Portland, CT 55+ active adult communities & homes for sale

125 communities near Portland

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3.6 rating (7 reviews)

Heritage Village

$200ks - $500ks

Heritage Village, Southbury, CT

Resale Only | 55+ age-restricted | Built 1967 - 2005 | 2,580 homes

Leisure Village

$100ks - $300ks

Leisure Village, Ridge, NY

Resale Only | 55+ age-restricted | Built 1969 - 1986 | 1,500 homes

Oronoque Village

$200ks - $400ks

Oronoque Village, Stratford, CT

Resale Only | 55+ age-restricted | Built 1971 - 1977 | 929 homes

3.7 rating (3 reviews)

Greenwood Village

$100ks

Greenwood Village, Manorville, NY

Resale Only | 55+ age-restricted | Built 1980 - 2000 | 512 homes

Leisure Knoll

$200ks - $400ks

Leisure Knoll, Ridge, NY

Resale Only | 55+ age-restricted | Built 1972 - 1982 | 701 homes

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

Questions? Call us: (860) 854-7490

The Greens at Half Hollow

$600ks - $1Ms

The Greens at Half Hollow, Melville, NY

Resale Only | 55+ age-restricted | Built 1994 - 2005 | 1,200 homes

The Waterways at Moriches

$300ks - $600ks

The Waterways at Moriches, Moriches, NY

Resale Only | 55+ age-restricted | Built 1985 - 1999 | 343 homes

4 rating (8 reviews)

Glenwood Village

$100ks - $200ks

Glenwood Village, Riverhead, NY

New and Resale | 55+ age-restricted | Built 1959 - present | 588 homes

The Manors at The Colony ...

$300ks - $400ks

The Manors at The Colony ..., Shirley, NY

New Construction | 55+ age-restricted | Built 2013 - present | 150 homes

Harmony Place

$400ks - $500ks

Harmony Place, Rutland, MA

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

5 rating (1 reviews)

The Villages at Mount Sin...

$600ks

The Villages at Mount Sin..., Mount Sinai, NY

Resale Only | 55+ age-restricted | Built 2005 - 2007 | 185 homes

The Village at Oxford Gre...

$400ks - $500ks

The Village at Oxford Gre..., Oxford, CT

New and Resale | 55+ age-restricted | Built 2004 - present | 835 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

5 rating (2 reviews)

Fairfield at St. James

$300ks - $500ks

Fairfield at St. James, St. James, NY

Resale Only | 55+ age-restricted | Built 1972 - 1989 | 653 homes

3.5 rating (2 reviews)

Foxwood Village

$200ks - $400ks

Foxwood Village, Calverton, NY

Resale Only | 55+ age-restricted | Built 1986 - 2007 | 294 homes

Leisure Glen

$300ks - $400ks

Leisure Glen, Ridge, NY

Resale Only | 55+ age-restricted | Built 1985 - 2010 | 646 homes

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

Questions? Call us: (860) 854-7490

The Seasons at Elwood

$800ks - $900ks

The Seasons at Elwood, East Northport, NY

Resale Only | 55+ age-restricted | Built 2018 - 2020 | 256 homes

5 rating (1 reviews)

Encore at Lake Grove

$500ks - $700ks

Encore at Lake Grove, Lake Grove, NY

Resale Only | 55+ age-restricted | Built 2006 - 2007 | 228 homes

5 rating (1 reviews)

Westhampton Pines

$900ks - $1Ms

Westhampton Pines, Westhampton, NY

Resale Only | 55+ age-restricted | Built 2005 - 2013 | 189 homes

Woodridge Strathmore Terr...

$200ks - $300ks

Woodridge Strathmore Terr..., Mount Sinai, NY

Resale Only | 55+ age-restricted | Built 1974 - 1985 | 226 homes

The Coves at Melville

$500ks

The Coves at Melville, Melville, NY

Resale Only | 62+ age-restricted | Built 2004 - 2005 | 175 homes

Country Pointe Preserve

$600ks - $900ks

Country Pointe PreserveYaphank, NY

New Construction | 55+ age-restricted | Built 2024 - present | 152 homes

5 rating (1 reviews)

Encore Atlantic Shores

$500ks - $800ks

Encore Atlantic Shores, Eastport, NY

Resale Only | 55+ age-restricted | Built 2004 - 2011 | 240 homes

Regency at Prospect

$300ks - $400ks

Regency at Prospect, Prospect, CT

Resale Only | 55+ age-restricted | Built 2006 - 2020 | 379 homes

Stoneleigh Woods at River...

$500ks

Stoneleigh Woods at River..., Riverhead, NY

Resale Only | 55+ age-restricted | Built 2007 - 2016 | 176 homes

Fairview at Oxford Greens

$400ks - $600ks

Fairview at Oxford Greens, Oxford, CT

New and Resale | 55+ age-restricted | Built 2019 - present | 125 homes

The Seasons at Seaford

$600ks

The Seasons at Seaford, Seaford, NY

Resale Only | 55+ age-restricted | Built 2015 - 2017 | 112 homes

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

Questions? Call us: (860) 854-7490

The Gardens of Wilbraham

$200ks - $400ks

The Gardens of Wilbraham, Wilbraham, MA

New and Resale | 55+ age-restricted | Built 2005 - present | 108 homes

Eagles Walk at East Quogu...

$300ks - $400ks

Eagles Walk at East Quogu..., East Quogue, NY

Resale Only | 55+ age-restricted | Built 2004 - 2014 | 67 homes

Village Estates

$300ks - $400ks

Village Estates, Amityville, NY

Resale Only | 55+ age-restricted | Built 2006 - 2008 | 138 homes

Rivington

$300ks - $900ks

Rivington, Danbury, CT

New and Resale | Age-targeted | Built 2006 - present | 1,050 homes

Country Pointe Plainview

$700ks - $1Ms

Country Pointe Plainview, Plainview, NY

New Construction | 55+ age-restricted | Built 2017 - present | 660 homes

The Summit at Bethel

$500ks - $700ks

The Summit at Bethel, Bethel, CT

Resale Only | 55+ age-restricted | Built 2010 - 2021 | 235 homes

South Pond Village

$300ks - $400ks

South Pond Village, Bloomfield, CT

Resale Only | 55+ age-restricted | Built 1999 - 2005 | 151 homes

The Vineyards at Miller P...

$500ks

The Vineyards at Miller P..., Miller Place, NY

Resale Only | 55+ age-restricted | Built 2004 - 2005 | 85 homes

Founders Village

$400ks - $500ks

Founders Village, Southold, NY

Resale Only | 55+ age-restricted | Built 1981 - 1985 | 92 homes

Applegate Estates

$500ks - $400ks

Applegate Estates, Southington, CT

New and Resale | 55+ age-restricted | Built 2010 - 2025 | 94 homes

1 rating (1 reviews)

Plymouth Estates at Mount...

$400ks - $500ks

Plymouth Estates at Mount..., Mount Sinai, NY

Resale Only | 55+ age-restricted | Built 2006 - 2013 | 285 homes

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

Questions? Call us: (860) 854-7490

Setauket Meadows

$500ks - $600ks

Setauket Meadows, Setauket, NY

Resale Only | 55+ age-restricted | Built 2005 - 2007 | 150 homes

Village Vistas

$800ks - $1Ms

50 GREAT HILL DR, BETHEL, CT, 06801

2 ASHTON LN 2, MILLBURY, MA, 01527

Community: Brierly Pond Village

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

Questions? Call us: (860) 854-7490

Founders Village

2555 YOUNGS AVE 1D, SOUTHOLD, NY, 11971, Southold, NY 11971

$560,000

2 beds

2 baths

1,100 sq ft

House

2555 YOUNGS AVE 1D, SOUTHOLD, NY, 11971

Community: Founders Village

Oronoque Village

13 ALGONQUIN LN B, STRATFORD, CT, 06614, Stratford, CT 06614

$396,000

1 beds

2 baths

1,480 sq ft

Condo

13 ALGONQUIN LN B, STRATFORD, CT, 06614

Community: Oronoque Village

Leisure Village

196 NEWCASTLE CT C, BROOKHAVEN, NY, 1196..., Brookhaven, NY 11961

$330,000

2 beds

1 baths

836 sq ft

Condo

196 NEWCASTLE CT C, BROOKHAVEN, NY, 1196...

Community: Leisure Village

The Coves at Melville

27 MORLEY CIR, HUNTINGTON, NY, 11747, Huntington, NY 11747

$585,000

2 beds

2 baths

1,109 sq ft

Condo

27 MORLEY CIR, HUNTINGTON, NY, 11747

Community: The Coves at Melville

Heritage Village

877 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488

$289,000

2 beds

2 baths

1,365 sq ft

Condo

877 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

The Village at Orchard Meadows

70 ORCHARD MEADOW DR 70, SHREWSBURY, MA,..., Shrewsbury, MA 01545

$649,000

2 beds

3 baths

1,896 sq ft

Condo

70 ORCHARD MEADOW DR 70, SHREWSBURY, MA,...

Community: The Village at Orchard Meadows

The Summit at Bethel

6 LOCKWOOD CIR 6, BETHEL, CT, 06801, Bethel, CT 06801

$619,000

3 beds

3 baths

1,771 sq ft

Condo

6 LOCKWOOD CIR 6, BETHEL, CT, 06801

Community: The Summit at Bethel

Greenwood Village

11 A DOGWOOD LN 11 A, BROOKHAVEN, NY, 11..., Brookhaven, NY 11949

$199,000

2 beds

2 baths

1,032 sq ft

Condo

11 A DOGWOOD LN 11 A, BROOKHAVEN, NY, 11...

Community: Greenwood Village

The Manors at The Colony Preserve

40 GREENTREE CT, BROOKHAVEN, NY, 11967, Brookhaven, NY 11967

$540,000

2 beds

2 baths

1,360 sq ft

Condo

40 GREENTREE CT, BROOKHAVEN, NY, 11967

Community: The Manors at The Colony Preserve

The Greens at Half Hollow

1075 SAVOY DR, HUNTINGTON, NY, 11747, Huntington, NY 11747

$699,000

2 beds

2 baths

1,166 sq ft

Condo

1075 SAVOY DR, HUNTINGTON, NY, 11747

Community: The Greens at Half Hollow

Pond Spring Village

37 SEPTEMBER LN 37, BEACON FALLS, CT, 06..., Beacon Falls, CT 06403

$450,000

2 beds

3 baths

1,328 sq ft

Condo

37 SEPTEMBER LN 37, BEACON FALLS, CT, 06...

Community: Pond Spring Village

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

Questions? Call us: (860) 854-7490

The Waterways at Moriches

188 RIVER DR, BROOKHAVEN, NY, 11955, Brookhaven, NY 11955

$729,000

2 beds

2 baths

2,100 sq ft

Condo

188 RIVER DR, BROOKHAVEN, NY, 11955

Community: The Waterways at Moriches

The Greens at Half Hollow

1053 SAVOY DR, HUNTINGTON, NY, 11747, Huntington, NY 11747

$739,900

2 beds

2 baths

1,100 sq ft

Condo

1053 SAVOY DR, HUNTINGTON, NY, 11747

Community: The Greens at Half Hollow

The Village at Orchard Meadows

7 BLOSSOM TREE DR 7, SHREWSBURY, MA, 015..., Shrewsbury, MA 01545

$525,000

2 beds

2 baths

1,370 sq ft

Condo

7 BLOSSOM TREE DR 7, SHREWSBURY, MA, 015...

Community: The Village at Orchard Meadows

Heritage Village

343 HERITAGE VLG D, SOUTHBURY, CT, 06488, Southbury, CT 06488

$215,000

2 beds

2 baths

1,044 sq ft

Condo

343 HERITAGE VLG D, SOUTHBURY, CT, 06488

Community: Heritage Village

Glenwood Village

1661 OLD COUNTRY RD 516, RIVERHEAD, NY, ..., Riverhead, NY 11901

$419,000

2 beds

2 baths

1,624 sq ft

Manufactured Home

1661 OLD COUNTRY RD 516, RIVERHEAD, NY, ...

Community: Glenwood Village

Rivington

925 OLD PASTURE DR 925, DANBURY, CT, 068..., Danbury, CT 06810

$510,000

2 beds

2 baths

1,258 sq ft

Condo

925 OLD PASTURE DR 925, DANBURY, CT, 068...

Community: Rivington

Leisure Knoll

379 LARCHMONT CT, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$539,000

2 beds

2 baths

1,070 sq ft

Condo

379 LARCHMONT CT, BROOKHAVEN, NY, 11961

Community: Leisure Knoll

The Greens at Half Hollow

562 BARDINI DR, HUNTINGTON, NY, 11747, Huntington, NY 11747

$949,888

2 beds

3 baths

1,941 sq ft

Condo

562 BARDINI DR, HUNTINGTON, NY, 11747

Community: The Greens at Half Hollow

Chatfield Farms

24 BAYBERRY CT 24, BEACON FALLS, CT, 064..., Beacon Falls, CT 06403

$725,000

3 beds

3 baths

1,981 sq ft

Condo

24 BAYBERRY CT 24, BEACON FALLS, CT, 064...

Community: Chatfield Farms

The Seasons at Elwood

53 WINTER PL 53, HUNTINGTON, NY, 11731, Huntington, NY 11731

$979,900

2 beds

3 baths

1,500 sq ft

Condo

53 WINTER PL 53, HUNTINGTON, NY, 11731

Community: The Seasons at Elwood

The Seasons at Elwood

240 FALL CT, HUNTINGTON, NY, 11731, Huntington, NY 11731

$1,299,999

2 beds

3 baths

2,329 sq ft

Condo

240 FALL CT, HUNTINGTON, NY, 11731

Community: The Seasons at Elwood

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

Questions? Call us: (860) 854-7490

Leisure Knoll

220 BELFAST LN, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$539,999

2 beds

2 baths

1,445 sq ft

Condo

220 BELFAST LN, BROOKHAVEN, NY, 11961

Community: Leisure Knoll

Leisure Glen

515 LEISURE DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$560,000

2 beds

2 baths

1,434 sq ft

House

515 LEISURE DR, BROOKHAVEN, NY, 11961

Community: Leisure Glen

Frequently Asked Questions

What size 55+ communities are there in Portland?

In Portland, there are no large communities, no medium communities, and 2 small communities with less than 500 homes.

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

The smallest 55+ communities in Portland has 56 homes, the largest has 82 homes, and the average communities consists of 69 homes.

Are there gated 55+ communities in Portland?

Yes, there is gated 55+ communities in Portland. Approximately 50.0% of 55+ communities in the area are gated. For instance, Bartlett Hill is a gated communities with 82 homes.

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

On average, listings in 55+ communities in Portland stay on the market for around 115 days. The average price of homes for sale in these communities is approximately $489,642, though prices can range widely based on the size, location, and amenities of the communities. For example, homes in Bartlett Hill average around $489,642.

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125 communities

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Portland, CT 55+ active adult communities & homes for sale

125 communities near Portland

231 homes near Portland

2 beds

3 baths

3,214 sq ft

Condo

2 beds

2 baths

1,076 sq ft

Condo

2 beds

3 baths

2,475 sq ft

House

2 beds

3 baths

1,620 sq ft

Condo

2 beds

3 baths

1,623 sq ft

Condo

2 beds

3 baths

2,067 sq ft

Condo

2 beds

2 baths

1,200 sq ft

Condo

2 beds

2 baths

1,535 sq ft

Condo

1 beds

3 baths

1,175 sq ft

Condo

2 beds

2 baths

1,398 sq ft

Condo

2 beds

1 baths

Condo

2 beds

2 baths

1,392 sq ft

Condo

2 beds

2 baths

1,486 sq ft

Condo

2 beds

2 baths

1,501 sq ft

Condo

2 beds

2 baths

1,432 sq ft

Condo

2 beds

4 baths

1,949 sq ft

Condo

2 beds

2 baths

1,100 sq ft

House

1 beds

2 baths

1,480 sq ft

Condo

2 beds

1 baths

836 sq ft

Condo

2 beds

2 baths