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

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

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

The Waterways at Moriches

$300ks - $600ks

The Waterways at Moriches, Moriches, NY

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

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

Questions? Call us: (860) 854-7490

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

The Manors at The Colony ...

$300ks - $400ks

The Manors at The Colony ..., Shirley, NY

New Construction | 55+ age-restricted | Built 2013 - present | 150 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 reviews)

Encore Atlantic Shores

$500ks - $800ks

Encore Atlantic Shores, Eastport, NY

Resale Only | 55+ age-restricted | Built 2004 - 2011 | 240 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 (1 reviews)

Westhampton Pines

$900ks - $1Ms

Westhampton Pines, Westhampton, NY

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

4 rating (8 reviews)

Glenwood Village

$100ks - $200ks

Glenwood Village, Riverhead, NY

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

Country Pointe Plainview

$700ks - $1Ms

Country Pointe Plainview, Plainview, NY

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

The Powder Forest Homes

$500ks - $700ks

The Powder Forest Homes, Simsbury, CT

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

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

Questions? Call us: (860) 854-7490

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

5 rating (1 reviews)

Sunken Pond Estates

$400ks

Sunken Pond Estates, Riverhead, NY

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

Brierly Pond Village

$300ks - $400ks

Brierly Pond Village, Millbury, MA

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

Leisure Knoll

$200ks - $400ks

Leisure Knoll, Ridge, NY

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

Spring Lake Village

$100ks - $200ks

Spring Lake Village, Southington, CT

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

Fairview at Oxford Greens

$400ks - $600ks

Fairview at Oxford Greens, Oxford, CT

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

Strathmore Gate East

$300ks

Strathmore Gate East, Coram, NY

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

Liberty at Newtown

$300ks - $400ks

Liberty at Newtown, Newtown, CT

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

3.5 rating (2 reviews)

Foxwood Village

$200ks - $400ks

Foxwood Village, Calverton, NY

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

Leisure Glen

$300ks - $400ks

Leisure Glen, Ridge, NY

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

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Questions? Call us: (860) 854-7490

Country Pointe Preserve

$600ks - $900ks

Country Pointe PreserveYaphank, NY

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

Rivington

$300ks - $900ks

Rivington, Danbury, CT

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

Stoneleigh Woods at River...

$500ks

Stoneleigh Woods at River..., Riverhead, NY

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

The Coves at Melville

$500ks

The Coves at Melville, Melville, NY

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

Regency at Prospect

$300ks - $400ks

Regency at Prospect, Prospect, CT

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

Kensington Estates

$1Ms

Kensington Estates, Woodbury, NY

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

The Summit at Bethel

$500ks - $700ks

The Summit at Bethel, Bethel, CT

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

Country Village Estates

$300ks

Country Village Estates, Coram, NY

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

Snug Harbor

$600ks - $700ks

Snug Harbor, Amityville, NY

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

Vineyards at Brookfield

$400ks - $500ks

Vineyards at Brookfield, Center Moriches, NY

New Construction | 55+ age-restricted | Built 2019 - present | 146 homes

Village Vistas

$800ks - $1Ms

Village Vistas, Port Jefferson, NY

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

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

Questions? Call us: (860) 854-7490

The Seasons at Plainview

$500ks - $600ks

The Seasons at Plainview, Plainview, NY

Resale Only | 55+ age-restricted | Built 2006 - 2007 | 134 homes

Meadow Brook Estates

$300ks - $400ks

Meadow Brook Estates, Oxford, CT

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

1 2 3...4

New Greenwood Village

5190 VILLAGE CIR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949

$239,000

2 beds

2 baths

1,258 sq ft

Condo

5190 VILLAGE CIR, BROOKHAVEN, NY, 11949

Community: Greenwood Village

Glenwood Village

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

$419,000

2 beds

2 baths

1,624 sq ft

Manufactured Home

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

Community: Glenwood Village

New Heritage Village

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

$259,000

2 beds

2 baths

1,432 sq ft

Condo

804 HERITAGE VLG B, SOUTHBURY, CT, 06488

Community: Heritage Village

New Strathmore Gate East

4 FLAIR WAY, BROOKHAVEN, NY, 11727, Brookhaven, NY 11727

$495,000

2 beds

2 baths

1,112 sq ft

House

4 FLAIR WAY, BROOKHAVEN, NY, 11727

Community: Strathmore Gate East

New The Village at Orchard Meadows

31 CORTLAND 31, SHREWSBURY, MA, 01545, Shrewsbury, MA 01545

$675,000

3 beds

4 baths

2,848 sq ft

Condo

31 CORTLAND 31, SHREWSBURY, MA, 01545

Community: The Village at Orchard Meadows

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

Questions? Call us: (860) 854-7490

New The Greens at Half Hollow

1130 SAVOY DR, HUNTINGTON, NY, 11747, Huntington, NY 11747

$710,000

2 beds

2 baths

1,140 sq ft

Condo

1130 SAVOY DR, HUNTINGTON, NY, 11747

Community: The Greens at Half Hollow

New Oronoque Village

89 S TRL A, STRATFORD, CT, 06614, Stratford, CT 06614

$649,000

1 beds

3 baths

1,438 sq ft

Condo

89 S TRL A, STRATFORD, CT, 06614

Community: Oronoque Village

New Oak Meadow Estates

197 OAK MEADOW LN 197, TORRINGTON, CT, 0..., Torrington, CT 06790

$399,000

2 beds

2 baths

1,419 sq ft

Condo

197 OAK MEADOW LN 197, TORRINGTON, CT, 0...

Community: Oak Meadow Estates

New Strathmore Gate East

9 FREEDOM LN, BROOKHAVEN, NY, 11727, Brookhaven, NY 11727

$289,000

1 beds

1 baths

728 sq ft

Condo

9 FREEDOM LN, BROOKHAVEN, NY, 11727

Community: Strathmore Gate East

New Heritage Village

301 HERRITAGE VLG B, SOUTHBURY, CT, 0648..., Southbury, CT 06488

$235,000

2 beds

2 baths

1,365 sq ft

Condo

301 HERRITAGE VLG B, SOUTHBURY, CT, 0648...

Community: Heritage Village

New Leisure Knoll

338 EDINBURGH DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$419,990

2 beds

1 baths

960 sq ft

Condo

338 EDINBURGH DR, BROOKHAVEN, NY, 11961

Community: Leisure Knoll

New Greenwood Village

5127 VILLAGE CIR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949

$227,000

2 beds

2 baths

1,291 sq ft

Condo

5127 VILLAGE CIR, BROOKHAVEN, NY, 11949

Community: Greenwood Village

New Billingsgate

14 BILLINGSGATE DR 14, SIMSBURY, CT, 060..., Simsbury, CT 06070

$750,000

2 beds

3 baths

2,729 sq ft

Condo

14 BILLINGSGATE DR 14, SIMSBURY, CT, 060...

Community: Billingsgate

New Encore Atlantic Shores

11 OVATION PL, BROOKHAVEN, NY, 11941, Brookhaven, NY 11941

$925,000

2 beds

3 baths

2,900 sq ft

Condo

11 OVATION PL, BROOKHAVEN, NY, 11941

Community: Encore Atlantic Shores

New Leisure Village

312 WOODBRIDGE DR B, BROOKHAVEN, NY, 119..., Brookhaven, NY 11961

$239,000

1 beds

1 baths

684 sq ft

Condo

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

Community: Leisure Village

New Heritage Village

184 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488

$209,000

1 beds

1 baths

928 sq ft

Condo

184 HERITAGE VLG A, SOUTHBURY, CT, 06488

Community: Heritage Village

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

Questions? Call us: (860) 854-7490

New The Powder Forest Homes

6 PROSPECT RDG 6, SIMSBURY, CT, 06070, Simsbury, CT 06070

2 beds

2 baths

1,976 sq ft

Condo

33204 SPRUCE POND CIR, OYSTER BAY, NY, 1...

Community: Country Pointe Plainview

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

Questions? Call us: (860) 854-7490

New Leisure Village

158 FALMOUTH CT A, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$228,888

2 beds

1 baths

836 sq ft

Condo

158 FALMOUTH CT A, BROOKHAVEN, NY, 11961

Community: Leisure Village

New The Village at Oxford Greens

443 TEE SHOT DR 443, OXFORD, CT, 06478, Oxford, CT 06478

$689,900

3 beds

3 baths

2,759 sq ft

Condo

443 TEE SHOT DR 443, OXFORD, CT, 06478

Community: The Village at Oxford Greens

New Hopmeadow Place

1 W ST 310, SIMSBURY, CT, 06070, Simsbury, CT 06070

$385,000

2 beds

2 baths

1,430 sq ft

Condo

1 W ST 310, SIMSBURY, CT, 06070

Community: Hopmeadow Place

New Leisure Knoll

152B LAURANCE LN, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961

$374,000

1 beds

1 baths

530 sq ft

Condo

152B LAURANCE LN, BROOKHAVEN, NY, 11961

Community: Leisure Knoll

Oronoque Village

448 HAMMERSTONE LN B, STRATFORD, CT, 066..., Stratford, CT 06614

$525,000

1 beds

3 baths

1,438 sq ft

Condo

448 HAMMERSTONE LN B, STRATFORD, CT, 066...

Community: Oronoque Village

The Powder Forest Homes

6 RONAN WAY 6, SIMSBURY, CT, 06070, Simsbury, CT 06070

$739,900

2 beds

3 baths

1,864 sq ft

115 AUTUMN DR, OYSTER BAY, NY, 11803

Community: The Seasons at Plainview

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

Questions? Call us: (860) 854-7490

Fairfield at St. James

1305 GOTHAM CT, SMITHTOWN, NY, 11780, Smithtown, NY 11780

$518,400

2 beds

2 baths

954 sq ft

Condo

1305 GOTHAM CT, SMITHTOWN, NY, 11780

Community: Fairfield at St. James

Meadowbrook Pointe Links & Spa

163 AUGUSTA DR, BROOKHAVEN, NY, 11763, Brookhaven, NY 11763

$699,990

2 beds

3 baths

1,558 sq ft

Condo

163 AUGUSTA DR, BROOKHAVEN, NY, 11763

Community: Meadowbrook Pointe Links & Spa

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

240 homes near Portland

2 beds

2 baths

1,258 sq ft

Condo

2 beds

2 baths

1,624 sq ft

Manufactured Home

2 beds

2 baths

1,432 sq ft

Condo

2 beds

2 baths

1,112 sq ft

House

3 beds

4 baths

2,848 sq ft

Condo

2 beds

2 baths

1,140 sq ft

Condo

1 beds

3 baths

1,438 sq ft

Condo

2 beds

2 baths

1,419 sq ft

Condo

1 beds

1 baths

728 sq ft

Condo

2 beds

2 baths

1,365 sq ft

Condo

2 beds

1 baths

960 sq ft

Condo

2 beds

2 baths

1,291 sq ft

Condo

2 beds

3 baths

2,729 sq ft

Condo

2 beds

3 baths

2,900 sq ft

Condo

1 beds

1 baths

684 sq ft

Condo

1 beds

1 baths

928 sq ft

Condo

3 beds

3 baths

2,183 sq ft

2 beds

3 baths

1,735 sq ft

Condo

2 beds

2 baths

1,500 sq ft

Condo

2 beds

3 baths