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

123 communities near Portland

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Bartlett Hill

$500Ks

Bartlett Hill, Portland, CT

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

The Atrium of Portland

<$100k

The Atrium of Portland, Portland, CT

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

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

$200Ks - $400Ks

Leisure Village, Ridge, NY

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

The Greens at Half Hollow

$500Ks - $1Ms

The Greens at Half Hollow, Melville, NY

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

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Questions? Call us: (860) 854-7490

Rivington

$600Ks

Rivington, Danbury, CT

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

Oronoque Village

$300Ks - $600Ks

Oronoque Village, Stratford, CT

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

The Village at Oxford Gre...

$500Ks - $600Ks

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

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

Leisure Knoll

$300Ks - $400Ks

Leisure Knoll, Ridge, NY

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

Country Pointe Plainview

$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

Fairfield at St. James, St. James, NY

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

Leisure Glen

$400Ks

Leisure Glen, Ridge, NY

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

Spring Lake Village

$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

Regency at Prospect

$300Ks - $500Ks

Regency at Prospect, Prospect, CT

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

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

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

Vineyards at Blue Point, Blue Point, NY

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

The Club at Melville

$500Ks

The Club at Melville, Melville, NY

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

The Seasons at Elwood

$800Ks - $900Ks

The Seasons at Elwood, East Northport, NY

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

Meadow Brook Estates

$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

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

Questions? Call us: (860) 854-7490

The Summit at Bethel

$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

Woodridge Strathmore Terr...

$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

Brierly Pond Village

$400Ks

Brierly Pond Village, Millbury, MA

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

Saddle Lakes

$400Ks

Saddle Lakes, Riverhead, NY

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

Country Village Estates

$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

The Seasons at East North...

$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

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 - $500Ks

Newtown Woods, Newtown, CT

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

Stoneleigh Woods at River...

$600Ks

Stoneleigh Woods at River..., Riverhead, NY

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

677 BALFOUR PL, MELVILLE, NY, 11747

Community: The Greens at Half Hollow

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

Questions? Call us: (860) 854-7490

The Greens at Half Hollow

259 ALTESSA BLVD, MELVILLE, NY, 11747, Melville, NY 11747

$1,499,000

3 beds

4 baths

3,100 sq ft

Condo

259 ALTESSA BLVD, MELVILLE, NY, 11747

Community: The Greens at Half Hollow

The Greens at Half Hollow

1082 SAVOY DR, MELVILLE, NY, 11747, Melville, NY 11747

$599,999

2 beds

2 baths

1,000 sq ft

Condo

1082 SAVOY DR, MELVILLE, NY, 11747

Community: The Greens at Half Hollow

The Greens at Half Hollow

423 FLORENCIA PL, MELVILLE, NY, 11747, Melville, NY 11747

$1,225,000

3 beds

3 baths

2,500 sq ft

Condo

423 FLORENCIA PL, MELVILLE, NY, 11747

Community: The Greens at Half Hollow

Fairfield at St. James

401 CABOT CT, SMITHTOWN, NY, 11780, Smithtown, NY 11780

$499,000

1 beds

2 baths

900 sq ft

Condo

401 CABOT CT, SMITHTOWN, NY, 11780

Community: Fairfield at St. James

New Leisure Knoll

145 EDINBURGH DR, RIDGE, NY, 11961, Ridge, NY 11961

$499,999

2 beds

2 baths

913 sq ft

House

145 EDINBURGH DR, RIDGE, NY, 11961

Community: Leisure Knoll

New Greenwood Village

91 VILLAGE CIR, MANORVILLE, NY, 11949, Manorville, NY 11949

$155,000

2 beds

2 baths

938 sq ft

Condo

91 VILLAGE CIR, MANORVILLE, NY, 11949

Community: Greenwood Village

Glenwood Village

1661 OLD COUNTRY RD 506, RIVERHEAD, NY, ..., Riverhead, NY 11901

$329,999

2 beds

2 baths

1,232 sq ft

Manufactured Home

1661 OLD COUNTRY RD 506, RIVERHEAD, NY, ...

Community: Glenwood Village

Encore Atlantic Shores

113 OVERTURE PL, EASTPORT, NY, 11941, Eastport, NY 11941

$895,000

2 beds

3 baths

3,037 sq ft

Condo

113 OVERTURE PL, EASTPORT, NY, 11941

Community: Encore Atlantic Shores

Stoneleigh Woods at Riverhead

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

$680,000

2 beds

3 baths

2,175 sq ft

Condo

159 STONELEIGH DR, RIVERHEAD, NY, 11901

Community: Stoneleigh Woods at Riverhead

Fairfield at St. James

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

$450,000

1 beds

2 baths

929 sq ft

Condo

607 CABOT CT 607, SMITHTOWN, NY, 11780

Community: Fairfield at St. James

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

Strathmore Gate East

53 FREEDOM LN, CORAM, NY, 11727, Coram, NY 11727

$440,000

2 beds

1 baths

1,036 sq ft

Condo

53 FREEDOM LN, CORAM, NY, 11727

Community: Strathmore Gate East

Leisure Village

474 DARWEN DR B, RIDGE, NY, 11961, Ridge, NY 11961

$400,000

2 beds

2 baths

1,200 sq ft

Condo

474 DARWEN DR B, RIDGE, NY, 11961

Community: Leisure Village

The Greens at Half Hollow

652 BALFOUR PL, MELVILLE, NY, 11747, Melville, NY 11747

$1,199,000

3 beds

3 baths

2,400 sq ft

Condo

652 BALFOUR PL, MELVILLE, NY, 11747

Community: The Greens at Half Hollow

Setauket Meadows

95 COVE LN, EAST SETAUKET, NY, 11733, East Setauket, NY 11733

$749,990

2 beds

3 baths

1,991 sq ft

Condo

95 COVE LN, EAST SETAUKET, NY, 11733

Community: Setauket Meadows

Foxwood Village

1407 MIDDLE RD UNIT 258, CALVERTON, NY, ..., Calverton, NY 11933

$525,000

3 beds

2 baths

1,568 sq ft

Manufactured Home

1407 MIDDLE RD UNIT 258, CALVERTON, NY, ...

Community: Foxwood Village

Stoneleigh Woods at Riverhead

4 HAVERTON CT, RIVERHEAD, NY, 11901, Riverhead, NY 11901

$660,000

2 beds

3 baths

2,175 sq ft

Condo

4 HAVERTON CT, RIVERHEAD, NY, 11901

Community: Stoneleigh Woods at Riverhead

Glenwood Village

1661 OLD COUNTRY RD 69, RIVERHEAD, NY, 1..., Riverhead, NY 11901

$239,999

2 beds

2 baths

924 sq ft

Manufactured Home

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

Community: Glenwood Village

Leisure Village

405 WOODBRIDGE DR D, RIDGE, NY, 11961, Ridge, NY 11961

$290,000

2 beds

1 baths

874 sq ft

Condo

405 WOODBRIDGE DR D, RIDGE, NY, 11961

Community: Leisure Village

Stoneleigh Woods at Riverhead

67 STONELEIGH DR, RIVERHEAD, NY, 11901, Riverhead, NY 11901

$640,000

2 beds

3 baths

1,972 sq ft

Condo

67 STONELEIGH DR, RIVERHEAD, NY, 11901

Community: Stoneleigh Woods at Riverhead

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

Questions? Call us: (860) 854-7490

Leisure Knoll

323 BROWNFIELD DR, RIDGE, NY, 11961, Ridge, NY 11961

$360,000

2 beds

1 baths

655 sq ft

Condo

323 BROWNFIELD DR, RIDGE, NY, 11961

Community: Leisure Knoll

Plymouth Estates at Mount Sinai

230 IRA RD # 230, MOUNT SINAI, NY, 11766, Mount Sinai, NY 11766

$589,999

2 beds

2 baths

1,317 sq ft

Condo

230 IRA RD # 230, MOUNT SINAI, NY, 11766

Community: Plymouth Estates at Mount Sinai

Strathmore Gate East

49 FREEDOM LN, CORAM, NY, 11727, Coram, NY 11727

$370,000

2 beds

1 baths

964 sq ft

House

49 FREEDOM LN, CORAM, NY, 11727

Community: Strathmore Gate East

Greenwood Village

145 VILLAGE CIR, MANORVILLE, NY, 11949, Manorville, NY 11949

$199,900

2 beds

2 baths

1,100 sq ft

Condo

145 VILLAGE CIR, MANORVILLE, NY, 11949

Community: Greenwood Village

Greenwood Village

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

$275,000

2 beds

2 baths

1,100 sq ft

Condo

53 VILLAGE CIR, BROOKHAVEN, NY, 11949

Community: Greenwood Village

Glenwood Village

1661 OLD COUNTRY RD UNIT 280, RIVERHEAD,..., Riverhead, NY 11901

$205,000

2 beds

2 baths

1,008 sq ft

Manufactured Home

1661 OLD COUNTRY RD UNIT 280, RIVERHEAD,...

Community: Glenwood Village

Greenwood Village

19 DOGWOOD LN, MANORVILLE, NY, 11949, Manorville, NY 11949

$167,500

2 beds

2 baths

871 sq ft

Condo

19 DOGWOOD LN, MANORVILLE, NY, 11949

Community: Greenwood Village

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

Greenwood Village

1 WILLOW CT, MANORVILLE, NY, 11949, Manorville, NY 11949

$229,900

2 beds

2 baths

1,450 sq ft

Condo

1 WILLOW CT, MANORVILLE, NY, 11949

Community: Greenwood Village

Westhampton Pines

112 ASHLEY DR, WESTHAMPTON, NY, 11977, Westhampton, NY 11977

$1,295,000

3 beds

3 baths

2,306 sq ft

Condo

112 ASHLEY DR, WESTHAMPTON, NY, 11977

Condo

46 TRENT CT C, RIDGE, NY, 11961

Community: Leisure 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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Call us: (860) 854-7490

123 communities near Portland

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

123 communities near Portland

218 homes near Portland

2 beds

2 baths

1,429 sq ft

Condo

2 beds

1 baths

1,085 sq ft

Condo

1 beds

2 baths

963 sq ft

Condo

2 beds

2 baths

1,134 sq ft

Condo

2 beds

3 baths

1,900 sq ft

Condo

3 beds

4 baths

3,100 sq ft

Condo

2 beds

2 baths

1,000 sq ft

Condo

3 beds

3 baths

2,500 sq ft

Condo

1 beds

2 baths

900 sq ft

Condo

2 beds

2 baths

913 sq ft

House

2 beds

2 baths

938 sq ft

Condo

2 beds

2 baths

1,232 sq ft

Manufactured Home

2 beds

3 baths

3,037 sq ft

Condo

2 beds

3 baths

2,175 sq ft

Condo

1 beds

2 baths

929 sq ft

Condo

2 beds

2 baths

1,736 sq ft

Condo

2 beds

1 baths

1,036 sq ft

Condo

2 beds

2 baths

1,200 sq ft

Condo

3 beds

3 baths

2,400 sq ft

Condo

2 beds