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Westport, CT 55+ active adult communities & homes for sale - Page 4

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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Leisure Glen 187 GLEN DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$525,000

2 beds

|

2 baths

|

1,451 sq ft

|

Condo

187 GLEN DR, BROOKHAVEN, NY, 11961
Community: Leisure Glen
The Waterways at Moriches 216 RIVER DR, BROOKHAVEN, NY, 11955, Brookhaven, NY 11955
$510,000

2 beds

|

2 baths

|

1,544 sq ft

|

Condo

216 RIVER DR, BROOKHAVEN, NY, 11955
Heritage Hills 128 HERITAGE HILLS DR B, SOMERS, NY, 105..., Somers, NY 10589
$450,000

1 beds

|

1 baths

|

955 sq ft

|

Condo

128 HERITAGE HILLS DR B, SOMERS, NY, 105...
Community: Heritage Hills
Heritage Hills 156 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589
$649,000

3 beds

|

2 baths

|

1,689 sq ft

|

Condo

156 HERITAGE HLS A, SOMERS, NY, 10589
Community: Heritage Hills
Heritage Village 874 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$275,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

874 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
Surrey Downs 13 GATLEY CLOSE, FREEHOLD, NJ, 07728, Freehold, NJ 07728
$479,000

2 beds

|

2 baths

|

1,261 sq ft

|

Ranch

13 GATLEY CLOSE, FREEHOLD, NJ, 07728
Community: Surrey Downs
Chelsea Square 105 POTTS RD, MORGANVILLE, NJ, 07751, Morganville, NJ 07751
$499,000

2 beds

|

2 baths

|

1,568 sq ft

|

Adult Community

105 POTTS RD, MORGANVILLE, NJ, 07751
Community: Chelsea Square
Greenwood Village 16 DOGWOOD LN, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949
$299,999

2 beds

|

2 baths

|

1,288 sq ft

|

Condo

16 DOGWOOD LN, BROOKHAVEN, NY, 11949
Community: Greenwood Village
Vineyards at Moriches 27 EMILIE DR, BROOKHAVEN, NY, 11934, Brookhaven, NY 11934
$785,000

2 beds

|

3 baths

|

2,335 sq ft

|

Condo

27 EMILIE DR, BROOKHAVEN, NY, 11934
Rivington 11 MERCY ST 11, DANBURY, CT, 06810, Danbury, CT 06810
$630,000

2 beds

|

4 baths

|

1,572 sq ft

11 MERCY ST 11, DANBURY, CT, 06810
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.
Heritage Village 701 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$399,900

2 beds

|

2 baths

|

1,398 sq ft

|

Condo

701 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 191 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$589,900

3 beds

|

2 baths

|

1,716 sq ft

|

Condo

191 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Windmill Gate 7 DARIA DR, ISLIP, NY, 11769, Islip, NY 11769
$599,000

2 beds

|

2 baths

|

1,175 sq ft

|

Condo

7 DARIA DR, ISLIP, NY, 11769
Community: Windmill Gate
Surrey Downs 7 KINGSTON CLOSE 1000, FREEHOLD, NJ, 077..., Freehold, NJ 07728
$399,000

2 beds

|

2 baths

|

1,261 sq ft

|

Ranch

7 KINGSTON CLOSE 1000, FREEHOLD, NJ, 077...
Community: Surrey Downs
Sunrise Village 113 REVERE DR, ISLIP, NY, 11782, Islip, NY 11782
$469,000

2 beds

|

2 baths

|

1,141 sq ft

|

Condo

113 REVERE DR, ISLIP, NY, 11782
Community: Sunrise Village
Dutchgate 1120 WILLOW LN, HEMPSTEAD, NY, 11580, Hempstead, NY 11580
$510,000

2 beds

|

2 baths

|

941 sq ft

|

Condo

1120 WILLOW LN, HEMPSTEAD, NY, 11580
Community: Dutchgate
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
Overlook 2059 SUMMIT LOOP 97, CARMEL, NY, 10512, Carmel, NY 10512
$920,000

2 beds

|

3 baths

|

2,873 sq ft

|

Condo

2059 SUMMIT LOOP 97, CARMEL, NY, 10512
Community: Overlook
Overlook 2057 SUMMIT LOOP 96, CARMEL, NY, 10512, Carmel, NY 10512
$885,000

2 beds

|

2 baths

|

1,948 sq ft

|

Condo

2057 SUMMIT LOOP 96, CARMEL, NY, 10512
Community: Overlook
Overlook 4091 FAIRWAYS DR 146, CARMEL, NY, 10512, Carmel, NY 10512
$772,000

3 beds

|

4 baths

|

2,131 sq ft

|

Condo

4091 FAIRWAYS DR 146, CARMEL, NY, 10512
Community: Overlook
Overlook 4085 FAIRWAYS DR 143, CARMEL, NY, 10512, Carmel, NY 10512
$689,000

3 beds

|

3 baths

|

1,931 sq ft

|

Condo

4085 FAIRWAYS DR 143, CARMEL, NY, 10512
Community: Overlook
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 24-B HERITAGE CRST B, SOUTHBURY, CT, 064..., Southbury, CT 06488
$419,900

2 beds

|

2 baths

|

1,217 sq ft

|

Condo

24-B HERITAGE CRST B, SOUTHBURY, CT, 064...
Community: Heritage Village
Heritage Village 593 HERITAGE VLG D, SOUTHBURY, CT, 06488, Southbury, CT 06488
$205,000

2 beds

|

2 baths

|

1,044 sq ft

|

Condo

593 HERITAGE VLG D, SOUTHBURY, CT, 06488
Community: Heritage Village
Stoneleigh Woods at Carmel 205 EGRETS LNDG 205, CARMEL, NY, 10512, Carmel, NY 10512
$475,000

2 beds

|

2 baths

|

1,344 sq ft

|

Condo

205 EGRETS LNDG 205, CARMEL, NY, 10512
Heritage Village 147 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$235,000

2 beds

|

2 baths

|

1,076 sq ft

|

Condo

147 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Shadow Lake Village 10D LEXINGTON CT, RED BANK, NJ, 07701, Red Bank, NJ 07701
$315,000

2 beds

|

1 baths

|

1,021 sq ft

|

Adult Community

10D LEXINGTON CT, RED BANK, NJ, 07701
Community: Shadow Lake Village
Four Seasons at Great Notch Spa and Club 3 BEDROCK CT A3, WOODLAND PARK, NJ, 0742..., Woodland Park, NJ 07424
$599,000

2 beds

|

2 baths

|

Condo

3 BEDROCK CT A3, WOODLAND PARK, NJ, 0742...
Heritage Village 22 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$204,000

2 beds

|

2 baths

|

1,032 sq ft

|

Condo

22 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
Greenwood Village 130 VILLAGE CIR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949
$129,000

2 beds

|

2 baths

|

1,177 sq ft

|

Condo

130 VILLAGE CIR, BROOKHAVEN, NY, 11949
Community: Greenwood Village
Jefferson Village 5 DEVON CT B, YORKTOWN, NY, 10598, Yorktown, NY 10598
$385,000

2 beds

|

1 baths

|

989 sq ft

|

Condo

5 DEVON CT B, YORKTOWN, NY, 10598
Community: Jefferson Village
The Villages NJ 128 KORN MARKET A, FREEHOLD, NJ, 07728, Freehold, NJ 07728
$365,000

2 beds

|

1 baths

|

1,088 sq ft

|

Ranch

128 KORN MARKET A, FREEHOLD, NJ, 07728
Community: The Villages NJ
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 258 NEWCASTLE CT F, BROOKHAVEN, NY, 1196..., Brookhaven, NY 11961
$299,000

2 beds

|

1 baths

|

875 sq ft

|

Condo

258 NEWCASTLE CT F, BROOKHAVEN, NY, 1196...
Community: Leisure Village
Country Pointe Plainview 17101 ASPENWOOD DR, OYSTER BAY, NY, 1180..., Oyster Bay, NY 11803
$1,100,000

2 beds

|

2 baths

|

1,400 sq ft

|

Condo

17101 ASPENWOOD DR, OYSTER BAY, NY, 1180...
Liberty at Newtown 76 SUZIE DR 76, NEWTOWN, CT, 06470, Newtown, CT 06470
$648,000

2 beds

|

3 baths

|

2,341 sq ft

|

Condo

76 SUZIE DR 76, NEWTOWN, CT, 06470
Community: Liberty at Newtown
Heritage Village 804 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$259,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

804 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
The Greens at Half Hollow 1130 SAVOY DR, HUNTINGTON, NY, 11747, Huntington, NY 11747
$710,000

2 beds

|

2 baths

|

1,140 sq ft

|

Condo

1130 SAVOY DR, HUNTINGTON, NY, 11747
Oronoque Village 89 S TRL A, STRATFORD, CT, 06614, Stratford, CT 06614
$649,000

1 beds

|

3 baths

|

1,438 sq ft

|

Condo

89 S TRL A, STRATFORD, CT, 06614
Community: Oronoque Village
Oak Meadow Estates 197 OAK MEADOW LN 197, TORRINGTON, CT, 0..., Torrington, CT 06790
$399,000

2 beds

|

2 baths

|

1,419 sq ft

|

Condo

197 OAK MEADOW LN 197, TORRINGTON, CT, 0...
Community: Oak Meadow Estates
Strathmore Gate East 9 FREEDOM LN, BROOKHAVEN, NY, 11727, Brookhaven, NY 11727
$289,000

1 beds

|

1 baths

|

728 sq ft

|

Condo

9 FREEDOM LN, BROOKHAVEN, NY, 11727
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
Jefferson Village 27 WALDEN CT J, YORKTOWN, NY, 10598, Yorktown, NY 10598
$349,900

1 beds

|

1 baths

|

800 sq ft

|

Condo

27 WALDEN CT J, YORKTOWN, NY, 10598
Community: Jefferson Village
Parker Village Estates 29 VILLAGE DR, EATONTOWN, NJ, 07724, Eatontown, NJ 07724
$669,900

2 beds

|

3 baths

|

2,308 sq ft

|

Townhouse

29 VILLAGE DR, EATONTOWN, NJ, 07724
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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