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Westport, CT 55+ active adult communities & homes for sale - Page 3
168 communities near Westport
305 homes near Westport
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$400ks
- $600ks
Harbor View Estates, Copiague, NY
New Construction
|
55+ age-restricted
|
Built 2017 - 2018
|
40 homes
$500ks
- $600ks
The Residences at Butterf..., Cold Spring, NY
Resale Only
|
55+ age-restricted
|
Built 2018 - 2023
|
49 homes
$800ks
- $900ks
The Seasons at Elwood, East Northport, NY
Resale Only
|
55+ age-restricted
|
Built 2018 - 2020
|
256 homes
$1Ms
Jessup's Landing, Quogue, NY
New and Resale
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55+ age-restricted
|
Built 2009 - 2016
|
31 homes
$500ks
- $600ks
Meadowbrooke Pointe East ..., East Meadow, NY
New Construction
|
62+ age-restricted
|
Built 2019 - present
|
104 homes
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$500ks
- $600ks
Hidden Harbor Estates, Copiague, NY
Resale Only
|
55+ age-restricted
|
Built 2010 - 2015
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38 homes
$400ks
- $500ks
Vineyards at Brookfield, Center Moriches, NY
New Construction
|
55+ age-restricted
|
Built 2019 - present
|
146 homes
$400ks
- $500ks
The Pines at Bohemia, Bohemia, NY
New Construction
|
55+ age-restricted
|
Built 2019 - present
|
20 homes
$600ks
- $700ks
The Polo Club at Islandia, Islandia, NY
New Construction
|
55+ age-restricted
|
Built 2019 - present
|
72 homes
Download the Ultimate 55+ Homebuying Guide
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$600ks
- $800ks
Stratford Park, Melville, NY
Resale Only
|
55+ age-restricted
|
Built 2011 - 2013
|
36 homes
Read the Ultimate 55+ Rental Guide
Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
$500ks
- $700ks
The Village Grande at Hol..., Holmdel, NJ
Resale Only
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55+ age-restricted
|
Built 1998 - present
|
115 homes
$600ks
The Bridges at Oxford Gre..., Oxford, CT
New Construction
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55+ age-restricted
|
Built 2025 - present
|
99 homes
$500ks
- $400ks
Applegate Estates, Southington, CT
New and Resale
|
55+ age-restricted
|
Built 2010 - 2025
|
94 homes
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$300ks
- $400ks
Regency at Prospect, Prospect, CT
Resale Only
|
55+ age-restricted
|
Built 2006 - 2020
|
379 homes
$800ks
West End Crossing, Long Branch, NJ
Resale Only
|
55+ age-restricted
|
Built 2023 - 2023
|
41 homes
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5 rating (2 reviews)
![Benson Woods]()
$400ks
- $600ks
Benson Woods, Middlebury, CT
New and Resale
|
55+ age-restricted
|
Built 2004 - present
|
79 homes
$400ks
- $500ks
Newbury Village, Brookfield, CT
New and Resale
|
55+ age-restricted
|
Built 2005 - present
|
120 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.
$500ks
- $700ks
The Summit at Bethel, Bethel, CT
Resale Only
|
55+ age-restricted
|
Built 2010 - 2021
|
235 homes
$100ks
Clockmaker's Hill, Winsted, CT
Resale Only
|
55+ age-restricted
|
Built 2005 - 2014
|
38 homes
$300ks
- $400ks
The Village at Buckingham, Avon, CT
Resale Only
|
55+ age-restricted
|
Built 2002 - 2006
|
56 homes
Read the Ultimate 55+ Rental Guide
Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
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$500ks
- $800ks
Fieldstone Village, Orange, CT
Resale Only
|
55+ age-restricted
|
Built 2010 - 2018
|
142 homes
$300ks
Pond Spring Village, Beacon Falls, CT
New and Resale
|
55+ age-restricted
|
Built 2005 - present
|
92 homes
$300ks
- $400ks
Beckley Farms, Berlin, CT
New and Resale
|
55+ age-restricted
|
Built 2010 - present
|
170 homes
$500ks
- $600ks
Castle Heights of Cheshir..., Cheshire, CT
Resale Only
|
55+ age-restricted
|
Built 2007 - 2022
|
88 homes
Want to learn more about 55+ rental communities in Westport?
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$500ks
- $700ks
Chimney Hill, Farmington, CT
Resale Only
|
55+ age-restricted
|
Built 2006 - 2013
|
44 homes
$500ks
- $600ks
RiverWalk, Branford, CT
New and Resale
|
55+ age-restricted
|
Built 2007 - present
|
60 homes
$300ks
- $400ks
Newington Ridge Preserve, Newington, CT
New Construction
|
55+ age-restricted
|
Built 2014 - present
|
16 homes
$500ks
- $700ks
The Powder Forest Homes, Simsbury, CT
Resale Only
|
55+ age-restricted
|
Built 2006 - 2016
|
182 homes
5 rating (3 reviews)
![Founders Ridge]()
$300ks
- $400ks
Founders Ridge, Middletown, CT
New Construction
|
55+ age-restricted
|
Built 2017 - present
|
75 homes
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Read the Ultimate 55+ Rental Guide
Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
$400ks
- $700ks
77 Sunset Lane, Ridgefield, CT
Resale Only
|
55+ age-restricted
|
Built 2016 - 2018
|
54 homes
$200ks
- $400ks
Bartlett Hollow, Middletown, CT
New Construction
|
55+ age-restricted
|
Built 2015 - present
|
25 homes
$500ks
- $600ks
Autumn Estates, Farmington, CT
Resale Only
|
55+ age-restricted
|
Built 2011 - 2017
|
30 homes
<$100k
The Atrium of Portland, Portland, CT
Resale Only
|
55+ age-restricted
|
Built 2004 - 2004
|
56 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
Billingsgate, Simsbury, CT
Resale Only
|
55+ age-restricted
|
Built 2003 - 2006
|
37 homes
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$200ks
- $300ks
Gloria Commons, Milford, CT
Resale Only
|
55+ age-restricted
|
Built 2007 - 2015
|
50 homes
$200ks
- $300ks
Hopmeadow Place, Simsbury, CT
Resale Only
|
55+ age-restricted
|
Built 2005 - 2005
|
66 homes
Want to learn more about 55+ communities in Westport?
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Questions? Call us:
(475) 471-1908
$300ks
- $400ks
Long Hill Village, Trumbull, CT
Resale Only
|
55+ age-restricted
|
Built 1997 - 1999
|
71 homes
New
Greenwood Village
![43 VILLAGE CIR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949]()
2 beds
|2 baths
|1,164 sq ft
|Mobile Home
43 VILLAGE CIR, BROOKHAVEN, NY, 11949
Community: Greenwood Village
MLS 965436 • Engel & Volkers North Fork, Therese ...
New
Sunken Pond Estates
![1403 PEBBLE BEACH PATH, RIVERHEAD, NY, 1..., Riverhead, NY 11901]()
2 beds
|3 baths
|1,350 sq ft
|Condo
1403 PEBBLE BEACH PATH, RIVERHEAD, NY, 1...
Community: Sunken Pond Estates
MLS 969799 • Signature Premier Properties, Ryan F...
New
Jefferson Village
![68A INDEPENDENCE CT A, YORKTOWN, NY, 105..., Yorktown, NY 10598]()
2 beds
|2 baths
|1,050 sq ft
|Condo
68A INDEPENDENCE CT A, YORKTOWN, NY, 105...
Community: Jefferson Village
MLS 963380 • Houlihan Lawrence Inc., Jo-Ella Deli...
New
Jefferson Village
![26 DORSET CT A, YORKTOWN, NY, 10598, Yorktown, NY 10598]()
MLS 966532 • Coldwell Banker Realty, Jo Ann Cooga...
New
The Seasons at East Meadow
![394 SPRING DR, HEMPSTEAD, NY, 11554, Hempstead, NY 11554]()
2 beds
|2 baths
|1,670 sq ft
|Condo
394 SPRING DR, HEMPSTEAD, NY, 11554
Community: The Seasons at East Meadow
MLS 969443 • Howard Hanna Coach, Lynn D. Witz
Want to learn more about 55+ communities in Westport?
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New
Leisure Knoll
![506 LANCASTER CT, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961]()
2 beds
|2 baths
|1,394 sq ft
|House
506 LANCASTER CT, BROOKHAVEN, NY, 11961
Community: Leisure Knoll
MLS 969385 • Coldwell Banker American Homes, Kath...
New
Heritage Hills
![392 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589]()
3 beds
|2 baths
|1,793 sq ft
|Condo
392 HERITAGE HLS A, SOMERS, NY, 10589
Community: Heritage Hills
MLS 968792 • Coldwell Banker Realty, Hope Ross Ma...
New
Heritage Village
![41 E MEADOW RD, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|3 baths
|1,479 sq ft
|Condo
41 E MEADOW RD, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24158313 • Century 21 Bette Real Estate, Just...
New
Four Seasons at Great Notch Spa and Club
![4 SLATE CT C1, WOODLAND PARK, NJ, 07424, Woodland Park, NJ 07424]()
2 beds
|2 baths
4 SLATE CT C1, WOODLAND PARK, NJ, 07424
Community: Four Seasons at Great Notch Spa and Club
MLS 4013303 • PROMINENT PROPERTIES SIR, PROMINENT...
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
The Villages NJ
![93 HALLS CROFT RD E, FREEHOLD, NJ, 07728, Freehold, NJ 07728]()
1 beds
|1 baths
|952 sq ft
|Adult Community
93 HALLS CROFT RD E, FREEHOLD, NJ, 07728
Community: The Villages NJ
MLS 22605902 • Melrose Realty, LLC, David Sgalamb...
Read the Ultimate 55+ Rental Guide
Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
New
Greenwood Village
![65A VILLAGE CIR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949]()
1 beds
|1 baths
|672 sq ft
|Condo
65A VILLAGE CIR, BROOKHAVEN, NY, 11949
Community: Greenwood Village
MLS 968217 • Gateway to The Hamptons R E, Vivian ...
New
Overlook
![3004 EASTVIEW DR 105, CARMEL, NY, 10512, Carmel, NY 10512]()
MLS 968639 • Toll Brothers Real Estate Inc., Thom...
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(475) 471-1908
New
Overlook
![2031 SUMMIT LOOP 89, CARMEL, NY, 10512, Carmel, NY 10512]()
MLS 968627 • Toll Brothers Real Estate Inc., Thom...
New
Greenwood Village
![135 VILLAGE CIR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949]()
2 beds
|1 baths
|938 sq ft
|House
135 VILLAGE CIR, BROOKHAVEN, NY, 11949
Community: Greenwood Village
MLS 968575 • Dream Select Realty Corp, LeVar D. C...
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Surrey Downs
![67 FARNWORTH CLOSE 1000, FREEHOLD, NJ, 0..., Freehold, NJ 07728]()
2 beds
|2 baths
|1,089 sq ft
|House
67 FARNWORTH CLOSE 1000, FREEHOLD, NJ, 0...
Community: Surrey Downs
MLS 22605742 • Compass New Jersey , LLC, Lori Mer...
The Vineyards at Mount Sinai
![59 FARM ACRE CIR, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766]()
2 beds
|4 baths
|1,982 sq ft
|Condo
59 FARM ACRE CIR, BROOKHAVEN, NY, 11766
Community: The Vineyards at Mount Sinai
MLS 966736 • Pinpoint Realty LI, Maryann Kelly
Download the Ultimate 55+ Homebuying Guide
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Regency at Fishkill
![323 REGENCY DR 323, FISHKILL, NY, 12524, Fishkill, NY 12524]()
1 beds
|2 baths
|1,450 sq ft
|House
323 REGENCY DR 323, FISHKILL, NY, 12524
Community: Regency at Fishkill
MLS 964999 • KW MidHudson, Philip E. Risi
Shadow Lake Village
![22 CLAREMONT CT, RED BANK, NJ, 07701, Red Bank, NJ 07701]()
2 beds
|2 baths
|1,272 sq ft
|House
22 CLAREMONT CT, RED BANK, NJ, 07701
Community: Shadow Lake Village
MLS 22605677 • Weichert Realtors-Holmdel, Sheryl ...
Dutchgate
![418 WILLOW LN, HEMPSTEAD, NY, 11580, Hempstead, NY 11580]()
MLS 961250 • Newman Realty Inc, Giacomo Sorrentin...
Read the Ultimate 55+ Rental Guide
Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
Greenwood Village
![21 LIMETREE DR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949]()
2 beds
|2 baths
|1,100 sq ft
|Condo
21 LIMETREE DR, BROOKHAVEN, NY, 11949
Community: Greenwood Village
MLS 967878 • Signature Premier Properties, Meliss...
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Leisure Village
![421 WEYMOUTH CT D, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961]()
2 beds
|1 baths
|875 sq ft
|Condo
421 WEYMOUTH CT D, BROOKHAVEN, NY, 11961
Community: Leisure Village
MLS 967775 • Leisure Living Realty Inc, Laura Ruh...
Leisure Village
![260 NEWCASTLE CT B, BROOKHAVEN, NY, 1196..., Brookhaven, NY 11961]()
1 beds
|1 baths
|684 sq ft
|Condo
260 NEWCASTLE CT B, BROOKHAVEN, NY, 1196...
Community: Leisure Village
MLS 967462 • RE/MAX Reliance, Lisa A. Camarda CBR...
Meadow Brook Estates
![312 SPRUCE HILL DR 312, OXFORD, CT, 0647..., Oxford, CT 06478]()
2 beds
|3 baths
|1,564 sq ft
|Condo
312 SPRUCE HILL DR 312, OXFORD, CT, 0647...
Community: Meadow Brook Estates
MLS 24156976 • RE/MAX Right Choice, Eric Schuell
Cedar Village at Ocean
![21 BENN LN, OCEAN TWP, NJ, 07712, Ocean Twp, NJ 07712]()
2 beds
|2 baths
|1,857 sq ft
|Ranch
21 BENN LN, OCEAN TWP, NJ, 07712
Community: Cedar Village at Ocean
MLS 22605539 • O'Brien Realty, LLC, Edwin Oels
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Regency at Holmdel
![17 SPALDING DR, HOLMDEL, NJ, 07733, Holmdel, NJ 07733]()
3 beds
|4 baths
|3,490 sq ft
|Adult Community
17 SPALDING DR, HOLMDEL, NJ, 07733
Community: Regency at Holmdel
MLS 22605537 • Keller Williams Realty Central Mon...
Leisure Knoll
![151 LAURANCE LN, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961]()
2 beds
|1 baths
|1,000 sq ft
|Condo
151 LAURANCE LN, BROOKHAVEN, NY, 11961
Community: Leisure Knoll
MLS 967646 • Howard Hanna Coach, Kalliopi C. Suar...
Four Seasons at Great Notch Spa and Club
![104 QUARRY DR, WOODLAND PARK, NJ, 07424, Woodland Park, NJ 07424]()
2 beds
|2 baths
|Townhouse
104 QUARRY DR, WOODLAND PARK, NJ, 07424
Community: Four Seasons at Great Notch Spa and Club
MLS 26007104 • Coldwell Banker, Upper Montclair, ...
Fairfield at St. James
![1205 GOTHAM DR, SMITHTOWN, NY, 11780, Smithtown, NY 11780]()
1 beds
|2 baths
|948 sq ft
|Condo
1205 GOTHAM DR, SMITHTOWN, NY, 11780
Community: Fairfield at St. James
MLS 967542 • Realty Connect USA LLC, Annmarie Rig...
The Bel Aire at East Meadow
![50 MERRICK AVE, HEMPSTEAD, NY, 11554, Hempstead, NY 11554]()
2 beds
|2 baths
|915 sq ft
|Condo
50 MERRICK AVE, HEMPSTEAD, NY, 11554
Community: The Bel Aire at East Meadow
MLS 967306 • Coldwell Banker American Homes, Rich...
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Read the Ultimate 55+ Rental Guide
Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
Heritage Hills
![769 HERITAGE HLS C, SOMERS, NY, 10589, Somers, NY 10589]()
1 beds
|2 baths
|1,296 sq ft
|Condo
769 HERITAGE HLS C, SOMERS, NY, 10589
Community: Heritage Hills
MLS 966722 • Houlihan Lawrence Inc., Eugenio Serm...
The Seasons at East Meadow
![403 AUTUMN DR, HEMPSTEAD, NY, 11554, Hempstead, NY 11554]()
2 beds
|2 baths
|1,272 sq ft
|Condo
403 AUTUMN DR, HEMPSTEAD, NY, 11554
Community: The Seasons at East Meadow
MLS 963914 • Coldwell Banker American Homes, Patr...
Heritage Village
![665 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
3 beds
|2 baths
|1,716 sq ft
|Condo
665 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24156576 • Berkshire Hathaway NE Prop., Miche...
Four Seasons at Great Notch Spa and Club
![7 GRAPHITE DR, LITTLE FALLS, NJ, 07424, Little Falls, NJ 07424]()
2 beds
|3 baths
7 GRAPHITE DR, LITTLE FALLS, NJ, 07424
Community: Four Seasons at Great Notch Spa and Club
MLS 26006656 • Coldwell Banker, Clifton, Arlene F...
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.
Four Seasons at Great Notch Spa and Club
![7 GRAPHITE DR, WOODLAND PARK, NJ, 07424, Woodland Park, NJ 07424]()
2 beds
|3 baths
|1,835 sq ft
7 GRAPHITE DR, WOODLAND PARK, NJ, 07424
Community: Four Seasons at Great Notch Spa and Club
MLS 4012405 • COLDWELL BANKER REALTY, COLDWELL BA...
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Newtown Woods
![433 BROOKSIDE CT 433, NEWTOWN, CT, 06470, Newtown, CT 06470]()
2 beds
|2 baths
|1,504 sq ft
|Condo
433 BROOKSIDE CT 433, NEWTOWN, CT, 06470
Community: Newtown Woods
MLS 24157176 • Coldwell Banker Realty, Linda McCa...
Glenwood Village
![1661 OLD COUNTRY RD 69, RIVERHEAD, NY, 1..., Riverhead, NY 11901]()
2 beds
|2 baths
|924 sq ft
|Manufactured Home
1661 OLD COUNTRY RD 69, RIVERHEAD, NY, 1...
Community: Glenwood Village
MLS 966254 • Signature Premier Properties, Noreen...
Oronoque Village
![261 AGAWAM DR A, STRATFORD, CT, 06614, Stratford, CT 06614]()
2 beds
|3 baths
|1,620 sq ft
|Condo
261 AGAWAM DR A, STRATFORD, CT, 06614
Community: Oronoque Village
MLS 24152511 • Higgins Group Real Estate, Sharon ...
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The Waterways at Moriches
![548 HIGHLAND CT, BROOKHAVEN, NY, 11955, Brookhaven, NY 11955]()
2 beds
|2 baths
|1,771 sq ft
|Condo
548 HIGHLAND CT, BROOKHAVEN, NY, 11955
Community: The Waterways at Moriches
MLS 963708 • Douglas Elliman Real Estate, Jo Ann ...
The Village at Oxford Greens
![1125 ST ANDREWS DR 47, OXFORD, CT, 06478, Oxford, CT 06478]()
2 beds
|3 baths
|2,454 sq ft
|Condo
1125 ST ANDREWS DR 47, OXFORD, CT, 06478
Community: The Village at Oxford Greens
MLS 24155601 • EG Group Realty LLC, Shabnam Sadat
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?
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REIN updates its listings on a daily basis. Data last updated: Mar 11, 2026.
This application does not include information on all of the properties available for sale at this time.
