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 5

170 communities near Westport

Sort by:

Relevance

Relevance

Village Vistas
$800ks - $1Ms
Village Vistas, Port Jefferson, NY
Resale Only | 55+ age-restricted | Built 2013 - 2017 | 43 homes
Boulder Brook
$200ks
Boulder Brook, Prospect, CT
Resale Only | 55+ age-restricted | Built 2004 - 2006 | 35 homes
Gloria Commons
$200ks - $300ks
Gloria Commons, Milford, CT
Resale Only | 55+ age-restricted | Built 2007 - 2015 | 50 homes
Regency at Woodbridge
$500ks - $700ks
Regency at Woodbridge, Woodbridge, CT
New Construction | 55+ age-restricted | Built 2023 - present | 70 homes
Granite Woods
$600ks - $700ks
Granite Woods, Middlebury, CT
New Construction | 55+ age-restricted | Built 2020 - present | 24 homes
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
Apple Ridge
$500ks - $1Ms
Apple Ridge, Mahwah, NJ
Resale Only | Age-targeted | Built 1977 - 1991 | 276 homes
Long Hill Village
$300ks - $400ks
Long Hill Village, Trumbull, CT
Resale Only | 55+ age-restricted | Built 1997 - 1999 | 71 homes
Hopmeadow Place
$200ks - $300ks
Hopmeadow Place, Simsbury, CT
Resale Only | 55+ age-restricted | Built 2005 - 2005 | 66 homes
Regency at Allaire
$700ks - $900ks
Regency at Allaire, Farmingdale, NJ
New Construction | 55+ age-restricted | Built 2020 - present | 98 homes
The Villas at Narraganset...
$400ks
The Villas at Narraganset..., Lindenhurst, NY
Resale Only | 55+ age-restricted | Built 2004 - 2005 | 138 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.
New Greenwood Village 105 W VILLAGE CIR 105, BROOKHAVEN, NY, 1..., Brookhaven, NY 11949
$245,000

2 beds

|

2 baths

|

1,130 sq ft

|

Condo

105 W VILLAGE CIR 105, BROOKHAVEN, NY, 1...
Community: Greenwood Village
The Villages NJ 41 PIAZZA SAN PAOLA C, FREEHOLD, NJ, 077..., Freehold, NJ 07728
$410,000

2 beds

|

2 baths

|

1,008 sq ft

|

Ranch

41 PIAZZA SAN PAOLA C, FREEHOLD, NJ, 077...
Community: The Villages NJ
Glenwood Village 1661 OLD COUNTRY RD 516, RIVERHEAD, NY, ..., Riverhead, NY 11901
$419,000

2 beds

|

2 baths

|

1,624 sq ft

|

Manufactured Home

1661 OLD COUNTRY RD 516, RIVERHEAD, NY, ...
Community: Glenwood Village
New Village Estates 130 FRANCESCA WAY, BABYLON, NY, 11701, Babylon, NY 11701
$639,000

2 beds

|

2 baths

|

1,243 sq ft

|

Condo

130 FRANCESCA WAY, BABYLON, NY, 11701
Community: Village Estates
New Jefferson Village 90 MOLLY PITCHER LN F, YORKTOWN, NY, 105..., Yorktown, NY 10598
$359,900

1 beds

|

1 baths

|

800 sq ft

|

Condo

90 MOLLY PITCHER LN F, YORKTOWN, NY, 105...
Community: Jefferson Village
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
New Eagles Walk at East Quogue 1204 AERIE WAY 1204, SOUTHAMPTON, NY, 11..., Southampton, NY 11942
$565,000

2 beds

|

2 baths

|

1,341 sq ft

|

Condo

1204 AERIE WAY 1204, SOUTHAMPTON, NY, 11...
New Cheesequake Village 10 HAVEN DR B, MATAWAN, NJ, 07747, Matawan, NJ 07747
$283,000

1 beds

|

1 baths

|

664 sq ft

|

Adult Community

10 HAVEN DR B, MATAWAN, NJ, 07747
Community: Cheesequake Village
New Woodridge Strathmore Terrace 89 STANDISH DR, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766
$500,000

2 beds

|

2 baths

|

1,240 sq ft

|

House

89 STANDISH DR, BROOKHAVEN, NY, 11766
New Jefferson Village 149 FLINTLOCK WAY E, YORKTOWN, NY, 10598, Yorktown, NY 10598
$375,000

1 beds

|

1 baths

|

853 sq ft

|

Condo

149 FLINTLOCK WAY E, YORKTOWN, NY, 10598
Community: Jefferson Village
New Leisure Village 231 BLACKPOOL CT, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$299,000

2 beds

|

1 baths

|

836 sq ft

|

Condo

231 BLACKPOOL CT, BROOKHAVEN, NY, 11961
Community: Leisure 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.
New The Greens at Half Hollow 742 VERONA DR, HUNTINGTON, NY, 11747, Huntington, NY 11747
$1,099,000

2 beds

|

3 baths

|

1,940 sq ft

|

Condo

742 VERONA DR, HUNTINGTON, NY, 11747
New Dutchgate 301 WILLOW LN, HEMPSTEAD, NY, 11580, Hempstead, NY 11580
$510,000

2 beds

|

2 baths

|

941 sq ft

|

Condo

301 WILLOW LN, HEMPSTEAD, NY, 11580
Community: Dutchgate
New Overlook 4095 FAIRWAYS DR 148, CARMEL, NY, 10512, Carmel, NY 10512
$699,000

3 beds

|

3 baths

|

1,914 sq ft

|

Condo

4095 FAIRWAYS DR 148, CARMEL, NY, 10512
Community: Overlook
New Heritage Hills 241 HERITAGE HLS D, SOMERS, NY, 10589, Somers, NY 10589
$499,900

2 beds

|

2 baths

|

1,138 sq ft

|

Condo

241 HERITAGE HLS D, SOMERS, NY, 10589
Community: Heritage Hills
New Four Seasons at Great Notch Spa and Club 8 PEBBLE RD C2, WOODLAND PARK, NJ, 07424, Woodland Park, NJ 07424
$699,900

2 beds

|

2 baths

|

Townhouse

8 PEBBLE RD C2, WOODLAND PARK, NJ, 07424
New Country Pointe Plainview 52102 BEECH TREE LN, OYSTER BAY, NY, 118..., Oyster Bay, NY 11803
$1,649,990

2 beds

|

3 baths

|

1,750 sq ft

|

Condo

52102 BEECH TREE LN, OYSTER BAY, NY, 118...
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
New Encore Atlantic Shores 216 SONATA CT, BROOKHAVEN, NY, 11941, Brookhaven, NY 11941
$899,000

2 beds

|

3 baths

|

2,439 sq ft

|

Condo

216 SONATA CT, BROOKHAVEN, NY, 11941
New The Waterways at Moriches 132 CAPTAINS CT, BROOKHAVEN, NY, 11955, Brookhaven, NY 11955
$550,000

2 beds

|

2 baths

|

1,544 sq ft

|

Condo

132 CAPTAINS CT, BROOKHAVEN, NY, 11955
New Vineyards at Blue Point 37 HALLEY DR 17, BROOKHAVEN, NY, 11772, Brookhaven, NY 11772
$660,000

2 beds

|

2 baths

|

1,220 sq ft

|

Condo

37 HALLEY DR 17, BROOKHAVEN, NY, 11772
New Surrey Downs 39 DATCHET CLOSE, FREEHOLD, NJ, 07728, Freehold, NJ 07728
$445,000

2 beds

|

2 baths

|

1,146 sq ft

|

Ranch

39 DATCHET CLOSE, FREEHOLD, NJ, 07728
Community: Surrey Downs
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.
Woodridge Strathmore Terrace 32 CHIPPENDALE DR, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766
$579,999

2 beds

|

2 baths

|

1,501 sq ft

|

Condo

32 CHIPPENDALE DR, BROOKHAVEN, NY, 11766
Heritage Village 786 HERITAGE VLG C, SOUTHBURY, CT, 06488, Southbury, CT 06488
$200,000

2 beds

|

2 baths

|

1,000 sq ft

|

Condo

786 HERITAGE VLG C, SOUTHBURY, CT, 06488
Community: Heritage Village
Newtown Woods 1227 BROOKSIDE CT 1227, NEWTOWN, CT, 064..., Newtown, CT 06470
$500,000

2 beds

|

2 baths

|

1,483 sq ft

|

Condo

1227 BROOKSIDE CT 1227, NEWTOWN, CT, 064...
Community: Newtown Woods
Newtown Woods 23 WOODS LN 23, NEWTOWN, CT, 06470, Newtown, CT 06470
$600,000

2 beds

|

3 baths

|

2,073 sq ft

|

Condo

23 WOODS LN 23, NEWTOWN, CT, 06470
Community: Newtown Woods
Greenwood Village 5127 VILLAGE CIR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949
$227,000

2 beds

|

2 baths

|

1,291 sq ft

|

Condo

5127 VILLAGE CIR, BROOKHAVEN, NY, 11949
Community: Greenwood Village
HarborView 100 HARBOR VIEW DR 335, NORTH HEMPSTEAD,..., North Hempstead, NY 11050
$1,199,000

3 beds

|

3 baths

|

2,216 sq ft

|

Condo

100 HARBOR VIEW DR 335, NORTH HEMPSTEAD,...
Community: HarborView
HarborView 123 LINKS CT, NORTH HEMPSTEAD, NY, 11050, North Hempstead, NY 11050
$1,299,000

3 beds

|

3 baths

|

2,160 sq ft

|

Condo

123 LINKS CT, NORTH HEMPSTEAD, NY, 11050
Community: HarborView
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
Heritage Village 581 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$350,000

2 beds

|

2 baths

|

1,398 sq ft

|

Condo

581 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Rosemont Estates 207 BRADWICK WAY, MARLBORO, NJ, 07746, Marlboro, NJ 07746
$960,000

2 beds

|

3 baths

|

2,551 sq ft

|

House

207 BRADWICK WAY, MARLBORO, NJ, 07746
Community: Rosemont Estates
Jefferson Village 56 KIRBY CLOSE B, YORKTOWN, NY, 10598, Yorktown, NY 10598
$489,500

2 beds

|

2 baths

|

970 sq ft

|

Condo

56 KIRBY CLOSE B, YORKTOWN, NY, 10598
Community: Jefferson 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.
Cheesequake Village 11 ALABAMA CT, OLD BRIDGE, NJ, 07747, Old Bridge, NJ 07747
$335,000

2 beds

|

2 baths

|

Townhouse,Condominium

11 ALABAMA CT, OLD BRIDGE, NJ, 07747
Community: Cheesequake Village
Cheesequake Village 11 ALABAMA CT 835, MATAWAN, NJ, 07747, Matawan, NJ 07747
$335,000

2 beds

|

2 baths

|

976 sq ft

|

Adult Community

11 ALABAMA CT 835, MATAWAN, NJ, 07747
Community: Cheesequake Village
Cheesequake Village 72 HAVEN DR D, MATAWAN, NJ, 07747, Matawan, NJ 07747
$310,000

2 beds

|

1 baths

|

949 sq ft

|

Adult Community

72 HAVEN DR D, MATAWAN, NJ, 07747
Community: Cheesequake Village
Cheesequake Village 72-D HAVEN DR 500, OLD BRIDGE, NJ, 07747, Old Bridge, NJ 07747
$310,000

2 beds

|

1 baths

|

Condo

72-D HAVEN DR 500, OLD BRIDGE, NJ, 07747
Community: Cheesequake Village
Heritage Hills 828 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589
$650,000

2 beds

|

2 baths

|

1,296 sq ft

|

Condo

828 HERITAGE HLS B, SOMERS, NY, 10589
Community: Heritage Hills
Windcrest East 5 GREEN ASH ST, RIVERHEAD, NY, 11933, Riverhead, NY 11933
$775,000

3 beds

|

3 baths

|

2,449 sq ft

|

House

5 GREEN ASH ST, RIVERHEAD, NY, 11933
Community: Windcrest East
Oronoque Village 212 AGAWAM DR B, STRATFORD, CT, 06614, Stratford, CT 06614
$319,000

1 beds

|

2 baths

|

1,426 sq ft

|

Condo

212 AGAWAM DR B, STRATFORD, CT, 06614
Community: Oronoque Village
The Views at Pomona 2202 VIEWS WAY, RAMAPO, NY, 10970, Ramapo, NY 10970
$469,000

2 beds

|

2 baths

|

1,360 sq ft

|

Condo

2202 VIEWS WAY, RAMAPO, NY, 10970
Community: The Views at Pomona
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
Oronoque Village 383 SEQUOIA LN B, STRATFORD, CT, 06614, Stratford, CT 06614
$485,000

1 beds

|

3 baths

|

1,360 sq ft

|

Condo

383 SEQUOIA LN B, STRATFORD, CT, 06614
Community: Oronoque Village
Glassbury Court at Cold Spring 1 MAGGIE MAY WAY, PHILIPSTOWN, NY, 10516, Philipstown, NY 10516
$715,000

2 beds

|

2 baths

|

1,974 sq ft

|

House

1 MAGGIE MAY WAY, PHILIPSTOWN, NY, 10516
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 optout@55places.com. 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
170 communities
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: Jul 27, 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