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Westport, CT 55+ active adult communities & homes for sale - Page 9
172 communities near Westport
404 homes near Westport
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3.6 rating (7 reviews)
$200ks
- $500ks
Heritage Village, Southbury, CT
Resale Only |
55+ age-restricted |
Built 1967 - 2005 |
2,580 homes
3 rating (2 reviews)
$400ks
- $900ks
Heritage Hills, Somers, NY
Resale Only |
Age-targeted |
Built 1974 - 2006 |
2,600 homes
2.8 rating (5 reviews)
$200ks
- $300ks
The Villages NJ, Howell, NJ
Resale Only |
55+ age-restricted |
Built 1967 - 1975 |
670 homes
4 rating (1 review)
$100ks
- $500ks
Jefferson Village, Yorktown Heights, NY
Resale Only |
55+ age-restricted |
Built 1967 - 1982 |
1,000 homes
2.8 rating (4 reviews)
$200ks
- $300ks
Cheesequake Village, Old Bridge, NJ
Resale Only |
55+ age-restricted |
Built 1965 - 1971 |
713 homes
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3.7 rating (3 reviews)
$100ks
Greenwood Village, Manorville, NY
Resale Only |
55+ age-restricted |
Built 1980 - 2000 |
512 homes
$400ks
- $500ks
The Village at Oxford Gre..., Oxford, CT
New and Resale |
55+ age-restricted |
Built 2004 - present |
835 homes
$200ks
- $400ks
Leisure Knoll, Ridge, NY
Resale Only |
55+ age-restricted |
Built 1972 - 1982 |
701 homes
$300ks
- $400ks
Leisure Glen, Ridge, NY
Resale Only |
55+ age-restricted |
Built 1985 - 2010 |
646 homes
$100ks
- $300ks
Leisure Village, Ridge, NY
Resale Only |
55+ age-restricted |
Built 1969 - 1986 |
1,500 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)
$200ks
- $400ks
Oronoque Village, Stratford, CT
Resale Only |
55+ age-restricted |
Built 1971 - 1977 |
929 homes
$300ks
- $900ks
Rivington, Danbury, CT
New and Resale |
Age-targeted |
Built 2006 - present |
1,050 homes
5 rating (2 reviews)
$200ks
- $500ks
Shadow Lake Village, Red Bank, NJ
Resale Only |
55+ age-restricted |
Built 1972 - 1980 |
952 homes
$300ks
- $600ks
The Waterways at Moriches, Moriches, NY
Resale Only |
55+ age-restricted |
Built 1985 - 1999 |
343 homes
5 rating (2 reviews)
$300ks
- $500ks
Fairfield at St. James, St. James, NY
Resale Only |
55+ age-restricted |
Built 1972 - 1989 |
653 homes
4 rating (8 reviews)
$100ks
- $200ks
Glenwood Village, Riverhead, NY
New and Resale |
55+ age-restricted |
Built 1959 - present |
588 homes
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(475) 471-1908
5 rating (1 review)
$400ks
- $700ks
Four Seasons at Great Not..., Woodland Park, NJ
Resale Only |
55+ age-restricted |
Built 2005 - 2018 |
814 homes
$600ks
- $1Ms
The Greens at Half Hollow, Melville, NY
Resale Only |
55+ age-restricted |
Built 1994 - 2005 |
1,200 homes
$600ks
- $1Ms
HarborView, Port Washington, NY
Resale Only |
55+ age-restricted |
Built 2002 - 2004 |
270 homes
4.2 rating (12 reviews)
$200ks
- $300ks
Surrey Downs, Freehold, NJ
Resale Only |
55+ age-restricted |
Built 1986 - 1997 |
443 homes
Download the Ultimate 55+ Homebuying Guide
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$300ks
- $400ks
The Manors at The Colony ..., Shirley, NY
New Construction |
55+ age-restricted |
Built 2013 - present |
150 homes
$400ks
- $600ks
Fairview at Oxford Greens, Oxford, CT
New and Resale |
55+ age-restricted |
Built 2019 - present |
125 homes
5 rating (1 review)
$500ks
- $700ks
Encore at Lake Grove, Lake Grove, NY
Resale Only |
55+ age-restricted |
Built 2006 - 2007 |
228 homes
5 rating (1 review)
$900ks
- $1Ms
Westhampton Pines, Westhampton, NY
Resale Only |
55+ age-restricted |
Built 2005 - 2013 |
189 homes
3.5 rating (2 reviews)
$200ks
- $400ks
Foxwood Village, Calverton, NY
Resale Only |
55+ age-restricted |
Built 1986 - 2007 |
294 homes
5 rating (1 review)
$500ks
- $800ks
Encore Atlantic Shores, Eastport, NY
Resale Only |
55+ age-restricted |
Built 2004 - 2011 |
240 homes
5 rating (1 review)
$300ks
- $500ks
Newtown Woods, Newtown, CT
New and Resale |
55+ age-restricted |
Built 2011 - present |
178 homes
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Questions? Call us:
(475) 471-1908
$300ks
- $500ks
Dutchgate, Valley Stream, NY
Resale Only |
55+ age-restricted |
Built 2009 - 2015 |
348 homes
$700ks
- $1Ms
Country Pointe Plainview, Plainview, NY
New Construction |
55+ age-restricted |
Built 2017 - present |
660 homes
$300ks
- $400ks
Meadow Brook Estates, Oxford, CT
Resale Only |
55+ age-restricted |
Built 2003 - 2020 |
246 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.
1 rating (1 review)
$400ks
- $500ks
Plymouth Estates at Mount..., Mount Sinai, NY
Resale Only |
55+ age-restricted |
Built 2006 - 2013 |
285 homes
$700ks
- $1Ms
Meadowbrook Pointe Athlet..., Westbury, NY
Resale Only |
55+ age-restricted |
Built 2015 - 2016 |
720 homes
$100ks
- $200ks
Spring Lake Village, Southington, CT
Resale Only |
55+ age-restricted |
Built 1970 - 2004 |
640 homes
$300ks
- $400ks
Regency at Fishkill, Fishkill, NY
Resale Only |
55+ age-restricted |
Built 2008 - 2020 |
164 homes
5 rating (1 review)
$400ks
Sunken Pond Estates, Riverhead, NY
Resale Only |
55+ age-restricted |
Built 2003 - 2005 |
194 homes
$400ks
- $500ks
Windcrest East, Calverton, NY
Resale Only |
55+ age-restricted |
Built 2004 - 2005 |
126 homes
$400ks
- $600ks
The Seasons at East Meado..., East Meadow, NY
Resale Only |
55+ age-restricted |
Built 2009 - 2012 |
404 homes
Want to learn more about 55+ communities in Westport?
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Questions? Call us:
(475) 471-1908
$600ks
- $700ks
Glassbury Court at Cold S..., Cold Spring, NY
Resale Only |
55+ age-restricted |
Built 2009 - 2014 |
90 homes
$400ks
- $500ks
Saddle Lakes, Riverhead, NY
Resale Only |
55+ age-restricted |
Built 2000 - 2002 |
196 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.
HarborView
3 beds
|3 baths
|2,160 sq ft
|Condo
123 LINKS CT, NORTH HEMPSTEAD, NY, 11050
Community: HarborView
MLS 1027930 • Evelyn Richards Inc, Maria Giacalon... • Evelyn Richards Inc
Rosemont Estates
2 beds
|3 baths
|2,551 sq ft
|House
207 BRADWICK WAY, MARLBORO, NJ, 07746
Community: Rosemont Estates
MLS 22622146 • NJ Elite Group LLC, Nicholas Sinop... • NJ Elite Group LLC
Heritage Village
2 beds
|2 baths
|1,398 sq ft
|Condo
895 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24191530 • Century 21 Bette Real Estate, Debo... • Century 21 Bette Real Estate
Heritage Village
2 beds
|2 baths
|1,432 sq ft
|Condo
16 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24191044 • Century 21 Bette Real Estate, Cynt... • Century 21 Bette Real Estate
Heritage Village
2 beds
|2 baths
|1,032 sq ft
|Condo
38 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24192310 • Berkshire Hathaway NE Prop., Jacek... • Berkshire Hathaway NE Prop.
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(475) 471-1908
Oronoque Village
1 beds
|2 baths
|1,360 sq ft
|Condo
407 MONTAUK LN B, STRATFORD, CT, 06614
Community: Oronoque Village
MLS 24186313 • Coldwell Banker Realty, Mary Kelle... • Coldwell Banker Realty
The Villas at Jumping Brook
2 beds
|2 baths
|1,992 sq ft
|House
8 TALL PINES DR, NEPTUNE TOWNSHIP, NJ, 0...
Community: The Villas at Jumping Brook
MLS 22621752 • Ward Wight Sotheby's International... • Ward Wight Sotheby's International Realty
The Village at Oxford Greens
2 beds
|2 baths
|1,682 sq ft
941 MACKENZIE LN 941, OXFORD, CT, 06478
Community: The Village at Oxford Greens
MLS 24192068 • Real Estate Two, Karen Berwick • Real Estate Two
Fairview at Oxford Greens
2 beds
|2 baths
|1,682 sq ft
941 MACKENZIE LN 941, OXFORD, CT, 06478
Community: Fairview at Oxford Greens
MLS 24192068 • Real Estate Two, Karen Berwick • Real Estate Two
Snug Harbor
MLS 992241 • Daniel Gale Sothebys Intl Rlty, Kim ... • Daniel Gale Sothebys Intl Rlty
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.
Rivington
3 beds
|3 baths
|1,600 sq ft
|Condo
64 WARRINGTON ROUND 64, DANBURY, CT, 068...
Community: Rivington
MLS 24191321 • Coldwell Banker Realty, Antonio Za... • Coldwell Banker Realty
Shadow Lake Village
2 beds
|2 baths
|1,423 sq ft
|House
10 DANBURY CT, RED BANK, NJ, 07701
Community: Shadow Lake Village
MLS 22621670 • Compass New Jersey , LLC, Karen Sl... • Compass New Jersey , LLC
Glenwood Village
2 beds
|2 baths
|1,500 sq ft
|Manufactured Home
1661 OLD COUNTRY RD 156D, RIVERHEAD, NY,...
Community: Glenwood Village
MLS 1025609 • R & R Duo Realty Inc, Irina V. Renn... • R & R Duo Realty Inc
Meadowbrook Pointe Athletic Club & Spa
2 beds
|2 baths
|1,319 sq ft
|Condo
348 TROTTING LN, HEMPSTEAD, NY, 11590
Community: Meadowbrook Pointe Athletic Club & Spa
MLS 1024788 • Douglas Elliman Real Estate, Matthe... • Douglas Elliman Real Estate
Winthrop Court
MLS 26026448 • Keller Williams Prosperity Realty,... • Keller Williams Prosperity Realty
Greenwood Village
1 beds
|1 baths
|812 sq ft
|Condo
89 VILLAGE CIR, BROOKHAVEN, NY, 11949
Community: Greenwood Village
MLS 1025221 • Coldwell Banker American Homes, Kel... • Coldwell Banker American Homes
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(475) 471-1908
Heritage Hills
2 beds
|3 baths
|1,550 sq ft
|Condo
358 HERITAGE HLS C, SOMERS, NY, 10589
Community: Heritage Hills
MLS 1024317 • Houlihan Lawrence Inc., Annpauline ... • Houlihan Lawrence Inc.
Newtown Woods
2 beds
|2 baths
|1,747 sq ft
|Condo
232 BROOKSIDE CT 232, NEWTOWN, CT, 06470
Community: Newtown Woods
MLS 24190305 • McGrath Realty Inc., Claudia Jiskr... • McGrath Realty Inc.
Glassbury Court at Cold Spring
2 beds
|2 baths
|1,974 sq ft
|Condo
10 MAGGIE MAY WAY, PHILIPSTOWN, NY, 1051...
Community: Glassbury Court at Cold Spring
MLS 1024506 • Keller Williams Realty Partner, Chr... • Keller Williams Realty Partner
Glenwood Village
2 beds
|2 baths
|980 sq ft
|Manufactured Home
1661 OLD COUNTRY RD 233, RIVERHEAD, NY, ...
Community: Glenwood Village
MLS 1024299 • Signature Premier Properties, Noree... • Signature Premier Properties
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.
Country Pointe Plainview
2 beds
|2 baths
|1,335 sq ft
|Condo
19303 ASPENWOOD DR, OYSTER BAY, NY, 1180...
Community: Country Pointe Plainview
MLS 1024039 • Douglas Elliman Real Estate, Patric... • Douglas Elliman Real Estate
Heritage Village
2 beds
|2 baths
|1,432 sq ft
|Condo
972 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24189835 • Century 21 Classic Homes, Linda Mu... • Century 21 Classic Homes
The Manors at The Colony Preserve
2 beds
|2 baths
|1,557 sq ft
|Condo
33 GREENTREE CT, BROOKHAVEN, NY, 11967
Community: The Manors at The Colony Preserve
MLS 1022293 • Howard Hanna Coach, Heather N. Malo... • Howard Hanna Coach
The Seasons at Elwood
2 beds
|3 baths
|2,900 sq ft
|Condo
178 SUMMER CIR, HUNTINGTON, NY, 11731
Community: The Seasons at Elwood
MLS 1020053 • LAFFEY REAL ESTATE, Pauline Conti • LAFFEY REAL ESTATE
Greenwood Village
2 beds
|2 baths
|987 sq ft
|House
5131 VILLAGE CIR, BROOKHAVEN, NY, 11949
Community: Greenwood Village
MLS 1021408 • Belzak & Bodkin Realty Corp, Susan ... • Belzak & Bodkin Realty Corp
Fairfield at St. James
2 beds
|2 baths
|948 sq ft
|Condo
1205 GOTHAM DR, SMITHTOWN, NY, 11780
Community: Fairfield at St. James
MLS 1021169 • Compass Greater NY LLC, Batul N. Mo... • Compass Greater NY LLC
Cheesequake Village
2 beds
|1 baths
|949 sq ft
|Adult Community
1 ALABAMA CT 820, MATAWAN, NJ, 07747
Community: Cheesequake Village
MLS 22620464 • Coldwell Banker Realty, Agostino S... • Coldwell Banker Realty
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Cheesequake Village
2 beds
|1 baths
|949 sq ft
|Condo
1-D ALABAMA CT D, OLD BRIDGE, NJ, 07747
Community: Cheesequake Village
MLS 2700173R • COLDWELL BANKER REALTY, AGOSTINO S... • COLDWELL BANKER REALTY
Oronoque Village
1 beds
|2 baths
|1,375 sq ft
|Condo
46 BUCKSKIN LN A, STRATFORD, CT, 06614
Community: Oronoque Village
MLS 24161546 • Sarah Harrower Realty, Sarah Harro... • Sarah Harrower Realty
Heritage Hills
3 beds
|2 baths
|1,689 sq ft
|Condo
156 HERITAGE HLS A, SOMERS, NY, 10589
Community: Heritage Hills
MLS 1019576 • William Raveis-New York LLC, Alexan... • William Raveis-New York LLC
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.
Surrey Downs
MLS 22620266 • RE/MAX Central, Lucy H Starr • RE/MAX Central
Heritage Village
3 beds
|2 baths
|1,716 sq ft
|Condo
191 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24188677 • Century 21 Bette Real Estate, Just... • Century 21 Bette Real Estate
Dutchgate
MLS 1021041 • OverSouth LLC, Michael J. Rose • OverSouth LLC
The Cottages at Wire Mill
3 beds
|4 baths
|3,244 sq ft
16 WIRE MILL RD A, STAMFORD, CT, 06903
Community: The Cottages at Wire Mill
MLS 24186279 • Houlihan Lawrence, Joy Kim Metalio... • Houlihan Lawrence
Jefferson Village
MLS 1019790 • River Realty Services, Inc., Meliss... • River Realty Services, Inc.
The Villages NJ
2 beds
|1 baths
|1,088 sq ft
|Ranch
128 KORN MARKET A, FREEHOLD, NJ, 07728
Community: The Villages NJ
MLS 22619554 • Keller Williams Realty Freehold, J... • Keller Williams Realty Freehold
Country Pointe Plainview
2 beds
|2 baths
|1,400 sq ft
|Condo
17101 ASPENWOOD DR, OYSTER BAY, NY, 1180...
Community: Country Pointe Plainview
MLS 1006877 • BH&G R E Realty Connect, Caryn D. T... • BH&G R E Realty Connect
Jefferson Village
1 beds
|1 baths
|800 sq ft
|Condo
27 WALDEN CT J, YORKTOWN, NY, 10598
Community: Jefferson Village
MLS 1017630 • Houlihan Lawrence Inc., Barbara J. ... • Houlihan Lawrence Inc.
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Billingsgate
2 beds
|3 baths
|2,729 sq ft
|Condo
14 BILLINGSGATE DR 14, SIMSBURY, CT, 060...
Community: Billingsgate
MLS 24184380 • William Pitt Sotheby's Int'l, Dian... • William Pitt Sotheby's Int'l
The Manors at The Colony Preserve
2 beds
|2 baths
|1,500 sq ft
|Condo
22 CRICKET CT, BROOKHAVEN, NY, 11967
Community: The Manors at The Colony Preserve
MLS 1018240 • Gateway to The Hamptons R E, Dari A... • Gateway to The Hamptons R E
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.
Frequently Asked Questions
Of the 1 55+ community in Westport, it is for sale. By size, 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?
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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: Oct 26, 2026.
This application does not include information on all of the properties available for sale at this time.
