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Westport, CT 55+ active adult communities & homes for sale - Page 2

369 homes 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
2.8 rating (4 reviews) Cheesequake Village
$100ks - $200ks
Cheesequake Village, Old Bridge, NJ
Resale Only | 55+ age-restricted | Built 1965 - 1971 | 713 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 - $800ks
Heritage Hills, Somers, NY
Resale Only | Age-targeted | Built 1974 - 2006 | 2,600 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
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4 rating (1 reviews) Jefferson Village
$100ks - $500ks
Jefferson Village, Yorktown Heights, NY
Resale Only | 55+ age-restricted | Built 1967 - 1982 | 1,000 homes
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
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
Country Pointe Plainview
$700ks - $1Ms
Country Pointe Plainview, Plainview, NY
New Construction | 55+ age-restricted | Built 2017 - present | 660 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 (2 reviews) Shadow Lake Village
$200ks - $500ks
Shadow Lake Village, Red Bank, NJ
Resale Only | 55+ age-restricted | Built 1972 - 1980 | 952 homes
3.7 rating (3 reviews) Greenwood Village
$100ks
Greenwood Village, Manorville, NY
Resale Only | 55+ age-restricted | Built 1980 - 2000 | 512 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
4.2 rating (12 reviews) Surrey Downs
$200ks - $300ks
Surrey Downs, Freehold, NJ
Resale Only | 55+ age-restricted | Built 1986 - 1997 | 443 homes
Leisure Village
$100ks - $300ks
Leisure Village, Ridge, NY
Resale Only | 55+ age-restricted | Built 1969 - 1986 | 1,500 homes
4 rating (8 reviews) Glenwood Village
$100ks - $200ks
Glenwood Village, Riverhead, NY
New and Resale | 55+ age-restricted | Built 1959 - present | 588 homes
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
The Manors at The Colony ...
$300ks - $400ks
The Manors at The Colony ..., Shirley, NY
New Construction | 55+ age-restricted | Built 2013 - present | 150 homes
Dutchgate
$300ks - $500ks
Dutchgate, Valley Stream, NY
Resale Only | 55+ age-restricted | Built 2009 - 2015 | 348 homes
Fairview at Oxford Greens
$400ks - $600ks
Fairview at Oxford Greens, Oxford, CT
New and Resale | 55+ age-restricted | Built 2019 - present | 125 homes
Rolling Meadows at Waysid...
$500ks - $600ks
Rolling Meadows at Waysid..., Ocean Township, NJ
Resale Only | 55+ age-restricted | Built 2002 - 2007 | 328 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
Regency at Fishkill
$300ks - $400ks
Regency at Fishkill, Fishkill, NY
Resale Only | 55+ age-restricted | Built 2008 - 2020 | 164 homes
Stoneleigh Woods at River...
$500ks
Stoneleigh Woods at River..., Riverhead, NY
Resale Only | 55+ age-restricted | Built 2007 - 2016 | 176 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
Liberty at Newtown
$300ks - $400ks
Liberty at Newtown, Newtown, CT
Resale Only | 55+ age-restricted | Built 2003 - 2007 | 96 homes
Leisure Glen
$300ks - $400ks
Leisure Glen, Ridge, NY
Resale Only | 55+ age-restricted | Built 1985 - 2010 | 646 homes
5 rating (1 reviews) Newtown Woods
$300ks - $500ks
Newtown Woods, Newtown, CT
New and Resale | 55+ age-restricted | Built 2011 - present | 178 homes
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Questions? Call us: (475) 471-1908
Woodridge Strathmore Terr...
$200ks - $300ks
Woodridge Strathmore Terr..., Mount Sinai, NY
Resale Only | 55+ age-restricted | Built 1974 - 1985 | 226 homes
Village Estates
$300ks - $400ks
Village Estates, Amityville, NY
Resale Only | 55+ age-restricted | Built 2006 - 2008 | 138 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
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.
Vineyards at Moriches
$500ks - $600ks
Vineyards at Moriches, Center Moriches, NY
Resale Only | 55+ age-restricted | Built 2008 - 2014 | 92 homes
5 rating (1 reviews) The Villas at Jumping Bro...
$300ks - $500ks
The Villas at Jumping Bro..., Neptune Township, NJ
Resale Only | 55+ age-restricted | Built 2001 - 2003 | 168 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
HarborView
$800ks - $1Ms
HarborView, Port Washington, NY
Resale Only | 55+ age-restricted | Built 2002 - 2004 | 270 homes
5 rating (1 reviews) Sunken Pond Estates
$400ks
Sunken Pond Estates, Riverhead, NY
Resale Only | 55+ age-restricted | Built 2003 - 2005 | 194 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
3.5 rating (2 reviews) Foxwood Village
$200ks - $400ks
Foxwood Village, Calverton, NY
Resale Only | 55+ age-restricted | Built 1986 - 2007 | 294 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) Westhampton Pines
$900ks - $1Ms
Westhampton Pines, Westhampton, NY
Resale Only | 55+ age-restricted | Built 2005 - 2013 | 189 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
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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Heritage Village 895 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$349,900

2 beds

|

2 baths

|

1,398 sq ft

|

Condo

895 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Stoneleigh Woods at Riverhead 159 STONELEIGH DR, RIVERHEAD, NY, 11901, Riverhead, NY 11901
$674,999

2 beds

|

3 baths

|

2,172 sq ft

|

Condo

159 STONELEIGH DR, RIVERHEAD, NY, 11901
Heritage Hills 181 HERITAGE HLS F, SOMERS, NY, 10589, Somers, NY 10589
$499,999

2 beds

|

2 baths

|

1,205 sq ft

|

Condo

181 HERITAGE HLS F, SOMERS, NY, 10589
Community: Heritage Hills
Heritage Village 16 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$389,900

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

16 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Leisure Village 274 BERWICK CT C, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$359,000

2 beds

|

1 baths

|

836 sq ft

|

Condo

274 BERWICK CT C, BROOKHAVEN, NY, 11961
Community: Leisure Village
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
Spring Lake Village 626 OVERLOOK PATH 626, SOUTHINGTON, CT, ..., Southington, CT 06489
$350,000

2 beds

|

2 baths

|

1,230 sq ft

|

Condo

626 OVERLOOK PATH 626, SOUTHINGTON, CT, ...
Community: Spring Lake Village
Bartlett Hill 19 PLUMROSE CT 19, PORTLAND, CT, 06480, Portland, CT 06480
$500,000

2 beds

|

3 baths

|

1,503 sq ft

19 PLUMROSE CT 19, PORTLAND, CT, 06480
Community: Bartlett Hill
Rolling Meadows at Wayside 12 BARBERRY DR, OCEAN TWP, NJ, 07712, Ocean Twp, NJ 07712
$939,900

2 beds

|

3 baths

|

House

12 BARBERRY DR, OCEAN TWP, NJ, 07712
Heritage Village 38 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$299,900

2 beds

|

2 baths

|

1,032 sq ft

|

Condo

38 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Oronoque Village 407 MONTAUK LN B, STRATFORD, CT, 06614, Stratford, CT 06614
$450,000

1 beds

|

2 baths

|

1,360 sq ft

|

Condo

407 MONTAUK LN B, STRATFORD, CT, 06614
Community: Oronoque 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.
Leisure Village 368 WOODBRIDGE DR A, BROOKHAVEN, NY, 119..., Brookhaven, NY 11961
$394,990

2 beds

|

1 baths

|

Condo

368 WOODBRIDGE DR A, BROOKHAVEN, NY, 119...
Community: Leisure Village
Baldwin Station 15 JASMINE CIR 15, MILFORD, CT, 06461, Milford, CT 06461
$599,000

2 beds

|

3 baths

|

2,331 sq ft

|

Condo

15 JASMINE CIR 15, MILFORD, CT, 06461
Community: Baldwin Station
The Villas at Jumping Brook 8 TALL PINES DR, NEPTUNE TOWNSHIP, NJ, 0..., Neptune Township, NJ 07753
$829,000

2 beds

|

2 baths

|

1,992 sq ft

|

House

8 TALL PINES DR, NEPTUNE TOWNSHIP, NJ, 0...
Country Pointe Plainview 67101 RED CEDAR RD, OYSTER BAY, NY, 1180..., Oyster Bay, NY 11803
$2,299,000

3 beds

|

4 baths

|

2,484 sq ft

|

House

67101 RED CEDAR RD, OYSTER BAY, NY, 1180...
Fairview at Oxford Greens 941 MACKENZIE LN 941, OXFORD, CT, 06478, Oxford, CT 06478
$699,900

2 beds

|

2 baths

|

1,682 sq ft

941 MACKENZIE LN 941, OXFORD, CT, 06478
The Village at Oxford Greens 941 MACKENZIE LN 941, OXFORD, CT, 06478, Oxford, CT 06478
$699,900

2 beds

|

2 baths

|

1,682 sq ft

941 MACKENZIE LN 941, OXFORD, CT, 06478
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
Leisure Glen 581 LEISURE DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$625,000

2 beds

|

2 baths

|

1,685 sq ft

|

Condo

581 LEISURE DR, BROOKHAVEN, NY, 11961
Community: Leisure Glen
Meadowbrook Pointe Links & Spa 252 SAND HILLS LN, BROOKHAVEN, NY, 11763, Brookhaven, NY 11763
$333,051

2 beds

|

2 baths

|

1,133 sq ft

|

Condo

252 SAND HILLS LN, BROOKHAVEN, NY, 11763
Snug Harbor 58 HARBOR RD, BABYLON, NY, 11701, Babylon, NY 11701
$495,000

1 beds

|

1 baths

|

727 sq ft

|

Condo

58 HARBOR RD, BABYLON, NY, 11701
Community: Snug Harbor
Rivington 64 WARRINGTON ROUND 64, DANBURY, CT, 068..., Danbury, CT 06810
$649,900

3 beds

|

3 baths

|

1,600 sq ft

|

Condo

64 WARRINGTON ROUND 64, DANBURY, CT, 068...
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.
Shadow Lake Village 10 DANBURY CT, RED BANK, NJ, 07701, Red Bank, NJ 07701
$630,000

2 beds

|

2 baths

|

1,423 sq ft

|

House

10 DANBURY CT, RED BANK, NJ, 07701
Community: Shadow Lake Village
Leisure Knoll 190 CANTERBURY DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$519,900

2 beds

|

1 baths

|

1,220 sq ft

|

Condo

190 CANTERBURY DR, BROOKHAVEN, NY, 11961
Community: Leisure Knoll
Glenwood Village 1661 OLD COUNTRY RD 156D, RIVERHEAD, NY,..., Riverhead, NY 11901
$469,000

2 beds

|

2 baths

|

1,500 sq ft

|

Manufactured Home

1661 OLD COUNTRY RD 156D, RIVERHEAD, NY,...
Community: Glenwood Village
Foxwood Village 1407 MIDDLE RD 277, RIVERHEAD, NY, 11933, Riverhead, NY 11933
$515,000

2 beds

|

2 baths

|

1,568 sq ft

|

Manufactured Home

1407 MIDDLE RD 277, RIVERHEAD, NY, 11933
Community: Foxwood Village
Meadowbrook Pointe Athletic Club & Spa 348 TROTTING LN, HEMPSTEAD, NY, 11590, Hempstead, NY 11590
$889,000

2 beds

|

2 baths

|

1,319 sq ft

|

Condo

348 TROTTING LN, HEMPSTEAD, NY, 11590
Regency at Wappinger 36 FARMINGTON RD, WAPPINGER, NY, 12590, Wappinger, NY 12590
$750,000

2 beds

|

3 baths

|

2,600 sq ft

|

House

36 FARMINGTON RD, WAPPINGER, NY, 12590
Encore at Lake Grove 189 SYMPHONY DR, BROOKHAVEN, NY, 11755, Brookhaven, NY 11755
$669,000

2 beds

|

3 baths

|

1,378 sq ft

|

Condo

189 SYMPHONY DR, BROOKHAVEN, NY, 11755
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
Heritage Village 1008 HERITAGE VLG A, SOUTHBURY, CT, 0648..., Southbury, CT 06488
$518,000

3 beds

|

2 baths

|

1,716 sq ft

|

Condo

1008 HERITAGE VLG A, SOUTHBURY, CT, 0648...
Community: Heritage Village
Rolling Meadows at Wayside 60 BARBERRY DR, OCEAN TWP, NJ, 07712, Ocean Twp, NJ 07712
$869,999

3 beds

|

3 baths

|

2,016 sq ft

|

Ranch

60 BARBERRY DR, OCEAN TWP, NJ, 07712
Jefferson Village 18 HASTINGS CT B, YORKTOWN, NY, 10598, Yorktown, NY 10598
$349,000

1 beds

|

1 baths

|

850 sq ft

|

Condo

18 HASTINGS CT B, YORKTOWN, NY, 10598
Community: Jefferson 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.
Winthrop Court 8205 HARCOURT 8205, CLIFTON, NJ, 07013, Clifton, NJ 07013
$499,000

2 beds

|

2 baths

|

Condo

8205 HARCOURT 8205, CLIFTON, NJ, 07013
Community: Winthrop Court
Heritage Village 76 HERITAGE VLG C, SOUTHBURY, CT, 06488, Southbury, CT 06488
$249,000

2 beds

|

2 baths

|

1,308 sq ft

|

Condo

76 HERITAGE VLG C, SOUTHBURY, CT, 06488
Community: Heritage Village
Cheesequake Village 5 PENNSYLVANIA DR, MATAWAN, NJ, 07747, Matawan, NJ 07747
$319,000

2 beds

|

1 baths

|

Condo

5 PENNSYLVANIA DR, MATAWAN, NJ, 07747
Community: Cheesequake Village
Cheesequake Village 10 C HAVEN DR, OLD BRIDGE TWP., NJ, 0774..., Old Bridge Twp., NJ 07747
$245,000

1 beds

|

1 baths

|

664 sq ft

10 C HAVEN DR, OLD BRIDGE TWP., NJ, 0774...
Community: Cheesequake Village
Greenwood Village 89 VILLAGE CIR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949
$99,999

1 beds

|

1 baths

|

812 sq ft

|

Condo

89 VILLAGE CIR, BROOKHAVEN, NY, 11949
Community: Greenwood Village
Setauket Meadows 66 BRIANNA DR, BROOKHAVEN, NY, 11733, Brookhaven, NY 11733
$739,999

2 beds

|

3 baths

|

1,878 sq ft

|

Condo

66 BRIANNA DR, BROOKHAVEN, NY, 11733
Community: Setauket Meadows
Winthrop Court 8205 HARCOURT RD, CLIFTON CITY, NJ, 0701..., Clifton City, NJ 07013
$499,000

2 beds

|

2 baths

|

1,534 sq ft

8205 HARCOURT RD, CLIFTON CITY, NJ, 0701...
Community: Winthrop Court
Shadow Lake Village 20 WESTERN REACH, RED BANK, NJ, 07701, Red Bank, NJ 07701
$350,000

2 beds

|

1 baths

|

973 sq ft

|

Adult Community

20 WESTERN REACH, RED BANK, NJ, 07701
Community: Shadow Lake Village
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
Dutchgate 1132 WILLOW LN 1131, HEMPSTEAD, NY, 1158..., Hempstead, NY 11580
$510,000

2 beds

|

2 baths

|

941 sq ft

|

Condo

1132 WILLOW LN 1131, HEMPSTEAD, NY, 1158...
Community: Dutchgate
Rolling Meadows at Wayside 15 MORNING GLORY DR, OCEAN TWP, NJ, 0771..., Ocean Twp, NJ 07712
$759,900

2 beds

|

2 baths

|

1,768 sq ft

|

Ranch

15 MORNING GLORY DR, OCEAN TWP, NJ, 0771...
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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