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

311 homes near Westport

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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
$200Ks - $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
$600Ks - $1Ms
The Greens at Half Hollow, Melville, NY
Resale Only | 55+ age-restricted | Built 1994 - 2005 | 1,200 homes
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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
$300Ks - $600Ks
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 - $600Ks
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
$100Ks - $300Ks
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
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
Leisure Glen, Ridge, NY
Resale Only | 55+ age-restricted | Built 1985 - 2010 | 646 homes
Spring Lake Village
$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
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Questions? Call us: (475) 471-1908
5 rating (1 reviews) Shady Oaks
$400Ks
Shady Oaks, Red Bank, NJ
Resale Only | 55+ age-restricted | Built 1982 - 1983 | 366 homes
Dutchgate
$400Ks
Dutchgate, Valley Stream, NY
Resale Only | 55+ age-restricted | Built 2009 - 2015 | 348 homes
The Waterways at Moriches
$400Ks - $700Ks
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 - $800Ks
Overlook, Carmel, NY
New Construction | 55+ age-restricted | 300 homes
Cedar Village at Ocean
$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
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
Vineyards at Blue Point, Blue Point, NY
Resale Only | 55+ age-restricted | Built 2016 - 2018 | 280 homes
Apple Ridge
$700Ks
Apple Ridge, Mahwah, NJ
Resale Only | Age-targeted | Built 1977 - 1991 | 276 homes
HarborView
$900Ks - $1Ms
HarborView, Port Washington, NY
Resale Only | 55+ age-restricted | Built 2002 - 2004 | 270 homes
Winthrop Court
$400Ks
Winthrop Court, Clifton, NJ
Resale Only | 55+ age-restricted | Built 2000 - 2010 | 270 homes
The Club at Melville
$500Ks
The Club at Melville, Melville, NY
Resale Only | 55+ age-restricted | Built 2015 - 2017 | 261 homes
Stoneleigh Woods at Riverhead 4 HAVERTON CT, RIVERHEAD, NY, 11901, Riverhead, NY 11901
$660,000

2 beds

|

3 baths

|

2,175 sq ft

|

Condo

4 HAVERTON CT, RIVERHEAD, NY, 11901
Glenwood Village 1661 OLD COUNTRY RD 69, RIVERHEAD, NY, 1..., Riverhead, NY 11901
$239,999

2 beds

|

2 baths

|

924 sq ft

|

Manufactured Home

1661 OLD COUNTRY RD 69, RIVERHEAD, NY, 1...
Community: Glenwood Village
Leisure Village 405 WOODBRIDGE DR D, RIDGE, NY, 11961, Ridge, NY 11961
$290,000

2 beds

|

1 baths

|

874 sq ft

|

Condo

405 WOODBRIDGE DR D, RIDGE, NY, 11961
Community: Leisure Village
The Seasons at East Meadow 383 SUMMER CT, EAST MEADOW, NY, 11554, East Meadow, NY 11554
$640,000

2 beds

|

2 baths

|

1,272 sq ft

|

Condo

383 SUMMER CT, EAST MEADOW, NY, 11554
Stoneleigh Woods at Riverhead 67 STONELEIGH DR, RIVERHEAD, NY, 11901, Riverhead, NY 11901
$640,000

2 beds

|

3 baths

|

1,972 sq ft

|

Condo

67 STONELEIGH DR, RIVERHEAD, NY, 11901
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
Leisure Knoll 323 BROWNFIELD DR, RIDGE, NY, 11961, Ridge, NY 11961
$360,000

2 beds

|

1 baths

|

655 sq ft

|

Condo

323 BROWNFIELD DR, RIDGE, NY, 11961
Community: Leisure Knoll
Plymouth Estates at Mount Sinai 230 IRA RD # 230, MOUNT SINAI, NY, 11766, Mount Sinai, NY 11766
$589,999

2 beds

|

2 baths

|

1,317 sq ft

|

Condo

230 IRA RD # 230, MOUNT SINAI, NY, 11766
Greenwood Village 145 VILLAGE CIR, MANORVILLE, NY, 11949, Manorville, NY 11949
$199,900

2 beds

|

2 baths

|

1,100 sq ft

|

Condo

145 VILLAGE CIR, MANORVILLE, NY, 11949
Community: Greenwood Village
Greenwood Village 53 VILLAGE CIR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949
$275,000

2 beds

|

2 baths

|

1,100 sq ft

|

Condo

53 VILLAGE CIR, BROOKHAVEN, NY, 11949
Community: Greenwood Village
Glenwood Village 1661 OLD COUNTRY RD UNIT 280, RIVERHEAD,..., Riverhead, NY 11901
$205,000

2 beds

|

2 baths

|

1,008 sq ft

|

Manufactured Home

1661 OLD COUNTRY RD UNIT 280, RIVERHEAD,...
Community: Glenwood 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 1 WILLOW CT, MANORVILLE, NY, 11949, Manorville, NY 11949
$229,900

2 beds

|

2 baths

|

1,450 sq ft

|

Condo

1 WILLOW CT, MANORVILLE, NY, 11949
Community: Greenwood Village
The Vineyards at Miller Place 48 AVERY LN, MILLER PLACE, NY, 11764, Miller Place, NY 11764
$679,900

2 beds

|

3 baths

|

1,486 sq ft

|

Condo

48 AVERY LN, MILLER PLACE, NY, 11764
Westhampton Pines 112 ASHLEY DR, WESTHAMPTON, NY, 11977, Westhampton, NY 11977
$1,295,000

3 beds

|

3 baths

|

2,306 sq ft

|

Condo

112 ASHLEY DR, WESTHAMPTON, NY, 11977
Community: Westhampton Pines
Jefferson Village 175 LONG HILL DR B, YORKTOWN HEIGHTS, NY..., Yorktown Heights, NY 10598
$425,000

2 beds

|

2 baths

|

1,159 sq ft

|

Condo

175 LONG HILL DR B, YORKTOWN HEIGHTS, NY...
Community: Jefferson Village
The Waterways at Moriches 509 OAK BLUFF CT, MORICHES, NY, 11955, Moriches, NY 11955
$755,000

2 beds

|

3 baths

|

1,875 sq ft

|

Condo

509 OAK BLUFF CT, MORICHES, NY, 11955
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
Greenwood Village 164 VILLAGE CIR, MANORVILLE, NY, 11949, Manorville, NY 11949
$174,990

2 beds

|

2 baths

|

938 sq ft

|

Manufactured Home

164 VILLAGE CIR, MANORVILLE, NY, 11949
Community: Greenwood Village
Leisure Glen 12 BALDWIN CT, RIDGE, NY, 11961, Ridge, NY 11961
$479,990

2 beds

|

2 baths

|

1,542 sq ft

|

Condo

12 BALDWIN CT, RIDGE, NY, 11961
Community: Leisure Glen
Jefferson Village 159 CARRIAGE CT C, YORKTOWN HEIGHTS, NY,..., Yorktown Heights, NY 10598
$569,999

2 beds

|

2 baths

|

1,300 sq ft

|

Condo

159 CARRIAGE CT C, YORKTOWN HEIGHTS, NY,...
Community: Jefferson Village
Greenwood Village 77 VILLAGE CIR, MANORVILLE, NY, 11949, Manorville, NY 11949
$155,900

2 beds

|

1 baths

|

1,000 sq ft

|

Condo

77 VILLAGE CIR, MANORVILLE, NY, 11949
Community: Greenwood Village
Leisure Village 46 TRENT CT C, RIDGE, NY, 11961, Ridge, NY 11961
$350,000

2 beds

|

1 baths

|

1,085 sq ft

|

Condo

46 TRENT CT C, RIDGE, 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.
Greenwood Village 99 VILLAGE CIR, MANORVILLE, NY, 11949, Manorville, NY 11949
$269,988

2 beds

|

2 baths

|

1,487 sq ft

|

Condo

99 VILLAGE CIR, MANORVILLE, NY, 11949
Community: Greenwood Village
Vineyards at Moriches 134 HALLEY DR, CENTER MORICHES, NY, 1193..., Center Moriches, NY 11934
$735,000

3 beds

|

3 baths

|

2,933 sq ft

|

Condo

134 HALLEY DR, CENTER MORICHES, NY, 1193...
Glenwood Village 1661 OLD COUNTRY RD 163, RIVERHEAD, NY, ..., Riverhead, NY 11901
$149,999

2 beds

|

1 baths

|

816 sq ft

|

Mobile Home

1661 OLD COUNTRY RD 163, RIVERHEAD, NY, ...
Community: Glenwood Village
Leisure Village 280 BERWICK CT A, RIDGE, NY, 11961, Ridge, NY 11961
$359,900

2 beds

|

1 baths

|

836 sq ft

|

Condo

280 BERWICK CT A, RIDGE, NY, 11961
Community: Leisure Village
Glenwood Village 1661 OLD COUNTRY RD UNIT 539, RIVERHEAD,..., Riverhead, NY 11901
$399,000

2 beds

|

2 baths

|

1,500 sq ft

|

Manufactured Home

1661 OLD COUNTRY RD UNIT 539, RIVERHEAD,...
Community: Glenwood Village
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
Heritage Hills 627 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589
$525,000

1 beds

|

2 baths

|

1,098 sq ft

|

Condo

627 HERITAGE HLS A, SOMERS, NY, 10589
Community: Heritage Hills
Leisure Knoll 190 CANTERBURY DR, RIDGE, NY, 11961, Ridge, NY 11961
$434,999

2 beds

|

1 baths

|

787 sq ft

|

Condo

190 CANTERBURY DR, RIDGE, NY, 11961
Community: Leisure Knoll
Meadowbrooke Pointe East Meadow 123 EMANUEL WAY, EAST MEADOW, NY, 11554, East Meadow, NY 11554
$729,000

2 beds

|

2 baths

|

1,390 sq ft

|

Condo

123 EMANUEL WAY, EAST MEADOW, NY, 11554
The Manors at The Colony Preserve 41 GREENTREE CT, SHIRLEY, NY, 11967, Shirley, NY 11967
$535,000

2 beds

|

2 baths

|

1,800 sq ft

|

Condo

41 GREENTREE CT, SHIRLEY, NY, 11967
Glenwood Village 1661 OLD COUNTRY RD UNIT 563, RIVERHEAD,..., Riverhead, NY 11901
$484,900

2 beds

|

2 baths

|

1,500 sq ft

|

Manufactured Home

1661 OLD COUNTRY RD UNIT 563, RIVERHEAD,...
Community: Glenwood 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.
Fairfield at St. James 914 FENWAY RD, SAINT JAMES, NY, 11780, Saint James, NY 11780
$470,000

2 beds

|

2 baths

|

1,200 sq ft

|

Condo

914 FENWAY RD, SAINT JAMES, NY, 11780
The Waterways at Moriches 546 HIGHLAND CT, MORICHES, NY, 11955, Moriches, NY 11955
$499,990

2 beds

|

2 baths

|

1,497 sq ft

|

Condo

546 HIGHLAND CT, MORICHES, NY, 11955
The Waterways at Moriches 414 LINDSAY LN, MORICHES, NY, 11955, Moriches, NY 11955
$535,000

2 beds

|

2 baths

|

2,141 sq ft

|

Condo

414 LINDSAY LN, MORICHES, NY, 11955
Jefferson Village 141 FLINTLOCK WAY B, YORKTOWN HEIGHTS, N..., Yorktown Heights, NY 10598
$675,000

2 beds

|

2 baths

|

1,555 sq ft

|

Condo

141 FLINTLOCK WAY B, YORKTOWN HEIGHTS, N...
Community: Jefferson Village
The Waterways at Moriches 244 RIVER DR, MORICHES, NY, 11955, Moriches, NY 11955
$625,000

2 beds

|

2 baths

|

1,960 sq ft

|

Condo

244 RIVER DR, MORICHES, NY, 11955
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
Stoneleigh Woods at Riverhead 18 KENNSINGTON CT, RIVERHEAD, NY, 11901, Riverhead, NY 11901
$665,000

2 beds

|

3 baths

|

2,172 sq ft

|

Condo

18 KENNSINGTON CT, RIVERHEAD, NY, 11901
Strathmore Gate East 141 FORGE LN, CORAM, NY, 11727, Coram, NY 11727
$319,000

1 beds

|

1 baths

|

728 sq ft

|

Condo

141 FORGE LN, CORAM, NY, 11727
Meadowbrook Pointe Athletic Club & Spa 323 ROOSEVELT WAY, WESTBURY, NY, 11590, Westbury, NY 11590
$875,000

2 beds

|

2 baths

|

1,328 sq ft

|

Condo

323 ROOSEVELT WAY, WESTBURY, NY, 11590
Country Village Estates 163 THEODORE DR, CORAM, NY, 11727, Coram, NY 11727
$472,000

2 beds

|

2 baths

|

1,261 sq ft

|

Condo

163 THEODORE DR, CORAM, NY, 11727
Greenwood Village 21 LIMETREE DR, MANORVILLE, NY, 11949, Manorville, NY 11949
$179,000

2 beds

|

2 baths

|

1,100 sq ft

|

Condo

21 LIMETREE DR, MANORVILLE, NY, 11949
Community: Greenwood Village
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311 homes near Westport
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