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Portland, CT 55+ active adult communities & homes for sale
123 communities near Portland
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
$100ks
- $300ks
Leisure Village, Ridge, NY
Resale Only
|
55+ age-restricted
|
Built 1969 - 1986
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1,500 homes
$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
$200ks
- $400ks
Leisure Knoll, Ridge, NY
Resale Only
|
55+ age-restricted
|
Built 1972 - 1982
|
701 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
$300ks
- $600ks
The Waterways at Moriches, Moriches, NY
Resale Only
|
55+ age-restricted
|
Built 1985 - 1999
|
343 homes
$600ks
- $1Ms
The Greens at Half Hollow, Melville, NY
Resale Only
|
55+ age-restricted
|
Built 1994 - 2005
|
1,200 homes
$100ks
- $200ks
Spring Lake Village, Southington, CT
Resale Only
|
55+ age-restricted
|
Built 1970 - 2004
|
640 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)
![Encore Atlantic Shores]()
$500ks
- $800ks
Encore Atlantic Shores, Eastport, NY
Resale Only
|
55+ age-restricted
|
Built 2004 - 2011
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240 homes
$400ks
- $500ks
Harmony Place, Rutland, MA
New Construction
|
55+ age-restricted
|
Built 2023 - present
|
142 homes
$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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$300ks
- $900ks
Rivington, Danbury, CT
New and Resale
|
Age-targeted
|
Built 2006 - present
|
1,050 homes
$400ks
The Villas at Narraganset..., Lindenhurst, NY
Resale Only
|
55+ age-restricted
|
Built 2004 - 2005
|
138 homes
5 rating (1 reviews)
![Newtown Woods]()
$300ks
- $500ks
Newtown Woods, Newtown, CT
New and Resale
|
55+ age-restricted
|
Built 2011 - present
|
178 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
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.
$500ks
- $700ks
Regency at Woodbridge, Woodbridge, CT
New Construction
|
55+ age-restricted
|
Built 2023 - present
|
70 homes
5 rating (1 reviews)
![Westhampton Pines]()
$900ks
- $1Ms
Westhampton Pines, Westhampton, NY
Resale Only
|
55+ age-restricted
|
Built 2005 - 2013
|
189 homes
$500ks
- $600ks
Stone Ridge Estates, Dix Hills, NY
Resale Only
|
55+ age-restricted
|
Built 2004 - 2013
|
76 homes
$500ks
The Coves at Melville, Melville, NY
Resale Only
|
62+ age-restricted
|
Built 2004 - 2005
|
175 homes
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(860) 854-7490
$300ks
- $400ks
Leisure Glen, Ridge, NY
Resale Only
|
55+ age-restricted
|
Built 1985 - 2010
|
646 homes
$1Ms
Kensington Estates, Woodbury, NY
New Construction
|
55+ age-restricted
|
Built 2019 - 2021
|
80 homes
$300ks
- $400ks
South Pond Village, Bloomfield, CT
Resale Only
|
55+ age-restricted
|
Built 1999 - 2005
|
151 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
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.
$400ks
- $600ks
Fairview at Oxford Greens, Oxford, CT
New and Resale
|
55+ age-restricted
|
Built 2019 - present
|
125 homes
$300ks
- $400ks
The Manors at The Colony ..., Shirley, NY
New Construction
|
55+ age-restricted
|
Built 2013 - present
|
150 homes
$300ks
- $400ks
Bartlett Hill, Portland, CT
Resale Only
|
55+ age-restricted
|
Built 2005 - 2011
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82 homes
$300ks
- $400ks
Liberty at Newtown, Newtown, CT
Resale Only
|
55+ age-restricted
|
Built 2003 - 2007
|
96 homes
$300ks
- $400ks
Meadow Brook Estates, Oxford, CT
Resale Only
|
55+ age-restricted
|
Built 2003 - 2020
|
246 homes
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Questions? Call us:
(860) 854-7490
$700ks
The Seasons at East North..., East Northport, NY
New Construction
|
55+ age-restricted
|
Built 2023 - present
|
190 homes
$300ks
- $400ks
Brierly Pond Village, Millbury, MA
Resale Only
|
55+ age-restricted
|
Built 2003 - 2013
|
199 homes
$200ks
- $300ks
Woodridge Strathmore Terr..., Mount Sinai, NY
Resale Only
|
55+ age-restricted
|
Built 1974 - 1985
|
226 homes
3.5 rating (2 reviews)
![Foxwood Village]()
$200ks
- $400ks
Foxwood Village, Calverton, NY
Resale Only
|
55+ age-restricted
|
Built 1986 - 2007
|
294 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.
$300ks
- $400ks
Regency at Prospect, Prospect, CT
Resale Only
|
55+ age-restricted
|
Built 2006 - 2020
|
379 homes
$300ks
- $400ks
Eagles Walk at East Quogu..., East Quogue, NY
Resale Only
|
55+ age-restricted
|
Built 2004 - 2014
|
67 homes
$600ks
- $700ks
Snug Harbor, Amityville, NY
Resale Only
|
55+ age-restricted
|
Built 1970 - 1974
|
176 homes
$700ks
- $1Ms
Country Pointe Plainview, Plainview, NY
New Construction
|
55+ age-restricted
|
Built 2017 - present
|
660 homes
Want to learn more about 55+ communities in Portland?
55places can help!
Questions? Call us:
(860) 854-7490
$300ks
- $400ks
Village Estates, Amityville, NY
Resale Only
|
55+ age-restricted
|
Built 2006 - 2008
|
138 homes
New
Oronoque Village
![483 COMMANCHE LN B, STRATFORD, CT, 06614, Stratford, CT 06614]()
1 beds
|2 baths
|1,454 sq ft
|Condo
483 COMMANCHE LN B, STRATFORD, CT, 06614
Community: Oronoque Village
MLS 24154522 • Coldwell Banker Realty, Christine ...
New
The Manors at The Colony Preserve
![21 GREENTREE CT, SHIRLEY, NY, 11967, Shirley, NY 11967]()
2 beds
|2 baths
|1,557 sq ft
|Condo
21 GREENTREE CT, SHIRLEY, NY, 11967
Community: The Manors at The Colony Preserve
MLS 963693 • Coldwell Banker M&D Good Life, There...
New
Encore Atlantic Shores
![135 CHOPIN PL, EASTPORT, NY, 11941, Eastport, NY 11941]()
2 beds
|2 baths
|2,233 sq ft
|Condo
135 CHOPIN PL, EASTPORT, NY, 11941
Community: Encore Atlantic Shores
MLS 961941 • Corcoran, Merle Buff
New
Heritage Village
![411 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,398 sq ft
|Condo
411 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24155104 • Berkshire Hathaway NE Prop., Bonni...
New
Sunrise Village
![71 REVERE DR, SAYVILLE, NY, 11782, Sayville, NY 11782]()
MLS 963805 • Signature Premier Properties, Debora...
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New
Spring Lake Village
![41 COACH DR # 41, SOUTHINGTON, CT, 06489, Southington, CT 06489]()
2 beds
|2 baths
|1,232 sq ft
|Condo
41 COACH DR # 41, SOUTHINGTON, CT, 06489
Community: Spring Lake Village
MLS 24154460 • Calcagni Real Estate, Donna Pelleg...
New
Rivington
![1025 COUNTRY VIEW RD # 1025, DANBURY, CT..., Danbury, CT 06810]()
2 beds
|2 baths
|1,292 sq ft
|Condo
1025 COUNTRY VIEW RD # 1025, DANBURY, CT...
Community: Rivington
MLS 24152848 • William Raveis Real Estate, SRIVID...
New
Heritage Village
![865 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,398 sq ft
|Condo
865 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24155103 • Showcase Realty, Inc., Gregory Bal...
New
Regency at Prospect
![50 LILAC LN # 50, PROSPECT, CT, 06712, Prospect, CT 06712]()
2 beds
|2 baths
|1,503 sq ft
|Condo
50 LILAC LN # 50, PROSPECT, CT, 06712
Community: Regency at Prospect
MLS 24154825 • Showcase Realty, Inc., Scott Marti...
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
Leisure Knoll
![498 CRANSTON LN, RIDGE, NY, 11961, Ridge, NY 11961]()
MLS 963436 • Coldwell Banker American Homes, Mary...
New
Fairfield at St. James
![1205 GOTHAM DR, SAINT JAMES, NY, 11780, Saint James, NY 11780]()
1 beds
|2 baths
|750 sq ft
|House
1205 GOTHAM DR, SAINT JAMES, NY, 11780
Community: Fairfield at St. James
MLS 963050 • Realty Connect USA LLC, Annmarie Rig...
New
Heritage Village
![1041 HERITAGE VLG A, SOUTHBURY, CT, 0648..., Southbury, CT 06488]()
2 beds
|2 baths
|1,044 sq ft
|Condo
1041 HERITAGE VLG A, SOUTHBURY, CT, 0648...
Community: Heritage Village
MLS 24154431 • Carey & Guarrera Real Estate, Alet...
Encore at Lake Grove
![51 SYMPHONY DR, LAKE GROVE, NY, 11755, Lake Grove, NY 11755]()
2 beds
|3 baths
|1,409 sq ft
|Condo
51 SYMPHONY DR, LAKE GROVE, NY, 11755
Community: Encore at Lake Grove
MLS 962663 • Signature Premier Properties, Karen ...
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The Seasons at Seaford
![28 SPRING DR, SEAFORD, NY, 11783, Seaford, NY 11783]()
2 beds
|2 baths
|1,034 sq ft
|Condo
28 SPRING DR, SEAFORD, NY, 11783
Community: The Seasons at Seaford
MLS 952881 • Douglas Elliman Real Estate, Norma Q...
Adams Farm
![40 ADAMS FARM RD 40, SHREWSBURY, MA, 015..., Shrewsbury, MA 01545]()
2 beds
|3 baths
|2,757 sq ft
|Condo
40 ADAMS FARM RD 40, SHREWSBURY, MA, 015...
Community: Adams Farm
MLS 73477916 • Mathieu Newton Sotheby's Internati...
Rivington
![13 MERCY ST 13, DANBURY, CT, 06810, Danbury, CT 06810]()
MLS 24153888 • William Pitt Sotheby's Int'l, Care...
Leisure Village
![306 TORQUAY CT E, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961]()
1 beds
|1 baths
|684 sq ft
|Condo
306 TORQUAY CT E, BROOKHAVEN, NY, 11961
Community: Leisure Village
MLS 960743 • Leisure Living Realty Inc, Paulina R...
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 Village at Orchard Meadows
![47 ORCHARD MEADOW DR 47, SHREWSBURY, MA,..., Shrewsbury, MA 01545]()
2 beds
|2 baths
|1,370 sq ft
|Condo
47 ORCHARD MEADOW DR 47, SHREWSBURY, MA,...
Community: The Village at Orchard Meadows
MLS 73477228 • RE/MAX Partners, Kris Koliss
Heritage Village
![972 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,432 sq ft
|Condo
972 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24154574 • Berkshire Hathaway NE Prop., Bonni...
Spring Lake Village
![6 LAKEVIEW DR 6, SOUTHINGTON, CT, 06489, Southington, CT 06489]()
3 beds
|3 baths
|1,471 sq ft
|Condo
6 LAKEVIEW DR 6, SOUTHINGTON, CT, 06489
Community: Spring Lake Village
MLS 24154583 • eXp Realty, Eric Christmas
Woodridge Strathmore Terrace
![35 CHIPPENDALE DR, MOUNT SINAI, NY, 1176..., Mount Sinai, NY 11766]()
2 beds
|2 baths
|1,240 sq ft
|Condo
35 CHIPPENDALE DR, MOUNT SINAI, NY, 1176...
Community: Woodridge Strathmore Terrace
MLS 959098 • Exit Realty Achieve, Laura Kraker E-...
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Glenwood Village
![181 GLYNWOOD 181, RIVERHEAD, NY, 11901, Riverhead, NY 11901]()
2 beds
|1 baths
|1,100 sq ft
|Manufactured On Land
181 GLYNWOOD 181, RIVERHEAD, NY, 11901
Community: Glenwood Village
MLS 958982 • Coldwell Banker M&D Good Life, Lynn ...
The Villas at Narragansett
![604 NARRAGANSETT VILLAS DR, BABYLON, NY,..., Babylon, NY 11757]()
2 beds
|2 baths
|1,227 sq ft
|Condo
604 NARRAGANSETT VILLAS DR, BABYLON, NY,...
Community: The Villas at Narragansett
MLS 961765 • Signature Premier Properties, Franci...
Encore Atlantic Shores
![179 MELODY CT, EASTPORT, NY, 11941, Eastport, NY 11941]()
2 beds
|3 baths
|2,900 sq ft
|Condo
179 MELODY CT, EASTPORT, NY, 11941
Community: Encore Atlantic Shores
MLS 959599 • Douglas Elliman Real Estate, Enzo Mo...
Oronoque Village
![488 COMMANCHE LN A, STRATFORD, CT, 06614, Stratford, CT 06614]()
1 beds
|3 baths
|2,199 sq ft
|Condo
488 COMMANCHE LN A, STRATFORD, CT, 06614
Community: Oronoque Village
MLS 24154316 • Serhant Connecticut, LLC, Carmen D...
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
![170 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,432 sq ft
|Condo
170 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24152831 • Ascend Realty LLC, Michael Monteir...
Park Glen
![4 BLOSSOM CT, NEW MILFORD, CT, 06776, New Milford, CT 06776]()
MLS 24153690 • William Raveis Real Estate, Pat Ca...
Leisure Knoll
![206 BELFAST LN, RIDGE, NY, 11961, Ridge, NY 11961]()
MLS 960634 • Leisure Living Realty Inc, Paulina R...
Glenwood Village
![1661 OLD COUNTRY RD 275, RIVERHEAD, NY, ..., Riverhead, NY 11901]()
2 beds
|2 baths
|1,050 sq ft
|Mobile Home
1661 OLD COUNTRY RD 275, RIVERHEAD, NY, ...
Community: Glenwood Village
MLS 960267 • Old Orchard Estates R E Inc, Matthew...
Leisure Glen
![530 LEISURE DR, RIDGE, NY, 11961, Ridge, NY 11961]()
MLS 957040 • Signature Premier Properties, Mildre...
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Questions? Call us:
(860) 854-7490
Brierly Pond Village
![100 HORNE WAY # 100, MILLBURY, MA, 01527, Millbury, MA 01527]()
2 beds
|3 baths
|2,021 sq ft
|Condo
100 HORNE WAY # 100, MILLBURY, MA, 01527
Community: Brierly Pond Village
MLS 73476625 • Century 21 XSELL REALTY, Lora Sava...
Spring Lake Village
![40 HICKORY HL # 40, SOUTHINGTON, CT, 064..., Southington, CT 06489]()
2 beds
|2 baths
|1,211 sq ft
|Condo
40 HICKORY HL # 40, SOUTHINGTON, CT, 064...
Community: Spring Lake Village
MLS 24153678 • Realty 3 CT, Shelly Meister Zamudi...
Woodridge Strathmore Terrace
![27 HEARTHSIDE DR, MOUNT SINAI, NY, 11766, Mount Sinai, NY 11766]()
1 beds
|1 baths
|844 sq ft
|Condo
27 HEARTHSIDE DR, MOUNT SINAI, NY, 11766
Community: Woodridge Strathmore Terrace
MLS 960957 • BERKSHIRE HATHAWAY, Michelle Madtes
Leisure Village
![418 WEYMOUTH CT C, RIDGE, NY, 11961, Ridge, NY 11961]()
2 beds
|1 baths
|1,036 sq ft
|Condo
418 WEYMOUTH CT C, RIDGE, NY, 11961
Community: Leisure Village
MLS 960927 • Signature Premier Properties, Adela ...
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
![575 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
3 beds
|2 baths
|1,716 sq ft
|Condo
575 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24152837 • Drakeley Real Estate, Inc., Shelle...
Heritage Village
![701 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,398 sq ft
|Condo
701 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24153612 • Century 21 Limitless, Kyle Seyboth
Leisure Village
![430 FALMOUTH CT A, RIDGE, NY, 11961, Ridge, NY 11961]()
2 beds
|2 baths
|1,200 sq ft
|House
430 FALMOUTH CT A, RIDGE, NY, 11961
Community: Leisure Village
MLS 960353 • OverSouth LLC, Sean Manning
Leisure Village
![258 NEWCASTLE CT F, RIDGE, NY, 11961, Ridge, NY 11961]()
2 beds
|1 baths
|875 sq ft
|Condo
258 NEWCASTLE CT F, RIDGE, NY, 11961
Community: Leisure Village
MLS 958463 • Leisure Living Realty Inc, Paulina R...
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Oak Meadow Estates
![65 OAK MEADOW LN # 65, HARWINTON, CT, 06..., Harwinton, CT 06791]()
2 beds
|4 baths
|2,164 sq ft
|Condo
65 OAK MEADOW LN # 65, HARWINTON, CT, 06...
Community: Oak Meadow Estates
MLS 24153507 • Northwest CT Realty, Leslie Tapia-...
The Greens at Half Hollow
![843 MADEIRA BLVD, HUNTINGTON, NY, 11747, Huntington, NY 11747]()
2 beds
|2 baths
|1,150 sq ft
|Condo
843 MADEIRA BLVD, HUNTINGTON, NY, 11747
Community: The Greens at Half Hollow
MLS 957971 • Compass Greater NY LLC, Andrea L. Co...
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?
192
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© 2026 REIN. REIN's listings Data and information is protected under federal copyright laws. Federal law prohibits, among other acts, the unauthorized copying or alteration of, or preparation of derivative works from, all or any part of copyrighted materials, including certain compilations of Data and information. COPYRIGHT VIOLATORS MAY BE SUBJECT TO SEVERE FINES AND PENALTIES UNDER FEDERAL LAW.
REIN updates its listings on a daily basis. Data last updated: Feb 24, 2026.
This application does not include information on all of the properties available for sale at this time.
