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 6

363 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
Leisure Village
$100ks - $300ks
Leisure Village, Ridge, NY
Resale Only | 55+ age-restricted | Built 1969 - 1986 | 1,500 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
3 rating (2 reviews) Heritage Hills
- $900ks
Heritage Hills, Somers, NY
Resale Only | Age-targeted | Built 1974 - 2006 | 2,600 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
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
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
The Waterways at Moriches
$300ks - $600ks
The Waterways at Moriches, Moriches, NY
Resale Only | 55+ age-restricted | Built 1985 - 1999 | 343 homes
3.7 rating (3 reviews) Greenwood Village
$100ks
Greenwood Village, Manorville, NY
Resale Only | 55+ age-restricted | Built 1980 - 2000 | 512 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.
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
4 rating (8 reviews) Glenwood Village
$100ks - $200ks
Glenwood Village, Riverhead, NY
New and Resale | 55+ age-restricted | Built 1959 - present | 588 homes
3.7 rating (3 reviews) Rosemont Estates
$500ks - $700ks
Rosemont Estates, Marlboro, NJ
Resale Only | 55+ age-restricted | Built 2004 - 2014 | 242 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
Leisure Knoll
$200ks - $400ks
Leisure Knoll, Ridge, NY
Resale Only | 55+ age-restricted | Built 1972 - 1982 | 701 homes
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
4.2 rating (12 reviews) Surrey Downs
$200ks - $300ks
Surrey Downs, Freehold, NJ
Resale Only | 55+ age-restricted | Built 1986 - 1997 | 443 homes
Fairview at Oxford Greens
$400ks - $600ks
Fairview at Oxford Greens, Oxford, CT
New and Resale | 55+ age-restricted | Built 2019 - present | 125 homes
Leisure Glen
$300ks - $400ks
Leisure Glen, Ridge, NY
Resale Only | 55+ age-restricted | Built 1985 - 2010 | 646 homes
HarborView
$600ks - $1Ms
HarborView, Port Washington, NY
Resale Only | 55+ age-restricted | Built 2002 - 2004 | 270 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.
Rivington
$300ks - $900ks
Rivington, Danbury, CT
New and Resale | Age-targeted | Built 2006 - present | 1,050 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
5 rating (1 reviews) Encore Atlantic Shores
$500ks - $800ks
Encore Atlantic Shores, Eastport, NY
Resale Only | 55+ age-restricted | Built 2004 - 2011 | 240 homes
The Coves at Melville
$500ks
The Coves at Melville, Melville, NY
Resale Only | 62+ age-restricted | Built 2004 - 2005 | 175 homes
The Retreat at Carmel
$300ks - $800ks
The Retreat at Carmel, Carmel, NY
Resale Only | 55+ age-restricted | Built 2008 - 2018 | 312 homes
5 rating (1 reviews) Newtown Woods
$300ks - $500ks
Newtown Woods, Newtown, CT
New and Resale | 55+ age-restricted | Built 2011 - present | 178 homes
5 rating (1 reviews) Sunrise Village
$400ks
Sunrise Village, Sayville, NY
Resale Only | 55+ age-restricted | Built 1985 - 1990 | 213 homes
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
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
Setauket Meadows
$500ks - $600ks
Setauket Meadows, Setauket, NY
Resale Only | 55+ age-restricted | Built 2005 - 2007 | 150 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
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.
Meadowbrook Pointe Athlet...
$700ks - $1Ms
Meadowbrook Pointe Athlet..., Westbury, NY
Resale Only | 55+ age-restricted | Built 2015 - 2016 | 720 homes
Kensington Estates
$1Ms
Kensington Estates, Woodbury, NY
New Construction | 55+ age-restricted | Built 2019 - 2021 | 80 homes
Village Estates
$300ks - $400ks
Village Estates, Amityville, NY
Resale Only | 55+ age-restricted | Built 2006 - 2008 | 138 homes
Winthrop Court
$400ks - $600ks
Winthrop Court, Clifton, NJ
Resale Only | 55+ age-restricted | Built 2000 - 2010 | 270 homes
Liberty at Newtown
$300ks - $400ks
Liberty at Newtown, Newtown, CT
Resale Only | 55+ age-restricted | Built 2003 - 2007 | 96 homes
Regency at Wappinger
$500ks
Regency at Wappinger, Wappingers Falls, NY
Resale Only | 55+ age-restricted | Built 2014 - 2020 | 225 homes
Parker Village Estates
$500ks - $600ks
Parker Village Estates, Eatontown, NJ
Resale Only | 55+ age-restricted | Built 2002 - 2002 | 66 homes
Glassbury Court at Cold S...
$500ks - $700ks
Glassbury Court at Cold S..., Cold Spring, NY
Resale Only | 55+ age-restricted | Built 2009 - 2014 | 90 homes
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
Spring Lake Village
$100ks - $200ks
Spring Lake Village, Southington, CT
Resale Only | 55+ age-restricted | Built 1970 - 2004 | 640 homes
Breton Hills
$500ks
Breton Hills, Glen Cove, NY
New Construction | 55+ age-restricted | Built 2019 - present | 72 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
Shadow Lake Village 11 MEDFORD CT, RED BANK, NJ, 07701, Red Bank, NJ 07701
$279,900

1 beds

|

2 baths

|

1,021 sq ft

|

Adult Community

11 MEDFORD CT, RED BANK, NJ, 07701
Community: Shadow Lake Village
Cheesequake Village 13 DELAWARE CT D, OLD BRIDGE, NJ, 07747, Old Bridge, NJ 07747
$279,900

2 beds

|

1 baths

|

949 sq ft

|

Condo

13 DELAWARE CT D, OLD BRIDGE, NJ, 07747
Community: Cheesequake Village
Jefferson Village 59 KIRBY CLOSE D, YORKTOWN, NY, 10598, Yorktown, NY 10598
$399,000

2 beds

|

2 baths

|

910 sq ft

|

Condo

59 KIRBY CLOSE D, YORKTOWN, NY, 10598
Community: Jefferson Village
Jefferson Village 51 JEFFERSON OVAL D, YORKTOWN, NY, 10598, Yorktown, NY 10598
$364,999

2 beds

|

2 baths

|

919 sq ft

|

Condo

51 JEFFERSON OVAL D, YORKTOWN, NY, 10598
Community: Jefferson Village
Heritage Village 401 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$353,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

401 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
Heritage Hills 415 HERITAGE HILLS DR D, SOMERS, NY, 105..., Somers, NY 10589
$875,000

2 beds

|

2 baths

|

1,663 sq ft

|

Condo

415 HERITAGE HILLS DR D, SOMERS, NY, 105...
Community: Heritage Hills
Heritage Village 25 HERITAGE CRST C, SOUTHBURY, CT, 06488, Southbury, CT 06488
$439,900

2 beds

|

2 baths

|

1,447 sq ft

|

Condo

25 HERITAGE CRST C, SOUTHBURY, CT, 06488
Community: Heritage Village
Sunken Pond Estates 3006 AMEN COR, RIVERHEAD, NY, 11901, Riverhead, NY 11901
$499,000

2 beds

|

2 baths

|

1,587 sq ft

|

Condo

3006 AMEN COR, RIVERHEAD, NY, 11901
Community: Sunken Pond Estates
Greenwood Village 2 DOGWOOD LN, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949
$192,500

2 beds

|

2 baths

|

1,064 sq ft

|

Condo

2 DOGWOOD LN, BROOKHAVEN, NY, 11949
Community: Greenwood Village
Heritage Village 1016 HERITAGE VLG B, SOUTHBURY, CT, 0648..., Southbury, CT 06488
$225,000

1 beds

|

1 baths

|

928 sq ft

|

Condo

1016 HERITAGE VLG B, SOUTHBURY, CT, 0648...
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.
Oronoque Village 72 DAKOTA LN B, STRATFORD, CT, 06614, Stratford, CT 06614
$539,500

1 beds

|

3 baths

|

1,118 sq ft

|

Condo

72 DAKOTA LN B, STRATFORD, CT, 06614
Community: Oronoque Village
Heritage Village 977 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$520,000

3 beds

|

2 baths

|

1,716 sq ft

|

Condo

977 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
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...
Shadow Lake Village 4 FRIENDSHIP CT, RED BANK, NJ, 07701, Red Bank, NJ 07701
$650,000

2 beds

|

2 baths

|

Ranch

4 FRIENDSHIP CT, RED BANK, NJ, 07701
Community: Shadow Lake Village
Jefferson Village 18L HASTINGS CT, YORKTOWN, NY, 10598, Yorktown, NY 10598
$395,000

2 beds

|

1 baths

|

1,000 sq ft

|

Condo

18L HASTINGS CT, YORKTOWN, NY, 10598
Community: Jefferson 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 8 QUARTZ WAY, WOODLAND PARK, NJ, 07424, Woodland Park, NJ 07424
$800,000

2 beds

|

2 baths

|

Townhouse

8 QUARTZ WAY, WOODLAND PARK, NJ, 07424
Heritage Village 151 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$199,999

2 beds

|

2 baths

|

1,032 sq ft

|

Condo

151 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Village Estates 137 FRANCESCA WAY, BABYLON, NY, 11701, Babylon, NY 11701
$599,999

2 beds

|

1 baths

|

1,245 sq ft

|

Condo

137 FRANCESCA WAY, BABYLON, NY, 11701
Community: Village Estates
Cheesequake Village 37 HAVEN DR, MATAWAN, NJ, 07747, Matawan, NJ 07747
$235,000

1 beds

|

1 baths

|

708 sq ft

|

Condo

37 HAVEN DR, MATAWAN, NJ, 07747
Community: Cheesequake 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.
Greenwood Village 43 VILLAGE CIR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949
$235,000

2 beds

|

2 baths

|

1,164 sq ft

|

Condo

43 VILLAGE CIR, BROOKHAVEN, NY, 11949
Community: Greenwood Village
Leisure Village 207 WOODBRIDGE DR B, BROOKHAVEN, NY, 119..., Brookhaven, NY 11961
$499,000

2 beds

|

2 baths

|

1,308 sq ft

|

Condo

207 WOODBRIDGE DR B, BROOKHAVEN, NY, 119...
Community: Leisure Village
Rolling Meadows at Wayside 250 ROLLING MEADOWS BLVD, OCEAN TWP, NJ,..., Ocean Twp, NJ 07712
$849,000

3 beds

|

3 baths

|

2,440 sq ft

|

House

250 ROLLING MEADOWS BLVD, OCEAN TWP, NJ,...
Leisure Village 427 AYLESBURY CT A, BROOKHAVEN, NY, 1196..., Brookhaven, NY 11961
$380,000

2 beds

|

2 baths

|

972 sq ft

|

Condo

427 AYLESBURY CT A, BROOKHAVEN, NY, 1196...
Community: Leisure Village
Fairfield at St. James 506 DREW DR, SMITHTOWN, NY, 11780, Smithtown, NY 11780
$585,000

3 beds

|

3 baths

|

1,716 sq ft

|

Condo

506 DREW DR, SMITHTOWN, NY, 11780
Heritage Village 644 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$509,000

3 beds

|

2 baths

|

1,716 sq ft

|

Condo

644 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Oronoque Village 86 S TRL A, STRATFORD, CT, 06614, Stratford, CT 06614
$535,000

2 beds

|

3 baths

|

2,734 sq ft

|

Condo

86 S TRL A, STRATFORD, CT, 06614
Community: Oronoque Village
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
Oronoque Village 252 AGAWAM DR A, STRATFORD, CT, 06614, Stratford, CT 06614
$639,000

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
$270,000

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
$489,900

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
Oronoque Village 639 ONONDAGA LN B, STRATFORD, CT, 06614, Stratford, CT 06614
$629,000

2 beds

|

3 baths

|

1,438 sq ft

|

Condo

639 ONONDAGA LN B, STRATFORD, CT, 06614
Community: Oronoque Village
Fairfield at St. James 908 DREW LN, SMITHTOWN, NY, 11780, Smithtown, NY 11780
$599,000

2 beds

|

2 baths

|

1,050 sq ft

|

Condo

908 DREW LN, SMITHTOWN, NY, 11780
The Villages at Mount Sinai Park 10 LOUDEN LOOP, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766
$749,000

3 beds

|

3 baths

|

2,455 sq ft

|

Condo

10 LOUDEN LOOP, BROOKHAVEN, NY, 11766
Sunken Pond Estates 1403 PEBBLE BEACH PATH, RIVERHEAD, NY, 1..., Riverhead, NY 11901
$489,000

2 beds

|

3 baths

|

1,350 sq ft

|

Condo

1403 PEBBLE BEACH PATH, RIVERHEAD, NY, 1...
Community: Sunken Pond Estates
Leisure Knoll 506 LANCASTER CT, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$549,000

2 beds

|

2 baths

|

1,394 sq ft

|

House

506 LANCASTER CT, BROOKHAVEN, NY, 11961
Community: Leisure Knoll
Heritage Hills 392 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589
$979,000

3 beds

|

2 baths

|

1,793 sq ft

|

Condo

392 HERITAGE HLS A, SOMERS, NY, 10589
Community: Heritage Hills
Heritage Village 41 E MEADOW RD, SOUTHBURY, CT, 06488, Southbury, CT 06488
$399,900

2 beds

|

3 baths

|

1,479 sq ft

|

Condo

41 E MEADOW RD, SOUTHBURY, CT, 06488
Community: Heritage Village
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
Paris Square 5201 RIO VISTA LN, NORTHVALE, NJ, 07647, Northvale, NJ 07647
$735,000

2 beds

|

2 baths

|

Condo

5201 RIO VISTA LN, NORTHVALE, NJ, 07647
Community: Paris Square
Shadow Lake Village 22 CLAREMONT CT, RED BANK, NJ, 07701, Red Bank, NJ 07701
$509,000

2 beds

|

2 baths

|

1,272 sq ft

|

House

22 CLAREMONT CT, RED BANK, NJ, 07701
Community: Shadow Lake 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.

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
363 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: Apr 26, 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