beds

2 baths

2,090 sq ft

Condo

2 beds

2 baths

1,512 sq ft

Condo

1 beds

1 baths

1,030 sq ft

Condo

1 beds

1 baths

956 sq ft

Condo

2 beds

2 baths

1,274 sq ft

Condo

2 beds

2 baths

1,258 sq ft

Condo

2 beds

2 baths

1,326 sq ft

Condo

2 beds

2 baths

1,475 sq ft

Condo

1 beds

1 baths

965 sq ft

Condo

2 beds

2 baths

1,496 sq ft

Condo

3 beds

3 baths

2,793 sq ft

Condo

2 beds

3 baths

2,956 sq ft

House

2 beds

2 baths

1,495 sq ft

Condo

2 beds

2 baths

1,584 sq ft

Condo

2 beds

3 baths

2,454 sq ft

Condo

2 beds