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

167 communities 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
$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!
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Rivington
$600Ks - $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 - $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 - $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 - $400Ks
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
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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 - $700Ks
The Waterways at Moriches, Moriches, NY
Resale Only | 55+ age-restricted | Built 1985 - 1999 | 343 homes
Rolling Meadows at Waysid...
$800Ks - $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 - $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 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
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
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
Apple Ridge
$700Ks - $700Ks
Apple Ridge, Mahwah, NJ
Resale Only | Age-targeted | Built 1977 - 1991 | 276 homes
Winthrop Court
$400Ks - $400Ks
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
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
Heritage Hills 349 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589
$625,000

2 beds

|

2 baths

|

1,484 sq ft

|

Condo

349 HERITAGE HLS B, SOMERS, NY, 10589
Community: Heritage Hills
Greenwood Village 45 DOGWOOD LN, MANORVILLE, NY, 11949, Manorville, NY 11949
$199,997

2 beds

|

2 baths

|

1,134 sq ft

|

Condo

45 DOGWOOD LN, MANORVILLE, NY, 11949
Community: Greenwood Village
Leisure Village 120 EXMORE CT D, RIDGE, NY, 11961, Ridge, NY 11961
$239,990

1 beds

|

1 baths

|

684 sq ft

|

Condo

120 EXMORE CT D, RIDGE, NY, 11961
Community: Leisure Village
Stoneleigh Woods at Riverhead 159 STONELEIGH DR, RIVERHEAD, NY, 11901, Riverhead, NY 11901
$680,000

2 beds

|

3 baths

|

2,175 sq ft

|

Condo

159 STONELEIGH DR, RIVERHEAD, NY, 11901
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
Leisure Village 96 ENFIELD CT B, RIDGE, NY, 11961, Ridge, NY 11961
$424,000

2 beds

|

2 baths

|

1,486 sq ft

|

Condo

96 ENFIELD CT B, RIDGE, NY, 11961
Community: Leisure Village
Overlook 4073 FAIRWAYS DR # 137, CARMEL, NY, 1051..., Carmel, NY 10512
$665,000

3 beds

|

3 baths

|

1,914 sq ft

|

Condo

4073 FAIRWAYS DR # 137, CARMEL, NY, 1051...
Community: Overlook
Regency at Fishkill 334 REGENCY DR, FISHKILL, NY, 12524, Fishkill, NY 12524
$539,900

2 beds

|

2 baths

|

1,499 sq ft

|

Condo

334 REGENCY DR, FISHKILL, NY, 12524
Community: Regency at Fishkill
New Fairfield at St. James 401 CABOT CT, SMITHTOWN, NY, 11780, Smithtown, NY 11780
$499,000

1 beds

|

2 baths

|

900 sq ft

|

Condo

401 CABOT CT, SMITHTOWN, NY, 11780
The Seasons at East Meadow 419 AUTUMN DR, EAST MEADOW, NY, 11554, East Meadow, NY 11554
$628,000

2 beds

|

2 baths

|

1,272 sq ft

|

Condo

419 AUTUMN DR, EAST MEADOW, NY, 11554
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 Leisure Knoll 145 EDINBURGH DR, RIDGE, NY, 11961, Ridge, NY 11961
$499,999

2 beds

|

2 baths

|

913 sq ft

|

House

145 EDINBURGH DR, RIDGE, NY, 11961
Community: Leisure Knoll
Heritage Hills 882 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589
$825,000

3 beds

|

2 baths

|

1,909 sq ft

|

Condo

882 HERITAGE HLS B, SOMERS, NY, 10589
Community: Heritage Hills
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
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
New Greenwood Village 91 VILLAGE CIR, MANORVILLE, NY, 11949, Manorville, NY 11949
$155,000

2 beds

|

2 baths

|

938 sq ft

|

Condo

91 VILLAGE CIR, MANORVILLE, NY, 11949
Community: Greenwood Village
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
Setauket Meadows 95 COVE LN, EAST SETAUKET, NY, 11733, East Setauket, NY 11733
$749,990

2 beds

|

3 baths

|

1,991 sq ft

|

Condo

95 COVE LN, EAST SETAUKET, NY, 11733
Community: Setauket Meadows
Heritage Hills 370 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589
$899,000

3 beds

|

2 baths

|

1,793 sq ft

|

Condo

370 HERITAGE HLS B, SOMERS, NY, 10589
Community: Heritage Hills
New Leisure Village 215 WOODBRIDGE DR A, RIDGE, NY, 11961, Ridge, NY 11961
$319,000

2 beds

|

1 baths

|

1,085 sq ft

|

Condo

215 WOODBRIDGE DR A, RIDGE, NY, 11961
Community: Leisure Village
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
The Greens at Half Hollow 259 ALTESSA BLVD, MELVILLE, NY, 11747, Melville, NY 11747
$1,499,000

3 beds

|

4 baths

|

3,100 sq ft

|

Condo

259 ALTESSA BLVD, MELVILLE, NY, 11747
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 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
Regency at Fishkill 736 REGENCY DR, FISHKILL, NY, 12524, Fishkill, NY 12524
$499,000

1 beds

|

2 baths

|

1,543 sq ft

|

House

736 REGENCY DR, FISHKILL, NY, 12524
Community: Regency at Fishkill
Foxwood Village 1407 MIDDLE RD UNIT 258, CALVERTON, NY, ..., Calverton, NY 11933
$525,000

3 beds

|

2 baths

|

1,568 sq ft

|

Manufactured Home

1407 MIDDLE RD UNIT 258, CALVERTON, NY, ...
Community: Foxwood Village
New The Greens at Half Hollow 652 BALFOUR PL, MELVILLE, NY, 11747, Melville, NY 11747
$1,199,000

3 beds

|

3 baths

|

2,400 sq ft

|

Condo

652 BALFOUR PL, MELVILLE, NY, 11747
Breton Hills 209 BRETON WAY, GLEN COVE, NY, 11542, Glen Cove, NY 11542
$699,888

2 beds

|

2 baths

|

1,300 sq ft

|

Condo

209 BRETON WAY, GLEN COVE, NY, 11542
Community: Breton Hills
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
The Hollows at Blue Hill 41 MICHAEL ROBERTS CT, PEARL RIVER, NY, ..., Pearl River, NY 10965
$999,000

2 beds

|

3 baths

|

2,210 sq ft

|

Condo

41 MICHAEL ROBERTS CT, PEARL RIVER, NY, ...
Heritage Hills 593 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589
$619,000

2 beds

|

2 baths

|

1,470 sq ft

|

Condo

593 HERITAGE HLS A, SOMERS, NY, 10589
Community: Heritage Hills
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
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
Heritage Hills 438 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589
$569,000

2 beds

|

2 baths

|

1,470 sq ft

|

Condo

438 HERITAGE HLS B, SOMERS, NY, 10589
Community: Heritage Hills
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.
Glassbury Court at Cold Spring 43 YESTERDAY DR, COLD SPRING, NY, 10516, Cold Spring, NY 10516
$729,000

2 beds

|

3 baths

|

2,620 sq ft

|

Condo

43 YESTERDAY DR, COLD SPRING, NY, 10516
Glassbury Court at Cold Spring 11 REVOLUTION RD, COLD SPRING, NY, 10516, Cold Spring, NY 10516
$515,000

2 beds

|

3 baths

|

1,806 sq ft

|

Condo

11 REVOLUTION RD, COLD SPRING, NY, 10516
Jefferson Village 170 LONG HILL DR A, YORKTOWN HEIGHTS, NY..., Yorktown Heights, NY 10598
$675,000

2 beds

|

2 baths

|

1,555 sq ft

|

Condo

170 LONG HILL DR A, YORKTOWN HEIGHTS, NY...
Community: Jefferson Village
Overlook 1037 COTTAGE DR 18, CARMEL, NY, 10512, Carmel, NY 10512
$898,000

2 beds

|

3 baths

|

2,496 sq ft

|

Condo

1037 COTTAGE DR 18, CARMEL, NY, 10512
Community: Overlook
Overlook 4071 FAIRWAYS DR 136, CARMEL, NY, 10512, Carmel, NY 10512
$668,000

3 beds

|

3 baths

|

1,914 sq ft

|

Condo

4071 FAIRWAYS DR 136, CARMEL, NY, 10512
Community: Overlook
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
Overlook 4057 FAIRWAYS DR # 129, CARMEL, NY, 1051..., Carmel, NY 10512
$699,000

3 beds

|

4 baths

|

2,131 sq ft

|

Condo

4057 FAIRWAYS DR # 129, CARMEL, NY, 1051...
Community: Overlook
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
Encore Atlantic Shores 113 OVERTURE PL, EASTPORT, NY, 11941, Eastport, NY 11941
$895,000

2 beds

|

3 baths

|

3,037 sq ft

|

Condo

113 OVERTURE PL, EASTPORT, NY, 11941
Heritage Hills 262 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589
$550,000

2 beds

|

2 baths

|

1,427 sq ft

|

Condo

262 HERITAGE HLS B, SOMERS, NY, 10589
Community: Heritage Hills
Strathmore Gate East 49 FREEDOM LN, CORAM, NY, 11727, Coram, NY 11727
$370,000

2 beds

|

1 baths

|

964 sq ft

|

House

49 FREEDOM LN, CORAM, NY, 11727

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167 communities near Westport
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