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

169 communities near Westport

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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
Oronoque Village
$200ks - $400ks
Oronoque Village, Stratford, CT
Resale Only | 55+ age-restricted | Built 1971 - 1977 | 929 homes
3 rating (2 reviews) Heritage Hills
$400ks - $900ks
Heritage Hills, Somers, NY
Resale Only | Age-targeted | Built 1974 - 2006 | 2,600 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
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Questions? Call us: (475) 471-1908
3.7 rating (3 reviews) Greenwood Village
$100ks
Greenwood Village, Manorville, NY
Resale Only | 55+ age-restricted | Built 1980 - 2000 | 512 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
2.8 rating (4 reviews) Cheesequake Village
$100ks - $200ks
Cheesequake Village, Old Bridge, NJ
Resale Only | 55+ age-restricted | Built 1965 - 1971 | 713 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
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
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
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) Rosemont Estates
$500ks - $700ks
Rosemont Estates, Marlboro, NJ
Resale Only | 55+ age-restricted | Built 2004 - 2014 | 242 homes
4 rating (8 reviews) Glenwood Village
$100ks - $200ks
Glenwood Village, Riverhead, NY
New and Resale | 55+ age-restricted | Built 1959 - present | 588 homes
Fairview at Oxford Greens
$400ks - $600ks
Fairview at Oxford Greens, Oxford, CT
New and Resale | 55+ age-restricted | Built 2019 - present | 125 homes
Winthrop Court
$400ks - $600ks
Winthrop Court, Clifton, NJ
Resale Only | 55+ age-restricted | Built 2000 - 2010 | 270 homes
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
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
4.2 rating (12 reviews) Surrey Downs
$200ks - $300ks
Surrey Downs, Freehold, NJ
Resale Only | 55+ age-restricted | Built 1986 - 1997 | 443 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 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.
Leisure Knoll
$200ks - $400ks
Leisure Knoll, Ridge, NY
Resale Only | 55+ age-restricted | Built 1972 - 1982 | 701 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
The Villas at Narraganset...
$400ks
The Villas at Narraganset..., Lindenhurst, NY
Resale Only | 55+ age-restricted | Built 2004 - 2005 | 138 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
5 rating (1 reviews) Newtown Woods
$300ks - $500ks
Newtown Woods, Newtown, CT
New and Resale | 55+ age-restricted | Built 2011 - present | 178 homes
Rivington
$300ks - $900ks
Rivington, Danbury, CT
New and Resale | Age-targeted | Built 2006 - present | 1,050 homes
Regency at Fishkill
$300ks - $400ks
Regency at Fishkill, Fishkill, NY
Resale Only | 55+ age-restricted | Built 2008 - 2020 | 164 homes
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Questions? Call us: (475) 471-1908
HarborView
$600ks - $1Ms
HarborView, Port Washington, NY
Resale Only | 55+ age-restricted | Built 2002 - 2004 | 270 homes
Spring Lake Village
$100ks - $200ks
Spring Lake Village, Southington, CT
Resale Only | 55+ age-restricted | Built 1970 - 2004 | 640 homes
Four Seasons at Cedar Gro...
$400ks - $600ks
Four Seasons at Cedar Gro..., Cedar Grove, NJ
Resale Only | 55+ age-restricted | Built 2000 - 2005 | 156 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.
Chelsea Square
$300ks - $400ks
Chelsea Square, Morganville, NJ
New and Resale | 55+ age-restricted | Built 2007 - present | 225 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
3.7 rating (3 reviews) Nobility Crest at Ocean
$300ks - $500ks
Nobility Crest at Ocean, Ocean Township, NJ
New and Resale | 55+ age-restricted | Built 2006 - present | 198 homes
5 rating (1 reviews) Westhampton Pines
$900ks - $1Ms
Westhampton Pines, Westhampton, NY
Resale Only | 55+ age-restricted | Built 2005 - 2013 | 189 homes
5 rating (1 reviews) Sunrise Village
$400ks
Sunrise Village, Sayville, NY
Resale Only | 55+ age-restricted | Built 1985 - 1990 | 213 homes
5 rating (1 reviews) Sunken Pond Estates
$400ks
Sunken Pond Estates, Riverhead, NY
Resale Only | 55+ age-restricted | Built 2003 - 2005 | 194 homes
Dutchgate
$300ks - $500ks
Dutchgate, Valley Stream, NY
Resale Only | 55+ age-restricted | Built 2009 - 2015 | 348 homes
Village Estates
$300ks - $400ks
Village Estates, Amityville, NY
Resale Only | 55+ age-restricted | Built 2006 - 2008 | 138 homes
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
Snug Harbor
$600ks - $700ks
Snug Harbor, Amityville, NY
Resale Only | 55+ age-restricted | Built 1970 - 1974 | 176 homes
The Retreat at Carmel
$300ks - $800ks
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.
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New Oronoque Village 377 PIUTE LN A, STRATFORD, CT, 06614, Stratford, CT 06614
$499,000

1 beds

|

3 baths

|

2,025 sq ft

|

Condo

377 PIUTE LN A, STRATFORD, CT, 06614
Community: Oronoque Village
New Knickerbocker Bay Club 433 MAIN ST 212, NORTH HEMPSTEAD, NY, 11..., North Hempstead, NY 11050
$2,300,000

3 beds

|

3 baths

|

2,544 sq ft

|

Condo

433 MAIN ST 212, NORTH HEMPSTEAD, NY, 11...
New Leisure Glen 12 BALDWIN CT, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$469,990

2 beds

|

2 baths

|

1,542 sq ft

|

Condo

12 BALDWIN CT, BROOKHAVEN, NY, 11961
Community: Leisure Glen
New The Villages at Mount Sinai Park 16 OAKHURST CT, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766
$789,000

2 beds

|

2 baths

|

1,929 sq ft

|

House

16 OAKHURST CT, BROOKHAVEN, NY, 11766
New The Waterways at Moriches 485 WOODSCREEK CT, BROOKHAVEN, NY, 11955, Brookhaven, NY 11955
$778,000

2 beds

|

3 baths

|

1,854 sq ft

|

Condo

485 WOODSCREEK CT, BROOKHAVEN, NY, 11955
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
New Leisure Village 404 WOODBRIDGE RD B, BROOKHAVEN, NY, 119..., Brookhaven, NY 11961
$359,900

2 beds

|

1 baths

|

907 sq ft

|

Condo

404 WOODBRIDGE RD B, BROOKHAVEN, NY, 119...
Community: Leisure Village
New Gloria Commons 32 LUCIUS CT 32, MILFORD, CT, 06460, Milford, CT 06460
$450,000

2 beds

|

3 baths

|

2,079 sq ft

|

Condo

32 LUCIUS CT 32, MILFORD, CT, 06460
Community: Gloria Commons
New HarborView 333 E OVERLOOK, NORTH HEMPSTEAD, NY, 110..., North Hempstead, NY 11050
$1,249,000

3 beds

|

3 baths

|

2,758 sq ft

|

Condo

333 E OVERLOOK, NORTH HEMPSTEAD, NY, 110...
Community: HarborView
New Shady Oaks 64 BOXWOOD TER, RED BANK, NJ, 07701, Red Bank, NJ 07701
$569,900

2 beds

|

2 baths

|

1,386 sq ft

|

House

64 BOXWOOD TER, RED BANK, NJ, 07701
Community: Shady Oaks
New Paris Square 2303 RIO VISTA LN, NORTHVALE, NJ, 07647, Northvale, NJ 07647
$575,000

2 beds

|

2 baths

|

Condo

2303 RIO VISTA LN, NORTHVALE, NJ, 07647
Community: Paris Square
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 Wolfe Landing 35 WOLFE CIR, CLARKSTOWN, NY, 10994, Clarkstown, NY 10994
$899,000

2 beds

|

3 baths

|

2,608 sq ft

|

House

35 WOLFE CIR, CLARKSTOWN, NY, 10994
Community: Wolfe Landing
New Beckley Farms 13 CONCORD DR 13, BERLIN, CT, 06037, Berlin, CT 06037
$624,900

3 beds

|

3 baths

|

2,030 sq ft

|

Condo

13 CONCORD DR 13, BERLIN, CT, 06037
Community: Beckley Farms
New The Villas at Narragansett 712 NARRAGANSETT VILLAS DR 712, BABYLON,..., Babylon, NY 11757
$619,999

2 beds

|

2 baths

|

1,231 sq ft

|

Condo

712 NARRAGANSETT VILLAS DR 712, BABYLON,...
New Newtown Woods 603 BROOKSIDE CT 603, NEWTOWN, CT, 06470, Newtown, CT 06470
$473,000

2 beds

|

2 baths

|

1,504 sq ft

|

Condo

603 BROOKSIDE CT 603, NEWTOWN, CT, 06470
Community: Newtown Woods
New Rosemont Estates 202 SCARBOROUGH WAY, MARLBORO, NJ, 07746, Marlboro, NJ 07746
$925,000

3 beds

|

4 baths

|

2,885 sq ft

|

Adult Community

202 SCARBOROUGH WAY, MARLBORO, NJ, 07746
Community: Rosemont Estates
New The Villages NJ 10 ZACATIN RD B, FREEHOLD, NJ, 07728, Freehold, NJ 07728
$429,000

2 beds

|

2 baths

|

1,248 sq ft

|

Adult Community

10 ZACATIN RD B, 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
New Glenwood Village 1661 OLD COUNTRY RD 516, RIVERHEAD, NY, ..., Riverhead, NY 11901
$499,999

2 beds

|

2 baths

|

1,624 sq ft

|

Manufactured Home

1661 OLD COUNTRY RD 516, RIVERHEAD, NY, ...
Community: Glenwood Village
New Heritage Village 29 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$253,900

2 beds

|

2 baths

|

1,076 sq ft

|

Condo

29 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
New Winthrop Court 1107 WICKHAM TER 374, CLIFTON CITY, NJ, ..., Clifton City, NJ 07013
$559,000

2 beds

|

2 baths

|

1,489 sq ft

1107 WICKHAM TER 374, CLIFTON CITY, NJ, ...
Community: Winthrop Court
New Shadow Lake Village 42 LEXINGTON CT, RED BANK, NJ, 07701, Red Bank, NJ 07701
$696,000

2 beds

|

2 baths

|

952 sq ft

|

Ranch

42 LEXINGTON 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.
New Meadow Brook Estates 521 HEATHERWOOD CT 521, OXFORD, CT, 0647..., Oxford, CT 06478
$599,900

2 beds

|

3 baths

|

1,866 sq ft

|

Condo

521 HEATHERWOOD CT 521, OXFORD, CT, 0647...
New Cheesequake Village 1 OKLAHOMA DR A, OLD BRIDGE, NJ, 07747, Old Bridge, NJ 07747
$299,000

2 beds

|

1 baths

|

Condo

1 OKLAHOMA DR A, OLD BRIDGE, NJ, 07747
Community: Cheesequake Village
New Glenwood Village 1661 OLD COUNTRY RD 417, RIVERHEAD, NY, ..., Riverhead, NY 11901
$339,000

2 beds

|

2 baths

|

1,344 sq ft

|

Manufactured Home

1661 OLD COUNTRY RD 417, RIVERHEAD, NY, ...
Community: Glenwood Village
New Setauket Meadows 86 BRIANNA DR, BROOKHAVEN, NY, 11733, Brookhaven, NY 11733
$775,000

2 beds

|

3 baths

|

1,991 sq ft

|

Condo

86 BRIANNA DR, BROOKHAVEN, NY, 11733
Community: Setauket Meadows
New Snug Harbor 65 HARBOR N, BABYLON, NY, 11701, Babylon, NY 11701
$629,000

2 beds

|

2 baths

|

935 sq ft

|

Condo

65 HARBOR N, BABYLON, NY, 11701
Community: Snug Harbor
New The Powder Forest Homes 37 BANTRY RD 37, SIMSBURY, CT, 06070, Simsbury, CT 06070
$899,000

3 beds

|

5 baths

|

2,724 sq ft

37 BANTRY RD 37, SIMSBURY, CT, 06070
New Jefferson Village 51 JEFFERSON OVAL F, YORKTOWN, NY, 10598, Yorktown, NY 10598
$448,500

2 beds

|

2 baths

|

1,100 sq ft

|

Condo

51 JEFFERSON OVAL F, YORKTOWN, NY, 10598
Community: Jefferson Village
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
New Regency at Wappinger 50 STRATFORD LN, WAPPINGER, NY, 12590, Wappinger, NY 12590
$689,000

2 beds

|

3 baths

|

1,823 sq ft

|

Condo

50 STRATFORD LN, WAPPINGER, NY, 12590
New Leisure Village 368 WOODBRIDGE DR A, BROOKHAVEN, NY, 119..., Brookhaven, NY 11961
$419,990

2 beds

|

1 baths

|

Condo

368 WOODBRIDGE DR A, BROOKHAVEN, NY, 119...
Community: Leisure Village
New The Village at Oxford Greens 114 COUNTRY CLUB DR 114, OXFORD, CT, 064..., Oxford, CT 06478
$575,000

2 beds

|

2 baths

|

1,590 sq ft

114 COUNTRY CLUB DR 114, OXFORD, CT, 064...
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 Cheesequake Village 52 GALEWOOD DR 637, MATAWAN, NJ, 07747, Matawan, NJ 07747
$359,000

2 beds

|

2 baths

|

976 sq ft

|

Townhouse

52 GALEWOOD DR 637, MATAWAN, NJ, 07747
Community: Cheesequake Village
New Shadow Lake Village 93 LEXINGTON CT, RED BANK, NJ, 07701, Red Bank, NJ 07701
$339,000

2 beds

|

1 baths

|

999 sq ft

|

Adult Community

93 LEXINGTON CT, RED BANK, NJ, 07701
Community: Shadow Lake Village
New Leisure Knoll 204 BELFAST LN, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$460,000

2 beds

|

2 baths

|

849 sq ft

|

House

204 BELFAST LN, BROOKHAVEN, NY, 11961
Community: Leisure Knoll
New Newtown Woods 1211 BROOKSIDE CT 1211, NEWTOWN, CT, 064..., Newtown, CT 06470
$485,000

2 beds

|

2 baths

|

1,483 sq ft

|

Condo

1211 BROOKSIDE CT 1211, NEWTOWN, CT, 064...
Community: Newtown Woods
New Heritage Village 930 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$489,900

2 beds

|

2 baths

|

1,398 sq ft

|

Condo

930 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
New Shadow Lake Village 56 CLAREMONT CT, RED BANK, NJ, 07701, Red Bank, NJ 07701
$390,000

1 beds

|

2 baths

|

1,186 sq ft

|

House

56 CLAREMONT CT, RED BANK, NJ, 07701
Community: Shadow Lake Village
New Leisure Village 124 EXMORE CT A, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$354,900

2 beds

|

1 baths

|

1,085 sq ft

|

Condo

124 EXMORE CT A, BROOKHAVEN, NY, 11961
Community: Leisure Village
New Liberty at Newtown 66 SUZIE DR 66, NEWTOWN, CT, 06470, Newtown, CT 06470
$636,000

2 beds

|

3 baths

|

2,407 sq ft

|

Condo

66 SUZIE DR 66, NEWTOWN, CT, 06470
Community: Liberty at Newtown
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
Glassbury Court at Cold Spring 19 REVOLUTION RD, PHILIPSTOWN, NY, 10516, Philipstown, NY 10516
$567,358

2 beds

|

3 baths

|

1,806 sq ft

|

Condo

19 REVOLUTION RD, PHILIPSTOWN, NY, 10516
The Manors at The Colony Preserve 15 CRICKET CT, BROOKHAVEN, NY, 11967, Brookhaven, NY 11967
$499,999

2 beds

|

2 baths

|

1,322 sq ft

|

Condo

15 CRICKET CT, BROOKHAVEN, NY, 11967
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.

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