Call us at (860) 854-7490 to learn more about active adult communities in Portland
Portland, CT 55+ active adult communities & homes for sale
123 communities near Portland
185 homes near Portland
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<$100k
The Atrium of Portland, Portland, CT
Resale Only
|
55+ age-restricted
|
Built 2004 - 2004
|
56 homes
3.6 rating (7 reviews)
![Heritage Village]()
$200Ks
- $500Ks
Heritage Village, Southbury, CT
Resale Only
|
55+ age-restricted
|
Built 1967 - 2005
|
2,580 homes
$200Ks
- $400Ks
Leisure Village, Ridge, NY
Resale Only
|
55+ age-restricted
|
Built 1969 - 1986
|
1,500 homes
$600Ks
- $1Ms
The Greens at Half Hollow, Melville, NY
Resale Only
|
55+ age-restricted
|
Built 1994 - 2005
|
1,200 homes
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$400Ks
- $600Ks
Rivington, Danbury, CT
New and Resale
|
Age-targeted
|
Built 2006 - present
|
1,050 homes
$300Ks
- $600Ks
Oronoque Village, Stratford, CT
Resale Only
|
55+ age-restricted
|
Built 1971 - 1977
|
929 homes
$500Ks
- $700Ks
The Village at Oxford Gre..., Oxford, CT
New and Resale
|
55+ age-restricted
|
Built 2004 - present
|
835 homes
Download the Ultimate 55+ Homebuying Guide
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$1Ms
Country Pointe Plainview, Plainview, NY
New Construction
|
55+ age-restricted
|
Built 2017 - present
|
660 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.
5 rating (2 reviews)
![Fairfield at St. James]()
$400Ks
- $500Ks
Fairfield at St. James, St. James, NY
Resale Only
|
55+ age-restricted
|
Built 1972 - 1989
|
653 homes
$400Ks
- $600Ks
Leisure Glen, Ridge, NY
Resale Only
|
55+ age-restricted
|
Built 1985 - 2010
|
646 homes
$200Ks
Spring Lake Village, Southington, CT
Resale Only
|
55+ age-restricted
|
Built 1970 - 2004
|
640 homes
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4 rating (8 reviews)
![Glenwood Village]()
$100Ks
- $200Ks
Glenwood Village, Riverhead, NY
New and Resale
|
55+ age-restricted
|
Built 1959 - present
|
588 homes
3.7 rating (3 reviews)
![Greenwood Village]()
$100Ks
- $200Ks
Greenwood Village, Manorville, NY
Resale Only
|
55+ age-restricted
|
Built 1980 - 2000
|
512 homes
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$400Ks
- $500Ks
Regency at Prospect, Prospect, CT
Resale Only
|
55+ age-restricted
|
Built 2006 - 2020
|
379 homes
$400Ks
- $500Ks
The Waterways at Moriches, Moriches, NY
Resale Only
|
55+ age-restricted
|
Built 1985 - 1999
|
343 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.
3.5 rating (2 reviews)
![Foxwood Village]()
$400Ks
- $500Ks
Foxwood Village, Calverton, NY
Resale Only
|
55+ age-restricted
|
Built 1986 - 2007
|
294 homes
1 rating (1 reviews)
![Plymouth Estates at Mount...]()
$500Ks
Plymouth Estates at Mount..., Mount Sinai, NY
Resale Only
|
55+ age-restricted
|
Built 2006 - 2013
|
285 homes
4.6 rating (9 reviews)
![Meadowbrook Pointe Links ...]()
$300Ks
- $700Ks
Meadowbrook Pointe Links ..., Medford, NY
New and Resale
|
55+ age-restricted
|
Built 2010 - present
|
280 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.
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
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$500Ks
The Club at Melville, Melville, NY
Resale Only
|
55+ age-restricted
|
Built 2015 - 2017
|
261 homes
$800Ks
- $900Ks
The Seasons at Elwood, East Northport, NY
Resale Only
|
55+ age-restricted
|
Built 2018 - 2020
|
256 homes
$500Ks
Meadow Brook Estates, Oxford, CT
Resale Only
|
55+ age-restricted
|
Built 2003 - 2020
|
246 homes
5 rating (1 reviews)
![Encore Atlantic Shores]()
$700Ks
- $800Ks
Encore Atlantic Shores, Eastport, NY
Resale Only
|
55+ age-restricted
|
Built 2004 - 2011
|
240 homes
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Download the Ultimate 55+ Homebuying Guide
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$600Ks
The Summit at Bethel, Bethel, CT
Resale Only
|
55+ age-restricted
|
Built 2010 - 2021
|
235 homes
4.9 rating (14 reviews)
![Chatfield Farms]()
$500Ks
- $600Ks
Chatfield Farms, Beacon Falls, CT
New Construction
|
55+ age-restricted
|
Built 2014 - present
|
231 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
$400Ks
Woodridge Strathmore Terr..., Mount Sinai, NY
Resale Only
|
55+ age-restricted
|
Built 1974 - 1985
|
226 homes
5 rating (1 reviews)
![Sunrise Village]()
$400Ks
- $500Ks
Sunrise Village, Sayville, NY
Resale Only
|
55+ age-restricted
|
Built 1985 - 1990
|
213 homes
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$400Ks
Brierly Pond Village, Millbury, MA
Resale Only
|
55+ age-restricted
|
Built 2003 - 2013
|
199 homes
$400Ks
Country Village Estates, Coram, NY
Resale Only
|
55+ age-restricted
|
Built 1993 - 2001
|
195 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
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.
$700Ks
The Seasons at East North..., East Northport, NY
New Construction
|
55+ age-restricted
|
Built 2023 - present
|
190 homes
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(860) 854-7490
5 rating (1 reviews)
![Westhampton Pines]()
$900Ks
- $1Ms
Westhampton Pines, Westhampton, NY
Resale Only
|
55+ age-restricted
|
Built 2005 - 2013
|
189 homes
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
$600Ks
- $700Ks
The Powder Forest Homes, Simsbury, CT
Resale Only
|
55+ age-restricted
|
Built 2006 - 2016
|
182 homes
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5 rating (1 reviews)
![Newtown Woods]()
$400Ks
- $500Ks
Newtown Woods, Newtown, CT
New and Resale
|
55+ age-restricted
|
Built 2011 - present
|
178 homes
Heritage Village
![60 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,365 sq ft
|Condo
60 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24137022 • William Raveis Real Estate, Ruth Z...
Heritage Village
![623 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
3 beds
|2 baths
|1,716 sq ft
|Condo
623 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24125367 • Showcase Realty, Inc., Jeff Colt
Heritage Village
![568A HERITAGE VLG, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,432 sq ft
|Condo
568A HERITAGE VLG, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24129707 • Showcase Realty, Inc., Jeff Colt
New
Regency at Woodbridge
![1 WHISPER RIDGE WAY # 51, WOODBRIDGE, CT..., Woodbridge, CT 06525]()
3 beds
|3 baths
|2,180 sq ft
|Condo
1 WHISPER RIDGE WAY # 51, WOODBRIDGE, CT...
Community: Regency at Woodbridge
MLS 24145819 • Thomas Jacovino, Kathy Childs
Regency at Woodbridge
![3 WHISPER RIDGE WAY # 50, WOODBRIDGE, CT..., Woodbridge, CT 06525]()
3 beds
|3 baths
|Condo
3 WHISPER RIDGE WAY # 50, WOODBRIDGE, CT...
Community: Regency at Woodbridge
MLS 24142176 • Thomas Jacovino, Kathy Childs
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New
Regency at Woodbridge
![8 WHISPER RIDGE WAY # 43, WOODBRIDGE, CT..., Woodbridge, CT 06525]()
3 beds
|3 baths
|Condo
8 WHISPER RIDGE WAY # 43, WOODBRIDGE, CT...
Community: Regency at Woodbridge
MLS 24145805 • Thomas Jacovino, Kathy Childs
Heritage Village
![331 HERITAGE VLG E, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,365 sq ft
|Condo
331 HERITAGE VLG E, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24143592 • Coldwell Banker Realty, Pamela Dos...
New
Heritage Village
![917 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
1 beds
|1 baths
|928 sq ft
|Condo
917 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24145119 • Joseph Bette REALTORS Inc, Cynthia...
Newbury Village
![332 STILL WATER CIR # 332, BROOKFIELD, C..., Brookfield, CT 06804]()
2 beds
|2 baths
|1,466 sq ft
|Condo
332 STILL WATER CIR # 332, BROOKFIELD, C...
Community: Newbury Village
MLS 24142328 • William Pitt Sotheby's Int'l, Bett...
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
![289 AGAWAM DR B, STRATFORD, CT, 06614, Stratford, CT 06614]()
1 beds
|3 baths
|1,620 sq ft
|Condo
289 AGAWAM DR B, STRATFORD, CT, 06614
Community: Oronoque Village
MLS 24138784 • Oronoque Real Estate, Monica Dalto...
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.
Oronoque Village
![766 NYACK LN B, STRATFORD, CT, 06614, Stratford, CT 06614]()
1 beds
|3 baths
|1,438 sq ft
|Condo
766 NYACK LN B, STRATFORD, CT, 06614
Community: Oronoque Village
MLS 24143831 • Coldwell Banker Realty, Christine ...
Regency at Prospect
![5 LILAC LN # 5, PROSPECT, CT, 06712, Prospect, CT 06712]()
2 beds
|3 baths
|1,503 sq ft
|Condo
5 LILAC LN # 5, PROSPECT, CT, 06712
Community: Regency at Prospect
MLS 24143185 • Century 21 Scala Group, Verzem Pov...
Oronoque Village
![183 APACHE LN A, STRATFORD, CT, 06614, Stratford, CT 06614]()
2 beds
|3 baths
|1,426 sq ft
|Condo
183 APACHE LN A, STRATFORD, CT, 06614
Community: Oronoque Village
MLS 24143262 • Preston Gray Real Estate, Tina Gam...
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Oronoque Village
![87 CREEK LN A, STRATFORD, CT, 06614, Stratford, CT 06614]()
1 beds
|2 baths
|1,454 sq ft
|Condo
87 CREEK LN A, STRATFORD, CT, 06614
Community: Oronoque Village
MLS 24140020 • Oronoque Real Estate, Monica Dalto...
Regency at Woodbridge
![12 WHISPER RIDGE WAY # 45, WOODBRIDGE, C..., Woodbridge, CT 06525]()
3 beds
|3 baths
|Condo
12 WHISPER RIDGE WAY # 45, WOODBRIDGE, C...
Community: Regency at Woodbridge
MLS 24136328 • Thomas Jacovino, Kathy Childs
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Oronoque Village
![383 SEQUOIA LN A, STRATFORD, CT, 06614, Stratford, CT 06614]()
1 beds
|3 baths
|1,360 sq ft
|Condo
383 SEQUOIA LN A, STRATFORD, CT, 06614
Community: Oronoque Village
MLS 24140690 • Coldwell Banker Realty, Mary Kelle...
Bartlett Hill
![9 PEAR ORCHARD RD # 9, PORTLAND, CT, 064..., Portland, CT 06480]()
MLS 24144542 • William Pitt Sotheby's Internation...
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.
Spring Lake Village
![85 CLEARVIEW CT # 85, SOUTHINGTON, CT, 0..., Southington, CT 06489]()
1 beds
|2 baths
|1,028 sq ft
|Condo
85 CLEARVIEW CT # 85, SOUTHINGTON, CT, 0...
Community: Spring Lake Village
MLS 24138605 • Century 21 AllPoints Realty, Jill ...
Heritage Village
![902 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,398 sq ft
|Condo
902 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24126334 • Joseph Bette REALTORS Inc, Justin ...
Oronoque Village
![511 OPA LN B, STRATFORD, CT, 06614, Stratford, CT 06614]()
2 beds
|2 baths
|1,454 sq ft
|Condo
511 OPA LN B, STRATFORD, CT, 06614
Community: Oronoque Village
MLS 24144925 • William Raveis Real Estate, Luke P...
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.
Oak Meadow Estates
![21 OAK MEADOW LN # 21, HARWINTON, CT, 06..., Harwinton, CT 06791]()
2 beds
|3 baths
|2,164 sq ft
|Condo
21 OAK MEADOW LN # 21, HARWINTON, CT, 06...
Community: Oak Meadow Estates
MLS 24142504 • William Pitt Sotheby's Int'l, Cath...
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Long Hill Village
![5 CIDER MILL LN, TRUMBULL, CT, 06611, Trumbull, CT 06611]()
2 beds
|2 baths
|1,370 sq ft
|Condo
5 CIDER MILL LN, TRUMBULL, CT, 06611
Community: Long Hill Village
MLS 24144185 • Higgins Group Real Estate, Fredda ...
Heritage Village
![191 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
3 beds
|2 baths
|1,716 sq ft
|Condo
191 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24122871 • Joseph Bette REALTORS Inc, Justin ...
The Summit at Bethel
![121 GREAT HILL DR # 121, BETHEL, CT, 068..., Bethel, CT 06801]()
3 beds
|3 baths
|2,652 sq ft
121 GREAT HILL DR # 121, BETHEL, CT, 068...
Community: The Summit at Bethel
MLS 24126832 • Warren Mitchell, Warren Mitchell
Oronoque Village
![522 IROQUOIS LN B, STRATFORD, CT, 06614, Stratford, CT 06614]()
3 beds
|3 baths
|1,426 sq ft
|Condo
522 IROQUOIS LN B, STRATFORD, CT, 06614
Community: Oronoque Village
MLS 24141511 • Fairfield County Real Estate, Terr...
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Download the Ultimate 55+ Homebuying Guide
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Heritage Village
![73 HERITAGE VLG D, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,044 sq ft
|Condo
73 HERITAGE VLG D, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24135925 • Berkshire Hathaway NE Prop., Maria...
Baldwin Station
![7 FIRE THORN LN # 7, MILFORD, CT, 06461, Milford, CT 06461]()
2 beds
|3 baths
|2,331 sq ft
|Condo
7 FIRE THORN LN # 7, MILFORD, CT, 06461
Community: Baldwin Station
MLS 24145318 • Coldwell Banker Realty, James Mont...
Oronoque Village
![736 QUINNIPIAC LN B, STRATFORD, CT, 0661..., Stratford, CT 06614]()
1 beds
|3 baths
|1,426 sq ft
|Condo
736 QUINNIPIAC LN B, STRATFORD, CT, 0661...
Community: Oronoque Village
MLS 24127108 • Coldwell Banker Realty, Larry Vecc...
Spring Lake Village
![889 GLACIER WAY # 889, SOUTHINGTON, CT, ..., Southington, CT 06489]()
3 beds
|2 baths
|1,923 sq ft
|Condo
889 GLACIER WAY # 889, SOUTHINGTON, CT, ...
Community: Spring Lake Village
MLS 24144794 • Putnam Agency Real Estate LLC, Reb...
Heritage Village
![123 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,398 sq ft
|Condo
123 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24145278 • Independent Realty Group, Tammi Li...
Want to learn more about 55+ communities in Portland?
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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.
Gloria Commons
![10 LUCIUS CT # 10, MILFORD, CT, 06461, Milford, CT 06461]()
2 beds
|3 baths
|2,061 sq ft
|Condo
10 LUCIUS CT # 10, MILFORD, CT, 06461
Community: Gloria Commons
MLS 24144529 • Preston Gray Real Estate, Katie Da...
Oronoque Village
![151 SOUTH TRL A, STRATFORD, CT, 06614, Stratford, CT 06614]()
2 beds
|2 baths
|1,426 sq ft
|Condo
151 SOUTH TRL A, STRATFORD, CT, 06614
Community: Oronoque Village
MLS 24144658 • Preston Gray Real Estate, Katie Da...
Oronoque Village
![488 COMMANCHE LN A, STRATFORD, CT, 06614, Stratford, CT 06614]()
2 beds
|3 baths
|1,438 sq ft
|Condo
488 COMMANCHE LN A, STRATFORD, CT, 06614
Community: Oronoque Village
MLS 24134368 • Higgins Group Real Estate, Carmen ...
Heritage Village
![876 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,398 sq ft
|Condo
876 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24139573 • William Raveis Real Estate, Ruth Z...
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
![701 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
3 beds
|2 baths
|1,716 sq ft
|Condo
701 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24137961 • Coldwell Banker Realty, Claudia Fo...
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Oronoque Village
![516 OPA LN A, STRATFORD, CT, 06614, Stratford, CT 06614]()
2 beds
|2 baths
|1,426 sq ft
|Condo
516 OPA LN A, STRATFORD, CT, 06614
Community: Oronoque Village
MLS 24139775 • Oronoque Real Estate, Monica Dalto...
Heritage Village
![132 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,432 sq ft
|Condo
132 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24118807 • William Raveis Real Estate, Ron Ne...
Spring Lake Village
![373 LAKEVIEW DR # 373, SOUTHINGTON, CT, ..., Southington, CT 06489]()
2 beds
|2 baths
|1,188 sq ft
|Condo
373 LAKEVIEW DR # 373, SOUTHINGTON, CT, ...
Community: Spring Lake Village
MLS 24138533 • Stacy Blake Realty LLC, Linda Faga...
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Oronoque Village
![195 BAYFIELD LN A, STRATFORD, CT, 06614, Stratford, CT 06614]()
1 beds
|3 baths
|1,575 sq ft
|Condo
195 BAYFIELD LN A, STRATFORD, CT, 06614
Community: Oronoque Village
MLS 24128861 • Property Choices Real Estate, Paul...
Heritage Village
![644 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
3 beds
|2 baths
|1,716 sq ft
|Condo
644 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24125882 • Berkshire Hathaway NE Prop., Miche...
Frequently Asked Questions
In Portland, there are no large communities, no medium communities, and 2 small communities with less than 500 homes.
The smallest 55+ communities in Portland has 56 homes, the largest has 82 homes, and the average communities consists of 69 homes.
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.
Want more information about active adult communities around Portland?
Want to learn more about 55+ communities in Portland?
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REIN updates its listings on a daily basis. Data last updated: Dec 25, 2025.
This application does not include information on all of the properties available for sale at this time.
