not an image

Call us at (475) 471-1908 to learn more about active adult communities in Westport

Westport, CT 55+ active adult communities & homes for sale - Page 8

348 homes near Westport

Sort by:

Relevance

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
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
Oronoque Village
$200ks - $400ks
Oronoque Village, Stratford, CT
Resale Only | 55+ age-restricted | Built 1971 - 1977 | 929 homes
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
Leisure Village
$100ks - $300ks
Leisure Village, Ridge, NY
Resale Only | 55+ age-restricted | Built 1969 - 1986 | 1,500 homes
3 rating (2 reviews) Heritage Hills
$400ks - $800ks
Heritage Hills, Somers, NY
Resale Only | Age-targeted | Built 1974 - 2006 | 2,600 homes
The Waterways at Moriches
$300ks - $600ks
The Waterways at Moriches, Moriches, NY
Resale Only | 55+ age-restricted | Built 1985 - 1999 | 343 homes
4.2 rating (12 reviews) Surrey Downs
$200ks - $300ks
Surrey Downs, Freehold, NJ
Resale Only | 55+ age-restricted | Built 1986 - 1997 | 443 homes
The Greens at Half Hollow
$600ks - $1Ms
The Greens at Half Hollow, Melville, NY
Resale Only | 55+ age-restricted | Built 1994 - 2005 | 1,200 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.
Leisure Knoll
$200ks - $400ks
Leisure Knoll, Ridge, NY
Resale Only | 55+ age-restricted | Built 1972 - 1982 | 701 homes
Regency at Fishkill
$300ks - $400ks
Regency at Fishkill, Fishkill, NY
Resale Only | 55+ age-restricted | Built 2008 - 2020 | 164 homes
3.7 rating (3 reviews) Greenwood Village
$100ks
Greenwood Village, Manorville, NY
Resale Only | 55+ age-restricted | Built 1980 - 2000 | 512 homes
The Village at Oxford Gre...
$400ks - $500ks
The Village at Oxford Gre..., Oxford, CT
New and Resale | 55+ age-restricted | Built 2004 - present | 835 homes
Overlook
$600ks - $900ks
Overlook, Carmel, NY
New Construction | 55+ age-restricted | 300 homes
Apple Ridge
$500ks - $1Ms
Apple Ridge, Mahwah, NJ
Resale Only | Age-targeted | Built 1977 - 1991 | 276 homes
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
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
4 rating (8 reviews) Glenwood Village
$100ks - $200ks
Glenwood Village, Riverhead, NY
New and Resale | 55+ age-restricted | Built 1959 - present | 588 homes
The Manors at The Colony ...
$300ks - $400ks
The Manors at The Colony ..., Shirley, NY
New Construction | 55+ age-restricted | Built 2013 - present | 150 homes
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
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.
Fairview at Oxford Greens
$400ks - $600ks
Fairview at Oxford Greens, Oxford, CT
New and Resale | 55+ age-restricted | Built 2019 - present | 125 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
The Summit at Bethel
$500ks - $700ks
The Summit at Bethel, Bethel, CT
Resale Only | 55+ age-restricted | Built 2010 - 2021 | 235 homes
The Seasons at Elwood
$800ks - $900ks
The Seasons at Elwood, East Northport, NY
Resale Only | 55+ age-restricted | Built 2018 - 2020 | 256 homes
Equestra at Colts Neck Cr...
$600ks - $700ks
Equestra at Colts Neck Cr..., Farmingdale, NJ
Resale Only | 55+ age-restricted | Built 2007 - 2018 | 483 homes
3.7 rating (3 reviews) Rosemont Estates
$500ks - $700ks
Rosemont Estates, Marlboro, NJ
Resale Only | 55+ age-restricted | Built 2004 - 2014 | 242 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
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
Meadowbrook Pointe Athlet...
$700ks - $1Ms
Meadowbrook Pointe Athlet..., Westbury, NY
Resale Only | 55+ age-restricted | Built 2015 - 2016 | 720 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
Leisure Glen
$300ks - $400ks
Leisure Glen, Ridge, NY
Resale Only | 55+ age-restricted | Built 1985 - 2010 | 646 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.
South Pond Village
$300ks - $400ks
South Pond Village, Bloomfield, CT
Resale Only | 55+ age-restricted | Built 1999 - 2005 | 151 homes
Regency at Holmdel
$900ks - $1Ms
Regency at Holmdel, Holmdel, NJ
Resale Only | 55+ age-restricted | Built 2016 - 2019 | 181 homes
The Hollows at Blue Hill
$500ks - $700ks
The Hollows at Blue Hill, Pearl River, NY
Resale Only | 55+ age-restricted | Built 2008 - 2014 | 126 homes
5 rating (1 reviews) Shady Oaks
$200ks - $400ks
Shady Oaks, Red Bank, NJ
Resale Only | 55+ age-restricted | Built 1982 - 1983 | 366 homes
5 rating (1 reviews) Westhampton Pines
$900ks - $1Ms
Westhampton Pines, Westhampton, NY
Resale Only | 55+ age-restricted | Built 2005 - 2013 | 189 homes
Rivington
$300ks - $900ks
Rivington, Danbury, CT
New and Resale | Age-targeted | Built 2006 - present | 1,050 homes
3.5 rating (2 reviews) Foxwood Village
$200ks - $400ks
Foxwood Village, Calverton, NY
Resale Only | 55+ age-restricted | Built 1986 - 2007 | 294 homes
5 rating (1 reviews) Sunken Pond Estates
$400ks
Sunken Pond Estates, Riverhead, NY
Resale Only | 55+ age-restricted | Built 2003 - 2005 | 194 homes
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
Four Seasons at Colts Far...
$600ks - $800ks
Four Seasons at Colts Far..., Farmingdale, NJ
New Construction | 55+ age-restricted | Built 2021 - present | 111 homes
5 rating (1 reviews) Newtown Woods
$300ks - $500ks
Newtown Woods, Newtown, CT
New and Resale | 55+ age-restricted | Built 2011 - present | 178 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.
1234...5
Apple Ridge 89 FISHER RD, MAHWAH, NJ, 07430, Mahwah, NJ 07430
$899,999

3 beds

|

3 baths

|

Townhouse

89 FISHER RD, MAHWAH, NJ, 07430
Community: Apple Ridge
The Village at Oxford Greens 731 CHAMPIONSHIP DR 731, OXFORD, CT, 064..., Oxford, CT 06478
$629,900

2 beds

|

2 baths

|

1,539 sq ft

|

Condo

731 CHAMPIONSHIP DR 731, OXFORD, CT, 064...
Jefferson Village 18L HASTINGS CT, YORKTOWN, NY, 10598, Yorktown, NY 10598
$385,000

2 beds

|

1 baths

|

1,000 sq ft

|

Condo

18L HASTINGS CT, YORKTOWN, NY, 10598
Community: Jefferson Village
Heritage Village 22 HERITAGE CIR A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$345,000

2 beds

|

2 baths

|

1,398 sq ft

|

Condo

22 HERITAGE CIR A, SOUTHBURY, CT, 06488
Community: Heritage Village
Village Estates 137 FRANCESCA WAY, BABYLON, NY, 11701, Babylon, NY 11701
$589,000

2 beds

|

1 baths

|

1,245 sq ft

|

Condo

137 FRANCESCA WAY, BABYLON, NY, 11701
Community: Village Estates
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
Leisure Village 207 WOODBRIDGE DR B, BROOKHAVEN, NY, 119..., Brookhaven, NY 11961
$479,000

2 beds

|

2 baths

|

1,308 sq ft

|

Condo

207 WOODBRIDGE DR B, BROOKHAVEN, NY, 119...
Community: Leisure Village
Fairfield at St. James 506 DREW DR, SMITHTOWN, NY, 11780, Smithtown, NY 11780
$569,000

3 beds

|

3 baths

|

1,716 sq ft

|

Condo

506 DREW DR, SMITHTOWN, NY, 11780
Oronoque Village 252 AGAWAM DR A, STRATFORD, CT, 06614, Stratford, CT 06614
$595,000

2 beds

|

3 baths

|

2,494 sq ft

|

Condo

252 AGAWAM DR A, STRATFORD, CT, 06614
Community: Oronoque Village
Heritage Village 78 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$265,000

2 beds

|

2 baths

|

1,032 sq ft

|

Condo

78 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Rivington 424 CENTER MEADOW LN 424, DANBURY, CT, 0..., Danbury, CT 06810
$484,900

2 beds

|

2 baths

|

1,258 sq ft

|

Condo

424 CENTER MEADOW LN 424, DANBURY, CT, 0...
Community: Rivington
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.
Bartlett Hill 9 PEAR ORCHARD RD 9, PORTLAND, CT, 06480, Portland, CT 06480
$479,900

2 beds

|

3 baths

|

1,404 sq ft

9 PEAR ORCHARD RD 9, PORTLAND, CT, 06480
Community: Bartlett Hill
Heritage Village 41 E MEADOW RD, SOUTHBURY, CT, 06488, Southbury, CT 06488
$389,900

2 beds

|

3 baths

|

1,479 sq ft

|

Condo

41 E MEADOW RD, SOUTHBURY, CT, 06488
Community: Heritage Village
Overlook 3004 EASTVIEW DR 105, CARMEL, NY, 10512, Carmel, NY 10512
$737,000

2 beds

|

3 baths

|

2,040 sq ft

|

Condo

3004 EASTVIEW DR 105, CARMEL, NY, 10512
Community: Overlook
Heritage Village 665 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$499,000

3 beds

|

2 baths

|

1,716 sq ft

|

Condo

665 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Four Seasons at Great Notch Spa and Club 7 GRAPHITE DR, LITTLE FALLS, NJ, 07424, Little Falls, NJ 07424
$849,900

2 beds

|

3 baths

7 GRAPHITE DR, LITTLE FALLS, NJ, 07424
Newtown Woods 433 BROOKSIDE CT 433, NEWTOWN, CT, 06470, Newtown, CT 06470
$485,000

2 beds

|

2 baths

|

1,504 sq ft

|

Condo

433 BROOKSIDE CT 433, NEWTOWN, CT, 06470
Community: Newtown Woods
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
The Waterways at Moriches 548 HIGHLAND CT, BROOKHAVEN, NY, 11955, Brookhaven, NY 11955
$499,000

2 beds

|

2 baths

|

1,771 sq ft

|

Condo

548 HIGHLAND CT, BROOKHAVEN, NY, 11955
Fairview at Oxford Greens 1125 ST ANDREWS DR 47, OXFORD, CT, 06478, Oxford, CT 06478
$708,775

2 beds

|

3 baths

|

2,454 sq ft

|

Condo

1125 ST ANDREWS DR 47, OXFORD, CT, 06478
The Village at Oxford Greens 1125 ST ANDREWS DR 47, OXFORD, CT, 06478, Oxford, CT 06478
$708,775

2 beds

|

3 baths

|

2,454 sq ft

|

Condo

1125 ST ANDREWS DR 47, OXFORD, CT, 06478
Oronoque Village 383 SEQUOIA LN A, STRATFORD, CT, 06614, Stratford, CT 06614
$635,000

1 beds

|

2 baths

|

1,360 sq ft

|

Condo

383 SEQUOIA LN A, STRATFORD, CT, 06614
Community: Oronoque Village
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 Manors at The Colony Preserve 41 GREENTREE CT, BROOKHAVEN, NY, 11967, Brookhaven, NY 11967
$515,000

2 beds

|

2 baths

|

1,557 sq ft

|

Condo

41 GREENTREE CT, BROOKHAVEN, NY, 11967
Cheshire Square 55 CHESHIRE SQ, LITTLE SILVER, NJ, 07739, Little Silver, NJ 07739
$685,000

2 beds

|

3 baths

|

Townhouse

55 CHESHIRE SQ, LITTLE SILVER, NJ, 07739
Community: Cheshire Square
Heritage Village 191 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$589,900

3 beds

|

2 baths

|

1,716 sq ft

|

Condo

191 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
The Manors at The Colony Preserve 21 GREENTREE CT, BROOKHAVEN, NY, 11967, Brookhaven, NY 11967
$499,999

2 beds

|

2 baths

|

1,557 sq ft

|

Condo

21 GREENTREE CT, BROOKHAVEN, NY, 11967
Heritage Village 1041 HERITAGE VLG A, SOUTHBURY, CT, 0648..., Southbury, CT 06488
$259,900

2 beds

|

2 baths

|

1,000 sq ft

|

Condo

1041 HERITAGE VLG A, SOUTHBURY, CT, 0648...
Community: Heritage Village
Jefferson Village 41 JEFFERSON OVAL G, YORKTOWN, NY, 10598, Yorktown, NY 10598
$469,000

2 beds

|

2 baths

|

1,100 sq ft

|

Condo

41 JEFFERSON OVAL G, YORKTOWN, NY, 10598
Community: Jefferson Village
Spring Lake Village 6 LAKEVIEW DR 6, SOUTHINGTON, CT, 06489, Southington, CT 06489
$300,000

3 beds

|

3 baths

|

1,471 sq ft

|

Condo

6 LAKEVIEW DR 6, SOUTHINGTON, CT, 06489
Community: Spring Lake Village
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
Heritage Hills 40 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589
$615,000

2 beds

|

2 baths

|

1,139 sq ft

|

Condo

40 HERITAGE HLS A, SOMERS, NY, 10589
Community: Heritage Hills
Heritage Village 914 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$275,000

2 beds

|

2 baths

|

1,144 sq ft

|

Condo

914 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 419 HERITAGE VLG E, SOUTHBURY, CT, 06488, Southbury, CT 06488
$500,000

3 beds

|

2 baths

|

1,716 sq ft

|

Condo

419 HERITAGE VLG E, SOUTHBURY, CT, 06488
Community: Heritage Village
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.
Village Vistas 11 THERESA LN, BROOKHAVEN, NY, 11777, Brookhaven, NY 11777
$1,299,000

2 beds

|

4 baths

|

3,000 sq ft

|

Condo

11 THERESA LN, BROOKHAVEN, NY, 11777
Community: Village Vistas
Encore Atlantic Shores 236 ENCORE BLVD, BROOKHAVEN, NY, 11941, Brookhaven, NY 11941
$775,000

2 beds

|

2 baths

|

2,215 sq ft

|

Condo

236 ENCORE BLVD, BROOKHAVEN, NY, 11941
The Villages NJ 80 PARKWAY DR D, FREEHOLD, NJ, 07728, Freehold, NJ 07728
$409,900

2 beds

|

2 baths

|

1,262 sq ft

|

Ranch

80 PARKWAY DR D, FREEHOLD, NJ, 07728
Community: The Villages NJ
Glenwood Village 1661 OLD COUNTRY RD, RIVERHEAD, NY, 1190..., Riverhead, NY 11901
$245,000

2 beds

|

2 baths

|

1,156 sq ft

|

Manufactured Home

1661 OLD COUNTRY RD, RIVERHEAD, NY, 1190...
Community: Glenwood Village
Surrey Downs 95 FARNWORTH CLOSE, FREEHOLD, NJ, 07728, Freehold, NJ 07728
$385,000

2 beds

|

2 baths

|

1,295 sq ft

|

Ranch

95 FARNWORTH CLOSE, FREEHOLD, NJ, 07728
Community: Surrey Downs
Newtown Woods 23 WOODS LN 23, NEWTOWN, CT, 06470, Newtown, CT 06470
$610,000

2 beds

|

3 baths

|

2,073 sq ft

|

Condo

23 WOODS LN 23, NEWTOWN, CT, 06470
Community: Newtown Woods
Westhampton Pines 39 KIMBERLY DR 39, SOUTHAMPTON, NY, 1197..., Southampton, NY 11977
$1,495,000

3 beds

|

3 baths

|

2,500 sq ft

|

Condo

39 KIMBERLY DR 39, SOUTHAMPTON, NY, 1197...
Community: Westhampton Pines
The Villages NJ 139 WEIN MARKET F, FREEHOLD, NJ, 07728, Freehold, NJ 07728
$339,000

2 beds

|

2 baths

|

1,244 sq ft

|

Ranch

139 WEIN MARKET F, FREEHOLD, NJ, 07728
Community: The Villages NJ
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
The Villages NJ 139 WEIN MARKET C, FREEHOLD, NJ, 07728, Freehold, NJ 07728
$395,000

2 beds

|

2 baths

|

1,132 sq ft

|

Ranch

139 WEIN MARKET C, FREEHOLD, NJ, 07728
Community: The Villages NJ
The Villages NJ 112 PILATUS PLATZ D, FREEHOLD, NJ, 07728, Freehold, NJ 07728
$399,900

2 beds

|

1 baths

|

1,144 sq ft

112 PILATUS PLATZ D, FREEHOLD, NJ, 07728
Community: The Villages NJ
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


Want more information about active adult communities around Westport?

Global - Lead Form - Buyer or Renter
*55places does not provide or maintain community HOA information.
By requesting more information, you agree that 55places may call, text, or email you about your inquiry, which may be made with automated means (including recorded voice messages, SMS, or text messages). You understand that your consent is not a prerequisite for buying, selling or renting a property. You may revoke your consent at any time by contacting [email protected]. Message/data rates may apply. You also agree to 55places.com’s Privacy Policy and Terms of Use.

Want to learn more about 55+ communities in Westport?

Call us: (475) 471-1908
348 homes
Remove Boundaries ×
Map Satellite

Reinmlsx

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: Jun 10, 2026.
This application does not include information on all of the properties available for sale at this time.

Call Us Call Us
Scroll to Top