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Westport, CT 55+ active adult communities & homes for sale
167 communities near Westport
311 homes near Westport
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$500Ks
- $600Ks
Whitney Glen, Westport, CT
Resale Only
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55+ age-restricted
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Built 1982 - 1982
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62 homes
3 rating (2 reviews)
![Heritage Hills]()
$300Ks
- $900Ks
Heritage Hills, Somers, NY
Resale Only
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Age-targeted
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Built 1974 - 2006
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2,600 homes
3.6 rating (7 reviews)
![Heritage Village]()
$200Ks
- $500Ks
Heritage Village, Southbury, CT
Resale Only
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55+ age-restricted
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Built 1967 - 2005
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2,580 homes
$200Ks
- $400Ks
Leisure Village, Ridge, NY
Resale Only
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55+ age-restricted
|
Built 1969 - 1986
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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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(475) 471-1908
$400Ks
- $600Ks
Rivington, Danbury, CT
New and Resale
|
Age-targeted
|
Built 2006 - present
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1,050 homes
4 rating (1 reviews)
![Jefferson Village]()
$200Ks
- $600Ks
Jefferson Village, Yorktown Heights, NY
Resale Only
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55+ age-restricted
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Built 1967 - 1982
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1,000 homes
5 rating (2 reviews)
![Shadow Lake Village]()
$300Ks
- $600Ks
Shadow Lake Village, Red Bank, NJ
Resale Only
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55+ age-restricted
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Built 1972 - 1980
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952 homes
$200Ks
- $600Ks
Oronoque Village, Stratford, CT
Resale Only
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55+ age-restricted
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Built 1971 - 1977
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929 homes
$500Ks
- $600Ks
The Village at Oxford Gre..., Oxford, CT
New and Resale
|
55+ age-restricted
|
Built 2004 - present
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835 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)
![Four Seasons at Great Not...]()
$600Ks
- $800Ks
Four Seasons at Great Not..., Woodland Park, NJ
Resale Only
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55+ age-restricted
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Built 2005 - 2018
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814 homes
$800Ks
- $1Ms
Meadowbrook Pointe Athlet..., Westbury, NY
Resale Only
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55+ age-restricted
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Built 2015 - 2016
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720 homes
2.8 rating (4 reviews)
![Cheesequake Village]()
$100Ks
- $300Ks
Cheesequake Village, Old Bridge, NJ
Resale Only
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55+ age-restricted
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Built 1965 - 1971
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713 homes
$300Ks
- $400Ks
Leisure Knoll, Ridge, NY
Resale Only
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55+ age-restricted
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Built 1972 - 1982
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701 homes
2.8 rating (5 reviews)
![The Villages NJ]()
$200Ks
- $400Ks
The Villages NJ, Howell, NJ
Resale Only
|
55+ age-restricted
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Built 1967 - 1975
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670 homes
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$1Ms
Country Pointe Plainview, Plainview, NY
New Construction
|
55+ age-restricted
|
Built 2017 - present
|
660 homes
5 rating (2 reviews)
![Fairfield at St. James]()
$400Ks
- $500Ks
Fairfield at St. James, St. James, NY
Resale Only
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55+ age-restricted
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Built 1972 - 1989
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653 homes
$200Ks
Spring Lake Village, Southington, CT
Resale Only
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55+ age-restricted
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Built 1970 - 2004
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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
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.
3.7 rating (3 reviews)
![Greenwood Village]()
$100Ks
- $200Ks
Greenwood Village, Manorville, NY
Resale Only
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55+ age-restricted
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Built 1980 - 2000
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512 homes
$800Ks
- $900Ks
Equestra at Colts Neck Cr..., Farmingdale, NJ
Resale Only
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55+ age-restricted
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Built 2007 - 2018
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483 homes
4.2 rating (12 reviews)
![Surrey Downs]()
$300Ks
- $400Ks
Surrey Downs, Freehold, NJ
Resale Only
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55+ age-restricted
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Built 1986 - 1997
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443 homes
$500Ks
- $600Ks
The Seasons at East Meado..., East Meadow, NY
Resale Only
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55+ age-restricted
|
Built 2009 - 2012
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404 homes
$300Ks
- $500Ks
Regency at Prospect, Prospect, CT
Resale Only
|
55+ age-restricted
|
Built 2006 - 2020
|
379 homes
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Questions? Call us:
(475) 471-1908
5 rating (1 reviews)
![Shady Oaks]()
$400Ks
Shady Oaks, Red Bank, NJ
Resale Only
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55+ age-restricted
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Built 1982 - 1983
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366 homes
$400Ks
Dutchgate, Valley Stream, NY
Resale Only
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55+ age-restricted
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Built 2009 - 2015
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348 homes
$400Ks
- $700Ks
The Waterways at Moriches, Moriches, NY
Resale Only
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55+ age-restricted
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Built 1985 - 1999
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343 homes
$700Ks
- $800Ks
Rolling Meadows at Waysid..., Ocean Township, NJ
Resale Only
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55+ age-restricted
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Built 2002 - 2007
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328 homes
$400Ks
- $600Ks
The Retreat at Carmel, Carmel, NY
Resale Only
|
55+ age-restricted
|
Built 2008 - 2018
|
312 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
Cedar Village at Ocean, Ocean Township, NJ
Resale Only
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55+ age-restricted
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Built 2005 - 2014
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295 homes
3.5 rating (2 reviews)
![Foxwood Village]()
$300Ks
- $400Ks
Foxwood Village, Calverton, NY
Resale Only
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55+ age-restricted
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Built 1986 - 2007
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294 homes
1 rating (1 reviews)
![Plymouth Estates at Mount...]()
$500Ks
Plymouth Estates at Mount..., Mount Sinai, NY
Resale Only
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55+ age-restricted
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Built 2006 - 2013
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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
Want to learn more about 55+ communities in Westport?
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(475) 471-1908
4 rating (1 reviews)
![Vineyards at Blue Point]()
$800Ks
Vineyards at Blue Point, Blue Point, NY
Resale Only
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55+ age-restricted
|
Built 2016 - 2018
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280 homes
$900Ks
- $1Ms
HarborView, Port Washington, NY
Resale Only
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55+ age-restricted
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Built 2002 - 2004
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270 homes
Heritage Hills
![593 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589]()
3 beds
|2 baths
|1,905 sq ft
|Condo
593 HERITAGE HLS B, SOMERS, NY, 10589
Community: Heritage Hills
MLS 921343 • Douglas Elliman Real Estate, Frankli...
Regency at Fishkill
![423 REGENCY DR, FISHKILL, NY, 12524, Fishkill, NY 12524]()
1 beds
|2 baths
|1,450 sq ft
|Condo
423 REGENCY DR, FISHKILL, NY, 12524
Community: Regency at Fishkill
MLS 917650 • eXp Realty, Dvora E. Price
The Vineyards at Miller Place
![37 HALLEY LN, MILLER PLACE, NY, 11764, Miller Place, NY 11764]()
2 beds
|3 baths
|1,853 sq ft
|Condo
37 HALLEY LN, MILLER PLACE, NY, 11764
Community: The Vineyards at Miller Place
MLS 916715 • Shea & Sanders Real Estate Inc, Lisa...
Greenwood Village
![2 LIMETREE DR, MANORVILLE, NY, 11949, Manorville, NY 11949]()
2 beds
|2 baths
|1,242 sq ft
|House
2 LIMETREE DR, MANORVILLE, NY, 11949
Community: Greenwood Village
MLS 924086 • Legacy Capital Realty LLC, Anderson ...
Regency at Fishkill
![326 REGENCY DR, FISHKILL, NY, 12524, Fishkill, NY 12524]()
1 beds
|2 baths
|1,543 sq ft
|Condo
326 REGENCY DR, FISHKILL, NY, 12524
Community: Regency at Fishkill
MLS 890462 • RE/MAX Town & Country, Spyros Spyrou
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Stone Ridge Estates
![108 JOSEPH LN, DIX HILLS, NY, 11746, Dix Hills, NY 11746]()
2 beds
|2 baths
|1,695 sq ft
|Condo
108 JOSEPH LN, DIX HILLS, NY, 11746
Community: Stone Ridge Estates
MLS 903129 • Real Broker NY LLC, Matthew J. Lenne...
The Villages at Mount Sinai Park
![4 OAKHURST CT, MOUNT SINAI, NY, 11766, Mount Sinai, NY 11766]()
3 beds
|3 baths
|2,850 sq ft
|Condo
4 OAKHURST CT, MOUNT SINAI, NY, 11766
Community: The Villages at Mount Sinai Park
MLS 902444 • Douglas Elliman Real Estate, Lisa A....
Leisure Village
![195 E NEWCASTLE CT, BROOKHAVEN, NY, 1196..., Brookhaven, NY 11961]()
1 beds
|1 baths
|684 sq ft
|Condo
195 E NEWCASTLE CT, BROOKHAVEN, NY, 1196...
Community: Leisure Village
MLS 888315 • Integrity Core Realty, Patroy Quarry
Kensington Estates
![46 PLAINVIEW RD, WOODBURY, NY, 11797, Woodbury, NY 11797]()
6 beds
|5 baths
|4,333 sq ft
|House
46 PLAINVIEW RD, WOODBURY, NY, 11797
Community: Kensington Estates
MLS 929199 • SRG Residential LLC, Jared Sarney
Jefferson Village
![45 JEFFERSON OVAL D, YORKTOWN HEIGHTS, N..., Yorktown Heights, NY 10598]()
2 beds
|2 baths
|1,100 sq ft
|Condo
45 JEFFERSON OVAL D, YORKTOWN HEIGHTS, N...
Community: Jefferson Village
MLS 916000 • Compass Greater NY, LLC, Anna Priski...
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 Villages at Mount Sinai Park
![109 LOUDEN LOOP, MOUNT SINAI, NY, 11766, Mount Sinai, NY 11766]()
2 beds
|2 baths
|1,736 sq ft
|Condo
109 LOUDEN LOOP, MOUNT SINAI, NY, 11766
Community: The Villages at Mount Sinai Park
MLS 887250 • Douglas Elliman Real Estate, Nancy D...
Leisure Village
![69 ENFIELD CT UNIT B B, RIDGE, NY, 11961, Ridge, NY 11961]()
2 beds
|1 baths
|1,278 sq ft
|Condo
69 ENFIELD CT UNIT B B, RIDGE, NY, 11961
Community: Leisure Village
MLS 905718 • Leisure Living Realty Inc, Catherine...
Breton Hills
![704 BRETON WAY # 704, GLEN COVE, NY, 115..., Glen Cove, NY 11542]()
2 beds
|2 baths
|1,440 sq ft
|Condo
704 BRETON WAY # 704, GLEN COVE, NY, 115...
Community: Breton Hills
MLS 920295 • Keller Williams Realty Elite, Patric...
Leisure Village
![48 TRENT CT B, RIDGE, NY, 11961, Ridge, NY 11961]()
MLS 906943 • Coldwell Banker American Homes, Rona...
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...
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(475) 471-1908
The Seasons at East Meadow
![272 SPRING DR, EAST MEADOW, NY, 11554, East Meadow, NY 11554]()
2 beds
|3 baths
|1,030 sq ft
|Condo
272 SPRING DR, EAST MEADOW, NY, 11554
Community: The Seasons at East Meadow
MLS 924891 • Birch Hill Realty Consultants, Josep...
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
![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...
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...
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...
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.
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 ...
Dutchgate
![802 WILLOW LN UPPR LEVEL, VALLEY STREAM,..., Valley Stream, NY 11580]()
2 beds
|2 baths
|941 sq ft
|Condo
802 WILLOW LN UPPR LEVEL, VALLEY STREAM,...
Community: Dutchgate
MLS 912526 • Douglas Elliman Real Estate, Susan K...
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...
Regency at Fishkill
![145 REGENCY DR, FISHKILL, NY, 12524, Fishkill, NY 12524]()
2 beds
|2 baths
|1,803 sq ft
|Condo
145 REGENCY DR, FISHKILL, NY, 12524
Community: Regency at Fishkill
MLS 898170 • Realty Center Hudson Valley, Edwin D...
Leisure Village
![120 EXMORE CT D, RIDGE, NY, 11961, Ridge, NY 11961]()
MLS 908219 • HomeCoin.com, Jonathan Minerick
Want to learn more about 55+ communities in Westport?
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Questions? Call us:
(475) 471-1908
The Seasons at East Meadow
![133 SPRING DR # 133, EAST MEADOW, NY, 11..., East Meadow, NY 11554]()
2 beds
|2 baths
|1,272 sq ft
|Condo
133 SPRING DR # 133, EAST MEADOW, NY, 11...
Community: The Seasons at East Meadow
MLS 917397 • Coldwell Banker American Homes, Rich...
HarborView
![100 HARBOR VIEW DR 423, PORT WASHINGTON,..., Port Washington, NY 11050]()
1 beds
|2 baths
|1,161 sq ft
|Condo
100 HARBOR VIEW DR 423, PORT WASHINGTON,...
Community: HarborView
MLS 818836 • Evelyn Richards Inc, Maria Giacalone
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 ...
The Greens at Half Hollow
![382 ALTESSA BLVD, MELVILLE, NY, 11747, Melville, NY 11747]()
2 beds
|2 baths
|2,937 sq ft
|Condo
382 ALTESSA BLVD, MELVILLE, NY, 11747
Community: The Greens at Half Hollow
MLS 904079 • Daniel Gale Sothebys Intl Rlty, John...
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.
HarborView
![100 HARBOR VIEW DR 439, PORT WASHINGTON,..., Port Washington, NY 11050]()
2 beds
|3 baths
|1,420 sq ft
|Condo
100 HARBOR VIEW DR 439, PORT WASHINGTON,...
Community: HarborView
MLS 838453 • Evelyn Richards Inc, Maria Giacalone
Leisure Village
![166 VENTRY CT B, RIDGE, NY, 11961, Ridge, NY 11961]()
MLS 895352 • Voro LLC, Lauren A. Granger
The Waterways at Moriches
![107 E MIDLAND POND CT, MORICHES, NY, 119..., Moriches, NY 11955]()
2 beds
|2 baths
|2,141 sq ft
|Condo
107 E MIDLAND POND CT, MORICHES, NY, 119...
Community: The Waterways at Moriches
MLS 829455 • Douglas Elliman Real Estate, Jo Ann ...
Plymouth Estates at Mount Sinai
![166 IRA RD, MOUNT SINAI, NY, 11766, Mount Sinai, NY 11766]()
2 beds
|2 baths
|1,820 sq ft
|Townhouse
166 IRA RD, MOUNT SINAI, NY, 11766
Community: Plymouth Estates at Mount Sinai
MLS 878423 • Aliano Real Estate, Nicholas A. Colo...
Oronoque Village
![617 CHEROKEE LN B, STRATFORD, CT, 06614, Stratford, CT 06614]()
1 beds
|3 baths
|1,438 sq ft
|Condo
617 CHEROKEE LN B, STRATFORD, CT, 06614
Community: Oronoque Village
MLS 24132771 • William Raveis Real Estate, Kenny ...
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(475) 471-1908
Oronoque Village
![164 BISON LN A, STRATFORD, CT, 06614, Stratford, CT 06614]()
1 beds
|2 baths
|1,175 sq ft
|Condo
164 BISON LN A, STRATFORD, CT, 06614
Community: Oronoque Village
MLS 24139444 • Stacy Blake Realty LLC, Celina Cuo...
New
Oronoque Village
![383 SEQUOIA LN A, STRATFORD, CT, 06614, Stratford, CT 06614]()
2 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...
Heritage Village
![26 HERITAGE CRST C, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,217 sq ft
|Condo
26 HERITAGE CRST C, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24123450 • Joseph Bette REALTORS Inc, Justin ...
The Village at Oxford Greens
![712 CHAMPIONSHIP DR # 712, OXFORD, CT, 0..., Oxford, CT 06478]()
2 beds
|2 baths
|1,546 sq ft
|Condo
712 CHAMPIONSHIP DR # 712, OXFORD, CT, 0...
Community: The Village at Oxford Greens
MLS 24134777 • Coldwell Banker Realty, Chris LaCa...
Fairview at Oxford Greens
![712 CHAMPIONSHIP DR # 712, OXFORD, CT, 0..., Oxford, CT 06478]()
2 beds
|2 baths
|1,546 sq ft
|Condo
712 CHAMPIONSHIP DR # 712, OXFORD, CT, 0...
Community: Fairview at Oxford Greens
MLS 24134777 • Coldwell Banker Realty, Chris LaCa...
Frequently Asked Questions
In Westport, there is 1 small community with less than 500 homes.
The smallest 55+ community in Westport has 62 homes, the largest has 62 homes, and the average community consists of 62 homes.
No, there are no gated 55+ communities in Westport.
Want more information about active adult communities around Westport?
Want to learn more about 55+ communities in Westport?
311
homes
near Westport
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REIN updates its listings on a daily basis. Data last updated: Dec 05, 2025.
This application does not include information on all of the properties available for sale at this time.
