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Portland, CT 55+ active adult communities & homes for sale - Page 3

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 Village at Oxford Greens 185 COUNTRY CLUB DR # 185, OXFORD, CT, 0..., Oxford, CT 06478
$645,000

3 beds

|

3 baths

|

2,595 sq ft

|

Condo

185 COUNTRY CLUB DR # 185, OXFORD, CT, 0...
The Village at Oxford Greens 185 COUNTRY CLUB DR 185, OXFORD, CT, 064..., Oxford, CT 06478
$645,000

3 beds

|

3 baths

|

2,595 sq ft

185 COUNTRY CLUB DR 185, OXFORD, CT, 064...
Heritage Village 423 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$320,000

2 beds

|

2 baths

|

1,365 sq ft

|

Condo

423 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Leisure Village 278 BERWICK CT UNIT B B, RIDGE, NY, 1196..., Ridge, NY 11961
$359,900

2 beds

|

1 baths

|

875 sq ft

|

Condo

278 BERWICK CT UNIT B B, RIDGE, NY, 1196...
Community: Leisure Village
Regency at Woodbridge 3 EDGEWOOD WAY # 26, WOODBRIDGE, CT, 065..., Woodbridge, CT 06525
$629,000

3 beds

|

3 baths

|

Condo

3 EDGEWOOD WAY # 26, WOODBRIDGE, CT, 065...
Want to learn more about 55+ communities in Portland? 55places can help!
Questions? Call us: (860) 854-7490
Regency at Woodbridge 5 WHISPER RIDGE WAY 49, WOODBRIDGE, CT, ..., Woodbridge, CT 06525
$749,000

3 beds

|

3 baths

|

Condo

5 WHISPER RIDGE WAY 49, WOODBRIDGE, CT, ...
Heritage Village 405 HERITAGE VLG D, SOUTHBURY, CT, 06488, Southbury, CT 06488
$199,900

2 beds

|

2 baths

|

1,044 sq ft

|

Condo

405 HERITAGE VLG D, SOUTHBURY, CT, 06488
Community: Heritage Village
Leisure Village 418 WEYMOUTH CT B, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$359,900

2 beds

|

1 baths

|

1,036 sq ft

|

Condo

418 WEYMOUTH CT B, BROOKHAVEN, NY, 11961
Community: Leisure Village
The Waterways at Moriches 554 MIRROR POND CT, BROOKHAVEN, NY, 1195..., Brookhaven, NY 11955
$499,000

2 beds

|

2 baths

|

1,497 sq ft

|

Condo

554 MIRROR POND CT, BROOKHAVEN, NY, 1195...
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 446 HAMMERSTONE LN B, STRATFORD, CT, 066..., Stratford, CT 06614
$635,000

3 beds

|

3 baths

|

1,426 sq ft

|

Condo

446 HAMMERSTONE LN B, STRATFORD, CT, 066...
Community: Oronoque Village
Oronoque Village 151 S TRL B, STRATFORD, CT, 06614, Stratford, CT 06614
$460,000

1 beds

|

3 baths

|

1,426 sq ft

|

Condo

151 S TRL B, STRATFORD, CT, 06614
Community: Oronoque Village
Heritage Village 761 HERITAGE VLG D, SOUTHBURY, CT, 06488, Southbury, CT 06488
$339,900

2 beds

|

2 baths

|

1,063 sq ft

|

Condo

761 HERITAGE VLG D, SOUTHBURY, CT, 06488
Community: Heritage Village
Liberty at Newtown 79 SUZIE DR # 79, NEWTOWN, CT, 06470, Newtown, CT 06470
$575,000

2 beds

|

3 baths

|

2,317 sq ft

|

Condo

79 SUZIE DR # 79, NEWTOWN, CT, 06470
Community: Liberty at Newtown
Want to learn more about 55+ communities in Portland? 55places can help!
Questions? Call us: (860) 854-7490
Fairfield at St. James 901 FENWAY RD, SAINT JAMES, NY, 11780, Saint James, NY 11780
$499,000

2 beds

|

2 baths

|

1,230 sq ft

|

Condo

901 FENWAY RD, SAINT JAMES, NY, 11780
Harmony Place 18 FIDELITY DR # 9, RUTLAND, MA, 01543, Rutland, MA 01543
$498,000

2 beds

|

2 baths

|

1,582 sq ft

|

Condo

18 FIDELITY DR # 9, RUTLAND, MA, 01543
Community: Harmony Place
Leisure Glen 10 OAKDALE CT, RIDGE, NY, 11961, Ridge, NY 11961
$599,900

2 beds

|

2 baths

|

1,666 sq ft

|

Condo

10 OAKDALE CT, RIDGE, NY, 11961
Community: Leisure Glen
Heritage Village 891 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$310,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

891 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 Coves at Melville 6 MORLEY CIR, MELVILLE, NY, 11747, Melville, NY 11747
$530,000

2 beds

|

2 baths

|

Condo

6 MORLEY CIR, MELVILLE, NY, 11747
Encore Atlantic Shores 6 OVATION PL, EASTPORT, NY, 11941, Eastport, NY 11941
$795,000

2 beds

|

2 baths

|

2,150 sq ft

|

Condo

6 OVATION PL, EASTPORT, NY, 11941
Rivington 85 WINDING RIDGE WAY # 85, DANBURY, CT, ..., Danbury, CT 06810
$825,000

3 beds

|

4 baths

|

1,794 sq ft

|

Condo

85 WINDING RIDGE WAY # 85, DANBURY, CT, ...
Community: Rivington
Stone Ridge Estates 153 CHRISTINE DR, DIX HILLS, NY, 11746, Dix Hills, NY 11746
$775,000

2 beds

|

2 baths

|

1,415 sq ft

|

Condo

153 CHRISTINE DR, DIX HILLS, NY, 11746
Community: Stone Ridge Estates
Want to learn more about 55+ communities in Portland? 55places can help!
Questions? Call us: (860) 854-7490
Leisure Village 186 VENTRY CT UNIT C, RIDGE, NY, 11961, Ridge, NY 11961
$289,000

2 beds

|

1 baths

|

900 sq ft

|

Condo

186 VENTRY CT UNIT C, RIDGE, NY, 11961
Community: Leisure Village
Leisure Village 116 EXMORE CT UNIT B, RIDGE, NY, 11961, Ridge, NY 11961
$299,000

2 beds

|

1 baths

|

875 sq ft

|

Condo

116 EXMORE CT UNIT B, RIDGE, NY, 11961
Community: Leisure Village
The Summit at Bethel 32 HUNTING RIDGE LN # 32, BETHEL, CT, 06..., Bethel, CT 06801
$689,000

3 beds

|

4 baths

|

2,090 sq ft

|

Condo

32 HUNTING RIDGE LN # 32, BETHEL, CT, 06...
Country Pointe Plainview 21105 ASPENWOOD DR, PLAINVIEW, NY, 11803, Plainview, NY 11803
$1,250,000

2 beds

|

2 baths

|

1,475 sq ft

|

Condo

21105 ASPENWOOD DR, PLAINVIEW, NY, 11803
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 Village 373 WOODBRIDGE DR B, RIDGE, NY, 11961, Ridge, NY 11961
$415,000

2 beds

|

1 baths

|

1,171 sq ft

|

Condo

373 WOODBRIDGE DR B, RIDGE, NY, 11961
Community: Leisure Village
The Villas at Narragansett 816 NARRAGANSETT VILLAS DR 816, BABYLON,..., Babylon, NY 11757
$549,999

2 beds

|

2 baths

|

1,215 sq ft

|

Condo

816 NARRAGANSETT VILLAS DR 816, BABYLON,...
Leisure Village 164 FALMOUTH CT E, RIDGE, NY, 11961, Ridge, NY 11961
$279,000

2 beds

|

1 baths

|

819 sq ft

|

Condo

164 FALMOUTH CT E, RIDGE, NY, 11961
Community: Leisure Village
Spring Lake Village 1 COACH DR # 1, SOUTHINGTON, CT, 06489, Southington, CT 06489
$279,900

2 beds

|

2 baths

|

1,323 sq ft

|

Condo

1 COACH DR # 1, SOUTHINGTON, CT, 06489
Community: Spring Lake Village
Harmony Place 10 FIDELITY DR # 5, RUTLAND, MA, 01543, Rutland, MA 01543
$498,000

2 beds

|

2 baths

|

1,582 sq ft

|

Condo

10 FIDELITY DR # 5, RUTLAND, MA, 01543
Community: Harmony Place
Want to learn more about 55+ communities in Portland? 55places can help!
Questions? Call us: (860) 854-7490
The Village at Oxford Greens 520 TRADITIONS CT N # 520, OXFORD, CT, 0..., Oxford, CT 06478
$629,000

2 beds

|

2 baths

|

1,590 sq ft

|

Condo

520 TRADITIONS CT N # 520, OXFORD, CT, 0...
Leisure Village 432A FALMOUTH CT # 432A, RIDGE, NY, 1196..., Ridge, NY 11961
$389,000

2 beds

|

1 baths

|

1,074 sq ft

|

Condo

432A FALMOUTH CT # 432A, RIDGE, NY, 1196...
Community: Leisure Village
Spring Lake Village 621 OVERLOOK PATH # 621, SOUTHINGTON, CT..., Southington, CT 06489
$340,000

2 beds

|

3 baths

|

1,133 sq ft

|

Condo

621 OVERLOOK PATH # 621, SOUTHINGTON, CT...
Community: Spring Lake Village
Greenwood Village 164 VILLAGE CIR, MANORVILLE, NY, 11949, Manorville, NY 11949
$149,997

2 beds

|

2 baths

|

938 sq ft

|

Condo

164 VILLAGE CIR, MANORVILLE, NY, 11949
Community: Greenwood 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.
Leisure Village 360 WOODBRIDGE DR A, RIDGE, NY, 11961, Ridge, NY 11961
$459,000

2 beds

|

2 baths

|

1,250 sq ft

|

Condo

360 WOODBRIDGE DR A, RIDGE, NY, 11961
Community: Leisure Village
Oronoque Village 617 CHEROKEE LN B, STRATFORD, CT, 06614, Stratford, CT 06614
$524,900

1 beds

|

3 baths

|

1,438 sq ft

|

Condo

617 CHEROKEE LN B, STRATFORD, CT, 06614
Community: Oronoque Village
Heritage Village 98 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$319,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

98 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Eagles Walk at East Quogue 104 AERIE WAY, EAST QUOGUE, NY, 11942, East Quogue, NY 11942
$549,900

2 beds

|

2 baths

|

1,341 sq ft

|

Condo

104 AERIE WAY, EAST QUOGUE, NY, 11942
Want to learn more about 55+ communities in Portland? 55places can help!
Questions? Call us: (860) 854-7490
Heritage Village 123 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$364,900

2 beds

|

2 baths

|

1,398 sq ft

|

Condo

123 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Baldwin Station 7 FIRE THORN LN # 7, MILFORD, CT, 06461, Milford, CT 06461
$679,950

2 beds

|

3 baths

|

2,331 sq ft

|

Condo

7 FIRE THORN LN # 7, MILFORD, CT, 06461
Community: Baldwin Station
1234…5

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