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Portland, CT 55+ active adult communities & homes for sale - Page 4

192 homes 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
Leisure Village
$100ks - $300ks
Leisure Village, Ridge, NY
Resale Only | 55+ age-restricted | Built 1969 - 1986 | 1,500 homes
Oronoque Village
$200ks - $400ks
Oronoque Village, Stratford, CT
Resale Only | 55+ age-restricted | Built 1971 - 1977 | 929 homes
3.7 rating (3 reviews) Greenwood Village
$100ks
Greenwood Village, Manorville, NY
Resale Only | 55+ age-restricted | Built 1980 - 2000 | 512 homes
4 rating (8 reviews) Glenwood Village
$100ks - $200ks
Glenwood Village, Riverhead, NY
New and Resale | 55+ age-restricted | Built 1959 - present | 588 homes
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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
Spring Lake Village
$100ks - $200ks
Spring Lake Village, Southington, CT
Resale Only | 55+ age-restricted | Built 1970 - 2004 | 640 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
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.
Harmony Place
$400ks - $500ks
Harmony Place, Rutland, MA
New Construction | 55+ age-restricted | Built 2023 - present | 142 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
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
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
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Rivington
$300ks - $900ks
Rivington, Danbury, CT
New and Resale | Age-targeted | Built 2006 - present | 1,050 homes
The Villas at Narraganset...
$400ks
The Villas at Narraganset..., Lindenhurst, NY
Resale Only | 55+ age-restricted | Built 2004 - 2005 | 138 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) Westhampton Pines
$900ks - $1Ms
Westhampton Pines, Westhampton, NY
Resale Only | 55+ age-restricted | Built 2005 - 2013 | 189 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 Glen
$300ks - $400ks
Leisure Glen, Ridge, NY
Resale Only | 55+ age-restricted | Built 1985 - 2010 | 646 homes
5 rating (1 reviews) Newtown Woods
$300ks - $500ks
Newtown Woods, Newtown, CT
New and Resale | 55+ age-restricted | Built 2011 - present | 178 homes
Regency at Woodbridge
$500ks - $700ks
Regency at Woodbridge, Woodbridge, CT
New Construction | 55+ age-restricted | Built 2023 - present | 70 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
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Stone Ridge Estates
$500ks - $600ks
Stone Ridge Estates, Dix Hills, NY
Resale Only | 55+ age-restricted | Built 2004 - 2013 | 76 homes
Kensington Estates
$1Ms
Kensington Estates, Woodbury, NY
New Construction | 55+ age-restricted | Built 2019 - 2021 | 80 homes
South Pond Village
$300ks - $400ks
South Pond Village, Bloomfield, CT
Resale Only | 55+ age-restricted | Built 1999 - 2005 | 151 homes
Fairview at Oxford Greens
$400ks - $600ks
Fairview at Oxford Greens, Oxford, CT
New and Resale | 55+ age-restricted | Built 2019 - present | 125 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 Coves at Melville
$500ks
The Coves at Melville, Melville, NY
Resale Only | 62+ age-restricted | Built 2004 - 2005 | 175 homes
Country Village Estates
$300ks
Country Village Estates, Coram, NY
Resale Only | 55+ age-restricted | Built 1993 - 2001 | 195 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
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
3.5 rating (2 reviews) Foxwood Village
$200ks - $400ks
Foxwood Village, Calverton, NY
Resale Only | 55+ age-restricted | Built 1986 - 2007 | 294 homes
Village Estates
$300ks - $400ks
Village Estates, Amityville, NY
Resale Only | 55+ age-restricted | Built 2006 - 2008 | 138 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
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.
Park Glen
$300ks - $500ks
Park Glen, New Milford, CT
Resale Only | 55+ age-restricted | Built 2006 - 2015 | 17 homes
Brierly Pond Village
$300ks - $400ks
Brierly Pond Village, Millbury, MA
Resale Only | 55+ age-restricted | Built 2003 - 2013 | 199 homes
Oak Meadow Estates
$200ks - $300ks
Oak Meadow Estates, Torrington, CT
New and Resale | 55+ age-restricted | Built 2013 - present | 31 homes
Regency at Prospect
$300ks - $400ks
Regency at Prospect, Prospect, CT
Resale Only | 55+ age-restricted | Built 2006 - 2020 | 379 homes
Want to learn more about 55+ communities in Portland? 55places can help!
Questions? Call us: (860) 854-7490
The Village at Orchard Me...
$400ks - $500ks
The Village at Orchard Me..., Shrewsbury, MA
Resale Only | 55+ age-restricted | Built 2002 - 2007 | 114 homes
Evergreen
$400ks - $500ks
Evergreen, Cromwell, CT
New and Resale | 55+ age-restricted | Built 2005 - present | 52 homes
123...4
The Waterways at Moriches 477 WOODSCREEK CT, MORICHES, NY, 11955, Moriches, NY 11955
$565,000

3 beds

|

2 baths

|

1,839 sq ft

|

Condo

477 WOODSCREEK CT, MORICHES, NY, 11955
Oronoque Village 766 NYACK LN B, STRATFORD, CT, 06614, Stratford, CT 06614
$649,000

1 beds

|

3 baths

|

1,438 sq ft

|

Condo

766 NYACK LN B, STRATFORD, CT, 06614
Community: Oronoque Village
Bartlett Hill 9 PEAR ORCHARD RD # 9, PORTLAND, CT, 064..., Portland, CT 06480
$505,000

2 beds

|

3 baths

|

1,404 sq ft

9 PEAR ORCHARD RD # 9, PORTLAND, CT, 064...
Community: Bartlett Hill
The Greens at Half Hollow 910 ALTESSA BLVD, HUNTINGTON, NY, 11747, Huntington, NY 11747
$779,000

2 beds

|

2 baths

|

1,120 sq ft

|

Condo

910 ALTESSA BLVD, HUNTINGTON, NY, 11747
Harmony Place 12 FIDELITY DR # 6, RUTLAND, MA, 01543, Rutland, MA 01543
$498,000

2 beds

|

2 baths

|

1,582 sq ft

|

Condo

12 FIDELITY DR # 6, RUTLAND, MA, 01543
Community: Harmony Place
Want to learn more about 55+ communities in Portland? 55places can help!
Questions? Call us: (860) 854-7490
Leisure Village 380 WOODBRIDGE DR D, RIDGE, NY, 11961, Ridge, NY 11961
$439,000

2 beds

|

2 baths

|

1,147 sq ft

|

Condo

380 WOODBRIDGE DR D, RIDGE, NY, 11961
Community: Leisure Village
Foxwood Village 1407 MIDDLE RD 275, RIVERHEAD, NY, 11933, Riverhead, NY 11933
$425,000

3 beds

|

2 baths

|

1,530 sq ft

|

House

1407 MIDDLE RD 275, RIVERHEAD, NY, 11933
Community: Foxwood Village
The Villas at Narragansett 512 NARRAGANSETT VILLAS DR, LINDENHURST,..., Lindenhurst, NY 11757
$599,000

2 beds

|

2 baths

|

1,227 sq ft

|

Condo

512 NARRAGANSETT VILLAS DR, LINDENHURST,...
Encore Atlantic Shores 177 MELODY CT, EASTPORT, NY, 11941, Eastport, NY 11941
$795,000

2 beds

|

2 baths

|

2,150 sq ft

|

Condo

177 MELODY CT, EASTPORT, NY, 11941
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.
Heritage Village 25 HERITAGE CRST C, SOUTHBURY, CT, 06488, Southbury, CT 06488
$449,000

2 beds

|

2 baths

|

1,447 sq ft

|

Condo

25 HERITAGE CRST C, SOUTHBURY, CT, 06488
Community: Heritage Village
Rivington 1 RIVINGTON WAY UNIT 201, DANBURY, CT, 0..., Danbury, CT 06810
$499,900

2 beds

|

2 baths

|

1,229 sq ft

|

Condo

1 RIVINGTON WAY UNIT 201, DANBURY, CT, 0...
Community: Rivington
Heritage Village 723 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$259,900

2 beds

|

2 baths

|

1,365 sq ft

|

Condo

723 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Greenwood Village 91 VILLAGE CIR, MANORVILLE, NY, 11949, Manorville, NY 11949
$149,000

2 beds

|

2 baths

|

938 sq ft

|

Condo

91 VILLAGE CIR, MANORVILLE, NY, 11949
Community: Greenwood Village
Want to learn more about 55+ communities in Portland? 55places can help!
Questions? Call us: (860) 854-7490
Fairfield at St. James 401 CABOT CT, SMITHTOWN, NY, 11780, Smithtown, NY 11780
$485,000

1 beds

|

2 baths

|

900 sq ft

|

Condo

401 CABOT CT, SMITHTOWN, NY, 11780
Oronoque Village 87 CREEK LN A, STRATFORD, CT, 06614, Stratford, CT 06614
$420,000

1 beds

|

2 baths

|

1,454 sq ft

|

Condo

87 CREEK LN A, STRATFORD, CT, 06614
Community: Oronoque Village
Oronoque Village 35 ALGONQUIN LN D, STRATFORD, CT, 06614, Stratford, CT 06614
$399,000

2 beds

|

2 baths

|

1,300 sq ft

|

Condo

35 ALGONQUIN LN D, STRATFORD, CT, 06614
Community: Oronoque Village
Oronoque Village 164 BISON LN A, STRATFORD, CT, 06614, Stratford, CT 06614
$465,000

1 beds

|

2 baths

|

1,175 sq ft

|

Condo

164 BISON LN A, STRATFORD, CT, 06614
Community: Oronoque Village
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.
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
Newtown Woods 433 BROOKSIDE CT 433, NEWTOWN, CT, 06470, Newtown, CT 06470
$500,000

2 beds

|

2 baths

|

1,504 sq ft

|

Condo

433 BROOKSIDE CT 433, NEWTOWN, CT, 06470
Community: Newtown Woods
Heritage Village 876 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$356,000

2 beds

|

2 baths

|

1,398 sq ft

|

Condo

876 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Greenwood Village 19 DOGWOOD LN, MANORVILLE, NY, 11949, Manorville, NY 11949
$149,900

2 beds

|

2 baths

|

871 sq ft

|

Condo

19 DOGWOOD LN, MANORVILLE, NY, 11949
Community: Greenwood Village
Want to learn more about 55+ communities in Portland? 55places can help!
Questions? Call us: (860) 854-7490
Leisure Village 169 VENTRY CT A, RIDGE, NY, 11961, Ridge, NY 11961
$289,000

2 beds

|

1 baths

|

875 sq ft

|

Condo

169 VENTRY CT A, RIDGE, NY, 11961
Community: Leisure Village
Heritage Village 929 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$499,900

3 beds

|

2 baths

|

1,716 sq ft

|

Condo

929 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 701 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$329,000

3 beds

|

2 baths

|

1,716 sq ft

|

Condo

701 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 889 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$374,500

2 beds

|

2 baths

|

1,398 sq ft

|

Condo

889 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
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 Gardens of Wilbraham 32 LODGE LN # 32, WILBRAHAM, MA, 01095, Wilbraham, MA 01095
$565,000

2 beds

|

2 baths

|

1,610 sq ft

|

Condo

32 LODGE LN # 32, WILBRAHAM, MA, 01095
The Waterways at Moriches 414 LINDSAY LN, MORICHES, NY, 11955, Moriches, NY 11955
$535,000

2 beds

|

2 baths

|

2,141 sq ft

|

Condo

414 LINDSAY LN, MORICHES, NY, 11955
Heritage Village 98 HERITAGE VLG D, SOUTHBURY, CT, 06488, Southbury, CT 06488
$298,000

2 beds

|

2 baths

|

1,044 sq ft

|

Condo

98 HERITAGE VLG D, SOUTHBURY, CT, 06488
Community: Heritage Village
The Village at Oxford Greens 930 TILLINGHAST DR 930, OXFORD, CT, 0647..., Oxford, CT 06478
$699,900

2 beds

|

3 baths

|

2,365 sq ft

930 TILLINGHAST DR 930, OXFORD, CT, 0647...
Heritage Village 73 HERITAGE VLG C, SOUTHBURY, CT, 06488, Southbury, CT 06488
$214,900

2 beds

|

2 baths

|

1,044 sq ft

|

Condo

73 HERITAGE VLG 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
Evergreen 34 WOODSBORO CIR # 34, CROMWELL, CT, 064..., Cromwell, CT 06416
$519,900

2 beds

|

2 baths

|

1,758 sq ft

|

Condo

34 WOODSBORO CIR # 34, CROMWELL, CT, 064...
Community: Evergreen
Kensington Estates 46 PLAINVIEW RD, WOODBURY, NY, 11797, Woodbury, NY 11797
$2,299,999

6 beds

|

5 baths

|

4,333 sq ft

|

House

46 PLAINVIEW RD, WOODBURY, NY, 11797
Community: Kensington Estates
Heritage Village 1008 HERITAGE VLG B, SOUTHBURY, CT, 0648..., Southbury, CT 06488
$385,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

1008 HERITAGE VLG B, SOUTHBURY, CT, 0648...
Community: Heritage Village
Heritage Village 862 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$499,900

3 beds

|

2 baths

|

1,716 sq ft

|

Condo

862 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
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 Waterways at Moriches 244 RIVER DR, BROOKHAVEN, NY, 11955, Brookhaven, NY 11955
$625,000

2 beds

|

2 baths

|

1,960 sq ft

|

Condo

244 RIVER DR, BROOKHAVEN, NY, 11955
The Village at Oxford Greens 712 CHAMPIONSHIP DR 712, OXFORD, CT, 064..., Oxford, CT 06478
$615,000

2 beds

|

2 baths

|

1,546 sq ft

|

Condo

712 CHAMPIONSHIP DR 712, OXFORD, CT, 064...
Fairview at Oxford Greens 712 CHAMPIONSHIP DR 712, OXFORD, CT, 064..., Oxford, CT 06478
$615,000

2 beds

|

2 baths

|

1,546 sq ft

|

Condo

712 CHAMPIONSHIP DR 712, OXFORD, CT, 064...
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
Want to learn more about 55+ communities in Portland? 55places can help!
Questions? Call us: (860) 854-7490
Heritage Village 176 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$249,900

2 beds

|

2 baths

|

1,032 sq ft

|

Condo

176 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Glenwood Village 1661 OLD COUNTRY RD 434, RIVERHEAD, NY, ..., Riverhead, NY 11901
$219,000

2 beds

|

2 baths

|

1,144 sq ft

|

Mobile Home

1661 OLD COUNTRY RD 434, RIVERHEAD, NY, ...
Community: Glenwood Village
1234…5

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