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

5 rating (2 reviews)

Oronoque Village

$200ks - $400ks

Oronoque Village, Stratford, CT

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

Leisure Glen

$300ks - $400ks

Leisure Glen, Ridge, NY

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

3.7 rating (3 reviews)

Greenwood Village

$100ks

Greenwood Village, Manorville, NY

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

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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

The Waterways at Moriches

$300ks - $600ks

The Waterways at Moriches, Moriches, NY

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

Leisure Village

$100ks - $300ks

Leisure Village, Ridge, NY

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

Rivington

$300ks - $900ks

Rivington, Danbury, CT

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

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.

Leisure Knoll

$200ks - $400ks

Leisure Knoll, Ridge, NY

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

Country Pointe Plainview

$700ks - $1Ms

Country Pointe Plainview, Plainview, NY

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

Harmony Place

$400ks - $500ks

Harmony Place, Rutland, MA

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

5 rating (1 reviews)

Newtown Woods

$300ks - $500ks

Newtown Woods, Newtown, CT

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

Fairview at Oxford Greens

$400ks - $600ks

Fairview at Oxford Greens, Oxford, CT

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

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

Questions? Call us: (860) 854-7490

Brierly Pond Village

$300ks - $400ks

Brierly Pond Village, Millbury, MA

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

Stoneleigh Woods at River...

$500ks

Stoneleigh Woods at River..., Riverhead, NY

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

5 rating (1 reviews)

Westhampton Pines

$900ks - $1Ms

Westhampton Pines, Westhampton, NY

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

Liberty at Newtown

$300ks - $400ks

Liberty at Newtown, Newtown, CT

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

The Summit at Bethel

$500ks - $700ks

The Summit at Bethel, Bethel, CT

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

Meadow Brook Estates

$300ks - $400ks

Meadow Brook Estates, Oxford, CT

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

Billingsgate

$400ks - $600ks

Billingsgate, Simsbury, CT

Resale Only | 55+ age-restricted | Built 2003 - 2006 | 37 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

Country Pointe Preserve

$600ks - $900ks

Country Pointe PreserveYaphank, NY

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

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Questions? Call us: (860) 854-7490

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

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

Saddle Lakes

$400ks - $500ks

Saddle Lakes, Riverhead, NY

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

3.5 rating (2 reviews)

Foxwood Village

$200ks - $400ks

Foxwood Village, Calverton, NY

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

Sunrise Village

$400ks

Sunrise Village, Sayville, NY

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

Snug Harbor

$600ks - $700ks

Snug Harbor, Amityville, NY

Resale Only | 55+ age-restricted | Built 1970 - 1974 | 176 homes

Woodridge Strathmore Terr...

$200ks - $300ks

Woodridge Strathmore Terr..., Mount Sinai, NY

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

Founders Village

$400ks - $500ks

Founders Village, Southold, NY

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

Harbor View Estates

$400ks - $600ks

Harbor View Estates, Copiague, NY

New Construction | 55+ age-restricted | Built 2017 - 2018 | 40 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

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

Questions? Call us: (860) 854-7490

Regency at Prospect

$300ks - $400ks

Regency at Prospect, Prospect, CT

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

Newbury Village

$400ks - $500ks

Newbury Village, Brookfield, CT

New and Resale | 55+ age-restricted | Built 2005 - present | 120 homes

1 2 3...4

New Greenwood Village

201 VILLAGE CIR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949

$250,000

2 beds

2 baths

1,078 sq ft

Condo

201 VILLAGE CIR, BROOKHAVEN, NY, 11949

Community: Greenwood Village

Greenwood Village

105 W VILLAGE CIR 105, BROOKHAVEN, NY, 1..., Brookhaven, NY 11949

$245,000

2 beds

2 baths

1,130 sq ft

Condo

105 W VILLAGE CIR 105, BROOKHAVEN, NY, 1...

Community: Greenwood Village

Glenwood Village

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

$410,000

2 beds

2 baths

1,624 sq ft

Manufactured Home

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

Community: Glenwood Village

New Heritage Village

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

$414,900

2 beds

2 baths

1,398 sq ft

Condo

886 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

New Encore at Lake Grove

39 SYMPHONY DR, BROOKHAVEN, NY, 11755, Brookhaven, NY 11755

$625,000

2 beds

3 baths

1,700 sq ft

Condo

39 SYMPHONY DR, BROOKHAVEN, NY, 11755

Community: Encore at Lake Grove

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New Regency Meadows

17 REGENCY CIR 17, TRUMBULL, CT, 06611, Trumbull, CT 06611

$765,000

4 beds

4 baths

2,597 sq ft

Condo

17 REGENCY CIR 17, TRUMBULL, CT, 06611

Community: Regency Meadows

New Billingsgate

8 BILLINGSGATE DR, SIMSBURY, CT, 06070, Simsbury, CT 06070

$700,000

2 beds

3 baths

2,471 sq ft

Condo

8 BILLINGSGATE DR, SIMSBURY, CT, 06070

Community: Billingsgate

New Oronoque Village

71 DAKOTA LN A, STRATFORD, CT, 06614, Stratford, CT 06614

$600,000

1 beds

2 baths

1,375 sq ft

Condo

71 DAKOTA LN A, STRATFORD, CT, 06614

Community: Oronoque Village

New Stone Ridge Estates

154 CHRISTINE DR, HUNTINGTON, NY, 11746, Huntington, NY 11746

$760,000

2 beds

2 baths

1,695 sq ft

Condo

154 CHRISTINE DR, HUNTINGTON, NY, 11746

Community: Stone Ridge Estates

New The Summit at Bethel

15 BRIAR RIDGE DR 15, BETHEL, CT, 06801, Bethel, CT 06801

$689,000

2 beds

3 baths

2,104 sq ft

Condo

15 BRIAR RIDGE DR 15, BETHEL, CT, 06801

Community: The Summit at Bethel

New The Waterways at Moriches

612 BAY VIEW CIR 12, BROOKHAVEN, NY, 119..., Brookhaven, NY 11955

$799,000

2 beds

3 baths

1,874 sq ft

Condo

612 BAY VIEW CIR 12, BROOKHAVEN, NY, 119...

Community: The Waterways at Moriches

New Country Pointe Preserve

128 JUNIPER LN 26, BROOKHAVEN, NY, 11980, Brookhaven, NY 11980

$895,000

2 beds

3 baths

1,998 sq ft

Condo

128 JUNIPER LN 26, BROOKHAVEN, NY, 11980

Community: Country Pointe Preserve

New Leisure Village

167 VENTRY CT D, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$259,000

1 beds

1 baths

684 sq ft

Condo

167 VENTRY CT D, BROOKHAVEN, NY, 11961

Community: Leisure Village

New Windcrest East

90 GOLDEN SPRUCE DR, RIVERHEAD, NY, 1193..., Riverhead, NY 11933

$799,000

3 beds

3 baths

2,620 sq ft

House

90 GOLDEN SPRUCE DR, RIVERHEAD, NY, 1193...

Community: Windcrest East

New Fairfield at St. James

111 FAIRFIELD DR 111, SMITHTOWN, NY, 117..., Smithtown, NY 11780

$599,999

2 beds

2 baths

1,733 sq ft

Condo

111 FAIRFIELD DR 111, SMITHTOWN, NY, 117...

Community: Fairfield at St. James

New Founders Village

2555 YOUNGS AVE 11A, SOUTHOLD, NY, 11971, Southold, NY 11971

$605,000

2 beds

2 baths

1,200 sq ft

Condo

2555 YOUNGS AVE 11A, SOUTHOLD, NY, 11971

Community: Founders Village

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

Questions? Call us: (860) 854-7490

New Oronoque Village

476 COMMANCHE LN A, STRATFORD, CT, 06614, Stratford, CT 06614

$565,000

1 beds

3 baths

1,426 sq ft

Condo

476 COMMANCHE LN A, STRATFORD, CT, 06614

Community: Oronoque Village

New Leisure Village

250A NEWCASTLE CT, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$359,000

2 beds

1 baths

1,085 sq ft

Condo

250A NEWCASTLE CT, BROOKHAVEN, NY, 11961

Community: Leisure Village

New Leisure Knoll

330 BROWNFIELD DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$429,000

2 beds

1 baths

1,020 sq ft

Condo

330 BROWNFIELD DR, BROOKHAVEN, NY, 11961

Community: Leisure Knoll

New Leisure Village

190 VENTRY CT F, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$269,000

1 beds

1 baths

684 sq ft

Condo

190 VENTRY CT F, BROOKHAVEN, NY, 11961

Community: Leisure Village

New Heritage Village

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

$215,000

2 beds

2 baths

1,000 sq ft

Condo

751 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

New Newtown Woods

1011 BROOKSIDE CT 1011, NEWTOWN, CT, 064..., Newtown, CT 06470

$495,000

2 beds

2 baths

1,483 sq ft

Condo

1011 BROOKSIDE CT 1011, NEWTOWN, CT, 064...

Community: Newtown Woods

New Leisure Glen

7 SAGAPONACK CT, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$599,000

2 beds

2 baths

1,867 sq ft

Condo

7 SAGAPONACK CT, BROOKHAVEN, NY, 11961

Community: Leisure Glen

New The Seasons at East Northport

157 AUGUST CIR, HUNTINGTON, NY, 11731, Huntington, NY 11731

$998,000

2 beds

3 baths

2,516 sq ft

Condo

157 AUGUST CIR, HUNTINGTON, NY, 11731

Community: The Seasons at East Northport

Regency at Prospect

112 CHERRY CIR 112, PROSPECT, CT, 06712, Prospect, CT 06712

$338,903

3 beds

2 baths

1,500 sq ft

Condo

112 CHERRY CIR 112, PROSPECT, CT, 06712

Community: Regency at Prospect

Fairfield at St. James

403 CABOT CT, SMITHTOWN, NY, 11780, Smithtown, NY 11780

$425,000

1 beds

1 baths

1,017 sq ft

Condo

403 CABOT CT, SMITHTOWN, NY, 11780

Community: Fairfield at St. James

Meadow Brook Estates

107 MEADOW BROOK RD 107, OXFORD, CT, 064..., Oxford, CT 06478

$625,000

3 beds

3 baths

1,922 sq ft

Condo

107 MEADOW BROOK RD 107, OXFORD, CT, 064...

Community: Meadow Brook Estates

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

Questions? Call us: (860) 854-7490

Heritage Village

40 HERITAGE VLG F, SOUTHBURY, CT, 06488, Southbury, CT 06488

$270,000

2 beds

2 baths

1,308 sq ft

Condo

40 HERITAGE VLG F, SOUTHBURY, CT, 06488

Community: Heritage Village

The Summit at Bethel

14 GREAT HILL DR 14, BETHEL, CT, 06801, Bethel, CT 06801

$699,000

3 beds

3 baths

2,744 sq ft

Condo

14 GREAT HILL DR 14, BETHEL, CT, 06801

Community: The Summit at Bethel

Oronoque Village

615 CHEROKEE LN A, STRATFORD, CT, 06614, Stratford, CT 06614

$574,900

2 beds

3 baths

1,426 sq ft

Condo

615 CHEROKEE LN A, STRATFORD, CT, 06614

Community: Oronoque Village

Harbor View Estates

301 ANCHOR CT, BABYLON, NY, 11726, Babylon, NY 11726

$625,000

1 beds

2 baths

1,213 sq ft

Condo

301 ANCHOR CT, BABYLON, NY, 11726

Community: Harbor View Estates

The Waterways at Moriches

606 BAY VIEW CIR 6, BROOKHAVEN, NY, 1195..., Brookhaven, NY 11955

$749,000

2 beds

3 baths

1,860 sq ft

Condo

606 BAY VIEW CIR 6, BROOKHAVEN, NY, 1195...

Community: The Waterways at Moriches

Founders Ridge

UNIT 2-41 WEBSTER LN 145, MIDDLETOWN, CT..., Middletown, CT 06457

$689,000

2 beds

2 baths

1,555 sq ft

UNIT 2-41 WEBSTER LN 145, MIDDLETOWN, CT...

Community: Founders Ridge

Leisure Glen

20 WAINSCOTT CT, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$599,999

2 beds

2 baths

1,666 sq ft

Condo

20 WAINSCOTT CT, BROOKHAVEN, NY, 11961

Community: Leisure Glen

Brierly Pond Village

97 HORNE WAY 97, MILLBURY, MA, 01527, Millbury, MA 01527

$450,000

2 beds

3 baths

1,746 sq ft

Condo

97 HORNE WAY 97, MILLBURY, MA, 01527

Community: Brierly Pond Village

Leisure Glen

9 OAKDALE CT, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$619,000

2 beds

2 baths

1,882 sq ft

House

9 OAKDALE CT, BROOKHAVEN, NY, 11961

Community: Leisure Glen

Country Pointe Plainview

43101 SILVER BIRCH LN, OYSTER BAY, NY, 1..., Oyster Bay, NY 11803

$1,750,000

2 beds

2 baths

2,178 sq ft

House

43101 SILVER BIRCH LN, OYSTER BAY, NY, 1...

Community: Country Pointe Plainview

Sunrise Village

97 REVERE DR, ISLIP, NY, 11782, Islip, NY 11782

$519,000

2 beds

2 baths

1,046 sq ft

Condo

97 REVERE DR, ISLIP, NY, 11782

Community: Sunrise Village

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

Questions? Call us: (860) 854-7490

Strathmore Gate East

39 FREEMONT LN, BROOKHAVEN, NY, 11727, Brookhaven, NY 11727

$375,000

2 beds

2 baths

1,112 sq ft

Condo

39 FREEMONT LN, BROOKHAVEN, NY, 11727

Community: Strathmore Gate East

Fairfield at St. James

704 FENWAY RD, SMITHTOWN, NY, 11780, Smithtown, NY 11780

$519,000

2 beds

2 baths

1,292 sq ft

Condo

704 FENWAY RD, 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.

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 149 days. The average price of homes for sale in these communities is approximately $493,052, though prices can range widely based on the size, location, and amenities of the communities. For example, homes in Bartlett Hill average around $493,052.

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125 communities

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

125 communities near Portland

257 homes near Portland

2 beds

2 baths

1,078 sq ft

Condo

2 beds

2 baths

1,130 sq ft

Condo

2 beds

2 baths

1,624 sq ft

Manufactured Home

2 beds

2 baths

1,398 sq ft

Condo

2 beds

3 baths

1,700 sq ft

Condo

4 beds

4 baths

2,597 sq ft

Condo

2 beds

3 baths

2,471 sq ft

Condo

1 beds

2 baths

1,375 sq ft

Condo

2 beds

2 baths

1,695 sq ft

Condo

2 beds

3 baths

2,104 sq ft

Condo

2 beds

3 baths

1,874 sq ft

Condo

2 beds

3 baths

1,998 sq ft

Condo

1 beds

1 baths

684 sq ft

Condo

3 beds

3 baths

2,620 sq ft

House

2 beds

2 baths

1,733 sq ft

Condo

2 beds

2 baths

1,200 sq ft

Condo

1 beds

3 baths

1,426 sq ft

Condo

2 beds

1 baths

1,085 sq ft

Condo

2 beds

1 baths

1,020 sq ft

Condo

1 beds