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

123 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

3.7 rating (3 reviews)

Greenwood Village

$100ks

Greenwood Village, Manorville, NY

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

Oronoque Village

$200ks - $400ks

Oronoque Village, Stratford, CT

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

Leisure Village

$100ks - $300ks

Leisure Village, Ridge, NY

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

Harmony Place

$400ks - $500ks

Harmony Place, Rutland, MA

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

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Questions? Call us: (860) 854-7490

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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

Leisure Knoll

$200ks - $400ks

Leisure Knoll, Ridge, NY

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

The Waterways at Moriches

$300ks - $600ks

The Waterways at Moriches, Moriches, NY

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

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.

Fairview at Oxford Greens

$400ks - $600ks

Fairview at Oxford Greens, Oxford, CT

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

Spring Lake Village

$100ks - $200ks

Spring Lake Village, Southington, CT

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

Leisure Glen

$300ks - $400ks

Leisure Glen, Ridge, NY

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

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

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

Questions? Call us: (860) 854-7490

Rivington

$300ks - $900ks

Rivington, Danbury, CT

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

5 rating (1 reviews)

Newtown Woods

$300ks - $500ks

Newtown Woods, Newtown, CT

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

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

Questions? Call us: (860) 854-7490

4 rating (8 reviews)

Glenwood Village

$100ks - $200ks

Glenwood Village, Riverhead, NY

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

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

5 rating (1 reviews)

Westhampton Pines

$900ks - $1Ms

Westhampton Pines, Westhampton, NY

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

Bartlett Hill

$300ks - $400ks

Bartlett Hill, Portland, CT

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

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Questions? Call us: (860) 854-7490

Kensington Estates

$1Ms

Kensington Estates, Woodbury, NY

New Construction | 55+ age-restricted | Built 2019 - 2021 | 80 homes

The Villas at Narraganset...

$400ks

The Villas at Narraganset..., Lindenhurst, NY

Resale Only | 55+ age-restricted | Built 2004 - 2005 | 138 homes

Country Village Estates

$300ks

Country Village Estates, Coram, NY

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

The Coves at Melville

$500ks

The Coves at Melville, Melville, NY

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

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Questions? Call us: (860) 854-7490

Strathmore Gate East

$300ks

Strathmore Gate East, Coram, NY

Resale Only | 55+ age-restricted | Built 1970 - 1975 | 174 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

Village Vistas

$800ks - $1Ms

Village Vistas, Port Jefferson, NY

Resale Only | 55+ age-restricted | Built 2013 - 2017 | 43 homes

4.9 rating (14 reviews)

Chatfield Farms

$400ks - $700ks

Chatfield Farms, Beacon Falls, CT

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

Baldwin Station

$400ks

Baldwin Station, Milford, CT

Resale Only | 55+ age-restricted | Built 2001 - 2003 | 82 homes

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Questions? Call us: (860) 854-7490

Liberty at Newtown

$300ks - $400ks

Liberty at Newtown, Newtown, CT

Resale Only | 55+ age-restricted | Built 2003 - 2007 | 96 homes

Regency at Woodbridge

$500ks - $700ks

Regency at Woodbridge, Woodbridge, CT

New Construction | 55+ age-restricted | Built 2023 - present | 70 homes

5 rating (1 reviews)

Sunken Pond Estates

$400ks

Sunken Pond Estates, Riverhead, NY

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

Meadow Brook Estates

$300ks - $400ks

Meadow Brook Estates, Oxford, CT

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

Stoneleigh Woods at River...

$500ks

Stoneleigh Woods at River..., Riverhead, NY

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

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

Questions? Call us: (860) 854-7490

Saddle Lakes

$400ks - $500ks

Saddle Lakes, Riverhead, NY

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

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

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

Questions? Call us: (860) 854-7490

Evergreen

$400ks - $500ks

Evergreen, Cromwell, CT

New and Resale | 55+ age-restricted | Built 2005 - present | 52 homes

Oak Meadow Estates

$200ks - $300ks

Oak Meadow Estates, Torrington, CT

New and Resale | 55+ age-restricted | Built 2013 - present | 31 homes

207 WOODBRIDGE DR B, BROOKHAVEN, NY, 119...

Community: Leisure Village

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Questions? Call us: (860) 854-7490

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252 AGAWAM DR A, STRATFORD, CT, 06614

Community: Oronoque Village

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Questions? Call us: (860) 854-7490

Fairfield at St. James

909 FENWAY RD, SMITHTOWN, NY, 11780, Smithtown, NY 11780

$489,000

2 beds

2 baths

1,230 sq ft

Condo

909 FENWAY RD, SMITHTOWN, NY, 11780

Community: Fairfield at St. James

Sunrise Village

4 REVERE DR, ISLIP, NY, 11782, Islip, NY 11782

$499,000

2 beds

2 baths

1,230 sq ft

Condo

4 REVERE DR, ISLIP, NY, 11782

Community: Sunrise Village

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

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Heritage Village

78 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488

$280,000

2 beds

2 baths

1,032 sq ft

Condo

78 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

The Villages at Mount Sinai Park

43 LOUDEN LOOP, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766

$799,000

3 beds

3 baths

2,455 sq ft

Condo

43 LOUDEN LOOP, BROOKHAVEN, NY, 11766

Community: The Villages at Mount Sinai Park

Rivington

424 CENTER MEADOW LN 424, DANBURY, CT, 0..., Danbury, CT 06810

$510,000

2 beds

2 baths

1,258 sq ft

Condo

424 CENTER MEADOW LN 424, DANBURY, CT, 0...

Community: Rivington

Bartlett Hill

9 PEAR ORCHARD RD 9, PORTLAND, CT, 06480, Portland, CT 06480

$479,900

2 beds

3 baths

1,404 sq ft

9 PEAR ORCHARD RD 9, PORTLAND, CT, 06480

Community: Bartlett Hill

Meadowbrook Pointe Links & Spa

83 PACIFIC DUNES CT 83, BROOKHAVEN, NY, ..., Brookhaven, NY 11763

$749,990

3 beds

3 baths

2,047 sq ft

Condo

83 PACIFIC DUNES CT 83, BROOKHAVEN, NY, ...

Community: Meadowbrook Pointe Links & Spa

Leisure Glen

263 GLEN DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$499,000

2 beds

2 baths

1,315 sq ft

Condo

263 GLEN DR, BROOKHAVEN, NY, 11961

Community: Leisure Glen

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

Questions? Call us: (860) 854-7490

Stoneleigh Woods at Riverhead

153 STONELEIGH DR 153, RIVERHEAD, NY, 11..., Riverhead, NY 11901

$699,000

3 beds

3 baths

2,107 sq ft

Condo

153 STONELEIGH DR 153, RIVERHEAD, NY, 11...

Community: Stoneleigh Woods at Riverhead

Strathmore Gate East

25 FREEMONT LN, BROOKHAVEN, NY, 11727, Brookhaven, NY 11727

$329,000

1 beds

1 baths

750 sq ft

Condo

25 FREEMONT LN, BROOKHAVEN, NY, 11727

Community: Strathmore Gate East

The Greens at Half Hollow

236 ALTESSA BLVD, HUNTINGTON, NY, 11747, Huntington, NY 11747

$1,698,000

2 beds

3 baths

2,500 sq ft

Condo

236 ALTESSA BLVD, HUNTINGTON, NY, 11747

Community: The Greens at Half Hollow

Leisure Glen

415 LEISURE DR 415, BROOKHAVEN, NY, 1196..., Brookhaven, NY 11961

$642,000

2 beds

2 baths

1,867 sq ft

Condo

415 LEISURE DR 415, BROOKHAVEN, NY, 1196...

House

506 LANCASTER CT, BROOKHAVEN, NY, 11961

Community: Leisure Knoll

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

Questions? Call us: (860) 854-7490

Heritage Village

41 E MEADOW RD, SOUTHBURY, CT, 06488, Southbury, CT 06488

$399,900

2 beds

3 baths

1,479 sq ft

Condo

41 E MEADOW RD, SOUTHBURY, CT, 06488

Community: Heritage Village

Greenwood Village

65A VILLAGE CIR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949

$134,900

1 beds

1 baths

864 sq ft

Condo

65A VILLAGE CIR, BROOKHAVEN, NY, 11949

Community: Greenwood Village

Greenwood Village

135 VILLAGE CIR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949

$139,999

2 beds

1 baths

938 sq ft

House

135 VILLAGE CIR, BROOKHAVEN, NY, 11949

Community: Greenwood Village

The Vineyards at Mount Sinai

59 FARM ACRE CIR, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766

$1,075,000

2 beds

4 baths

1,982 sq ft

Condo

59 FARM ACRE CIR, BROOKHAVEN, NY, 11766

Community: The Vineyards at Mount Sinai

Greenwood Village

21 LIMETREE DR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949

$169,000

2 beds

2 baths

1,100 sq ft

Condo

21 LIMETREE DR, BROOKHAVEN, NY, 11949

Community: Greenwood Village

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

Questions? Call us: (860) 854-7490

Leisure Village

421 WEYMOUTH CT D, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$349,000

2 beds

1 baths

875 sq ft

Condo

421 WEYMOUTH CT D, BROOKHAVEN, NY, 11961

Community: Leisure Village

Leisure Village

260 NEWCASTLE CT B, BROOKHAVEN, NY, 1196..., Brookhaven, NY 11961

$259,990

1 beds

1 baths

684 sq ft

Condo

260 NEWCASTLE CT B, BROOKHAVEN, NY, 1196...

Community: Leisure Village

Meadow Brook Estates

312 SPRUCE HILL DR 312, OXFORD, CT, 0647..., Oxford, CT 06478

$529,900

2 beds

3 baths

1,564 sq ft

Condo

312 SPRUCE HILL DR 312, OXFORD, CT, 0647...

Community: Meadow Brook Estates

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

Questions? Call us: (860) 854-7490

Leisure Knoll

151 LAURANCE LN, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$489,000

2 beds

1 baths

1,000 sq ft

Condo

151 LAURANCE LN, BROOKHAVEN, NY, 11961

Community: Leisure Knoll

Fairfield at St. James

1205 GOTHAM DR, SMITHTOWN, NY, 11780, Smithtown, NY 11780

$449,990

1 beds

2 baths

948 sq ft

Condo

1205 GOTHAM DR, SMITHTOWN, NY, 11780

Community: Fairfield at St. James

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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123 communities

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

123 communities near Portland

197 homes near Portland

2 beds

1 baths

1,245 sq ft

Condo

2 beds

2 baths

1,110 sq ft

Condo

2 beds

2 baths

1,164 sq ft

Condo

2 beds

2 baths

1,666 sq ft

Condo

2 beds

2 baths

1,308 sq ft

Condo

2 beds

2 baths

1,076 sq ft

Condo

2 beds

1 baths

874 sq ft

Condo

2 beds

2 baths

972 sq ft

Condo

2 beds

2 baths

1,386 sq ft

Condo

3 beds

3 baths

1,716 sq ft

Condo

3 beds

2 baths

1,716 sq ft

Condo

2 beds

3 baths

2,734 sq ft

Condo

2 beds

3 baths

2,823 sq ft

Condo

2 beds

2 baths

1,230 sq ft

Condo

2 beds

2 baths

1,230 sq ft

Condo

2 beds

2 baths

1,032 sq ft

Condo

3 beds

3 baths

2,455 sq ft

Condo

2 beds

2 baths

1,258 sq ft

Condo

2 beds

3 baths

1,404 sq ft

3 beds

3 baths