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
359 homes near Westport
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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
2.8 rating (4 reviews)
![Cheesequake Village]()
$100ks
- $200ks
Cheesequake Village, Old Bridge, NJ
Resale Only
|
55+ age-restricted
|
Built 1965 - 1971
|
713 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
4 rating (1 reviews)
![Jefferson Village]()
$100ks
- $500ks
Jefferson Village, Yorktown Heights, NY
Resale Only
|
55+ age-restricted
|
Built 1967 - 1982
|
1,000 homes
$100ks
- $300ks
Leisure Village, Ridge, NY
Resale Only
|
55+ age-restricted
|
Built 1969 - 1986
|
1,500 homes
Want to learn more about 55+ communities in Westport?
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(475) 471-1908
$200ks
- $400ks
Oronoque Village, Stratford, CT
Resale Only
|
55+ age-restricted
|
Built 1971 - 1977
|
929 homes
3 rating (2 reviews)
![Heritage Hills]()
$400ks
- $800ks
Heritage Hills, Somers, NY
Resale Only
|
Age-targeted
|
Built 1974 - 2006
|
2,600 homes
4.2 rating (12 reviews)
![Surrey Downs]()
$200ks
- $300ks
Surrey Downs, Freehold, NJ
Resale Only
|
55+ age-restricted
|
Built 1986 - 1997
|
443 homes
$300ks
- $600ks
The Waterways at Moriches, Moriches, NY
Resale Only
|
55+ age-restricted
|
Built 1985 - 1999
|
343 homes
$200ks
- $400ks
Leisure Knoll, Ridge, NY
Resale Only
|
55+ age-restricted
|
Built 1972 - 1982
|
701 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
Greenwood Village, Manorville, NY
Resale Only
|
55+ age-restricted
|
Built 1980 - 2000
|
512 homes
$600ks
- $1Ms
The Greens at Half Hollow, Melville, NY
Resale Only
|
55+ age-restricted
|
Built 1994 - 2005
|
1,200 homes
$300ks
- $400ks
Regency at Fishkill, Fishkill, NY
Resale Only
|
55+ age-restricted
|
Built 2008 - 2020
|
164 homes
$400ks
- $500ks
The Village at Oxford Gre..., Oxford, CT
New and Resale
|
55+ age-restricted
|
Built 2004 - present
|
835 homes
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(475) 471-1908
$300ks
- $400ks
The Manors at The Colony ..., Shirley, NY
New Construction
|
55+ age-restricted
|
Built 2013 - present
|
150 homes
4 rating (8 reviews)
![Glenwood Village]()
$100ks
- $200ks
Glenwood Village, Riverhead, NY
New and Resale
|
55+ age-restricted
|
Built 1959 - present
|
588 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
$700ks
- $1Ms
Meadowbrook Pointe Athlet..., Westbury, NY
Resale Only
|
55+ age-restricted
|
Built 2015 - 2016
|
720 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)
![The Villages at Mount Sin...]()
$600ks
The Villages at Mount Sin..., Mount Sinai, NY
Resale Only
|
55+ age-restricted
|
Built 2005 - 2007
|
185 homes
$600ks
- $700ks
Equestra at Colts Neck Cr..., Farmingdale, NJ
Resale Only
|
55+ age-restricted
|
Built 2007 - 2018
|
483 homes
$800ks
- $900ks
The Seasons at Elwood, East Northport, NY
Resale Only
|
55+ age-restricted
|
Built 2018 - 2020
|
256 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
$600ks
The Seasons at Seaford, Seaford, NY
Resale Only
|
55+ age-restricted
|
Built 2015 - 2017
|
112 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
5 rating (1 reviews)
![Four Seasons at Great Not...]()
$400ks
- $700ks
Four Seasons at Great Not..., Woodland Park, NJ
Resale Only
|
55+ age-restricted
|
Built 2005 - 2018
|
814 homes
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(475) 471-1908
$500ks
- $700ks
The Summit at Bethel, Bethel, CT
Resale Only
|
55+ age-restricted
|
Built 2010 - 2021
|
235 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
$300ks
- $400ks
South Pond Village, Bloomfield, CT
Resale Only
|
55+ age-restricted
|
Built 1999 - 2005
|
151 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
3.7 rating (3 reviews)
![Rosemont Estates]()
$500ks
- $700ks
Rosemont Estates, Marlboro, NJ
Resale Only
|
55+ age-restricted
|
Built 2004 - 2014
|
242 homes
$300ks
- $400ks
Eagles Walk at East Quogu..., East Quogue, NY
Resale Only
|
55+ age-restricted
|
Built 2004 - 2014
|
67 homes
$700ks
- $1Ms
Country Pointe Plainview, Plainview, NY
New Construction
|
55+ age-restricted
|
Built 2017 - present
|
660 homes
$600ks
- $1Ms
HarborView, Port Washington, NY
Resale Only
|
55+ age-restricted
|
Built 2002 - 2004
|
270 homes
5 rating (1 reviews)
![Sunken Pond Estates]()
$400ks
Sunken Pond Estates, Riverhead, NY
Resale Only
|
55+ age-restricted
|
Built 2003 - 2005
|
194 homes
$500ks
Breton Hills, Glen Cove, NY
New Construction
|
55+ age-restricted
|
Built 2019 - present
|
72 homes
$500ks
Stoneleigh Woods at River..., Riverhead, NY
Resale Only
|
55+ age-restricted
|
Built 2007 - 2016
|
176 homes
Want to learn more about 55+ communities in Westport?
55places can help!
Questions? Call us:
(475) 471-1908
3.5 rating (2 reviews)
![Foxwood Village]()
$200ks
- $400ks
Foxwood Village, Calverton, NY
Resale Only
|
55+ age-restricted
|
Built 1986 - 2007
|
294 homes
$300ks
- $400ks
Regency at Prospect, Prospect, CT
Resale Only
|
55+ age-restricted
|
Built 2006 - 2020
|
379 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.
Heritage Hills
![567 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589]()
1 beds
|2 baths
|967 sq ft
|Condo
567 HERITAGE HLS B, SOMERS, NY, 10589
Community: Heritage Hills
MLS 987091 • Coldwell Banker Realty, Sherri Malon...
New
Glassbury Court at Cold Spring
![28 YESTERDAY DR, PHILIPSTOWN, NY, 10516, Philipstown, NY 10516]()
2 beds
|2 baths
|2,071 sq ft
|House
28 YESTERDAY DR, PHILIPSTOWN, NY, 10516
Community: Glassbury Court at Cold Spring
MLS 1010018 • William Raveis-New York LLC, Lance ...
New
Four Seasons at Great Notch Spa and Club
![5 SLATE CT A3, WOODLAND PARK, NJ, 07424, Woodland Park, NJ 07424]()
2 beds
|2 baths
|Condo
5 SLATE CT A3, WOODLAND PARK, NJ, 07424
Community: Four Seasons at Great Notch Spa and Club
MLS 26020991 • Berkshire Hathaway Home Services V...
New
Heritage Village
![18 HERITAGE CRST D, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
3 beds
|2 baths
|1,735 sq ft
|Condo
18 HERITAGE CRST D, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24181734 • William Raveis Real Estate, Betty ...
New
Fairview at Oxford Greens
![1131 ST ANDREWS DR 50, OXFORD, CT, 06478, Oxford, CT 06478]()
2 beds
|3 baths
|2,536 sq ft
|Condo
1131 ST ANDREWS DR 50, OXFORD, CT, 06478
Community: Fairview at Oxford Greens
MLS 24181733 • EG Group Realty LLC, Jason Helton
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(475) 471-1908
New
The Village at Oxford Greens
![1131 ST ANDREWS DR 50, OXFORD, CT, 06478, Oxford, CT 06478]()
2 beds
|3 baths
|2,536 sq ft
|Condo
1131 ST ANDREWS DR 50, OXFORD, CT, 06478
Community: The Village at Oxford Greens
MLS 24181733 • EG Group Realty LLC, Jason Helton
New
Country Village Estates
![114 THEODORE DR, BROOKHAVEN, NY, 11727, Brookhaven, NY 11727]()
2 beds
|2 baths
|1,198 sq ft
|Condo
114 THEODORE DR, BROOKHAVEN, NY, 11727
Community: Country Village Estates
MLS 1008742 • Coldwell Banker American Homes, Ang...
New
The Seasons at Seaford
![54 SPRING DR, HEMPSTEAD, NY, 11783, Hempstead, NY 11783]()
2 beds
|2 baths
|1,034 sq ft
|Condo
54 SPRING DR, HEMPSTEAD, NY, 11783
Community: The Seasons at Seaford
MLS 1009935 • Signature Premier Properties, Valer...
New
Heritage Village
![28 HERITAGE CRST E, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
3 beds
|2 baths
|1,735 sq ft
|Condo
28 HERITAGE CRST E, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24180783 • Berkshire Hathaway NE Prop., Maria...
New
Sunken Pond Estates
![2201 PEBBLE BEACH PATH 2201, RIVERHEAD, ..., Riverhead, NY 11901]()
2 beds
|2 baths
|1,258 sq ft
|Condo
2201 PEBBLE BEACH PATH 2201, RIVERHEAD, ...
Community: Sunken Pond Estates
MLS 1004037 • Douglas Elliman Real Estate, Patric...
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
Encore Atlantic Shores
![177 MELODY CT, BROOKHAVEN, NY, 11941, Brookhaven, NY 11941]()
2 beds
|2 baths
|2,150 sq ft
|Condo
177 MELODY CT, BROOKHAVEN, NY, 11941
Community: Encore Atlantic Shores
MLS 1008548 • Corcoran, Merle Buff
New
The Village Grande at Holmdel
![22 HYACINTH CT, HOLMDEL, NJ, 07733, Holmdel, NJ 07733]()
2 beds
|3 baths
|2,273 sq ft
|House
22 HYACINTH CT, HOLMDEL, NJ, 07733
Community: The Village Grande at Holmdel
MLS 22616840 • Heritage House Sotheby's Internati...
New
Shadow Lake Village
![46 FRIENDSHIP CT, RED BANK, NJ, 07701, Red Bank, NJ 07701]()
2 beds
|2 baths
|1,108 sq ft
|House
46 FRIENDSHIP CT, RED BANK, NJ, 07701
Community: Shadow Lake Village
MLS 22616805 • RE/MAX Central, Nancy Coviello
New
The Seasons at East Meadow
![115 SPRING DR, HEMPSTEAD, NY, 11554, Hempstead, NY 11554]()
2 beds
|2 baths
|1,367 sq ft
|Condo
115 SPRING DR, HEMPSTEAD, NY, 11554
Community: The Seasons at East Meadow
MLS 1008332 • Howard Hanna Coach, Lynn D. Witz
New
The Waterways at Moriches
![376 QUARRY POND CT, BROOKHAVEN, NY, 1195..., Brookhaven, NY 11955]()
2 beds
|2 baths
|1,440 sq ft
|Condo
376 QUARRY POND CT, BROOKHAVEN, NY, 1195...
Community: The Waterways at Moriches
MLS 1009291 • Realty Connect USA L I Inc, Roseann...
Want to learn more about 55+ communities in Westport?
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Questions? Call us:
(475) 471-1908
New
Meadowbrook Pointe Athletic Club & Spa
![236 ROOSEVELT WAY 3306, HEMPSTEAD, NY, 1..., Hempstead, NY 11590]()
2 beds
|2 baths
|1,349 sq ft
|Condo
236 ROOSEVELT WAY 3306, HEMPSTEAD, NY, 1...
Community: Meadowbrook Pointe Athletic Club & Spa
MLS 1003898 • Douglas Elliman Real Estate, Matthe...
New
Cheesequake Village
![67 GALEWOOD DR B, OLD BRIDGE, NJ, 07747, Old Bridge, NJ 07747]()
MLS 2617001R • EXP REALTY, LLC, THEODORE KOCZON
New
The Waterways at Moriches
![519 HIGHLAND CT, BROOKHAVEN, NY, 11955, Brookhaven, NY 11955]()
2 beds
|2 baths
|1,497 sq ft
|Condo
519 HIGHLAND CT, BROOKHAVEN, NY, 11955
Community: The Waterways at Moriches
MLS 1008592 • Douglas Elliman Real Estate, Jo Ann...
New
Fairfield at St. James
![1003 GOTHAM DR, SMITHTOWN, NY, 11780, Smithtown, NY 11780]()
2 beds
|2 baths
|1,321 sq ft
|Condo
1003 GOTHAM DR, SMITHTOWN, NY, 11780
Community: Fairfield at St. James
MLS 1008586 • Signature Premier Properties, Debor...
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
Fairfield at St. James
![409 ELTON CT, SMITHTOWN, NY, 11780, Smithtown, NY 11780]()
3 beds
|3 baths
|1,733 sq ft
|Condo
409 ELTON CT, SMITHTOWN, NY, 11780
Community: Fairfield at St. James
MLS 1008656 • Signature Premier Properties, Debor...
New
Country Pointe Plainview
![15103 ASPENWOOD DR, OYSTER BAY, NY, 1180..., Oyster Bay, NY 11803]()
2 beds
|2 baths
|1,335 sq ft
|Condo
15103 ASPENWOOD DR, OYSTER BAY, NY, 1180...
Community: Country Pointe Plainview
MLS 1006637 • Realty Connect USA LLC, Caryn D. Ty...
New
Jefferson Village
![51 JEFFERSON OVAL E, YORKTOWN, NY, 10598, Yorktown, NY 10598]()
2 beds
|2 baths
|1,100 sq ft
|Condo
51 JEFFERSON OVAL E, YORKTOWN, NY, 10598
Community: Jefferson Village
MLS 1008809 • DeMarsh Properties Inc., Carla DeMa...
New
Oronoque Village
![44 BUCKSKIN LN A, STRATFORD, CT, 06614, Stratford, CT 06614]()
2 beds
|2 baths
|1,400 sq ft
|Condo
44 BUCKSKIN LN A, STRATFORD, CT, 06614
Community: Oronoque Village
MLS 24180732 • Coldwell Banker Realty, Alicia Hal...
New
Cheesequake Village
![67 GALEWOOD DR B, MATAWAN, NJ, 07747, Matawan, NJ 07747]()
2 beds
|1 baths
|914 sq ft
|Adult Community
67 GALEWOOD DR B, MATAWAN, NJ, 07747
Community: Cheesequake Village
MLS 22616622 • EXP Realty, Theodore Koczon
New
The Vineyards at Mount Sinai
![51 FARM ACRE CIR, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766]()
2 beds
|3 baths
|3,214 sq ft
|Condo
51 FARM ACRE CIR, BROOKHAVEN, NY, 11766
Community: The Vineyards at Mount Sinai
MLS 1008377 • Pinpoint Realty LI, Maryann Kelly
Want to learn more about 55+ communities in Westport?
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(475) 471-1908
New
Heritage Village
![29 HERITAGE VLG D, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,076 sq ft
|Condo
29 HERITAGE VLG D, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24180713 • Berkshire Hathaway NE Prop., Jacqu...
New
Oronoque Village
![513 OPA LN A, STRATFORD, CT, 06614, Stratford, CT 06614]()
2 beds
|3 baths
|1,620 sq ft
|Condo
513 OPA LN A, STRATFORD, CT, 06614
Community: Oronoque Village
MLS 24178763 • Coldwell Banker Realty, Michael Si...
New
Heritage Hills
![900 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589]()
2 beds
|3 baths
|1,552 sq ft
|Condo
900 HERITAGE HLS B, SOMERS, NY, 10589
Community: Heritage Hills
MLS 1007130 • Houlihan Lawrence Inc., Barbara Har...
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
Meadowbrook Pointe Athletic Club & Spa
![318 ROOSEVELT WAY, NORTH HEMPSTEAD, NY, ..., North Hempstead, NY 11590]()
2 beds
|2 baths
|1,438 sq ft
|Condo
318 ROOSEVELT WAY, NORTH HEMPSTEAD, NY, ...
Community: Meadowbrook Pointe Athletic Club & Spa
MLS 1006313 • Realty Connect USA LLC, Nancy J. Pe...
New
Apple Ridge
![143 FISHER RD, MAHWAH TWP., NJ, 07430, Mahwah Twp., NJ 07430]()
MLS 4031895 • TERRIE O'CONNOR REALTORS, TERRIE O'...
New
The Summit at Bethel
![50 GREAT HILL DR, BETHEL, CT, 06801, Bethel, CT 06801]()
2 beds
|3 baths
|1,623 sq ft
|Condo
50 GREAT HILL DR, BETHEL, CT, 06801
Community: The Summit at Bethel
MLS 24178005 • Coldwell Banker Realty, Kim Giffor...
New
Regency at Prospect
![59 CHERRY CIR 59, PROSPECT, CT, 06712, Prospect, CT 06712]()
2 beds
|3 baths
|2,067 sq ft
|Condo
59 CHERRY CIR 59, PROSPECT, CT, 06712
Community: Regency at Prospect
MLS 24176447 • Pavlik Real Estate LLC, Deborah Ri...
New
Harbor View Estates
![206 ANCHOR CT, BABYLON, NY, 11726, Babylon, NY 11726]()
2 beds
|2 baths
|1,200 sq ft
|Condo
206 ANCHOR CT, BABYLON, NY, 11726
Community: Harbor View Estates
MLS 1004792 • Douglas Elliman Real Estate, Phoebe...
Regency at Fishkill
![835 REGENCY DR, FISHKILL, NY, 12524, Fishkill, NY 12524]()
2 beds
|2 baths
|1,803 sq ft
|Condo
835 REGENCY DR, FISHKILL, NY, 12524
Community: Regency at Fishkill
MLS 1007847 • Houlihan Lawrence Inc., Jennifer St...
Four Seasons at Colts Farm
![62 SANCTUARY LN, FARMINGDALE, NJ, 07727, Farmingdale, NJ 07727]()
2 beds
|2 baths
|2,023 sq ft
|House
62 SANCTUARY LN, FARMINGDALE, NJ, 07727
Community: Four Seasons at Colts Farm
MLS 22616356 • Christie's Int'l RE Group, Ruth Bl...
Want to learn more about 55+ communities in Westport?
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(475) 471-1908
South Pond Village
![174 THISTLE POND DR 174, BLOOMFIELD, CT,..., Bloomfield, CT 06002]()
2 beds
|2 baths
|1,535 sq ft
|Condo
174 THISTLE POND DR 174, BLOOMFIELD, CT,...
Community: South Pond Village
MLS 24180284 • Berkshire Hathaway NE Prop., Lisa ...
Oronoque Village
![778 QUINNIPIAC LN A, STRATFORD, CT, 0661..., Stratford, CT 06614]()
1 beds
|3 baths
|1,175 sq ft
|Condo
778 QUINNIPIAC LN A, STRATFORD, CT, 0661...
Community: Oronoque Village
MLS 24176136 • Coldwell Banker Realty, Mary Kelle...
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 13 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?
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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: Jun 07, 2026.
This application does not include information on all of the properties available for sale at this time.
