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 4

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
Spring Lake Village 214 WATERS EDGE DR 214, SOUTHINGTON, CT,..., Southington, CT 06489
$317,000

2 beds

|

3 baths

|

1,564 sq ft

|

Condo

214 WATERS EDGE DR 214, SOUTHINGTON, CT,...
Community: Spring Lake Village
Heritage Village 889 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$358,000

2 beds

|

2 baths

|

1,398 sq ft

|

Condo

889 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Woodridge Strathmore Terrace 7 COBBLESTONE WAY, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766
$449,000

2 beds

|

2 baths

|

840 sq ft

|

Condo

7 COBBLESTONE WAY, BROOKHAVEN, NY, 11766
The Villas at Jumping Brook 3 DORAL WAY, NEPTUNE TOWNSHIP, NJ, 07753, Neptune Township, NJ 07753
$724,900

2 beds

|

2 baths

|

1,742 sq ft

|

Ranch

3 DORAL WAY, NEPTUNE TOWNSHIP, NJ, 07753
The Villages NJ 24 CALLE DE ELVIRA F, FREEHOLD, NJ, 0772..., Freehold, NJ 07728
$330,000

2 beds

|

1 baths

|

1,008 sq ft

|

Adult Community

24 CALLE DE ELVIRA F, FREEHOLD, NJ, 0772...
Community: The Villages NJ
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
Greenwood Village 191 VILLAGE CIR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949
$139,999

2 beds

|

2 baths

|

1,032 sq ft

|

Condo

191 VILLAGE CIR, BROOKHAVEN, NY, 11949
Community: Greenwood Village
Oronoque Village 402 MONTAUK LN B, STRATFORD, CT, 06614, Stratford, CT 06614
$515,000

2 beds

|

3 baths

|

1,118 sq ft

|

Condo

402 MONTAUK LN B, STRATFORD, CT, 06614
Community: Oronoque Village
The Waterways at Moriches 549 HIGHLAND CT, BROOKHAVEN, NY, 11955, Brookhaven, NY 11955
$649,000

2 beds

|

2 baths

|

1,497 sq ft

|

Condo

549 HIGHLAND CT, BROOKHAVEN, NY, 11955
Leisure Village 248 NEWCASTLE CT A, BROOKHAVEN, NY, 1196..., Brookhaven, NY 11961
$415,000

2 beds

|

1 baths

|

1,085 sq ft

|

Condo

248 NEWCASTLE CT A, BROOKHAVEN, NY, 1196...
Community: Leisure Village
Leisure Village 375 WOODBRIDGE DR C, BROOKHAVEN, NY, 119..., Brookhaven, NY 11961
$389,000

2 beds

|

1 baths

|

1,171 sq ft

|

Condo

375 WOODBRIDGE DR C, BROOKHAVEN, NY, 119...
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.
Cheesequake Village 10 MAINE CT 734, MATAWAN, NJ, 07747, Matawan, NJ 07747
$325,000

2 beds

|

1 baths

|

949 sq ft

|

Adult Community

10 MAINE CT 734, MATAWAN, NJ, 07747
Community: Cheesequake Village
The Manors at The Colony Preserve 94 LAKESIDE CT, BROOKHAVEN, NY, 11967, Brookhaven, NY 11967
$529,999

2 beds

|

2 baths

|

1,360 sq ft

|

Condo

94 LAKESIDE CT, BROOKHAVEN, NY, 11967
Strathmore Gate East 22 FREEMONT LN, BROOKHAVEN, NY, 11727, Brookhaven, NY 11727
$429,000

2 beds

|

2 baths

|

1,112 sq ft

|

Condo

22 FREEMONT LN, BROOKHAVEN, NY, 11727
Heritage Village 36 HERITAGE CIR B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$525,000

3 beds

|

2 baths

|

1,716 sq ft

|

Condo

36 HERITAGE CIR B, SOUTHBURY, CT, 06488
Community: Heritage Village
South Pond Village 78 SILO WAY 78, BLOOMFIELD, CT, 06002, Bloomfield, CT 06002
$289,900

3 beds

|

3 baths

|

1,639 sq ft

|

Condo

78 SILO WAY 78, BLOOMFIELD, CT, 06002
Community: South Pond Village
The Powder Forest Homes 3 RONAN WAY 3, SIMSBURY, CT, 06070, Simsbury, CT 06070
$629,900

2 beds

|

3 baths

|

1,284 sq ft

|

Condo

3 RONAN WAY 3, SIMSBURY, CT, 06070
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
Heritage Hills 272 HERITAGE HLS C, SOMERS, NY, 10589, Somers, NY 10589
$569,900

2 beds

|

2 baths

|

1,500 sq ft

|

Condo

272 HERITAGE HLS C, SOMERS, NY, 10589
Community: Heritage Hills
The Village at Oxford Greens 575 INVERNESS CT 575, OXFORD, CT, 06478, Oxford, CT 06478
$699,900

3 beds

|

3 baths

|

2,008 sq ft

575 INVERNESS CT 575, OXFORD, CT, 06478
Cheesequake Village 11 ALABAMA CT 835, MATAWAN, NJ, 07747, Matawan, NJ 07747
$375,000

2 beds

|

2 baths

|

976 sq ft

|

Adult Community

11 ALABAMA CT 835, MATAWAN, NJ, 07747
Community: Cheesequake Village
Cheesequake Village 11 ALABAMA CT, OLD BRIDGE, NJ, 07747, Old Bridge, NJ 07747
$375,000

2 beds

|

2 baths

|

976 sq ft

|

Condo

11 ALABAMA CT, OLD BRIDGE, 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.
Cheesequake Village 1 CONNECTICUT CT, OLD BRIDGE, NJ, 07747, Old Bridge, NJ 07747
$249,500

1 beds

|

1 baths

|

708 sq ft

|

Condo

1 CONNECTICUT CT, OLD BRIDGE, NJ, 07747
Community: Cheesequake Village
Cedar Village at Ocean 14 DOGWOOD DR, OCEAN TWP, NJ, 07712, Ocean Twp, NJ 07712
$748,900

2 beds

|

2 baths

|

1,831 sq ft

|

House

14 DOGWOOD DR, OCEAN TWP, NJ, 07712
Cheesequake Village 1 CONNECTICUT CT 843, MATAWAN, NJ, 07747, Matawan, NJ 07747
$249,500

1 beds

|

1 baths

|

708 sq ft

|

Ranch

1 CONNECTICUT CT 843, MATAWAN, NJ, 07747
Community: Cheesequake Village
Regency at Holmdel 17 SPALDING DR, HOLMDEL, NJ, 07733, Holmdel, NJ 07733
$1,333,000

3 beds

|

4 baths

|

3,490 sq ft

|

Adult Community

17 SPALDING DR, HOLMDEL, NJ, 07733
Community: Regency at Holmdel
Oak Meadow Estates 65 OAK MEADOW LN 65, TORRINGTON, CT, 067..., Torrington, CT 06790
$485,000

2 beds

|

4 baths

|

2,164 sq ft

|

Condo

65 OAK MEADOW LN 65, TORRINGTON, CT, 067...
Community: Oak Meadow Estates
Four Seasons at Wayne 703 FOUR SEASONS DR, WAYNE, NJ, 07470, Wayne, NJ 07470
$510,000

2 beds

|

2 baths

|

Condo

703 FOUR SEASONS DR, WAYNE, NJ, 07470
Jefferson Village 119 VILLAGE RD H, YORKTOWN, NY, 10598, Yorktown, NY 10598
$439,000

2 beds

|

2 baths

|

1,100 sq ft

|

Condo

119 VILLAGE RD H, YORKTOWN, NY, 10598
Community: Jefferson Village
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
HarborView 626 VILLAGE GRN, NORTH HEMPSTEAD, NY, 11..., North Hempstead, NY 11050
$1,199,000

3 beds

|

3 baths

|

2,424 sq ft

|

Condo

626 VILLAGE GRN, NORTH HEMPSTEAD, NY, 11...
Community: HarborView
Rosemont Estates 329 VAN DUSEN DR, MARLBORO, NJ, 07746, Marlboro, NJ 07746
$959,900

3 beds

|

4 baths

|

2,885 sq ft

|

House

329 VAN DUSEN DR, MARLBORO, NJ, 07746
Community: Rosemont Estates
Heritage Village 4 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$249,000

1 beds

|

1 baths

|

928 sq ft

|

Condo

4 HERITAGE VLG A, 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.
Jefferson Village 129 COLUMBIA CT D, YORKTOWN, NY, 10598, Yorktown, NY 10598
$469,999

2 beds

|

2 baths

|

1,100 sq ft

|

Condo

129 COLUMBIA CT D, YORKTOWN, NY, 10598
Community: Jefferson Village
Fairview at Oxford Greens 1077 AUGUSTA DR 1077, OXFORD, CT, 06478, Oxford, CT 06478
$664,900

3 beds

|

3 baths

|

2,256 sq ft

|

Condo

1077 AUGUSTA DR 1077, OXFORD, CT, 06478
The Village at Oxford Greens 1077 AUGUSTA DR 1077, OXFORD, CT, 06478, Oxford, CT 06478
$664,900

3 beds

|

3 baths

|

2,256 sq ft

|

Condo

1077 AUGUSTA DR 1077, OXFORD, CT, 06478
Village Estates 105 FRANCESCA WAY 105, BABYLON, NY, 1170..., Babylon, NY 11701
$559,000

2 beds

|

1 baths

|

1,229 sq ft

|

Condo

105 FRANCESCA WAY 105, BABYLON, NY, 1170...
Community: Village Estates
Overlook 2079 SUMMIT LOOP 103, CARMEL, NY, 10512, Carmel, NY 10512
$899,000

2 beds

|

2 baths

|

1,948 sq ft

|

Condo

2079 SUMMIT LOOP 103, CARMEL, NY, 10512
Community: Overlook
Glenwood Village 1661 OLD COUNTRY RD 62, RIVERHEAD, NY, 1..., Riverhead, NY 11901
$425,000

3 beds

|

2 baths

|

1,680 sq ft

|

Manufactured Home

1661 OLD COUNTRY RD 62, RIVERHEAD, NY, 1...
Community: Glenwood Village
Leisure Village 72 ENFIELD CT A, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$359,900

2 beds

|

1 baths

|

1,085 sq ft

|

Condo

72 ENFIELD CT A, BROOKHAVEN, NY, 11961
Community: Leisure Village
Four Seasons at Great Notch Spa and Club 5 SLATE CT A3, WOODLAND PARK, NJ, 07424, Woodland Park, NJ 07424
$615,000

2 beds

|

2 baths

|

Condo

5 SLATE CT A3, WOODLAND PARK, NJ, 07424
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
Winthrop Court 1107 WICKHAM TER 374, CLIFTON, NJ, 07013, Clifton, NJ 07013
$559,000

2 beds

|

2 baths

|

Condo

1107 WICKHAM TER 374, CLIFTON, NJ, 07013
Community: Winthrop Court
Pond Spring Village 17 PONDVIEW CIR 17, BEACON FALLS, CT, 06..., Beacon Falls, CT 06403
$474,900

2 beds

|

2 baths

|

1,474 sq ft

|

Condo

17 PONDVIEW CIR 17, BEACON FALLS, CT, 06...
Community: Pond Spring 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