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Westport, CT 55+ active adult communities & homes for sale - Page 6

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
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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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Shadow Lake Village 115 LEXINGTON CT, RED BANK, NJ, 07701, Red Bank, NJ 07701
$339,000

2 beds

|

1 baths

|

1,021 sq ft

|

Adult Community

115 LEXINGTON CT, RED BANK, NJ, 07701
Community: Shadow Lake Village
The Powder Forest Homes 15 BANTRY RD 15, SIMSBURY, CT, 06070, Simsbury, CT 06070
$935,000

4 beds

|

3 baths

|

1,878 sq ft

15 BANTRY RD 15, SIMSBURY, CT, 06070
Oronoque Village 283 AGAWAM DR A, STRATFORD, CT, 06614, Stratford, CT 06614
$625,000

2 beds

|

3 baths

|

1,415 sq ft

|

Condo

283 AGAWAM DR A, STRATFORD, CT, 06614
Community: Oronoque Village
The Greens at Half Hollow 283 ALTESSA BLVD, HUNTINGTON, NY, 11747, Huntington, NY 11747
$1,395,000

3 beds

|

3 baths

|

2,700 sq ft

|

Condo

283 ALTESSA BLVD, HUNTINGTON, NY, 11747
Apple Ridge 227 WESTERVELT LN, MAHWAH, NJ, 07430, Mahwah, NJ 07430
$830,000

3 beds

|

3 baths

|

Townhouse

227 WESTERVELT LN, MAHWAH, NJ, 07430
Community: Apple Ridge
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
Cheesequake Village 5 PENNSYLVANIA DR 454, OLD BRIDGE, NJ, 0..., Old Bridge, NJ 07747
$299,500

2 beds

|

1 baths

|

Condo

5 PENNSYLVANIA DR 454, OLD BRIDGE, NJ, 0...
Community: Cheesequake Village
The Waterways at Moriches 605 BAY VIEW CIR 5, BROOKHAVEN, NY, 1195..., Brookhaven, NY 11955
$649,000

2 beds

|

3 baths

|

1,485 sq ft

|

Condo

605 BAY VIEW CIR 5, BROOKHAVEN, NY, 1195...
Heritage Village 10 HERITAGE CIR A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$353,900

3 beds

|

2 baths

|

1,716 sq ft

|

Condo

10 HERITAGE CIR A, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Hills 879 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589
$750,000

2 beds

|

2 baths

|

1,549 sq ft

|

Condo

879 HERITAGE HLS B, SOMERS, NY, 10589
Community: Heritage Hills
Liberty at Newtown 49 JO AL CT 49, NEWTOWN, CT, 06470, Newtown, CT 06470
$635,000

2 beds

|

3 baths

|

2,341 sq ft

|

Condo

49 JO AL CT 49, NEWTOWN, CT, 06470
Community: Liberty at Newtown
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.
Heritage Village 1 HERITAGE VLG C, SOUTHBURY, CT, 06488, Southbury, CT 06488
$225,000

2 beds

|

2 baths

|

1,044 sq ft

|

Condo

1 HERITAGE VLG C, SOUTHBURY, CT, 06488
Community: Heritage Village
Cheesequake Village 31 HAVEN DR, OLD BRIDGE, NJ, 07747, Old Bridge, NJ 07747
$350,000

2 beds

|

1 baths

|

875 sq ft

|

Condo

31 HAVEN DR, OLD BRIDGE, NJ, 07747
Community: Cheesequake Village
Heritage Village 24 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$230,000

2 beds

|

2 baths

|

1,076 sq ft

|

Condo

24 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 59 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$245,000

2 beds

|

2 baths

|

1,076 sq ft

|

Condo

59 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Oronoque Village 93 SEMINOLE LN B, STRATFORD, CT, 06614, Stratford, CT 06614
$559,000

2 beds

|

3 baths

|

2,542 sq ft

|

Condo

93 SEMINOLE LN B, STRATFORD, CT, 06614
Community: Oronoque Village
The Villas at Jumping Brook 94 TALL PINES DR, NEPTUNE TOWNSHIP, NJ, ..., Neptune Township, NJ 07753
$799,900

2 beds

|

2 baths

|

1,688 sq ft

|

Ranch

94 TALL PINES DR, NEPTUNE TOWNSHIP, NJ, ...
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
Four Seasons at Colts Farm 4 PASTURE DR, FARMINGDALE, NJ, 07727, Farmingdale, NJ 07727
$1,220,000

4 beds

|

3 baths

|

3,040 sq ft

|

Adult Community

4 PASTURE DR, FARMINGDALE, NJ, 07727
Newbury Village 46 GREAT HERON LN 46, BROOKFIELD, CT, 06..., Brookfield, CT 06804
$689,000

2 beds

|

4 baths

|

2,560 sq ft

|

Condo

46 GREAT HERON LN 46, BROOKFIELD, CT, 06...
Community: Newbury Village
Liberty at Newtown 25 FRANKLIN CT 25, NEWTOWN, CT, 06470, Newtown, CT 06470
$529,000

2 beds

|

2 baths

|

1,413 sq ft

|

Condo

25 FRANKLIN CT 25, NEWTOWN, CT, 06470
Community: Liberty at Newtown
Heritage Hills 300 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589
$575,000

2 beds

|

2 baths

|

1,500 sq ft

|

Condo

300 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.
Rivington 11 ORWICH CT 11, DANBURY, CT, 06810, Danbury, CT 06810
$649,900

3 beds

|

4 baths

|

1,572 sq ft

|

Condo

11 ORWICH CT 11, DANBURY, CT, 06810
Community: Rivington
The Villages NJ 63 CORSO ITALIA D D, FREEHOLD, NJ, 07728, Freehold, NJ 07728
$355,000

2 beds

|

1 baths

|

1,008 sq ft

|

Condo

63 CORSO ITALIA D D, FREEHOLD, NJ, 07728
Community: The Villages NJ
The Village at Oxford Greens 527 PUTTING GREEN LN 527, OXFORD, CT, 06..., Oxford, CT 06478
$650,000

3 beds

|

3 baths

|

2,008 sq ft

|

Condo

527 PUTTING GREEN LN 527, OXFORD, CT, 06...
Regency at Prospect 10 ASH LN 10, PROSPECT, CT, 06712, Prospect, CT 06712
$539,000

2 beds

|

3 baths

|

1,928 sq ft

|

Condo

10 ASH LN 10, PROSPECT, CT, 06712
Community: Regency at Prospect
Regency at Fishkill 811 REGENCY DR 802, FISHKILL, NY, 12524, Fishkill, NY 12524
$161,450

2 beds

|

2 baths

|

1,100 sq ft

|

Condo

811 REGENCY DR 802, FISHKILL, NY, 12524
Community: Regency at Fishkill
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
Heritage Village 18 HERITAGE CRST D, SOUTHBURY, CT, 06488, Southbury, CT 06488
$419,981

3 beds

|

2 baths

|

1,735 sq ft

|

Condo

18 HERITAGE CRST D, SOUTHBURY, CT, 06488
Community: Heritage Village
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
Fairview at Oxford Greens 1131 ST ANDREWS DR 50, OXFORD, CT, 06478, Oxford, CT 06478
$713,775

2 beds

|

3 baths

|

2,536 sq ft

|

Condo

1131 ST ANDREWS DR 50, OXFORD, CT, 06478
The Village at Oxford Greens 1131 ST ANDREWS DR 50, OXFORD, CT, 06478, Oxford, CT 06478
$713,775

2 beds

|

3 baths

|

2,536 sq ft

|

Condo

1131 ST ANDREWS DR 50, OXFORD, CT, 06478
Heritage Village 28 HERITAGE CRST E, SOUTHBURY, CT, 06488, Southbury, CT 06488
$615,000

3 beds

|

2 baths

|

1,735 sq ft

|

Condo

28 HERITAGE CRST E, 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.
The Village Grande at Holmdel 22 HYACINTH CT, HOLMDEL, NJ, 07733, Holmdel, NJ 07733
$925,000

2 beds

|

3 baths

|

2,273 sq ft

|

House

22 HYACINTH CT, HOLMDEL, NJ, 07733
Paris Square 1302 RIO VISTA LN, NORTHVALE, NJ, 07647, Northvale, NJ 07647
$750,000

3 beds

|

2 baths

|

Condo

1302 RIO VISTA LN, NORTHVALE, NJ, 07647
Community: Paris Square
Shadow Lake Village 46 FRIENDSHIP CT, RED BANK, NJ, 07701, Red Bank, NJ 07701
$499,000

2 beds

|

2 baths

|

1,108 sq ft

|

House

46 FRIENDSHIP CT, RED BANK, NJ, 07701
Community: Shadow Lake Village
The Waterways at Moriches 376 QUARRY POND CT, BROOKHAVEN, NY, 1195..., Brookhaven, NY 11955
$519,000

2 beds

|

2 baths

|

1,440 sq ft

|

Condo

376 QUARRY POND CT, BROOKHAVEN, NY, 1195...
Cheesequake Village 67 GALEWOOD DR B, OLD BRIDGE, NJ, 07747, Old Bridge, NJ 07747
$330,000

2 beds

|

1 baths

|

Condo

67 GALEWOOD DR B, OLD BRIDGE, NJ, 07747
Community: Cheesequake Village
Country Pointe Plainview 15103 ASPENWOOD DR, OYSTER BAY, NY, 1180..., Oyster Bay, NY 11803
$1,075,000

2 beds

|

2 baths

|

1,335 sq ft

|

Condo

15103 ASPENWOOD DR, OYSTER BAY, NY, 1180...
Jefferson Village 51 JEFFERSON OVAL E, YORKTOWN, NY, 10598, Yorktown, NY 10598
$455,000

2 beds

|

2 baths

|

1,100 sq ft

|

Condo

51 JEFFERSON OVAL E, YORKTOWN, NY, 10598
Community: Jefferson Village
Cheesequake Village 67 GALEWOOD DR B, MATAWAN, NJ, 07747, Matawan, NJ 07747
$330,000

2 beds

|

1 baths

|

914 sq ft

|

Adult Community

67 GALEWOOD DR B, MATAWAN, NJ, 07747
Community: Cheesequake Village
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
The Vineyards at Mount Sinai 51 FARM ACRE CIR, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766
$1,050,000

2 beds

|

3 baths

|

3,214 sq ft

|

Condo

51 FARM ACRE CIR, BROOKHAVEN, NY, 11766
Heritage Hills 900 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589
$742,000

2 beds

|

3 baths

|

1,552 sq ft

|

Condo

900 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.

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