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Portland, CT 55+ active adult communities & homes for sale - Page 2

123 communities near Portland

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5 rating (1 reviews) The Villages at Mount Sin...
$500Ks - $700Ks
The Villages at Mount Sin..., Mount Sinai, NY
Resale Only | 55+ age-restricted | Built 2005 - 2007 | 185 homes
5 rating (1 reviews) Encore at Lake Grove
$600Ks - $800Ks
Encore at Lake Grove, Lake Grove, NY
Resale Only | 55+ age-restricted | Built 2006 - 2007 | 228 homes
Snug Harbor
$600Ks - $700Ks
Snug Harbor, Amityville, NY
Resale Only | 55+ age-restricted | Built 1970 - 1974 | 176 homes
The Coves at Melville
$500Ks
The Coves at Melville, Melville, NY
Resale Only | 62+ age-restricted | Built 2004 - 2005 | 175 homes
Meadow Brook Estates
$500Ks
Meadow Brook Estates, Oxford, CT
Resale Only | 55+ age-restricted | Built 2003 - 2020 | 246 homes
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4.9 rating (14 reviews) Chatfield Farms
$500Ks
Chatfield Farms, Beacon Falls, CT
New Construction | 55+ age-restricted | Built 2014 - present | 231 homes
The Seasons at Plainview
$600Ks - $700Ks
The Seasons at Plainview, Plainview, NY
Resale Only | 55+ age-restricted | Built 2006 - 2007 | 134 homes
3.5 rating (2 reviews) Foxwood Village
$400Ks - $500Ks
Foxwood Village, Calverton, NY
Resale Only | 55+ age-restricted | Built 1986 - 2007 | 294 homes
The Seasons at Salisbury
$600Ks
The Seasons at Salisbury, Holden, MA
Resale Only | 55+ age-restricted | Built 2002 - 2006 | 91 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.
Brierly Pond Village
$400Ks
Brierly Pond Village, Millbury, MA
Resale Only | 55+ age-restricted | Built 2003 - 2013 | 199 homes
Read the Ultimate 55+ Rental Guide Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
The Bridges at Oxford Gre...
$600Ks
The Bridges at Oxford Gre..., Oxford, CT
New Construction | 55+ age-restricted | Built 2025 - present | 99 homes
Vineyards at Moriches
$700Ks
Vineyards at Moriches, Center Moriches, NY
Resale Only | 55+ age-restricted | Built 2008 - 2014 | 92 homes
Eastport Meadows
$400Ks
Eastport Meadows, Eastport, NY
Resale Only | 55+ age-restricted | Built 2009 - 2016 | 50 homes
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Saddle Lakes
$400Ks
Saddle Lakes, Riverhead, NY
Resale Only | 55+ age-restricted | Built 2000 - 2002 | 196 homes
5 rating (1 reviews) Sunken Pond Estates
$400Ks - $500Ks
Sunken Pond Estates, Riverhead, NY
Resale Only | 55+ age-restricted | Built 2003 - 2005 | 194 homes
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Village Vistas
$800Ks - $1Ms
Village Vistas, Port Jefferson, NY
Resale Only | 55+ age-restricted | Built 2013 - 2017 | 43 homes
Setauket Meadows
$600Ks - $700Ks
Setauket Meadows, Setauket, NY
Resale Only | 55+ age-restricted | Built 2005 - 2007 | 150 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) Sunrise Village
$400Ks - $500Ks
Sunrise Village, Sayville, NY
Resale Only | 55+ age-restricted | Built 1985 - 1990 | 213 homes
Windcrest East
$600Ks
Windcrest East, Calverton, NY
Resale Only | 55+ age-restricted | Built 2004 - 2005 | 126 homes
Windmill Gate
$300Ks - $400Ks
Windmill Gate, Oakdale, NY
Resale Only | 55+ age-restricted | Built 1989 - 1991 | 110 homes
Read the Ultimate 55+ Rental Guide Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
Woodridge Strathmore Terr...
$400Ks
Woodridge Strathmore Terr..., Mount Sinai, NY
Resale Only | 55+ age-restricted | Built 1974 - 1985 | 226 homes
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Founders Village
$500Ks - $600Ks
Founders Village, Southold, NY
Resale Only | 55+ age-restricted | Built 1981 - 1985 | 92 homes
The Club at Melville
$500Ks
The Club at Melville, Melville, NY
Resale Only | 55+ age-restricted | Built 2015 - 2017 | 261 homes
The Seasons at Seaford
$700Ks
The Seasons at Seaford, Seaford, NY
Resale Only | 55+ age-restricted | Built 2015 - 2017 | 112 homes
4 rating (1 reviews) Vineyards at Blue Point
$800Ks
Vineyards at Blue Point, Blue Point, NY
Resale Only | 55+ age-restricted | Built 2016 - 2018 | 280 homes
Want to learn more about 55+ rental communities in Portland? 55places can help!
Questions? Call us: (860) 854-7490
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.
3.5 rating (2 reviews) Harvest Pointe
$800Ks - $3Ms
Harvest Pointe, Cutchogue, NY
New Construction | 55+ age-restricted | Built 2017 - present | 124 homes
Harbor View Estates
$400Ks - $600Ks
Harbor View Estates, Copiague, NY
New Construction | 55+ age-restricted | Built 2017 - 2018 | 40 homes
The Seasons at Elwood
$800Ks - $900Ks
The Seasons at Elwood, East Northport, NY
Resale Only | 55+ age-restricted | Built 2018 - 2020 | 256 homes
Jessup's Landing
$1Ms
Jessup's Landing, Quogue, NY
New and Resale | 55+ age-restricted | Built 2009 - 2016 | 31 homes
Hidden Harbor Estates
$500Ks - $600Ks
Hidden Harbor Estates, Copiague, NY
Resale Only | 55+ age-restricted | Built 2010 - 2015 | 38 homes
Want to learn more about 55+ communities in Portland? 55places can help!
Questions? Call us: (860) 854-7490
Read the Ultimate 55+ Rental Guide Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
Vineyards at Brookfield
$700Ks
Vineyards at Brookfield, Center Moriches, NY
New Construction | 55+ age-restricted | Built 2019 - present | 146 homes
The Vineyards at Mount Si...
$800Ks - $1Ms
The Vineyards at Mount Si..., Mount Sinai, NY
New Construction | 55+ age-restricted | Built 2020 - present | 91 homes
The Pines at Bohemia
$400Ks - $500Ks
The Pines at Bohemia, Bohemia, NY
New Construction | 55+ age-restricted | Built 2019 - present | 20 homes
The Polo Club at Islandia
$600Ks
The Polo Club at Islandia, Islandia, NY
New Construction | 55+ age-restricted | Built 2019 - present | 72 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.
Stratford Park
$900Ks
Stratford Park, Melville, NY
Resale Only | 55+ age-restricted | Built 2011 - 2013 | 36 homes
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Questions? Call us: (860) 854-7490
Applegate Estates
$500Ks - $400Ks
Applegate Estates, Southington, CT
New and Resale | 55+ age-restricted | Built 2010 - 2025 | 94 homes
The Summit at Bethel
$600Ks
The Summit at Bethel, Bethel, CT
Resale Only | 55+ age-restricted | Built 2010 - 2021 | 235 homes
Fieldstone Village
$500Ks - $800Ks
Fieldstone Village, Orange, CT
Resale Only | 55+ age-restricted | Built 2010 - 2018 | 142 homes
Want to learn more about 55+ communities in Portland? 55places can help!
Questions? Call us: (860) 854-7490
Pond Spring Village
$300Ks
Pond Spring Village, Beacon Falls, CT
New and Resale | 55+ age-restricted | Built 2005 - present | 92 homes
RiverWalk
$500Ks - $600Ks
RiverWalk, Branford, CT
New and Resale | 55+ age-restricted | Built 2007 - present | 60 homes
Oronoque Village 13 ALGONQUIN LN C, STRATFORD, CT, 06614, Stratford, CT 06614
$399,000

1 beds

|

2 baths

|

1,330 sq ft

|

Condo

13 ALGONQUIN LN C, STRATFORD, CT, 06614
Community: Oronoque Village
Greenwood Village 42 VILLAGE CIR, MANORVILLE, NY, 11949, Manorville, NY 11949
$99,000

2 beds

|

2 baths

|

960 sq ft

|

Condo

42 VILLAGE CIR, MANORVILLE, NY, 11949
Community: Greenwood Village
Harmony Place 20 FIDELITY DR # 10, RUTLAND, MA, 01543, Rutland, MA 01543
$498,000

2 beds

|

2 baths

|

1,582 sq ft

|

Condo

20 FIDELITY DR # 10, RUTLAND, MA, 01543
Community: Harmony Place
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...
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
Want to learn more about 55+ communities in Portland? 55places can help!
Questions? Call us: (860) 854-7490
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Questions? Call us: (860) 854-7490
Oronoque Village 315 NAVAJO LN A, STRATFORD, CT, 06614, Stratford, CT 06614
$531,500

2 beds

|

3 baths

|

1,590 sq ft

|

Condo

315 NAVAJO LN A, STRATFORD, CT, 06614
Community: Oronoque Village
Leisure Village 278 BERWICK CT UNIT B B, RIDGE, NY, 1196..., Ridge, NY 11961
$369,900

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...
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, ...
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.
Regency at Woodbridge 5 EDGEWOOD WAY # 25, WOODBRIDGE, CT, 065..., Woodbridge, CT 06525
$649,000

3 beds

|

3 baths

|

Condo

5 EDGEWOOD WAY # 25, WOODBRIDGE, CT, 065...
Read the Ultimate 55+ Rental Guide Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
Country Pointe Plainview 25102 ASPENWOOD DR, PLAINVIEW, NY, 11803, Plainview, NY 11803
$1,649,888

3 beds

|

2 baths

|

2,056 sq ft

|

Condo

25102 ASPENWOOD DR, PLAINVIEW, NY, 11803
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, RIDGE, NY, 11961, Ridge, NY 11961
$364,999

2 beds

|

1 baths

|

1,036 sq ft

|

Condo

418 WEYMOUTH CT B, RIDGE, NY, 11961
Community: Leisure Village
Want to learn more about 55+ communities in Portland? 55places can help!
Questions? Call us: (860) 854-7490
The Waterways at Moriches 554 MIRROR POND CT, MORICHES, NY, 11955, Moriches, NY 11955
$525,000

2 beds

|

2 baths

|

1,497 sq ft

|

Condo

554 MIRROR POND CT, MORICHES, NY, 11955
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
Want to learn more about 55+ rental communities in Portland? 55places can help!
Questions? Call us: (860) 854-7490
Oronoque Village 151 SOUTH TRL B, STRATFORD, CT, 06614, Stratford, CT 06614
$460,000

1 beds

|

3 baths

|

1,426 sq ft

|

Condo

151 SOUTH 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
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.
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
Stoneleigh Woods at Riverhead 23 GOOSE NECK LN, RIVERHEAD, NY, 11901, Riverhead, NY 11901
$585,000

2 beds

|

3 baths

|

1,631 sq ft

|

Condo

23 GOOSE NECK LN, RIVERHEAD, NY, 11901
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
Read the Ultimate 55+ Rental Guide Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
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
Want to learn more about 55+ communities in Portland? 55places can help!
Questions? Call us: (860) 854-7490
Harmony Place 212 FIDELITY DR 83, RUTLAND, MA, 01543, Rutland, MA 01543
$498,000

2 beds

|

2 baths

|

1,582 sq ft

|

Condo

212 FIDELITY DR 83, 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
Rivington 184 WARRINGTON ROUND # 184, DANBURY, CT,..., Danbury, CT 06810
$599,000

3 beds

|

3 baths

|

1,600 sq ft

|

Condo

184 WARRINGTON ROUND # 184, DANBURY, CT,...
Community: Rivington
Want to learn more about 55+ rental communities in Portland? 55places can help!
Questions? Call us: (860) 854-7490
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
Oronoque Village 195 BAYFIELD LN A, STRATFORD, CT, 06614, Stratford, CT 06614
$499,000

2 beds

|

3 baths

|

1,575 sq ft

|

Condo

195 BAYFIELD LN A, STRATFORD, CT, 06614
Community: Oronoque Village
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
Heritage Village 162 HERITAGE VLG D, SOUTHBURY, CT, 06488, Southbury, CT 06488
$235,000

2 beds

|

2 baths

|

1,076 sq ft

|

Condo

162 HERITAGE VLG D, SOUTHBURY, CT, 06488
Community: Heritage Village
Want to learn more about 55+ communities in Portland? 55places can help!
Questions? Call us: (860) 854-7490
Read the Ultimate 55+ Rental Guide Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
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
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
Stoneleigh Woods at Riverhead 5 NEWCASTLE CT, RIVERHEAD, NY, 11901, Riverhead, NY 11901
$635,000

2 beds

|

3 baths

|

1,942 sq ft

|

Condo

5 NEWCASTLE CT, RIVERHEAD, NY, 11901
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 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...
Want to learn more about 55+ rental communities in Portland? 55places can help!
Questions? Call us: (860) 854-7490
Village Estates 119 FRANCESCA WAY # 119, AMITYVILLE, NY,..., Amityville, NY 11701
$549,000

2 beds

|

1 baths

|

1,234 sq ft

|

Condo

119 FRANCESCA WAY # 119, AMITYVILLE, NY,...
Community: Village Estates
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
Leisure Village 274 BERWICK CT A, RIDGE, NY, 11961, Ridge, NY 11961
$349,999

2 beds

|

1 baths

|

836 sq ft

|

Condo

274 BERWICK CT A, RIDGE, NY, 11961
Community: Leisure Village
Want to learn more about 55+ communities in Portland? 55places can help!
Questions? Call us: (860) 854-7490
The Villages at Mount Sinai Park 4 OAKHURST CT, MOUNT SINAI, NY, 11766, Mount Sinai, NY 11766
$775,000

3 beds

|

3 baths

|

2,850 sq ft

|

House

4 OAKHURST CT, MOUNT SINAI, NY, 11766
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

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