Call us at (475) 471-1908 to learn more about active adult communities in Westport
Westport, CT 55+ active adult communities & homes for sale
170 communities near Westport
393 homes near Westport
Sort by:
Relevance
3.6 rating (7 reviews)
![Heritage Village]()
$200ks
- $500ks
Heritage Village, Southbury, CT
Resale Only
|
55+ age-restricted
|
Built 1967 - 2005
|
2,580 homes
2.8 rating (4 reviews)
![Cheesequake Village]()
$100ks
- $200ks
Cheesequake Village, Old Bridge, NJ
Resale Only
|
55+ age-restricted
|
Built 1965 - 1971
|
713 homes
3 rating (2 reviews)
![Heritage Hills]()
$400ks
- $800ks
Heritage Hills, Somers, NY
Resale Only
|
Age-targeted
|
Built 1974 - 2006
|
2,600 homes
4 rating (1 reviews)
![Jefferson Village]()
$100ks
- $500ks
Jefferson Village, Yorktown Heights, NY
Resale Only
|
55+ age-restricted
|
Built 1967 - 1982
|
1,000 homes
2.8 rating (5 reviews)
![The Villages NJ]()
$200ks
- $300ks
The Villages NJ, Howell, NJ
Resale Only
|
55+ age-restricted
|
Built 1967 - 1975
|
670 homes
Want to learn more about 55+ communities in Westport?
55places can help!
Questions? Call us:
(475) 471-1908
5 rating (2 reviews)
![Oronoque Village]()
$200ks
- $400ks
Oronoque Village, Stratford, CT
Resale Only
|
55+ age-restricted
|
Built 1971 - 1977
|
929 homes
4 rating (8 reviews)
![Glenwood Village]()
$100ks
- $200ks
Glenwood Village, Riverhead, NY
New and Resale
|
55+ age-restricted
|
Built 1959 - present
|
588 homes
$100ks
- $300ks
Leisure Village, Ridge, NY
Resale Only
|
55+ age-restricted
|
Built 1969 - 1986
|
1,500 homes
$300ks
- $600ks
The Waterways at Moriches, Moriches, NY
Resale Only
|
55+ age-restricted
|
Built 1985 - 1999
|
343 homes
3.7 rating (3 reviews)
![Greenwood Village]()
$100ks
Greenwood Village, Manorville, NY
Resale Only
|
55+ age-restricted
|
Built 1980 - 2000
|
512 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
- $500ks
The Village at Oxford Gre..., Oxford, CT
New and Resale
|
55+ age-restricted
|
Built 2004 - present
|
835 homes
5 rating (2 reviews)
![Shadow Lake Village]()
$200ks
- $500ks
Shadow Lake Village, Red Bank, NJ
Resale Only
|
55+ age-restricted
|
Built 1972 - 1980
|
952 homes
$300ks
- $400ks
The Manors at The Colony ..., Shirley, NY
New Construction
|
55+ age-restricted
|
Built 2013 - present
|
150 homes
5 rating (1 reviews)
![Encore Atlantic Shores]()
$500ks
- $800ks
Encore Atlantic Shores, Eastport, NY
Resale Only
|
55+ age-restricted
|
Built 2004 - 2011
|
240 homes
$600ks
- $1Ms
The Greens at Half Hollow, Melville, NY
Resale Only
|
55+ age-restricted
|
Built 1994 - 2005
|
1,200 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 Westport?
55places can help!
Questions? Call us:
(475) 471-1908
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
$400ks
- $600ks
Fairview at Oxford Greens, Oxford, CT
New and Resale
|
55+ age-restricted
|
Built 2019 - present
|
125 homes
4.2 rating (12 reviews)
![Surrey Downs]()
$200ks
- $300ks
Surrey Downs, Freehold, NJ
Resale Only
|
55+ age-restricted
|
Built 1986 - 1997
|
443 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
Leisure Glen, Ridge, NY
Resale Only
|
55+ age-restricted
|
Built 1985 - 2010
|
646 homes
$300ks
- $500ks
Dutchgate, Valley Stream, NY
Resale Only
|
55+ age-restricted
|
Built 2009 - 2015
|
348 homes
$500ks
Stoneleigh Woods at River..., Riverhead, NY
Resale Only
|
55+ age-restricted
|
Built 2007 - 2016
|
176 homes
$300ks
- $900ks
Rivington, Danbury, CT
New and Resale
|
Age-targeted
|
Built 2006 - present
|
1,050 homes
$300ks
- $400ks
Regency at Fishkill, Fishkill, NY
Resale Only
|
55+ age-restricted
|
Built 2008 - 2020
|
164 homes
$100ks
- $200ks
Spring Lake Village, Southington, CT
Resale Only
|
55+ age-restricted
|
Built 1970 - 2004
|
640 homes
Want to learn more about 55+ communities in Westport?
55places can help!
Questions? Call us:
(475) 471-1908
$500ks
- $700ks
Glassbury Court at Cold S..., Cold Spring, NY
Resale Only
|
55+ age-restricted
|
Built 2009 - 2014
|
90 homes
$200ks
- $400ks
Leisure Knoll, Ridge, NY
Resale Only
|
55+ age-restricted
|
Built 1972 - 1982
|
701 homes
$800ks
- $1Ms
HarborView, Port Washington, NY
Resale Only
|
55+ age-restricted
|
Built 2002 - 2004
|
270 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)
![Newtown Woods]()
$300ks
- $500ks
Newtown Woods, Newtown, CT
New and Resale
|
55+ age-restricted
|
Built 2011 - present
|
178 homes
5 rating (1 reviews)
![The Villas at Jumping Bro...]()
$300ks
- $500ks
The Villas at Jumping Bro..., Neptune Township, NJ
Resale Only
|
55+ age-restricted
|
Built 2001 - 2003
|
168 homes
$600ks
- $800ks
Four Seasons at Colts Far..., Farmingdale, NJ
New Construction
|
55+ age-restricted
|
Built 2021 - present
|
111 homes
5 rating (1 reviews)
![Westhampton Pines]()
$900ks
- $1Ms
Westhampton Pines, Westhampton, NY
Resale Only
|
55+ age-restricted
|
Built 2005 - 2013
|
189 homes
$600ks
- $700ks
Equestra at Colts Neck Cr..., Farmingdale, NJ
Resale Only
|
55+ age-restricted
|
Built 2007 - 2018
|
483 homes
$400ks
- $600ks
Winthrop Court, Clifton, NJ
Resale Only
|
55+ age-restricted
|
Built 2000 - 2010
|
270 homes
$800ks
- $900ks
The Seasons at Elwood, East Northport, NY
Resale Only
|
55+ age-restricted
|
Built 2018 - 2020
|
256 homes
$400ks
- $500ks
Vineyards at Brookfield, Center Moriches, NY
New Construction
|
55+ age-restricted
|
Built 2019 - present
|
146 homes
Want to learn more about 55+ communities in Westport?
55places can help!
Questions? Call us:
(475) 471-1908
$200ks
- $400ks
The Views at Pomona, Pomona, NY
Resale Only
|
55+ age-restricted
|
Built 2011 - 2011
|
56 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.
Jefferson Village
![39 SUSSEX DR B, YORKTOWN, NY, 10598, Yorktown, NY 10598]()
2 beds
|2 baths
|1,000 sq ft
|Condo
39 SUSSEX DR B, YORKTOWN, NY, 10598
Community: Jefferson Village
MLS 1028904 • Coldwell Banker Realty, Mary L. Cra... • Coldwell Banker Realty
Heritage Village
![345 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
3 beds
|2 baths
|1,716 sq ft
|Condo
345 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24196164 • Keller Williams Realty, Marvin Ben... • Keller Williams Realty
Greenwood Village
![105 W VILLAGE CIR 105, BROOKHAVEN, NY, 1..., Brookhaven, NY 11949]()
2 beds
|2 baths
|1,130 sq ft
|Condo
105 W VILLAGE CIR 105, BROOKHAVEN, NY, 1...
Community: Greenwood Village
MLS 1029061 • Gateway to The Hamptons R E, Janet ... • Gateway to The Hamptons R E
The Villages NJ
![41 PIAZZA SAN PAOLA C, FREEHOLD, NJ, 077..., Freehold, NJ 07728]()
2 beds
|2 baths
|1,008 sq ft
|Ranch
41 PIAZZA SAN PAOLA C, FREEHOLD, NJ, 077...
Community: The Villages NJ
MLS 22621215 • Coldwell Banker Realty, Karen Alba... • Coldwell Banker Realty
Glenwood Village
![1661 OLD COUNTRY RD 516, RIVERHEAD, NY, ..., Riverhead, NY 11901]()
2 beds
|2 baths
|1,624 sq ft
|Manufactured Home
1661 OLD COUNTRY RD 516, RIVERHEAD, NY, ...
Community: Glenwood Village
MLS 1011541 • Gateway to The Hamptons R E, Vivian... • Gateway to The Hamptons R E
Want to learn more about 55+ communities in Westport?
55places can help!
Questions? Call us:
(475) 471-1908
New
Rivington
![11 MERCY ST 11, DANBURY, CT, 06810, Danbury, CT 06810]()
MLS 24199575 • Keller Williams Realty Partner, Ce... • Keller Williams Realty Partner
New
Greenwood Village
![162 VILLAGE CIR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949]()
2 beds
|2 baths
|1,078 sq ft
|Condo
162 VILLAGE CIR, BROOKHAVEN, NY, 11949
Community: Greenwood Village
MLS 1039145 • Coldwell Banker American Homes, Rya... • Coldwell Banker American Homes
New
Jefferson Village
![45 JEFFERSON OVAL H, YORKTOWN, NY, 10598, Yorktown, NY 10598]()
2 beds
|2 baths
|1,100 sq ft
|Condo
45 JEFFERSON OVAL H, YORKTOWN, NY, 10598
Community: Jefferson Village
MLS 1031552 • Coldwell Banker Realty, Linda Gottl... • Coldwell Banker Realty
New
Leisure Glen
![272 GLEN DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961]()
MLS 1039018 • Signature Premier Properties, Mildr... • 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.
New
Shadow Lake Village
![52 EASTPORT CT, RED BANK, NJ, 07701, Red Bank, NJ 07701]()
MLS 22625378 • Coldwell Banker Realty, Christine ... • Coldwell Banker Realty
New
Spring Lake Village
![853 GLACIER WAY 853, SOUTHINGTON, CT, 06..., Southington, CT 06489]()
2 beds
|2 baths
|1,226 sq ft
|Condo
853 GLACIER WAY 853, SOUTHINGTON, CT, 06...
Community: Spring Lake Village
MLS 24199208 • Berkshire Hathaway NE Prop., Carri... • Berkshire Hathaway NE Prop.
New
Heritage Hills
![790 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589]()
2 beds
|2 baths
|1,296 sq ft
|Condo
790 HERITAGE HLS B, SOMERS, NY, 10589
Community: Heritage Hills
MLS 1036450 • Billingsley Realty, Maureen O'keefe... • Billingsley Realty
New
Woodridge Strathmore Terrace
![62 HEARTHSIDE DR, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766]()
2 beds
|2 baths
|1,105 sq ft
|Condo
62 HEARTHSIDE DR, BROOKHAVEN, NY, 11766
Community: Woodridge Strathmore Terrace
MLS 1033093 • Douglas Elliman Real Estate, Christ... • Douglas Elliman Real Estate
New
Shadow Lake Village
![48 ELLSWORTH CT, RED BANK, NJ, 07701, Red Bank, NJ 07701]()
MLS 22625205 • Compass New Jersey LLC, Leonora La... • Compass New Jersey LLC
New
The Villages NJ
![80 PARKWAY DR D, FREEHOLD, NJ, 07728, Freehold, NJ 07728]()
2 beds
|2 baths
|1,262 sq ft
|Adult Community
80 PARKWAY DR D, FREEHOLD, NJ, 07728
Community: The Villages NJ
MLS 22625226 • RE/MAX Realty 9, Jay Kline • RE/MAX Realty 9
Want to learn more about 55+ communities in Westport?
55places can help!
Questions? Call us:
(475) 471-1908
New
Meadow Brook Estates
![107 MEADOW BROOK RD 107, OXFORD, CT, 064..., Oxford, CT 06478]()
3 beds
|3 baths
|1,922 sq ft
107 MEADOW BROOK RD 107, OXFORD, CT, 064...
Community: Meadow Brook Estates
MLS 24197945 • Coldwell Banker Realty, Joseph Pau... • Coldwell Banker Realty
New
Shaker Heights
![12 COPLEY CIR 12, ENFIELD, CT, 06082, Enfield, CT 06082]()
2 beds
|2 baths
|1,897 sq ft
|Condo
12 COPLEY CIR 12, ENFIELD, CT, 06082
Community: Shaker Heights
MLS 24182563 • BHHS Realty Professionals, Jennife... • BHHS Realty Professionals
New
The Powder Forest Homes
![9 GRISWOLD PL 9, SIMSBURY, CT, 06070, Simsbury, CT 06070]()
3 beds
|5 baths
|2,774 sq ft
9 GRISWOLD PL 9, SIMSBURY, CT, 06070
Community: The Powder Forest Homes
MLS 24198799 • Berkshire Hathaway NE Prop., Kris ... • Berkshire Hathaway NE Prop.
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
Woodcrest at Jacobs Hill
![1104 JACOBS HILL RD, CORTLANDT, NY, 1056..., Cortlandt, NY 10567]()
2 beds
|2 baths
|1,145 sq ft
|House
1104 JACOBS HILL RD, CORTLANDT, NY, 1056...
Community: Woodcrest at Jacobs Hill
MLS 1031066 • Houlihan Lawrence Inc., Masayuki M.... • Houlihan Lawrence Inc.
New
Heritage Village
![65 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
1 beds
|1 baths
|928 sq ft
|Condo
65 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24198765 • Century 21 Bette Real Estate, Just... • Century 21 Bette Real Estate
New
Heritage Village
![261B HERITAGE VLG, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,032 sq ft
|Condo
261B HERITAGE VLG, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24198823 • Coldwell Banker Realty, Anne Stark • Coldwell Banker Realty
New
Westhampton Pines
![179 CARLY LN, SOUTHAMPTON, NY, 11977, Southampton, NY 11977]()
2 beds
|2 baths
|2,000 sq ft
|Condo
179 CARLY LN, SOUTHAMPTON, NY, 11977
Community: Westhampton Pines
MLS 1036953 • Compass Greater NY LLC, Maria C. Cu... • Compass Greater NY LLC
New
Heritage Village
![1016 HERITAGE VLG A, SOUTHBURY, CT, 0648..., Southbury, CT 06488]()
1 beds
|1 baths
|928 sq ft
|Condo
1016 HERITAGE VLG A, SOUTHBURY, CT, 0648...
Community: Heritage Village
MLS 24198857 • Century 21 Bette Real Estate, Just... • Century 21 Bette Real Estate
New
Nobility Crest at Ocean
![7 CENTRE ST 5301, OCEAN TWP, NJ, 07712, Ocean Twp, NJ 07712]()
2 beds
|2 baths
|1,327 sq ft
|Adult Community
7 CENTRE ST 5301, OCEAN TWP, NJ, 07712
Community: Nobility Crest at Ocean
MLS 22625070 • Coldwell Banker Realty, Kim L Spec... • Coldwell Banker Realty
New
Spring Lake Village
![504 CARRIAGE DR 504, SOUTHINGTON, CT, 06..., Southington, CT 06489]()
2 beds
|2 baths
|1,313 sq ft
|Condo
504 CARRIAGE DR 504, SOUTHINGTON, CT, 06...
Community: Spring Lake Village
MLS 24198897 • Beycome of Connecticut, Steven Kol... • Beycome of Connecticut
Want to learn more about 55+ communities in Westport?
55places can help!
Questions? Call us:
(475) 471-1908
New
Oronoque Village
![522 IROQUOIS LN B, STRATFORD, CT, 06614, Stratford, CT 06614]()
MLS 24176404 • Oronoque Real Estate, Monica Dalto... • Oronoque Real Estate
New
Shadow Lake Village
![76 MANCHESTER CT, RED BANK, NJ, 07701, Red Bank, NJ 07701]()
2 beds
|1 baths
|1,021 sq ft
|Adult Community
76 MANCHESTER CT, RED BANK, NJ, 07701
Community: Shadow Lake Village
MLS 22624976 • Real Broker, LLC- Red Bank, Kim Ta... • Real Broker, LLC- Red Bank
New
Stoneleigh Woods at Riverhead
![158 STONELEIGH DR, RIVERHEAD, NY, 11901, Riverhead, NY 11901]()
2 beds
|3 baths
|2,071 sq ft
|Condo
158 STONELEIGH DR, RIVERHEAD, NY, 11901
Community: Stoneleigh Woods at Riverhead
MLS 1036536 • Douglas Elliman Real Estate, Patric... • Douglas Elliman Real Estate
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
Heritage Hills
![220 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589]()
3 beds
|2 baths
|1,689 sq ft
|Condo
220 HERITAGE HLS B, SOMERS, NY, 10589
Community: Heritage Hills
MLS 1034987 • William Raveis Real Estate, Katheri... • William Raveis Real Estate
New
The Seasons at East Meadow
![421 AUTUMN DR, HEMPSTEAD, NY, 11554, Hempstead, NY 11554]()
2 beds
|2 baths
|1,272 sq ft
|Condo
421 AUTUMN DR, HEMPSTEAD, NY, 11554
Community: The Seasons at East Meadow
MLS 1036497 • BH&G R E Realty Connect, Kathleen A... • BH&G R E Realty Connect
New
Country Pointe Preserve
![128 JUNIPER LN 26, BROOKHAVEN, NY, 11980, Brookhaven, NY 11980]()
2 beds
|3 baths
|1,998 sq ft
|Condo
128 JUNIPER LN 26, BROOKHAVEN, NY, 11980
Community: Country Pointe Preserve
MLS 1037832 • Premier Prop At Meadowbrook Pt, Rob... • Premier Prop At Meadowbrook Pt
New
Apple Ridge
![239 WESTERVELT LN, MAHWAH TWP., NJ, 0743..., Mahwah Twp., NJ 07430]()
MLS 4046296 • KELLER WILLIAMS TOWN LIFE, KELLER W... • KELLER WILLIAMS TOWN LIFE
The Villages NJ
![42 PIAZZA CORREALE B, FREEHOLD, NJ, 0772..., Freehold, NJ 07728]()
MLS 22624876 • RE/MAX Central, Iris Silverberg • RE/MAX Central
Rivington
![424 CENTER MEADOW LN 424, DANBURY, CT, 0..., Danbury, CT 06810]()
2 beds
|2 baths
|1,258 sq ft
|Condo
424 CENTER MEADOW LN 424, DANBURY, CT, 0...
Community: Rivington
MLS 24198556 • Century 21 AllPoints Realty, Ginge... • Century 21 AllPoints Realty
Windmill Gate
![18 KATHLEEN DR, ISLIP, NY, 11769, Islip, NY 11769]()
MLS 1037151 • Keller Williams Realty Elite, Joan ... • Keller Williams Realty Elite
Country Pointe Plainview
![52102 BEECH TREE LN, OYSTER BAY, NY, 118..., Oyster Bay, NY 11803]()
2 beds
|3 baths
|1,750 sq ft
|Condo
52102 BEECH TREE LN, OYSTER BAY, NY, 118...
Community: Country Pointe Plainview
MLS 1037006 • Douglas Elliman Real Estate, Ronni ... • Douglas Elliman Real Estate
Want to learn more about 55+ communities in Westport?
55places can help!
Questions? Call us:
(475) 471-1908
Glenwood Village
![1661 OLD COUNTRY RD 454, RIVERHEAD, NY, ..., Riverhead, NY 11901]()
2 beds
|2 baths
|1,152 sq ft
|Manufactured Home
1661 OLD COUNTRY RD 454, RIVERHEAD, NY, ...
Community: Glenwood Village
MLS 1037492 • Signature Premier Properties, Noree... • Signature Premier Properties
The Seasons at Elwood
![63 WINTER PL, HUNTINGTON, NY, 11731, Huntington, NY 11731]()
2 beds
|2 baths
|1,108 sq ft
|Condo
63 WINTER PL, HUNTINGTON, NY, 11731
Community: The Seasons at Elwood
MLS 1037047 • Michael J Watts & Assoc Inc, Michae... • Michael J Watts & Assoc Inc
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
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.
On average, listings in 55+ community in Westport stay on the market for around 19 days. The average price of homes for sale in this community is approximately $459,000, though prices can range widely based on the size, location, and amenities of the community. For example, homes in Whitney Glen average around $459,000.
Want more information about active adult communities around Westport?
Want to learn more about 55+ communities in Westport?
170
communities
Remove Boundaries ×
Map
Satellite
The listings data displayed on this medium comes in part from the Real Estate Information Network Inc. (REIN) and has been authorized by participating listing Broker Members of REIN for display. REIN's listings are based upon Data submitted by its Broker Members, and REIN therefore makes no representation or warranty regarding the accuracy of the Data. All users of REIN's listings database should confirm the accuracy of the listing information directly with the listing agent.
© 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: Aug 17, 2026.
This application does not include information on all of the properties available for sale at this time.
