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Westport, CT 55+ active adult communities & homes for sale - Page 5

310 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 (5 reviews) The Villages NJ
$200ks - $300ks
The Villages NJ, Howell, NJ
Resale Only | 55+ age-restricted | Built 1967 - 1975 | 670 homes
3 rating (2 reviews) Heritage Hills
$400ks - $1Ms
Heritage Hills, Somers, NY
Resale Only | Age-targeted | Built 1974 - 2006 | 2,600 homes
Leisure Village
$100ks - $300ks
Leisure Village, Ridge, NY
Resale Only | 55+ age-restricted | Built 1969 - 1986 | 1,500 homes
Oronoque Village
$200ks - $400ks
Oronoque Village, Stratford, CT
Resale Only | 55+ age-restricted | Built 1971 - 1977 | 929 homes
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2.8 rating (4 reviews) Cheesequake Village
$100ks - $200ks
Cheesequake Village, Old Bridge, NJ
Resale Only | 55+ age-restricted | Built 1965 - 1971 | 713 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
Overlook
$600ks - $900ks
Overlook, Carmel, NY
New Construction | 55+ age-restricted | 300 homes
Fairview at Oxford Greens
$400ks - $600ks
Fairview at Oxford Greens, Oxford, CT
New and Resale | 55+ age-restricted | Built 2019 - present | 125 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
Greenwood Village, Manorville, NY
Resale Only | 55+ age-restricted | Built 1980 - 2000 | 512 homes
4 rating (1 reviews) Jefferson Village
$100ks - $500ks
Jefferson Village, Yorktown Heights, NY
Resale Only | 55+ age-restricted | Built 1967 - 1982 | 1,000 homes
Leisure Knoll
$200ks - $400ks
Leisure Knoll, Ridge, NY
Resale Only | 55+ age-restricted | Built 1972 - 1982 | 701 homes
4.2 rating (12 reviews) Surrey Downs
$200ks - $300ks
Surrey Downs, Freehold, NJ
Resale Only | 55+ age-restricted | Built 1986 - 1997 | 443 homes
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The Waterways at Moriches
$300ks - $600ks
The Waterways at Moriches, Moriches, NY
Resale Only | 55+ age-restricted | Built 1985 - 1999 | 343 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 rating (8 reviews) Glenwood Village
$100ks - $200ks
Glenwood Village, Riverhead, NY
New and Resale | 55+ age-restricted | Built 1959 - present | 588 homes
5 rating (2 reviews) Fairfield at St. James
$300ks - $500ks
Fairfield at St. James, St. James, NY
Resale Only | 55+ age-restricted | Built 1972 - 1989 | 653 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) Encore Atlantic Shores
$500ks - $800ks
Encore Atlantic Shores, Eastport, NY
Resale Only | 55+ age-restricted | Built 2004 - 2011 | 240 homes
The Retreat at Carmel
$300ks - $800ks
The Retreat at Carmel, Carmel, NY
Resale Only | 55+ age-restricted | Built 2008 - 2018 | 312 homes
Meadowbrook Pointe Athlet...
$700ks - $1Ms
Meadowbrook Pointe Athlet..., Westbury, NY
Resale Only | 55+ age-restricted | Built 2015 - 2016 | 720 homes
Rivington
$300ks - $900ks
Rivington, Danbury, CT
New and Resale | Age-targeted | Built 2006 - present | 1,050 homes
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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
Spring Lake Village
$100ks - $200ks
Spring Lake Village, Southington, CT
Resale Only | 55+ age-restricted | Built 1970 - 2004 | 640 homes
5 rating (1 reviews) Four Seasons at Great Not...
$400ks - $700ks
Four Seasons at Great Not..., Woodland Park, NJ
Resale Only | 55+ age-restricted | Built 2005 - 2018 | 814 homes
Dutchgate
$300ks - $500ks
Dutchgate, Valley Stream, NY
Resale Only | 55+ age-restricted | Built 2009 - 2015 | 348 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.
The Villas at Narraganset...
$400ks
The Villas at Narraganset..., Lindenhurst, NY
Resale Only | 55+ age-restricted | Built 2004 - 2005 | 138 homes
3.7 rating (3 reviews) Rosemont Estates
$500ks - $700ks
Rosemont Estates, Marlboro, NJ
Resale Only | 55+ age-restricted | Built 2004 - 2014 | 242 homes
Leisure Glen
$300ks - $400ks
Leisure Glen, Ridge, NY
Resale Only | 55+ age-restricted | Built 1985 - 2010 | 646 homes
Kensington Estates
$1Ms
Kensington Estates, Woodbury, NY
New Construction | 55+ age-restricted | Built 2019 - 2021 | 80 homes
South Pond Village
$300ks - $400ks
South Pond Village, Bloomfield, CT
Resale Only | 55+ age-restricted | Built 1999 - 2005 | 151 homes
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Questions? Call us: (475) 471-1908
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
4.9 rating (14 reviews) Chatfield Farms
$400ks - $700ks
Chatfield Farms, Beacon Falls, CT
New Construction | 55+ age-restricted | Built 2014 - present | 231 homes
5 rating (1 reviews) Westhampton Pines
$900ks - $1Ms
Westhampton Pines, Westhampton, NY
Resale Only | 55+ age-restricted | Built 2005 - 2013 | 189 homes
The Manors at The Colony ...
$300ks - $400ks
The Manors at The Colony ..., Shirley, NY
New Construction | 55+ age-restricted | Built 2013 - present | 150 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.
Bartlett Hill
$300ks - $400ks
Bartlett Hill, Portland, CT
Resale Only | 55+ age-restricted | Built 2005 - 2011 | 82 homes
5 rating (1 reviews) Newtown Woods
$300ks - $500ks
Newtown Woods, Newtown, CT
New and Resale | 55+ age-restricted | Built 2011 - present | 178 homes
The Coves at Melville
$500ks
The Coves at Melville, Melville, NY
Resale Only | 62+ age-restricted | Built 2004 - 2005 | 175 homes
Four Seasons at Wayne
$300ks - $400ks
Four Seasons at Wayne, Wayne, NJ
Resale Only | 55+ age-restricted | Built 1999 - 2001 | 230 homes
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
Chelsea Square
$300ks - $400ks
Chelsea Square, Morganville, NJ
New and Resale | 55+ age-restricted | Built 2007 - present | 225 homes
Autumn Fields
$200ks - $300ks
Autumn Fields, Enfield, CT
Resale Only | 55+ age-restricted | Built 2004 - 2006 | 56 homes
1234...5
The Village at Oxford Greens 185 COUNTRY CLUB DR 185, OXFORD, CT, 064..., Oxford, CT 06478
$645,000

3 beds

|

3 baths

|

2,595 sq ft

185 COUNTRY CLUB DR 185, OXFORD, CT, 064...
Leisure Village 278 BERWICK CT B, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$359,900

2 beds

|

1 baths

|

875 sq ft

|

Condo

278 BERWICK CT B, BROOKHAVEN, NY, 11961
Community: Leisure Village
Regency at Woodbridge 3 EDGEWOOD WAY 26, WOODBRIDGE, CT, 06525, Woodbridge, CT 06525
$629,000

3 beds

|

3 baths

|

Condo

3 EDGEWOOD WAY 26, WOODBRIDGE, CT, 06525
Regency at Woodbridge 5 WHISPER RIDGE WAY 49, WOODBRIDGE, CT, ..., Woodbridge, CT 06525
$699,000

3 beds

|

3 baths

|

Condo

5 WHISPER RIDGE WAY 49, WOODBRIDGE, CT, ...
Heritage Village 405 HERITAGE VLG D, SOUTHBURY, CT, 06488, Southbury, CT 06488
$199,900

2 beds

|

2 baths

|

1,044 sq ft

|

Condo

405 HERITAGE VLG 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
Leisure Village 418 WEYMOUTH CT B, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$359,900

2 beds

|

1 baths

|

1,036 sq ft

|

Condo

418 WEYMOUTH CT B, BROOKHAVEN, NY, 11961
Community: Leisure Village
The Waterways at Moriches 554 MIRROR POND CT, BROOKHAVEN, NY, 1195..., Brookhaven, NY 11955
$499,000

2 beds

|

2 baths

|

1,497 sq ft

|

Condo

554 MIRROR POND CT, BROOKHAVEN, NY, 1195...
Oronoque Village 446 HAMMERSTONE LN B, STRATFORD, CT, 066..., Stratford, CT 06614
$635,000

3 beds

|

3 baths

|

1,426 sq ft

|

Condo

446 HAMMERSTONE LN B, STRATFORD, CT, 066...
Community: Oronoque Village
Heritage Hills 182 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589
$475,000

2 beds

|

2 baths

|

1,205 sq ft

|

Condo

182 HERITAGE HLS A, 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.
Oronoque Village 151 S TRL B, STRATFORD, CT, 06614, Stratford, CT 06614
$449,000

1 beds

|

3 baths

|

1,426 sq ft

|

Condo

151 S TRL B, STRATFORD, CT, 06614
Community: Oronoque Village
The Retreat at Carmel 4 FROST CT, CARMEL, NY, 10512, Carmel, NY 10512
$759,900

2 beds

|

3 baths

|

2,035 sq ft

|

Condo

4 FROST CT, CARMEL, NY, 10512
Heritage Village 761 HERITAGE VLG D, SOUTHBURY, CT, 06488, Southbury, CT 06488
$329,900

2 beds

|

2 baths

|

1,063 sq ft

|

Condo

761 HERITAGE VLG D, SOUTHBURY, CT, 06488
Community: Heritage Village
Liberty at Newtown 79 SUZIE DR 79, NEWTOWN, CT, 06470, Newtown, CT 06470
$575,000

2 beds

|

3 baths

|

2,317 sq ft

|

Condo

79 SUZIE DR 79, NEWTOWN, CT, 06470
Community: Liberty at Newtown
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
Fairfield at St. James 901 FENWAY RD, SAINT JAMES, NY, 11780, Saint James, NY 11780
$499,000

2 beds

|

2 baths

|

1,230 sq ft

|

Condo

901 FENWAY RD, SAINT JAMES, NY, 11780
Leisure Glen 10 OAKDALE CT, RIDGE, NY, 11961, Ridge, NY 11961
$599,900

2 beds

|

2 baths

|

1,666 sq ft

|

Condo

10 OAKDALE CT, RIDGE, NY, 11961
Community: Leisure Glen
Heritage Village 891 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$310,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

891 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
The Coves at Melville 6 MORLEY CIR, MELVILLE, NY, 11747, Melville, NY 11747
$530,000

2 beds

|

2 baths

|

Condo

6 MORLEY CIR, 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.
Encore Atlantic Shores 6 OVATION PL, BROOKHAVEN, NY, 11941, Brookhaven, NY 11941
$795,000

2 beds

|

2 baths

|

2,150 sq ft

|

Condo

6 OVATION PL, BROOKHAVEN, NY, 11941
The Villages NJ 82 PARKWAY DR B, FREEHOLD, NJ, 07728, Freehold, NJ 07728
$459,900

2 beds

|

2 baths

|

1,168 sq ft

|

Ranch

82 PARKWAY DR B, FREEHOLD, NJ, 07728
Community: The Villages NJ
Surrey Downs 3 GATLEY CLOSE 1000, FREEHOLD, NJ, 07728, Freehold, NJ 07728
$469,900

2 beds

|

2 baths

|

1,261 sq ft

|

Ranch

3 GATLEY CLOSE 1000, FREEHOLD, NJ, 07728
Community: Surrey Downs
Apple Ridge 272 BELMONT PL # 272, MAHWAH, NJ, 07430, Mahwah, NJ 07430
$869,000

3 beds

|

3 baths

|

Townhouse

272 BELMONT PL # 272, MAHWAH, NJ, 07430
Community: Apple Ridge
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
Rivington 85 WINDING RIDGE WAY 85, DANBURY, CT, 06..., Danbury, CT 06810
$825,000

3 beds

|

4 baths

|

1,794 sq ft

|

Condo

85 WINDING RIDGE WAY 85, DANBURY, CT, 06...
Community: Rivington
Surrey Downs 47 CARNABY CLOSE, FREEHOLD, NJ, 07728, Freehold, NJ 07728
$384,999

2 beds

|

2 baths

|

1,074 sq ft

|

Ranch

47 CARNABY CLOSE, FREEHOLD, NJ, 07728
Community: Surrey Downs
Leisure Village 116 EXMORE CT UNIT B, RIDGE, NY, 11961, Ridge, NY 11961
$299,000

2 beds

|

1 baths

|

875 sq ft

|

Condo

116 EXMORE CT UNIT B, RIDGE, NY, 11961
Community: Leisure Village
The Retreat at Carmel 2 BLAIR HEIGHTS 3317, CARMEL, NY, 10512, Carmel, NY 10512
$459,900

2 beds

|

2 baths

|

1,323 sq ft

|

Condo

2 BLAIR HEIGHTS 3317, CARMEL, NY, 10512
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.
Dutchgate 817 WILLOW LN, VALLEY STREAM, NY, 11580, Valley Stream, NY 11580
$514,990

2 beds

|

2 baths

|

941 sq ft

|

Condo

817 WILLOW LN, VALLEY STREAM, NY, 11580
Community: Dutchgate
Meadowbrook Pointe Athletic Club & Spa 365 TROTTING LN, WESTBURY, NY, 11590, Westbury, NY 11590
$799,999

1 beds

|

2 baths

|

1,128 sq ft

|

Condo

365 TROTTING LN, WESTBURY, NY, 11590
Heritage Hills 537 HERITAGE HLS D, SOMERS, NY, 10589, Somers, NY 10589
$600,000

2 beds

|

2 baths

|

1,470 sq ft

|

Condo

537 HERITAGE HLS D, SOMERS, NY, 10589
Community: Heritage Hills
The Summit at Bethel 32 HUNTING RIDGE LN # 32, BETHEL, CT, 06..., Bethel, CT 06801
$689,000

3 beds

|

4 baths

|

2,090 sq ft

|

Condo

32 HUNTING RIDGE LN # 32, BETHEL, CT, 06...
Country Pointe Plainview 21105 ASPENWOOD DR, PLAINVIEW, NY, 11803, Plainview, NY 11803
$1,250,000

2 beds

|

2 baths

|

1,475 sq ft

|

Condo

21105 ASPENWOOD DR, PLAINVIEW, NY, 11803
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
Leisure Village 373 WOODBRIDGE DR B, RIDGE, NY, 11961, Ridge, NY 11961
$415,000

2 beds

|

1 baths

|

1,171 sq ft

|

Condo

373 WOODBRIDGE DR B, RIDGE, NY, 11961
Community: Leisure Village
The Villas at Narragansett 816 NARRAGANSETT VILLAS DR 816, BABYLON,..., Babylon, NY 11757
$549,999

2 beds

|

2 baths

|

1,215 sq ft

|

Condo

816 NARRAGANSETT VILLAS DR 816, BABYLON,...
Apple Ridge 183 VAN WINKLE LN, MAHWAH, NJ, 07430, Mahwah, NJ 07430
$849,000

3 beds

|

3 baths

|

Townhouse

183 VAN WINKLE LN, MAHWAH, NJ, 07430
Community: Apple Ridge
Four Seasons at Wayne 511 FOUR SEASONS DR 511, WAYNE, NJ, 0747..., Wayne, NJ 07470
$545,000

2 beds

|

2 baths

|

Condo

511 FOUR SEASONS DR 511, WAYNE, NJ, 0747...
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.
Spring Lake Village 1 COACH DR 1, SOUTHINGTON, CT, 06489, Southington, CT 06489
$279,900

2 beds

|

2 baths

|

1,323 sq ft

|

Condo

1 COACH DR 1, SOUTHINGTON, CT, 06489
Community: Spring Lake Village
Cheesequake Village 14 CONNECTICUT CT # 869, MATAWAN, NJ, 07..., Matawan, NJ 07747
$249,999

2 beds

|

1 baths

|

914 sq ft

|

Duplex

14 CONNECTICUT CT # 869, MATAWAN, NJ, 07...
Community: Cheesequake Village
Bartlett Hill 9 PEAR ORCHARD RD # 9, PORTLAND, CT, 064..., Portland, CT 06480
$505,000

2 beds

|

3 baths

|

1,404 sq ft

|

Condo

9 PEAR ORCHARD RD # 9, PORTLAND, CT, 064...
Community: Bartlett Hill
Bartlett Hill 9 PEAR ORCHARD RD 9, PORTLAND, CT, 06480, Portland, CT 06480
$505,000

2 beds

|

3 baths

|

1,404 sq ft

|

Condo

9 PEAR ORCHARD RD 9, PORTLAND, CT, 06480
Community: Bartlett Hill
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
The Villages NJ 161A PARKWAY DR A, FREEHOLD, NJ, 07728, Freehold, NJ 07728
$335,000

2 beds

|

2 baths

|

1,262 sq ft

|

Adult Community

161A PARKWAY DR A, FREEHOLD, NJ, 07728
Community: The Villages NJ
The Retreat at Carmel 14 LANGDON GRV, CARMEL, NY, 10512, Carmel, NY 10512
$679,900

3 beds

|

3 baths

|

3,000 sq ft

|

Condo

14 LANGDON GRV, CARMEL, NY, 10512
1234567…8

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