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

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

Leisure Knoll

$200ks - $400ks

Leisure Knoll, Ridge, NY

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

5 rating (2 reviews)

Oronoque Village

$200ks - $400ks

Oronoque Village, Stratford, CT

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

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Questions? Call us: (860) 854-7490

Leisure Glen

$300ks - $400ks

Leisure Glen, Ridge, NY

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

Rivington

$300ks - $900ks

Rivington, Danbury, CT

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

Leisure Village

$100ks - $300ks

Leisure Village, Ridge, NY

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

The Waterways at Moriches

$300ks - $600ks

The Waterways at Moriches, Moriches, NY

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

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.

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

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

Fairview at Oxford Greens

$400ks - $600ks

Fairview at Oxford Greens, Oxford, CT

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

5 rating (1 review)

Encore Atlantic Shores

$500ks - $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

Country Pointe Plainview

$700ks - $1Ms

Country Pointe Plainview, Plainview, NY

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

5 rating (1 review)

Newtown Woods

$300ks - $500ks

Newtown Woods, Newtown, CT

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

Meadow Brook Estates

$300ks - $400ks

Meadow Brook Estates, Oxford, CT

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

5 rating (1 review)

Westhampton Pines

$900ks - $1Ms

Westhampton Pines, Westhampton, NY

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

Encore at Lake Grove

$500ks - $700ks

Encore at Lake Grove, Lake Grove, NY

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

Brierly Pond Village

$300ks - $400ks

Brierly Pond Village, Millbury, MA

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

1 rating (1 review)

Plymouth Estates at Mount...

$400ks - $500ks

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

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

Spring Lake Village

$100ks - $200ks

Spring Lake Village, Southington, CT

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

Stoneleigh Woods at River...

$500ks

Stoneleigh Woods at River..., Riverhead, NY

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

Saddle Lakes

$400ks - $500ks

Saddle Lakes, Riverhead, NY

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

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Questions? Call us: (860) 854-7490

Granite Woods

$600ks - $700ks

Granite Woods, Middlebury, CT

New Construction | 55+ age-restricted | Built 2020 - present | 24 homes

Windcrest East

$400ks - $500ks

Windcrest East, Calverton, NY

Resale Only | 55+ age-restricted | Built 2004 - 2005 | 126 homes

Woodridge Strathmore Terr...

$200ks - $300ks

Woodridge Strathmore Terr..., Mount Sinai, NY

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

The Villas at Narraganset...

$400ks

The Villas at Narraganset..., Lindenhurst, NY

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

Harbor View Estates

$400ks - $600ks

Harbor View Estates, Copiague, NY

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

Strathmore Gate East

$300ks

Strathmore Gate East, Coram, NY

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

Regency Meadows

$500ks

Regency Meadows, Trumbull, CT

Resale Only | 55+ age-restricted | Built 2003 - 2005 | 51 homes

5 rating (1 review)

Sunken Pond Estates

$400ks

Sunken Pond Estates, Riverhead, NY

Resale Only | 55+ age-restricted | Built 2003 - 2005 | 194 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 (1 review)

Sunrise Village

$400ks

Sunrise Village, Sayville, NY

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

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

Questions? Call us: (860) 854-7490

Kensington Estates

$1Ms

Kensington Estates, Woodbury, NY

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

Regency at Woodbridge

$500ks - $700ks

Regency at Woodbridge, Woodbridge, CT

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

1 2 3...4

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

Heritage Village

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

$339,900

2 beds

2 baths

1,432 sq ft

Condo

170 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$420,000

2 beds

2 baths

1,432 sq ft

Condo

778 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

Heritage Village

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

$274,900

2 beds

2 baths

1,044 sq ft

Condo

176 HERITAGE VLG D, SOUTHBURY, CT, 06488

Community: Heritage Village

Leisure Village

387 WOODBRIDGE DR A, BROOKHAVEN, NY, 119..., Brookhaven, NY 11961

$499,000

2 beds

2 baths

1,767 sq ft

Condo

387 WOODBRIDGE DR A, BROOKHAVEN, NY, 119...

Community: Leisure Village

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

Questions? Call us: (860) 854-7490

Glenwood Village

1661 OLD COUNTRY RD 77, RIVERHEAD, NY, 1..., Riverhead, NY 11901

$335,000

2 beds

2 baths

1,248 sq ft

Manufactured Home

1661 OLD COUNTRY RD 77, RIVERHEAD, NY, 1...

Community: Glenwood 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

Meadow Brook Estates

802 SAGE HILL DR 802, OXFORD, CT, 06478, Oxford, CT 06478

$675,000

2 beds

3 baths

2,258 sq ft

Condo

802 SAGE HILL DR 802, OXFORD, CT, 06478

Community: Meadow Brook Estates

Leisure Knoll

346 EDINBURGH DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$419,000

2 beds

1 baths

1,050 sq ft

Condo

346 EDINBURGH DR, BROOKHAVEN, NY, 11961

Community: Leisure Knoll

Sunken Pond Estates

3102 AMEN COR, RIVERHEAD, NY, 11901, Riverhead, NY 11901

$525,000

2 beds

2 baths

1,587 sq ft

Condo

3102 AMEN COR, RIVERHEAD, NY, 11901

Community: Sunken Pond Estates

Rivington

71 WARRINGTON ROUND 71, DANBURY, CT, 068..., Danbury, CT 06810

$669,900

3 beds

3 baths

1,704 sq ft

Condo

71 WARRINGTON ROUND 71, DANBURY, CT, 068...

Community: Rivington

Rivington

3 HUMBER HILL RD 3, DANBURY, CT, 06810, Danbury, CT 06810

$774,900

3 beds

4 baths

2,120 sq ft

Condo

3 HUMBER HILL RD 3, DANBURY, CT, 06810

Community: Rivington

Leisure Knoll

177 CANTERBURY DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$379,900

2 beds

1 baths

1,116 sq ft

Condo

177 CANTERBURY DR, BROOKHAVEN, NY, 11961

Community: Leisure Knoll

Sunrise Village

152 REVERE DR, ISLIP, NY, 11782, Islip, NY 11782

$519,990

2 beds

2 baths

1,230 sq ft

Condo

152 REVERE DR, ISLIP, NY, 11782

Community: Sunrise Village

The Greens at Half Hollow

1067 SAVOY DR, HUNTINGTON, NY, 11747, Huntington, NY 11747

$699,000

2 beds

2 baths

1,150 sq ft

Condo

1067 SAVOY DR, HUNTINGTON, NY, 11747

Community: The Greens at Half Hollow

Strathmore Gate East

46 FORGE LN, BROOKHAVEN, NY, 11727, Brookhaven, NY 11727

$429,999

2 beds

2 baths

1,112 sq ft

House

46 FORGE LN, BROOKHAVEN, NY, 11727

Community: Strathmore Gate East

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

Questions? Call us: (860) 854-7490

Foxwood Village

1407 MIDDLE RD 271, RIVERHEAD, NY, 11933, Riverhead, NY 11933

$465,000

3 beds

2 baths

1,792 sq ft

Manufactured Home

1407 MIDDLE RD 271, RIVERHEAD, NY, 11933

Community: Foxwood Village

The Greens at Half Hollow

581 VERONA DR, HUNTINGTON, NY, 11747, Huntington, NY 11747

$1,199,900

2 beds

3 baths

1,941 sq ft

Condo

581 VERONA DR, HUNTINGTON, NY, 11747

Community: The Greens at Half Hollow

Granite Woods

35 NUTMEG RD B5, MIDDLEBURY, CT, 06762, Middlebury, CT 06762

$250,000

2 beds

1 baths

890 sq ft

Condo

35 NUTMEG RD B5, MIDDLEBURY, CT, 06762

Community: Granite Woods

Kensington Estates

46 PLAINVIEW RD, OYSTER BAY, NY, 11797, Oyster Bay, NY 11797

$2,049,888

6 beds

5 baths

4,333 sq ft

House

46 PLAINVIEW RD, OYSTER BAY, NY, 11797

Community: Kensington Estates

Greenwood Village

33 DOGWOOD LN, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949

$225,000

2 beds

2 baths

1,134 sq ft

House

33 DOGWOOD LN, BROOKHAVEN, NY, 11949

Community: Greenwood Village

Windcrest East

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

$799,000

3 beds

3 baths

2,620 sq ft

Condo

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

Community: Windcrest East

Windcrest East

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

$799,990

3 beds

3 baths

2,531 sq ft

Condo

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

Community: Windcrest East

Leisure Glen

9 AMAGANSETT CT, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$519,900

2 beds

2 baths

1,476 sq ft

Condo

9 AMAGANSETT CT, BROOKHAVEN, NY, 11961

Community: Leisure Glen

Long Hill Village

48 CIDER MILL LN, TRUMBULL, CT, 06611, Trumbull, CT 06611

$499,900

2 beds

2 baths

1,070 sq ft

Condo

48 CIDER MILL LN, TRUMBULL, CT, 06611

Community: Long Hill Village

Meadow Brook Estates

130 MEADOW BROOK RD 130, OXFORD, CT, 064..., Oxford, CT 06478

$599,000

2 beds

3 baths

1,920 sq ft

Condo

130 MEADOW BROOK RD 130, OXFORD, CT, 064...

Community: Meadow Brook Estates

The Club at Melville

212 CLUBHOUSE CIR 212, HUNTINGTON, NY, 1..., Huntington, NY 11747

$584,000

2 beds

2 baths

1,226 sq ft

Condo

212 CLUBHOUSE CIR 212, HUNTINGTON, NY, 1...

Community: The Club at Melville

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

Questions? Call us: (860) 854-7490

Greenwood Village

10 GREENWOOD BLVD, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949

$179,999

2 beds

1 baths

938 sq ft

Condo

10 GREENWOOD BLVD, BROOKHAVEN, NY, 11949

Community: Greenwood Village

Leisure Knoll

148 LAURANCE LN, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$499,000

2 beds

2 baths

1,096 sq ft

Condo

148 LAURANCE LN, BROOKHAVEN, NY, 11961

Community: Leisure Knoll

Fairfield at St. James

1406 GOTHAM CT, SMITHTOWN, NY, 11780, Smithtown, NY 11780

$579,803

2 beds

2 baths

1,321 sq ft

Condo

1406 GOTHAM CT, SMITHTOWN, NY, 11780

Community: Fairfield at St. James

Long Hill Village

36 LONG HILL PL, TRUMBULL, CT, 06611, Trumbull, CT 06611

$550,000

2 beds

3 baths

1,370 sq ft

Condo

36 LONG HILL PL, TRUMBULL, CT, 06611

Community: Long Hill Village

Greenwood Village

1 LIMETREE DR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949

$268,833

2 beds

2 baths

1,027 sq ft

Condo

1 LIMETREE DR, BROOKHAVEN, NY, 11949

Community: Greenwood Village

Foxwood Village

1407 MIDDLE RD 245, RIVERHEAD, NY, 11933, Riverhead, NY 11933

$349,000

3 beds

2 baths

1,368 sq ft

House

1407 MIDDLE RD 245, RIVERHEAD, NY, 11933

Community: Foxwood Village

Setauket Meadows

33 BLAIR RD, BROOKHAVEN, NY, 11733, Brookhaven, NY 11733

$849,999

2 beds

3 baths

1,700 sq ft

Condo

33 BLAIR RD, BROOKHAVEN, NY, 11733

Community: Setauket Meadows

Encore at Lake Grove

163 SYMPHONY DR, BROOKHAVEN, NY, 11755, Brookhaven, NY 11755

$645,000

2 beds

3 baths

1,378 sq ft

Condo

163 SYMPHONY DR, BROOKHAVEN, NY, 11755

Community: Encore at Lake Grove

Rivington

$565,000

2 beds

2 baths

1,549 sq ft

Condo

1 RIVINGTON WAY 306, DANBURY, CT, 06810

Community: Rivington

Regency at Woodbridge

18 HILLCREST DR 18, WOODBRIDGE, CT, 0652..., Woodbridge, CT 06525

$829,900

3 beds

3 baths

2,412 sq ft

Condo

18 HILLCREST DR 18, WOODBRIDGE, CT, 0652...

Community: Regency at Woodbridge

Heritage Village

2 HERITAGE CRST C, SOUTHBURY, CT, 06488, Southbury, CT 06488

$469,900

2 beds

2 baths

1,420 sq ft

Condo

2 HERITAGE CRST C, SOUTHBURY, CT, 06488

Community: Heritage Village

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

Questions? Call us: (860) 854-7490

Spring Lake Village

19 HICKORY HL 19, SOUTHINGTON, CT, 06489, Southington, CT 06489

$256,000

2 beds

2 baths

1,285 sq ft

Condo

19 HICKORY HL 19, SOUTHINGTON, CT, 06489

Community: Spring Lake Village

Heritage Village

4 HERITAGE CRST C, SOUTHBURY, CT, 06488, Southbury, CT 06488

$399,000

2 beds

2 baths

1,306 sq ft

Condo

4 HERITAGE CRST C, SOUTHBURY, CT, 06488

Community: Heritage Village

Frequently Asked Questions

What size 55+ communities are there in Portland?

Of the 2 55+ communities in Portland, 2 are for sale and none are rentals. By size, 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 278 days. The average price of homes for sale in these communities is approximately $495,000, though prices can range widely based on the size, location, and amenities of the communities. For example, homes in Bartlett Hill average around $495,000.

Want more information about active adult communities around Portland?

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125 communities

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

125 communities near Portland

275 homes near Portland

2 beds

2 baths

1,078 sq ft

Condo

2 beds

2 baths

1,432 sq ft

Condo

2 beds

2 baths

1,432 sq ft

Condo

2 beds

2 baths

1,044 sq ft

Condo

2 beds

2 baths

1,767 sq ft

Condo

2 beds

2 baths

1,248 sq ft

Manufactured Home

2 beds

2 baths

1,624 sq ft

Manufactured Home

2 beds

3 baths

2,258 sq ft

Condo

2 beds

1 baths

1,050 sq ft

Condo

2 beds

2 baths

1,587 sq ft

Condo

3 beds

3 baths

1,704 sq ft

Condo

3 beds

4 baths

2,120 sq ft

Condo

2 beds

1 baths

1,116 sq ft

Condo

2 beds

2 baths

1,230 sq ft

Condo

2 beds

2 baths

1,150 sq ft

Condo

2 beds

2 baths

1,112 sq ft

House

3 beds

2 baths

1,792 sq ft

Manufactured Home

2 beds

3 baths

1,941 sq ft

Condo

2 beds

1 baths

890 sq ft

Condo

6 beds