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

260 homes near Portland

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Bartlett Hill

$500Ks - $500Ks

Bartlett Hill, Portland, CT

Resale Only | 55+ age-restricted | Built 2005 - 2011 | 82 homes

No reviews yet

The Atrium of Portland

<$100k - $100Ks

The Atrium of Portland, Portland, CT

Resale Only | 55+ age-restricted | Built 2004 - 2004 | 56 homes

3.6 rating (7 reviews)

Heritage Village

$100Ks - $500Ks

Heritage Village, Southbury, CT

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

No reviews yet

Leisure Village

$200Ks - $400Ks

Leisure Village, Ridge, NY

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

No reviews yet

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

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No reviews yet

Rivington

$400Ks - $500Ks

Rivington, Danbury, CT

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

No reviews yet

Oronoque Village

$300Ks - $600Ks

Oronoque Village, Stratford, CT

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

No reviews yet

The Village at Oxford Gre...

$500Ks - $700Ks

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

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

No reviews yet

Leisure Knoll

$300Ks - $500Ks

Leisure Knoll, Ridge, NY

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

No reviews yet

Country Pointe Plainview

$1Ms - $1Ms

Country Pointe Plainview, Plainview, NY

New Construction | 55+ age-restricted | Built 2017 - present | 660 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 (2 reviews)

Fairfield at St. James

$400Ks - $500Ks

Fairfield at St. James, St. James, NY

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

No reviews yet

Leisure Glen

$400Ks - $400Ks

Leisure Glen, Ridge, NY

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

No reviews yet

Spring Lake Village

$200Ks - $200Ks

Spring Lake Village, Southington, CT

Resale Only | 55+ age-restricted | Built 1970 - 2004 | 640 homes

4 rating (8 reviews)

Glenwood Village

$100Ks - $400Ks

Glenwood Village, Riverhead, NY

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

3.7 rating (3 reviews)

Greenwood Village

$100Ks - $200Ks

Greenwood Village, Manorville, NY

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

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

Questions? Call us: (860) 854-7490

No reviews yet

Regency at Prospect

$300Ks - $500Ks

Regency at Prospect, Prospect, CT

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

No reviews yet

The Waterways at Moriches

$400Ks - $700Ks

The Waterways at Moriches, Moriches, NY

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

3.5 rating (2 reviews)

Foxwood Village

$300Ks - $400Ks

Foxwood Village, Calverton, NY

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

1 rating (1 reviews)

Plymouth Estates at Mount...

$500Ks - $500Ks

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

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

4.6 rating (9 reviews)

Meadowbrook Pointe Links ...

$300Ks - $700Ks

Meadowbrook Pointe Links ..., Medford, NY

New and Resale | 55+ age-restricted | Built 2010 - present | 280 homes

4 rating (1 reviews)

Vineyards at Blue Point

$800Ks - $800Ks

Vineyards at Blue Point, Blue Point, NY

Resale Only | 55+ age-restricted | Built 2016 - 2018 | 280 homes

No reviews yet

The Club at Melville

$500Ks - $500Ks

The Club at Melville, Melville, NY

Resale Only | 55+ age-restricted | Built 2015 - 2017 | 261 homes

No reviews yet

The Seasons at Elwood

$800Ks - $900Ks

The Seasons at Elwood, East Northport, NY

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

No reviews yet

Meadow Brook Estates

$500Ks - $500Ks

Meadow Brook Estates, Oxford, CT

Resale Only | 55+ age-restricted | Built 2003 - 2020 | 246 homes

5 rating (1 reviews)

Encore Atlantic Shores

$600Ks - $800Ks

Encore Atlantic Shores, Eastport, NY

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

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Questions? Call us: (860) 854-7490

No reviews yet

The Summit at Bethel

$600Ks - $600Ks

The Summit at Bethel, Bethel, CT

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

4.9 rating (14 reviews)

Chatfield Farms

$500Ks - $600Ks

Chatfield Farms, Beacon Falls, CT

New Construction | 55+ age-restricted | Built 2014 - present | 231 homes

5 rating (1 reviews)

Encore at Lake Grove

$600Ks - $800Ks

Encore at Lake Grove, Lake Grove, NY

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

No reviews yet

Woodridge Strathmore Terr...

$400Ks - $400Ks

Woodridge Strathmore Terr..., Mount Sinai, NY

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

5 rating (1 reviews)

Sunrise Village

$400Ks - $500Ks

Sunrise Village, Sayville, NY

Resale Only | 55+ age-restricted | Built 1985 - 1990 | 213 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

Saddle Lakes

$400Ks - $400Ks

Saddle Lakes, Riverhead, NY

Resale Only | 55+ age-restricted | Built 2000 - 2002 | 196 homes

No reviews yet

Country Village Estates

$400Ks - $400Ks

Country Village Estates, Coram, NY

Resale Only | 55+ age-restricted | Built 1993 - 2001 | 195 homes

5 rating (1 reviews)

Sunken Pond Estates

$400Ks - $500Ks

Sunken Pond Estates, Riverhead, NY

Resale Only | 55+ age-restricted | Built 2003 - 2005 | 194 homes

No reviews yet

The Seasons at East North...

$700Ks - $700Ks

The Seasons at East North..., East Northport, NY

New Construction | 55+ age-restricted | Built 2023 - present | 190 homes

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

Questions? Call us: (860) 854-7490

5 rating (1 reviews)

Westhampton Pines

$900Ks - $1Ms

Westhampton Pines, Westhampton, NY

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

5 rating (1 reviews)

The Villages at Mount Sin...

$600Ks - $700Ks

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

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

No reviews yet

The Powder Forest Homes

$600Ks - $700Ks

The Powder Forest Homes, Simsbury, CT

Resale Only | 55+ age-restricted | Built 2006 - 2016 | 182 homes

5 rating (1 reviews)

Newtown Woods

$400Ks - $400Ks

Newtown Woods, Newtown, CT

New and Resale | 55+ age-restricted | Built 2011 - present | 178 homes

No reviews yet

Stoneleigh Woods at River...

$600Ks - $600Ks

Stoneleigh Woods at River..., Riverhead, NY

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

1661 OLD COUNTRY RD 69, RIVERHEAD, NY, 1...

Community: Glenwood Village

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

Questions? Call us: (860) 854-7490

The Villages at Mount Sinai Park

68 LOUDEN LOOP, MOUNT SINAI, NY, 11766, Mount Sinai, NY 11766

$657,000

2 beds

2 baths

1,736 sq ft

Condo

68 LOUDEN LOOP, MOUNT SINAI, NY, 11766

Community: The Villages at Mount Sinai Park

Leisure Village

69 ENFIELD CT UNIT B B, RIDGE, NY, 11961, Ridge, NY 11961

$359,900

2 beds

1 baths

1,278 sq ft

Condo

69 ENFIELD CT UNIT B B, RIDGE, NY, 11961

Community: Leisure Village

Fairfield at St. James

204 BENTLEY CT 204, SMITHTOWN, NY, 11780, Smithtown, NY 11780

$439,000

1 beds

1 baths

750 sq ft

Condo

204 BENTLEY CT 204, SMITHTOWN, NY, 11780

Community: Fairfield at St. James

Leisure Village

171B VENTRY CT 171B, BROOKHAVEN, NY, 119..., Brookhaven, NY 11961

$249,000

1 beds

1 baths

679 sq ft

Condo

171B VENTRY CT 171B, BROOKHAVEN, NY, 119...

Community: Leisure Village

Greenwood Village

16 VILLAGE CIR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949

$169,900

2 beds

2 baths

1,200 sq ft

Condo

16 VILLAGE CIR, BROOKHAVEN, NY, 11949

Community: Greenwood Village

Leisure Village

65 ENFIELD CT UNIT A A, RIDGE, NY, 11961, Ridge, NY 11961

$349,999

2 beds

1 baths

1,085 sq ft

Condo

65 ENFIELD CT UNIT A A, RIDGE, NY, 11961

Community: Leisure Village

The Waterways at Moriches

244 RIVER DR, MORICHES, NY, 11955, Moriches, NY 11955

$675,000

2 beds

2 baths

1,960 sq ft

Condo

244 RIVER DR, MORICHES, NY, 11955

Community: The Waterways at Moriches

Greenwood Village

21 LIMETREE DR, MANORVILLE, NY, 11949, Manorville, NY 11949

$179,000

2 beds

2 baths

1,100 sq ft

Condo

21 LIMETREE DR, MANORVILLE, NY, 11949

Community: Greenwood Village

Leisure Glen

12 BALDWIN CT, RIDGE, NY, 11961, Ridge, NY 11961

$489,990

2 beds

2 baths

1,542 sq ft

Condo

12 BALDWIN CT, RIDGE, NY, 11961

Community: Leisure Glen

Leisure Village

261 NEWCASTLE CT UNIT D, RIDGE, NY, 1196..., Ridge, NY 11961

$215,000

1 beds

1 baths

800 sq ft

Condo

261 NEWCASTLE CT UNIT D, RIDGE, NY, 1196...

Condo

4 GUILFORD CT UNIT C, RIDGE, NY, 11961

Community: Leisure Village

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

Questions? Call us: (860) 854-7490

The Waterways at Moriches

204 RIVER DR, MORICHES, NY, 11955, Moriches, NY 11955

$789,000

2 beds

2 baths

1,790 sq ft

Condo

204 RIVER DR, MORICHES, NY, 11955

Community: The Waterways at Moriches

The Villages at Mount Sinai Park

4 OAKHURST CT, MOUNT SINAI, NY, 11766, Mount Sinai, NY 11766

$799,999

3 beds

3 baths

2,850 sq ft

Condo

4 OAKHURST CT, MOUNT SINAI, NY, 11766

Community: The Villages at Mount Sinai Park

Fairfield at St. James

607 CABOT CT 607, SMITHTOWN, NY, 11780, Smithtown, NY 11780

$499,000

1 beds

2 baths

929 sq ft

Condo

607 CABOT CT 607, SMITHTOWN, NY, 11780

Community: Fairfield at St. James

The Vineyards at Miller Place

48 AVERY LN, MILLER PLACE, NY, 11764, Miller Place, NY 11764

$679,900

2 beds

3 baths

1,486 sq ft

Condo

48 AVERY LN, MILLER PLACE, NY, 11764

Community: The Vineyards at Miller Place

Leisure Village

48 TRENT CT B, RIDGE, NY, 11961, Ridge, NY 11961

$355,000

2 beds

1 baths

1,278 sq ft

Condo

48 TRENT CT B, RIDGE, NY, 11961

Community: Leisure Village

Stoneleigh Woods at Riverhead

159 STONELEIGH DR, RIVERHEAD, NY, 11901, Riverhead, NY 11901

$699,999

2 beds

3 baths

2,172 sq ft

House

159 STONELEIGH DR, RIVERHEAD, NY, 11901

Community: Stoneleigh Woods at Riverhead

The Greens at Half Hollow

1126 SAVOY DR, MELVILLE, NY, 11747, Melville, NY 11747

$629,888

2 beds

2 baths

1,150 sq ft

Condo

1126 SAVOY DR, MELVILLE, NY, 11747

Community: The Greens at Half Hollow

Village Estates

6 SARAH CT, AMITYVILLE, NY, 11701, Amityville, NY 11701

$579,000

2 beds

2 baths

1,243 sq ft

Condo

6 SARAH CT, AMITYVILLE, NY, 11701

Community: Village Estates

Glenwood Village

1661 OLD COUNTRY RD UNIT 563, RIVERHEAD,..., Riverhead, NY 11901

$489,000

2 beds

2 baths

1,500 sq ft

Manufactured Home

1661 OLD COUNTRY RD UNIT 563, RIVERHEAD,...

Community: Glenwood Village

Leisure Glen

13 OAKDALE CT, RIDGE, NY, 11961, Ridge, NY 11961

$449,999

2 beds

2 baths

1,140 sq ft

House

13 OAKDALE CT, RIDGE, NY, 11961

Community: Leisure Glen

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

Questions? Call us: (860) 854-7490

The Vineyards at Miller Place

37 HALLEY LN, MILLER PLACE, NY, 11764, Miller Place, NY 11764

$680,000

2 beds

3 baths

1,853 sq ft

Condo

37 HALLEY LN, MILLER PLACE, NY, 11764

Community: The Vineyards at Miller Place

Greenwood Village

53 VILLAGE CIR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949

$295,000

2 beds

2 baths

1,100 sq ft

Condo

53 VILLAGE CIR, BROOKHAVEN, NY, 11949

Community: Greenwood Village

Greenwood Village

2 LIMETREE DR, MANORVILLE, NY, 11949, Manorville, NY 11949

$250,000

2 beds

2 baths

1,242 sq ft

House

2 LIMETREE DR, MANORVILLE, NY, 11949

Community: Greenwood Village

Leisure Village

311 WOODBRIDGE DR 311-C, RIDGE, NY, 1196..., Ridge, NY 11961

$225,000

1 beds

1 baths

684 sq ft

Condo

311 WOODBRIDGE DR 311-C, RIDGE, NY, 1196...

Community: Leisure Village

Glenwood Village

1661 OLD COUNTRY OLD COUNTRY RD, RIVERHE..., Riverhead, NY 11901

$285,000

2 beds

2 baths

1,232 sq ft

Manufactured Home

1661 OLD COUNTRY OLD COUNTRY RD, RIVERHE...

Community: Glenwood Village

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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.

Want more information about active adult communities around Portland?

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260 homes near Portland

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

123 communities near Portland

260 homes near Portland

2 beds

2 baths

1,130 sq ft

Condo

2 beds

3 baths

2,175 sq ft

Condo

2 beds

2 baths

1,134 sq ft

Condo

2 beds

1 baths

836 sq ft

Condo

2 beds

2 baths

924 sq ft

Manufactured Home

2 beds

2 baths

1,736 sq ft

Condo

2 beds

1 baths

1,278 sq ft

Condo

1 beds

1 baths

750 sq ft

Condo

1 beds

1 baths

679 sq ft

Condo

2 beds

2 baths

1,200 sq ft

Condo

2 beds

1 baths

1,085 sq ft

Condo

2 beds

2 baths

1,960 sq ft

Condo

2 beds

2 baths

1,100 sq ft

Condo

2 beds

2 baths

1,542 sq ft

Condo

1 beds

1 baths

800 sq ft

Condo

2 beds

2 baths

1,100 sq ft

Condo

2 beds

2 baths

1,200 sq ft

Condo

2 beds

2 baths

1,700 sq ft

Condo

2 beds

2 baths

1,800 sq ft

Condo

2 beds