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Portland, CT 55+ active adult communities & homes for sale
123 communities near Portland
260 homes near Portland
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![Bartlett Hill]()
$500Ks
- $500Ks
Bartlett Hill, Portland, CT
Resale Only
|
55+ age-restricted
|
Built 2005 - 2011
|
82 homes
No reviews yet
![The Atrium of Portland]()
<$100k
- $100Ks
The Atrium of Portland, Portland, CT
Resale Only
|
55+ age-restricted
|
Built 2004 - 2004
|
56 homes
3.6 rating (7 reviews)
![Heritage Village]()
$100Ks
- $500Ks
Heritage Village, Southbury, CT
Resale Only
|
55+ age-restricted
|
Built 1967 - 2005
|
2,580 homes
No reviews yet
![Leisure Village]()
$200Ks
- $400Ks
Leisure Village, Ridge, NY
Resale Only
|
55+ age-restricted
|
Built 1969 - 1986
|
1,500 homes
No reviews yet
![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
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No reviews yet
![Rivington]()
$400Ks
- $500Ks
Rivington, Danbury, CT
New and Resale
|
Age-targeted
|
Built 2006 - present
|
1,050 homes
No reviews yet
![Oronoque Village]()
$300Ks
- $600Ks
Oronoque Village, Stratford, CT
Resale Only
|
55+ age-restricted
|
Built 1971 - 1977
|
929 homes
No reviews yet
![The Village at Oxford Gre...]()
$500Ks
- $700Ks
The Village at Oxford Gre..., Oxford, CT
New and Resale
|
55+ age-restricted
|
Built 2004 - present
|
835 homes
No reviews yet
![Leisure Knoll]()
$300Ks
- $500Ks
Leisure Knoll, Ridge, NY
Resale Only
|
55+ age-restricted
|
Built 1972 - 1982
|
701 homes
No reviews yet
![Country Pointe Plainview]()
$1Ms
- $1Ms
Country Pointe Plainview, Plainview, NY
New Construction
|
55+ age-restricted
|
Built 2017 - present
|
660 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 (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
No reviews yet
![Leisure Glen]()
$400Ks
- $400Ks
Leisure Glen, Ridge, NY
Resale Only
|
55+ age-restricted
|
Built 1985 - 2010
|
646 homes
No reviews yet
![Spring Lake Village]()
$200Ks
- $200Ks
Spring Lake Village, Southington, CT
Resale Only
|
55+ age-restricted
|
Built 1970 - 2004
|
640 homes
4 rating (8 reviews)
![Glenwood Village]()
$100Ks
- $400Ks
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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No reviews yet
![Regency at Prospect]()
$300Ks
- $500Ks
Regency at Prospect, Prospect, CT
Resale Only
|
55+ age-restricted
|
Built 2006 - 2020
|
379 homes
No reviews yet
![The Waterways at Moriches]()
$400Ks
- $700Ks
The Waterways at Moriches, Moriches, NY
Resale Only
|
55+ age-restricted
|
Built 1985 - 1999
|
343 homes
3.5 rating (2 reviews)
![Foxwood Village]()
$300Ks
- $400Ks
Foxwood Village, Calverton, NY
Resale Only
|
55+ age-restricted
|
Built 1986 - 2007
|
294 homes
1 rating (1 reviews)
![Plymouth Estates at Mount...]()
$500Ks
- $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
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.
4 rating (1 reviews)
![Vineyards at Blue Point]()
$800Ks
- $800Ks
Vineyards at Blue Point, Blue Point, NY
Resale Only
|
55+ age-restricted
|
Built 2016 - 2018
|
280 homes
No reviews yet
![The Club at Melville]()
$500Ks
- $500Ks
The Club at Melville, Melville, NY
Resale Only
|
55+ age-restricted
|
Built 2015 - 2017
|
261 homes
No reviews yet
![The Seasons at Elwood]()
$800Ks
- $900Ks
The Seasons at Elwood, East Northport, NY
Resale Only
|
55+ age-restricted
|
Built 2018 - 2020
|
256 homes
No reviews yet
![Meadow Brook Estates]()
$500Ks
- $500Ks
Meadow Brook Estates, Oxford, CT
Resale Only
|
55+ age-restricted
|
Built 2003 - 2020
|
246 homes
5 rating (1 reviews)
![Encore Atlantic Shores]()
$600Ks
- $800Ks
Encore Atlantic Shores, Eastport, NY
Resale Only
|
55+ age-restricted
|
Built 2004 - 2011
|
240 homes
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No reviews yet
![The Summit at Bethel]()
$600Ks
- $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
No reviews yet
![Woodridge Strathmore Terr...]()
$400Ks
- $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
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.
No reviews yet
![Brierly Pond Village]()
$400Ks
- $400Ks
Brierly Pond Village, Millbury, MA
Resale Only
|
55+ age-restricted
|
Built 2003 - 2013
|
199 homes
No reviews yet
![Saddle Lakes]()
$400Ks
- $400Ks
Saddle Lakes, Riverhead, NY
Resale Only
|
55+ age-restricted
|
Built 2000 - 2002
|
196 homes
No reviews yet
![Country Village Estates]()
$400Ks
- $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
No reviews yet
![The Seasons at East North...]()
$700Ks
- $700Ks
The Seasons at East North..., East Northport, NY
New Construction
|
55+ age-restricted
|
Built 2023 - present
|
190 homes
Want to learn more about 55+ communities in Portland?
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Questions? Call us:
(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...]()
$600Ks
- $700Ks
The Villages at Mount Sin..., Mount Sinai, NY
Resale Only
|
55+ age-restricted
|
Built 2005 - 2007
|
185 homes
No reviews yet
![The Powder Forest Homes]()
$600Ks
- $700Ks
The Powder Forest Homes, Simsbury, CT
Resale Only
|
55+ age-restricted
|
Built 2006 - 2016
|
182 homes
5 rating (1 reviews)
![Newtown Woods]()
$400Ks
- $400Ks
Newtown Woods, Newtown, CT
New and Resale
|
55+ age-restricted
|
Built 2011 - present
|
178 homes
No reviews yet
![Stoneleigh Woods at River...]()
$600Ks
- $600Ks
Stoneleigh Woods at River..., Riverhead, NY
Resale Only
|
55+ age-restricted
|
Built 2007 - 2016
|
176 homes
Leisure Village
![449 ARLINGTON DR A, RIDGE, NY, 11961, Ridge, NY 11961]()
2 beds
|1 baths
|1,074 sq ft
|Condo
449 ARLINGTON DR A, RIDGE, NY, 11961
Community: Leisure Village
MLS 925505 • Exit Realty Island Elite, Michele L....
Leisure Village
![22B GUILFORD CT # 22B, RIDGE, NY, 11961, Ridge, NY 11961]()
2 beds
|1 baths
|1,085 sq ft
|Condo
22B GUILFORD CT # 22B, RIDGE, NY, 11961
Community: Leisure Village
MLS 923135 • Leisure Living Realty Inc, Heather B...
Glenwood Village
![1661 OLD COUNTRY RD UNIT 543, RIVERHEAD,..., Riverhead, NY 11901]()
2 beds
|2 baths
|1,632 sq ft
|Manufactured Home
1661 OLD COUNTRY RD UNIT 543, RIVERHEAD,...
Community: Glenwood Village
MLS 882046 • Howard Hanna Coach, Carol Giordano
Leisure Village
![412 WEYMOUTH CT UNIT B, RIDGE, NY, 11961, Ridge, NY 11961]()
2 beds
|1 baths
|1,100 sq ft
|Condo
412 WEYMOUTH CT UNIT B, RIDGE, NY, 11961
Community: Leisure Village
MLS 924555 • Keller Williams Rlty Landmark, Anton...
Leisure Village
![474 DARWEN DR B, RIDGE, NY, 11961, Ridge, NY 11961]()
MLS 911211 • Douglas Elliman Real Estate, Nicole ...
Want to learn more about 55+ communities in Portland?
55places can help!
Questions? Call us:
(860) 854-7490
Leisure Village
![259 NEWCASTLE CT E, RIDGE, NY, 11961, Ridge, NY 11961]()
1 beds
|1 baths
|875 sq ft
|Condo
259 NEWCASTLE CT E, RIDGE, NY, 11961
Community: Leisure Village
MLS 878336 • Barons Real Estate Associates, David...
The Coves at Melville
![95 MORLEY CIR, MELVILLE, NY, 11747, Melville, NY 11747]()
2 beds
|2 baths
|1,100 sq ft
|Condo
95 MORLEY CIR, MELVILLE, NY, 11747
Community: The Coves at Melville
MLS 923311 • Douglas Elliman Real Estate, Elyse B...
Leisure Village
![227 BLACKPOOL CT D, RIDGE, NY, 11961, Ridge, NY 11961]()
1 beds
|1 baths
|684 sq ft
|House
227 BLACKPOOL CT D, RIDGE, NY, 11961
Community: Leisure Village
MLS 910658 • Serhant LLC, Daniel T. Bourke
Leisure Village
![258 NEWCASTLE CT A, RIDGE, NY, 11961, Ridge, NY 11961]()
2 beds
|1 baths
|900 sq ft
|Condo
258 NEWCASTLE CT A, RIDGE, NY, 11961
Community: Leisure Village
MLS 923080 • Charles Rutenberg Realty Inc, Lawren...
Stoneleigh Woods at Riverhead
![18 KENNSINGTON CT -, RIVERHEAD, NY, 1190..., Riverhead, NY 11901]()
2 beds
|3 baths
|2,172 sq ft
|Stock Cooperative
18 KENNSINGTON CT -, RIVERHEAD, NY, 1190...
Community: Stoneleigh Woods at Riverhead
MLS 916048 • HomeCoin.com, Jonathan Minerick
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.
Meadowbrook Pointe Links & Spa
![60 PACIFIC DUNES CT, MEDFORD, NY, 11763, Medford, NY 11763]()
2 beds
|3 baths
|2,191 sq ft
|Condo
60 PACIFIC DUNES CT, MEDFORD, NY, 11763
Community: Meadowbrook Pointe Links & Spa
MLS 915123 • Signature Premier Properties, Matthe...
Leisure Knoll
![323 BROWNFIELD DR, RIDGE, NY, 11961, Ridge, NY 11961]()
MLS 919433 • Daniel Gale Sothebys Intl Rlty, Bonn...
Leisure Glen
![244 GLEN DR, RIDGE, NY, 11961, Ridge, NY 11961]()
MLS 916026 • Fiore Real Estate Sales Corp, Anna M...
Meadowbrook Pointe Links & Spa
![279 AUGUSTA DR, MEDFORD, NY, 11763, Medford, NY 11763]()
2 beds
|2 baths
|1,133 sq ft
|Condo
279 AUGUSTA DR, MEDFORD, NY, 11763
Community: Meadowbrook Pointe Links & Spa
MLS 901359 • Signature Premier Properties, Matthe...
Leisure Village
![310 WOODBRIDGE DR UNIT C, RIDGE, NY, 119..., Ridge, NY 11961]()
2 beds
|1 baths
|1,278 sq ft
|Condo
310 WOODBRIDGE DR UNIT C, RIDGE, NY, 119...
Community: Leisure Village
MLS 889288 • Coldwell Banker American Homes, Kath...
Want to learn more about 55+ communities in Portland?
55places can help!
Questions? Call us:
(860) 854-7490
Sunken Pond Estates
![4006 SAINT ANDREWS AVE, RIVERHEAD, NY, 1..., Riverhead, NY 11901]()
2 beds
|2 baths
|1,587 sq ft
|Condo
4006 SAINT ANDREWS AVE, RIVERHEAD, NY, 1...
Community: Sunken Pond Estates
MLS 917567 • Douglas Elliman Real Estate, Janet R...
Westhampton Pines
![112 ASHLEY DR, WESTHAMPTON, NY, 11977, Westhampton, NY 11977]()
3 beds
|3 baths
|2,306 sq ft
|Condo
112 ASHLEY DR, WESTHAMPTON, NY, 11977
Community: Westhampton Pines
MLS 907102 • William Raveis New York LLC, Margare...
Leisure Knoll
![407 BELFAST LN, RIDGE, NY, 11961, Ridge, NY 11961]()
MLS 918156 • Howard Hanna Coach, Kalliopi C. Suar...
Windmill Gate
![18 DAWN DR, OAKDALE, NY, 11769, Oakdale, NY 11769]()
MLS 922262 • S I Premiere Properties, Teresa Iera...
Glenwood Village
![1661 OLD COUNTRY RD 308, RIVERHEAD, NY, ..., Riverhead, NY 11901]()
2 beds
|1 baths
|840 sq ft
|Mobile Home
1661 OLD COUNTRY RD 308, RIVERHEAD, NY, ...
Community: Glenwood Village
MLS 922155 • Realty Connect USA L I Inc, Fengxia ...
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
![488A FAIRWAY CT # 488A, RIDGE, NY, 11961, Ridge, NY 11961]()
2 beds
|2 baths
|1,180 sq ft
|Condo
488A FAIRWAY CT # 488A, RIDGE, NY, 11961
Community: Leisure Village
MLS 921749 • Leisure Living Realty Inc, Laura Ruh...
Leisure Village
![46 TRENT CT C, RIDGE, NY, 11961, Ridge, NY 11961]()
MLS 916420 • Frontline Realty Group LLC, Lisa Kne...
Leisure Village
![231 BLACKPOOL CT F, RIDGE, NY, 11961, Ridge, NY 11961]()
2 beds
|1 baths
|875 sq ft
|Condo
231 BLACKPOOL CT F, RIDGE, NY, 11961
Community: Leisure Village
MLS 908850 • Leisure Living Realty Inc, Paulina R...
The Vineyards at Miller Place
![43 HALLEY LN, MILLER PLACE, NY, 11764, Miller Place, NY 11764]()
2 beds
|3 baths
|1,350 sq ft
|Condo
43 HALLEY LN, MILLER PLACE, NY, 11764
Community: The Vineyards at Miller Place
MLS 910906 • Douglas Elliman Real Estate, Carmela...
The Greens at Half Hollow
![285 MADEIRA BLVD # 285, MELVILLE, NY, 11..., Melville, NY 11747]()
3 beds
|3 baths
|3,200 sq ft
|Condo
285 MADEIRA BLVD # 285, MELVILLE, NY, 11...
Community: The Greens at Half Hollow
MLS 889597 • Compass Greater NY LLC, Diane Betz
Want to learn more about 55+ communities in Portland?
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Leisure Village
![405 WOODBRIDGE DR D, RIDGE, NY, 11961, Ridge, NY 11961]()
2 beds
|1 baths
|874 sq ft
|Condo
405 WOODBRIDGE DR D, RIDGE, NY, 11961
Community: Leisure Village
MLS 920854 • Coldwell Banker American Homes, Kath...
Stoneleigh Woods at Riverhead
![67 STONELEIGH DR, RIVERHEAD, NY, 11901, Riverhead, NY 11901]()
2 beds
|3 baths
|1,972 sq ft
|Condo
67 STONELEIGH DR, RIVERHEAD, NY, 11901
Community: Stoneleigh Woods at Riverhead
MLS 917715 • Douglas Elliman Real Estate, Mary El...
Country Village Estates
![163 THEODORE DR, CORAM, NY, 11727, Coram, NY 11727]()
2 beds
|2 baths
|1,261 sq ft
|Condo
163 THEODORE DR, CORAM, NY, 11727
Community: Country Village Estates
MLS 909033 • Coldwell Banker American Homes, Ange...
Leisure Village
![167 VENTRY CT UNIT C, RIDGE, NY, 11961, Ridge, NY 11961]()
1 beds
|1 baths
|684 sq ft
|Condo
167 VENTRY CT UNIT C, RIDGE, NY, 11961
Community: Leisure Village
MLS 919695 • Coldwell Banker American Homes, Laur...
Leisure Village
![120 EXMORE CT D, RIDGE, NY, 11961, Ridge, NY 11961]()
MLS 908219 • HomeCoin.com, Jonathan Minerick
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
![19 VILLANOVA CT, RIDGE, NY, 11961, Ridge, NY 11961]()
MLS 918889 • Realty Connect USA LI, Margaret Tsou...
Leisure Village
![96 ENFIELD CT B, RIDGE, NY, 11961, Ridge, NY 11961]()
MLS 877572 • Compass Greater NY LLC, Kenneth Hirs...
Fairfield at St. James
![102 GOTHAM WAY, SAINT JAMES, NY, 11780, Saint James, NY 11780]()
3 beds
|3 baths
|1,600 sq ft
|Condo
102 GOTHAM WAY, SAINT JAMES, NY, 11780
Community: Fairfield at St. James
MLS 901666 • Howard Hanna Coach, Christine Daddio...
Fairfield at St. James
![914 FENWAY RD, SAINT JAMES, NY, 11780, Saint James, NY 11780]()
2 beds
|2 baths
|1,200 sq ft
|Condo
914 FENWAY RD, SAINT JAMES, NY, 11780
Community: Fairfield at St. James
MLS 886931 • Douglas Elliman Real Estate, Laura R...
Leisure Village
![98 A EASTBOURNE, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961]()
2 beds
|2 baths
|1,486 sq ft
|Condo
98 A EASTBOURNE, BROOKHAVEN, NY, 11961
Community: Leisure Village
MLS 906713 • Coldwell Banker American Homes, Mary...
Want to learn more about 55+ communities in Portland?
55places can help!
Questions? Call us:
(860) 854-7490
Leisure Village
![269 BERWICK CT B, RIDGE, NY, 11961, Ridge, NY 11961]()
2 beds
|1 baths
|1,048 sq ft
|Condo
269 BERWICK CT B, RIDGE, NY, 11961
Community: Leisure Village
MLS 913579 • Howard Hanna Coach, Julie P. Lapasot...
Leisure Village
![350B WOODBRIDGE DR 350B, BROOKHAVEN, NY,..., Brookhaven, NY 11961]()
2 beds
|1 baths
|1,100 sq ft
|Condo
350B WOODBRIDGE DR 350B, BROOKHAVEN, NY,...
Community: Leisure Village
MLS 904734 • Leisure Living Realty Inc, Paulina R...
Greenwood Village
![38B VILLAGE CIR S, MANORVILLE, NY, 11949, Manorville, NY 11949]()
1 beds
|1 baths
|600 sq ft
|Condo
38B VILLAGE CIR S, MANORVILLE, NY, 11949
Community: Greenwood Village
MLS 913692 • Gateway to The Hamptons R E, Vivian ...
The Waterways at Moriches
![514 HIGHLAND CT # A3, MORICHES, NY, 1195..., Moriches, NY 11955]()
2 beds
|2 baths
|1,839 sq ft
|Condo
514 HIGHLAND CT # A3, MORICHES, NY, 1195...
Community: The Waterways at Moriches
MLS 913148 • Douglas Elliman Real Estate, Jo Ann ...
Greenwood Village
![77 VILLAGE CIR, MANORVILLE, NY, 11949, Manorville, NY 11949]()
2 beds
|1 baths
|1,000 sq ft
|Condo
77 VILLAGE CIR, MANORVILLE, NY, 11949
Community: Greenwood Village
MLS 853523 • Gateway to The Hamptons R E, Janet R...
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?
260
homes
near Portland
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© 2025 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: Oct 28, 2025.
This application does not include information on all of the properties available for sale at this time.
