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

123 communities near Portland

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Park Glen
$600Ks
Park Glen, New Milford, CT
Resale Only | 55+ age-restricted | Built 2006 - 2015 | 17 homes
Newington Ridge Preserve
$300Ks - $400Ks
Newington Ridge Preserve, Newington, CT
New Construction | 55+ age-restricted | Built 2014 - present | 16 homes
Cobblestone Court
$400Ks - $500Ks
Cobblestone Court, Essex, CT
New and Resale | 55+ age-restricted | Built 2017 - present | 8 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.
Want to learn more about 55+ communities in Portland? 55places can help!
Questions? Call us: (860) 854-7490
Oronoque Village 516 OPA LN A, STRATFORD, CT, 06614, Stratford, CT 06614
$459,900

2 beds

|

2 baths

|

1,426 sq ft

|

Condo

516 OPA LN A, STRATFORD, CT, 06614
Community: Oronoque Village
Regency at Woodbridge 21 HERITAGE LN # 60, WOODBRIDGE, CT, 065..., Woodbridge, CT 06525
$599,000

3 beds

|

3 baths

|

Condo

21 HERITAGE LN # 60, WOODBRIDGE, CT, 065...
Regency at Prospect 11 POPLAR DR # 11, PROSPECT, CT, 06712, Prospect, CT 06712
$549,000

3 beds

|

3 baths

|

2,058 sq ft

|

Condo

11 POPLAR DR # 11, PROSPECT, CT, 06712
Community: Regency at Prospect
New Oronoque Village 766 NYACK LN B, STRATFORD, CT, 06614, Stratford, CT 06614
$649,000

2 beds

|

3 baths

|

1,438 sq ft

|

Condo

766 NYACK LN B, STRATFORD, CT, 06614
Community: Oronoque Village
Oronoque Village 183 APACHE LN A, STRATFORD, CT, 06614, Stratford, CT 06614
$499,900

2 beds

|

3 baths

|

1,426 sq ft

|

Condo

183 APACHE LN A, STRATFORD, CT, 06614
Community: Oronoque Village
Want to learn more about 55+ communities in Portland? 55places can help!
Questions? Call us: (860) 854-7490
Oronoque Village 289 AGAWAM DR B, STRATFORD, CT, 06614, Stratford, CT 06614
$639,900

1 beds

|

3 baths

|

1,620 sq ft

|

Condo

289 AGAWAM DR B, STRATFORD, CT, 06614
Community: Oronoque Village
New Long Hill Village 5 CIDER MILL LN, TRUMBULL, CT, 06611, Trumbull, CT 06611
$479,900

2 beds

|

2 baths

|

1,370 sq ft

|

Condo

5 CIDER MILL LN, TRUMBULL, CT, 06611
Community: Long Hill Village
New Oronoque Village 151 SOUTH TRL A, STRATFORD, CT, 06614, Stratford, CT 06614
$494,900

2 beds

|

2 baths

|

1,426 sq ft

|

Condo

151 SOUTH TRL A, STRATFORD, CT, 06614
Community: Oronoque Village
Heritage Village 132 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$285,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

132 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Spring Lake Village 373 LAKEVIEW DR # 373, SOUTHINGTON, CT, ..., Southington, CT 06489
$259,900

2 beds

|

2 baths

|

1,188 sq ft

|

Condo

373 LAKEVIEW DR # 373, SOUTHINGTON, CT, ...
Community: Spring Lake 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.
Oronoque Village 87 CREEK LN A, STRATFORD, CT, 06614, Stratford, CT 06614
$439,900

1 beds

|

2 baths

|

1,454 sq ft

|

Condo

87 CREEK LN A, STRATFORD, CT, 06614
Community: Oronoque Village
Oronoque Village 195 BAYFIELD LN A, STRATFORD, CT, 06614, Stratford, CT 06614
$499,000

1 beds

|

3 baths

|

1,575 sq ft

|

Condo

195 BAYFIELD LN A, STRATFORD, CT, 06614
Community: Oronoque Village
Heritage Village 902 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$389,900

2 beds

|

2 baths

|

1,398 sq ft

|

Condo

902 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
New Gloria Commons 10 LUCIUS CT # 10, MILFORD, CT, 06461, Milford, CT 06461
$450,000

2 beds

|

3 baths

|

2,061 sq ft

|

Condo

10 LUCIUS CT # 10, MILFORD, CT, 06461
Community: Gloria Commons
Heritage Village 644 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$524,900

3 beds

|

2 baths

|

1,716 sq ft

|

Condo

644 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
Park Glen 1 BLOSSOM CT # 1, NEW MILFORD, CT, 06776, New Milford, CT 06776
$545,000

2 beds

|

2 baths

|

1,880 sq ft

|

Condo

1 BLOSSOM CT # 1, NEW MILFORD, CT, 06776
Community: Park Glen
Oronoque Village 617 CHEROKEE LN B, STRATFORD, CT, 06614, Stratford, CT 06614
$534,999

1 beds

|

3 baths

|

1,438 sq ft

|

Condo

617 CHEROKEE LN B, STRATFORD, CT, 06614
Community: Oronoque Village
Oronoque Village 133 BANNOCK LN A, STRATFORD, CT, 06614, Stratford, CT 06614
$629,900

3 beds

|

3 baths

|

1,438 sq ft

|

Condo

133 BANNOCK LN A, STRATFORD, CT, 06614
Community: Oronoque Village
Heritage Village 39 HERITAGE VLG C, SOUTHBURY, CT, 06488, Southbury, CT 06488
$238,000

2 beds

|

2 baths

|

1,044 sq ft

|

Condo

39 HERITAGE VLG C, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 953 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$264,900

1 beds

|

1 baths

|

928 sq ft

|

Condo

953 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.
New Heritage Village 20 HERITAGE CIR B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$290,000

2 beds

|

2 baths

|

1,000 sq ft

|

Condo

20 HERITAGE CIR B, SOUTHBURY, CT, 06488
Community: Heritage Village
The Woods at Dunham Pond 12 HERON VIEW RD # 12, NEW FAIRFIELD, CT..., New Fairfield, CT 06812
$409,900

1 beds

|

2 baths

|

1,550 sq ft

12 HERON VIEW RD # 12, NEW FAIRFIELD, CT...
The Village at Buckingham 8 KENINGTON RD # 8, AVON, CT, 06001, Avon, CT 06001
$599,900

3 beds

|

3 baths

|

2,430 sq ft

|

Condo

8 KENINGTON RD # 8, AVON, CT, 06001
Heritage Village 7 HERITAGE CRST B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$449,900

2 beds

|

2 baths

|

1,447 sq ft

|

Condo

7 HERITAGE CRST B, SOUTHBURY, CT, 06488
Community: Heritage Village
Oronoque Village 383 SEQUOIA LN A, STRATFORD, CT, 06614, Stratford, CT 06614
$635,000

2 beds

|

3 baths

|

1,360 sq ft

|

Condo

383 SEQUOIA LN A, STRATFORD, CT, 06614
Community: Oronoque Village
Want to learn more about 55+ communities in Portland? 55places can help!
Questions? Call us: (860) 854-7490
Rivington 47 WARRINGTON ROUND # 47, DANBURY, CT, 0..., Danbury, CT 06810
$650,000

3 beds

|

3 baths

|

1,704 sq ft

|

Condo

47 WARRINGTON ROUND # 47, DANBURY, CT, 0...
Community: Rivington
Newbury Village 332 STILL WATER CIR # 332, BROOKFIELD, C..., Brookfield, CT 06804
$525,000

2 beds

|

2 baths

|

1,466 sq ft

|

Condo

332 STILL WATER CIR # 332, BROOKFIELD, C...
Community: Newbury Village
Oronoque Village 164 BISON LN A, STRATFORD, CT, 06614, Stratford, CT 06614
$479,999

1 beds

|

2 baths

|

1,175 sq ft

|

Condo

164 BISON LN A, STRATFORD, CT, 06614
Community: Oronoque Village
Oronoque Village 543 NORTH TRL B, STRATFORD, CT, 06614, Stratford, CT 06614
$499,000

2 beds

|

3 baths

|

1,426 sq ft

|

Condo

543 NORTH TRL B, STRATFORD, CT, 06614
Community: Oronoque Village
Heritage Village 191 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$395,000

3 beds

|

2 baths

|

1,716 sq ft

|

Condo

191 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.
Oronoque Village 488 COMMANCHE LN A, STRATFORD, CT, 06614, Stratford, CT 06614
$619,000

2 beds

|

3 baths

|

1,438 sq ft

|

Condo

488 COMMANCHE LN A, STRATFORD, CT, 06614
Community: Oronoque Village
Rivington 13 MERCY ST # 13, DANBURY, CT, 06810, Danbury, CT 06810
$650,000

3 beds

|

3 baths

|

1,572 sq ft

|

Condo

13 MERCY ST # 13, DANBURY, CT, 06810
Community: Rivington
Heritage Village 44 HERITAGE VLG F, SOUTHBURY, CT, 06488, Southbury, CT 06488
$239,000

2 beds

|

2 baths

|

1,308 sq ft

|

Condo

44 HERITAGE VLG F, SOUTHBURY, CT, 06488
Community: Heritage Village
Oak Meadow Estates 21 OAK MEADOW LN # 21, HARWINTON, CT, 06..., Harwinton, CT 06791
$450,000

2 beds

|

3 baths

|

2,164 sq ft

|

Condo

21 OAK MEADOW LN # 21, HARWINTON, CT, 06...
Community: Oak Meadow Estates
The Village at Oxford Greens 930 TILLINGHAST DR # 930, OXFORD, CT, 06..., Oxford, CT 06478
$759,900

2 beds

|

3 baths

|

2,365 sq ft

930 TILLINGHAST DR # 930, OXFORD, CT, 06...
Want to learn more about 55+ communities in Portland? 55places can help!
Questions? Call us: (860) 854-7490
Heritage Village 761 HERITAGE VLG D, SOUTHBURY, CT, 06488, Southbury, CT 06488
$344,900

2 beds

|

2 baths

|

1,063 sq ft

|

Condo

761 HERITAGE VLG D, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 865 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$369,900

2 beds

|

2 baths

|

1,398 sq ft

|

Condo

865 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Oronoque Village 522 IROQUOIS LN B, STRATFORD, CT, 06614, Stratford, CT 06614
$399,000

3 beds

|

3 baths

|

1,426 sq ft

|

Condo

522 IROQUOIS LN B, STRATFORD, CT, 06614
Community: Oronoque Village
Spring Lake Village 1 COACH DR # 1, SOUTHINGTON, CT, 06489, Southington, CT 06489
$280,000

2 beds

|

2 baths

|

1,323 sq ft

|

Condo

1 COACH DR # 1, SOUTHINGTON, CT, 06489
Community: Spring Lake Village
Heritage Village 623 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$535,000

3 beds

|

2 baths

|

1,716 sq ft

|

Condo

623 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
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123 communities near Portland
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