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

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

167 communities near Westport

Sort by:

Relevance

Relevance

Whitney Glen
$500Ks - $600Ks
Whitney Glen, Westport, CT
Resale Only | 55+ age-restricted | Built 1982 - 1982 | 62 homes
3 rating (2 reviews) Heritage Hills
$300Ks - $900Ks
Heritage Hills, Somers, NY
Resale Only | Age-targeted | Built 1974 - 2006 | 2,600 homes
3.6 rating (7 reviews) Heritage Village
$100Ks - $500Ks
Heritage Village, Southbury, CT
Resale Only | 55+ age-restricted | Built 1967 - 2005 | 2,580 homes
Leisure Village
$200Ks - $400Ks
Leisure Village, Ridge, NY
Resale Only | 55+ age-restricted | Built 1969 - 1986 | 1,500 homes
The Greens at Half Hollow
$500Ks - $1Ms
The Greens at Half Hollow, Melville, NY
Resale Only | 55+ age-restricted | Built 1994 - 2005 | 1,200 homes
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
Rivington
$400Ks - $600Ks
Rivington, Danbury, CT
New and Resale | Age-targeted | Built 2006 - present | 1,050 homes
4 rating (1 reviews) Jefferson Village
$200Ks - $600Ks
Jefferson Village, Yorktown Heights, NY
Resale Only | 55+ age-restricted | Built 1967 - 1982 | 1,000 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
Oronoque Village
$200Ks - $600Ks
Oronoque Village, Stratford, CT
Resale Only | 55+ age-restricted | Built 1971 - 1977 | 929 homes
The Village at Oxford Gre...
$500Ks - $700Ks
The Village at Oxford Gre..., Oxford, CT
New and Resale | 55+ age-restricted | Built 2004 - present | 835 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) Four Seasons at Great Not...
$600Ks - $800Ks
Four Seasons at Great Not..., Woodland Park, NJ
Resale Only | 55+ age-restricted | Built 2005 - 2018 | 814 homes
Meadowbrook Pointe Athlet...
$800Ks - $1Ms
Meadowbrook Pointe Athlet..., Westbury, NY
Resale Only | 55+ age-restricted | Built 2015 - 2016 | 720 homes
2.8 rating (4 reviews) Cheesequake Village
$200Ks - $200Ks
Cheesequake Village, Old Bridge, NJ
Resale Only | 55+ age-restricted | Built 1965 - 1971 | 713 homes
Leisure Knoll
$300Ks - $400Ks
Leisure Knoll, Ridge, NY
Resale Only | 55+ age-restricted | Built 1972 - 1982 | 701 homes
2.8 rating (5 reviews) The Villages NJ
$200Ks - $400Ks
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
Country Pointe Plainview
$1Ms - $1Ms
Country Pointe Plainview, Plainview, NY
New Construction | 55+ age-restricted | Built 2017 - present | 660 homes
5 rating (2 reviews) Fairfield at St. James
$400Ks - $500Ks
Fairfield at St. James, St. James, NY
Resale Only | 55+ age-restricted | Built 1972 - 1989 | 653 homes
Leisure Glen
$400Ks - $400Ks
Leisure Glen, Ridge, NY
Resale Only | 55+ age-restricted | Built 1985 - 2010 | 646 homes
Spring Lake Village
$200Ks - $200Ks
Spring Lake Village, Southington, CT
Resale Only | 55+ age-restricted | Built 1970 - 2004 | 640 homes
4 rating (8 reviews) Glenwood Village
$100Ks - $400Ks
Glenwood Village, Riverhead, NY
New and Resale | 55+ age-restricted | Built 1959 - present | 588 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 - $200Ks
Greenwood Village, Manorville, NY
Resale Only | 55+ age-restricted | Built 1980 - 2000 | 512 homes
Equestra at Colts Neck Cr...
$800Ks - $900Ks
Equestra at Colts Neck Cr..., Farmingdale, NJ
Resale Only | 55+ age-restricted | Built 2007 - 2018 | 483 homes
4.2 rating (12 reviews) Surrey Downs
$300Ks - $400Ks
Surrey Downs, Freehold, NJ
Resale Only | 55+ age-restricted | Built 1986 - 1997 | 443 homes
The Seasons at East Meado...
$500Ks - $600Ks
The Seasons at East Meado..., East Meadow, NY
Resale Only | 55+ age-restricted | Built 2009 - 2012 | 404 homes
Regency at Prospect
$300Ks - $500Ks
Regency at Prospect, Prospect, CT
Resale Only | 55+ age-restricted | Built 2006 - 2020 | 379 homes
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
5 rating (1 reviews) Shady Oaks
$400Ks - $400Ks
Shady Oaks, Red Bank, NJ
Resale Only | 55+ age-restricted | Built 1982 - 1983 | 366 homes
Dutchgate
$400Ks - $400Ks
Dutchgate, Valley Stream, NY
Resale Only | 55+ age-restricted | Built 2009 - 2015 | 348 homes
The Waterways at Moriches
$400Ks - $600Ks
The Waterways at Moriches, Moriches, NY
Resale Only | 55+ age-restricted | Built 1985 - 1999 | 343 homes
Rolling Meadows at Waysid...
$700Ks - $800Ks
Rolling Meadows at Waysid..., Ocean Township, NJ
Resale Only | 55+ age-restricted | Built 2002 - 2007 | 328 homes
The Retreat at Carmel
$400Ks - $600Ks
The Retreat at Carmel, Carmel, NY
Resale Only | 55+ age-restricted | Built 2008 - 2018 | 312 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.
Overlook
$600Ks - $900Ks
Overlook, Carmel, NY
New Construction | 55+ age-restricted | 300 homes
Cedar Village at Ocean
$700Ks - $700Ks
Cedar Village at Ocean, Ocean Township, NJ
Resale Only | 55+ age-restricted | Built 2005 - 2014 | 295 homes
3.5 rating (2 reviews) Foxwood Village
$300Ks - $400Ks
Foxwood Village, Calverton, NY
Resale Only | 55+ age-restricted | Built 1986 - 2007 | 294 homes
1 rating (1 reviews) Plymouth Estates at Mount...
$500Ks - $500Ks
Plymouth Estates at Mount..., Mount Sinai, NY
Resale Only | 55+ age-restricted | Built 2006 - 2013 | 285 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
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
4 rating (1 reviews) Vineyards at Blue Point
$800Ks - $800Ks
Vineyards at Blue Point, Blue Point, NY
Resale Only | 55+ age-restricted | Built 2016 - 2018 | 280 homes
Apple Ridge
$700Ks - $700Ks
Apple Ridge, Mahwah, NJ
Resale Only | Age-targeted | Built 1977 - 1991 | 276 homes
Winthrop Court
$400Ks - $500Ks
Winthrop Court, Clifton, NJ
Resale Only | 55+ age-restricted | Built 2000 - 2010 | 270 homes
HarborView
$900Ks - $1Ms
HarborView, Port Washington, NY
Resale Only | 55+ age-restricted | Built 2002 - 2004 | 270 homes
The Club at Melville
$500Ks - $500Ks
The Club at Melville, Melville, NY
Resale Only | 55+ age-restricted | Built 2015 - 2017 | 261 homes
Rolling Meadows at Wayside 106 ROLLING MEADOWS BLVD, ASBURY PARK, N..., Asbury Park, NJ 07712
$739,000

2 beds

|

2 baths

|

Ranch

106 ROLLING MEADOWS BLVD, ASBURY PARK, N...
Surrey Downs 23 DATCHET CLOSE # 1000, FREEHOLD, NJ, 0..., Freehold, NJ 07728
$325,000

2 beds

|

1 baths

|

Ranch

23 DATCHET CLOSE # 1000, FREEHOLD, NJ, 0...
Community: Surrey Downs
The Villages NJ 138 WEIN MARKET C, FREEHOLD, NJ, 07728, Freehold, NJ 07728
$374,900

2 beds

|

2 baths

|

1,262 sq ft

|

Adult Community

138 WEIN MARKET C, FREEHOLD, NJ, 07728
Community: The Villages NJ
New Four Seasons at Cedar Grove 806 HOLLY LN, CEDAR GROVE, NJ, 07009, Cedar Grove, NJ 07009
$695,000

2 beds

|

2 baths

|

1,949 sq ft

806 HOLLY LN, CEDAR GROVE, NJ, 07009
Rosemont Estates 211 BRADWICK WAY, MARLBORO, NJ, 07746, Marlboro, NJ 07746
$799,900

2 beds

|

3 baths

|

2,452 sq ft

|

House

211 BRADWICK WAY, MARLBORO, NJ, 07746
Community: Rosemont Estates
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
Cheesequake Village 56 GALEWOOD DR A, MATAWAN, NJ, 07747, Matawan, NJ 07747
$315,000

2 beds

|

1 baths

|

914 sq ft

|

Condo

56 GALEWOOD DR A, MATAWAN, NJ, 07747
Community: Cheesequake Village
Shadow Lake Village 19 MANCHESTER CT, RED BANK, NJ, 07701, Red Bank, NJ 07701
$429,900

2 beds

|

1 baths

|

952 sq ft

|

Ranch

19 MANCHESTER CT, RED BANK, NJ, 07701
Community: Shadow Lake Village
Rolling Meadows at Wayside 4 MAGNOLIA CT, ASBURY PARK, NJ, 07712, Asbury Park, NJ 07712
$799,000

2 beds

|

2 baths

|

1,824 sq ft

|

Ranch

4 MAGNOLIA CT, ASBURY PARK, NJ, 07712
New Shadow Lake Village 163 LEXINGTON CT, RED BANK, NJ, 07701, Red Bank, NJ 07701
$315,000

2 beds

|

1 baths

|

1,021 sq ft

|

Adult Community

163 LEXINGTON CT, RED BANK, NJ, 07701
Community: Shadow Lake Village
New Nobility Crest at Ocean 7 CENTRE ST UNIT 2109, OCEAN, NJ, 07712, Ocean, NJ 07712
$445,000

1 beds

|

1 baths

|

1,058 sq ft

|

Condo

7 CENTRE ST UNIT 2109, OCEAN, NJ, 07712
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.
Enclave at Ocean 1218 W PARK AVE, OCEAN, NJ, 07712, Ocean, NJ 07712
$1,500,000

5 beds

|

7 baths

|

3,953 sq ft

|

House

1218 W PARK AVE, OCEAN, NJ, 07712
Community: Enclave at Ocean
Rolling Meadows at Wayside 11 ROLLING MEADOWS BLVD, ASBURY PARK, NJ..., Asbury Park, NJ 07712
$829,900

3 beds

|

3 baths

|

2,288 sq ft

|

House

11 ROLLING MEADOWS BLVD, ASBURY PARK, NJ...
Shadow Lake Village 50 HANCOCK CT, RED BANK, NJ, 07701, Red Bank, NJ 07701
$415,000

2 beds

|

2 baths

|

1,235 sq ft

|

Adult Community

50 HANCOCK CT, RED BANK, NJ, 07701
Community: Shadow Lake Village
Regency at Allaire 106 GRANDVIEW CIR, FARMINGDALE, NJ, 0772..., Farmingdale, NJ 07727
$1,350,000

4 beds

|

3 baths

|

2,928 sq ft

|

House

106 GRANDVIEW CIR, FARMINGDALE, NJ, 0772...
Community: Regency at Allaire
Winthrop Court 6102 HARCOURT RD # 519, CLIFTON, NJ, 070..., Clifton, NJ 07013
$515,000

2 beds

|

2 baths

|

Condo

6102 HARCOURT RD # 519, CLIFTON, NJ, 070...
Community: Winthrop Court
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
Winthrop Court 6102 HARCOURT RD # 102, CLIFTON, NJ, 070..., Clifton, NJ 07013
$515,000

2 beds

|

2 baths

6102 HARCOURT RD # 102, CLIFTON, NJ, 070...
Community: Winthrop Court
The Villages NJ 32 PLAZA DE LAS LOBOS C, FREEHOLD, NJ, 0..., Freehold, NJ 07728
$389,000

2 beds

|

2 baths

|

Adult Community

32 PLAZA DE LAS LOBOS C, FREEHOLD, NJ, 0...
Community: The Villages NJ
Regency at Holmdel 17 SPALDING DR, HOLMDEL, NJ, 07733, Holmdel, NJ 07733
$1,350,000

3 beds

|

4 baths

|

3,417 sq ft

|

Adult Community

17 SPALDING DR, HOLMDEL, NJ, 07733
Community: Regency at Holmdel
New Rolling Meadows at Wayside 41 ROLLING MEADOWS BLVD, ASBURY PARK, NJ..., Asbury Park, NJ 07712
$809,900

2 beds

|

3 baths

|

House

41 ROLLING MEADOWS BLVD, ASBURY PARK, NJ...
New Cedar Village at Ocean 67 SEQUOIA PKWY, ASBURY PARK, NJ, 07712, Asbury Park, NJ 07712
$795,000

2 beds

|

2 baths

|

1,859 sq ft

|

Ranch

67 SEQUOIA PKWY, ASBURY PARK, NJ, 07712
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.
Surrey Downs 32 CARNABY CLOSE, FREEHOLD, NJ, 07728, Freehold, NJ 07728
$339,000

2 beds

|

1 baths

|

Ranch

32 CARNABY CLOSE, FREEHOLD, NJ, 07728
Community: Surrey Downs
Cheesequake Village 7 GEORGIA CT D, MATAWAN, NJ, 07747, Matawan, NJ 07747
$299,000

2 beds

|

1 baths

|

Adult Community

7 GEORGIA CT D, MATAWAN, NJ, 07747
Community: Cheesequake Village
Cheesequake Village 10 CALIFORNIA CT A, MATAWAN, NJ, 07747, Matawan, NJ 07747
$290,000

2 beds

|

1 baths

|

914 sq ft

|

Condo

10 CALIFORNIA CT A, MATAWAN, NJ, 07747
Community: Cheesequake Village
Shadow Lake Village 12 ELLSWORTH CT, RED BANK, NJ, 07701, Red Bank, NJ 07701
$599,000

2 beds

|

2 baths

|

Ranch

12 ELLSWORTH CT, RED BANK, NJ, 07701
Community: Shadow Lake Village
Cheesequake Village 14 CONNECTICUT CT D, MATAWAN, NJ, 07747, Matawan, NJ 07747
$289,999

2 beds

|

1 baths

|

Adult Community

14 CONNECTICUT CT D, MATAWAN, NJ, 07747
Community: Cheesequake Village
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
Four Seasons at Great Notch Spa and Club 5 GRANITE RD UNIT D2, WOODLAND PARK, NJ,..., Woodland Park, NJ 07424
$699,900

2 beds

|

2 baths

|

Townhouse

5 GRANITE RD UNIT D2, WOODLAND PARK, NJ,...
Winthrop Court 8205 HARCOURT RD # 8205, CLIFTON, NJ, 07..., Clifton, NJ 07013
$499,000

2 beds

|

2 baths

|

Condo

8205 HARCOURT RD # 8205, CLIFTON, NJ, 07...
Community: Winthrop Court
Four Seasons at Wayne 511 FOUR SEASONS DR, WAYNE, NJ, 07470, Wayne, NJ 07470
$559,000

2 beds

|

2 baths

|

Condo

511 FOUR SEASONS DR, WAYNE, NJ, 07470
Shady Oaks 59 BOXWOOD TER, RED BANK, NJ, 07701, Red Bank, NJ 07701
$499,000

2 beds

|

2 baths

|

1,386 sq ft

|

Ranch

59 BOXWOOD TER, RED BANK, NJ, 07701
Community: Shady Oaks
Cedar Village at Ocean 41 REDWOOD DR, ASBURY PARK, NJ, 07712, Asbury Park, NJ 07712
$764,900

3 beds

|

2 baths

|

1,823 sq ft

|

Ranch

41 REDWOOD DR, ASBURY PARK, NJ, 07712
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.
Winthrop Court 1110 WICKHAM TER # 1110, CLIFTON, NJ, 07..., Clifton, NJ 07013
$599,500

2 beds

|

2 baths

|

Condo

1110 WICKHAM TER # 1110, CLIFTON, NJ, 07...
Community: Winthrop Court
New Rosemont Estates 219 EVERTON BLVD, MARLBORO, NJ, 07746, Marlboro, NJ 07746
$849,900

3 beds

|

3 baths

|

2,842 sq ft

|

House

219 EVERTON BLVD, MARLBORO, NJ, 07746
Community: Rosemont Estates
Four Seasons at Great Notch Spa and Club 23 COPPA RD, WOODLAND PARK, NJ, 07424, Woodland Park, NJ 07424
$849,000

2 beds

|

3 baths

|

Townhouse

23 COPPA RD, WOODLAND PARK, NJ, 07424
Regency at Allaire 11 WOODSPRING RD, FARMINGDALE, NJ, 07727, Farmingdale, NJ 07727
$899,999

2 beds

|

2 baths

|

2,005 sq ft

|

Ranch

11 WOODSPRING RD, FARMINGDALE, NJ, 07727
Community: Regency at Allaire
Rosemont Estates 142 SCARBOROUGH WAY, MARLBORO, NJ, 07746, Marlboro, NJ 07746
$879,000

3 beds

|

3 baths

|

2,790 sq ft

|

Adult Community

142 SCARBOROUGH WAY, MARLBORO, NJ, 07746
Community: Rosemont Estates
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
Surrey Downs 1 CARNABY CLOSE # 1000, FREEHOLD, NJ, 07..., Freehold, NJ 07728
$425,000

2 beds

|

2 baths

|

1,261 sq ft

|

Ranch

1 CARNABY CLOSE # 1000, FREEHOLD, NJ, 07...
Community: Surrey Downs
The Villages NJ 77 PARKWAY DR D, FREEHOLD, NJ, 07728, Freehold, NJ 07728
$316,999

2 beds

|

1 baths

|

1,188 sq ft

|

Ranch

77 PARKWAY DR D, FREEHOLD, NJ, 07728
Community: The Villages NJ
Surrey Downs 5 JAFFREYTON CLOSE, FREEHOLD, NJ, 07728, Freehold, NJ 07728
$385,000

2 beds

|

2 baths

|

1,144 sq ft

|

Ranch

5 JAFFREYTON CLOSE, FREEHOLD, NJ, 07728
Community: Surrey Downs
Shadow Lake Village 109 LEXINGTON CT, RED BANK, NJ, 07701, Red Bank, NJ 07701
$399,000

2 beds

|

1 baths

|

Ranch

109 LEXINGTON CT, RED BANK, NJ, 07701
Community: Shadow Lake Village
Shadow Lake Village 50 FRIENDSHIP CT, RED BANK, NJ, 07701, Red Bank, NJ 07701
$429,000

2 beds

|

2 baths

|

1,114 sq ft

|

Adult Community

50 FRIENDSHIP CT, RED BANK, NJ, 07701
Community: Shadow Lake Village

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
167 communities near Westport
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.
© 2025 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: Nov 07, 2025.
This application does not include information on all of the properties available for sale at this time.

Call Us Call Us
Scroll to Top