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Westport, CT 55+ active adult communities & homes for sale - Page 9

348 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
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
4 rating (1 reviews) Jefferson Village
$100ks - $500ks
Jefferson Village, Yorktown Heights, NY
Resale Only | 55+ age-restricted | Built 1967 - 1982 | 1,000 homes
Oronoque Village
$200ks - $400ks
Oronoque Village, Stratford, CT
Resale Only | 55+ age-restricted | Built 1971 - 1977 | 929 homes
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Questions? Call us: (475) 471-1908
Leisure Village
$100ks - $300ks
Leisure Village, Ridge, NY
Resale Only | 55+ age-restricted | Built 1969 - 1986 | 1,500 homes
3 rating (2 reviews) Heritage Hills
$400ks - $800ks
Heritage Hills, Somers, NY
Resale Only | Age-targeted | Built 1974 - 2006 | 2,600 homes
The Waterways at Moriches
$300ks - $600ks
The Waterways at Moriches, Moriches, NY
Resale Only | 55+ age-restricted | Built 1985 - 1999 | 343 homes
4.2 rating (12 reviews) Surrey Downs
$200ks - $300ks
Surrey Downs, Freehold, NJ
Resale Only | 55+ age-restricted | Built 1986 - 1997 | 443 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
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 Knoll
$200ks - $400ks
Leisure Knoll, Ridge, NY
Resale Only | 55+ age-restricted | Built 1972 - 1982 | 701 homes
Regency at Fishkill
$300ks - $400ks
Regency at Fishkill, Fishkill, NY
Resale Only | 55+ age-restricted | Built 2008 - 2020 | 164 homes
3.7 rating (3 reviews) Greenwood Village
$100ks
Greenwood Village, Manorville, NY
Resale Only | 55+ age-restricted | Built 1980 - 2000 | 512 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
Apple Ridge
$500ks - $1Ms
Apple Ridge, Mahwah, NJ
Resale Only | Age-targeted | Built 1977 - 1991 | 276 homes
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
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
4 rating (8 reviews) Glenwood Village
$100ks - $200ks
Glenwood Village, Riverhead, NY
New and Resale | 55+ age-restricted | Built 1959 - present | 588 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
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
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.
Fairview at Oxford Greens
$400ks - $600ks
Fairview at Oxford Greens, Oxford, CT
New and Resale | 55+ age-restricted | Built 2019 - present | 125 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
The Summit at Bethel
$500ks - $700ks
The Summit at Bethel, Bethel, CT
Resale Only | 55+ age-restricted | Built 2010 - 2021 | 235 homes
The Seasons at Elwood
$800ks - $900ks
The Seasons at Elwood, East Northport, NY
Resale Only | 55+ age-restricted | Built 2018 - 2020 | 256 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
3.7 rating (3 reviews) Rosemont Estates
$500ks - $700ks
Rosemont Estates, Marlboro, NJ
Resale Only | 55+ age-restricted | Built 2004 - 2014 | 242 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
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
Meadowbrook Pointe Athlet...
$700ks - $1Ms
Meadowbrook Pointe Athlet..., Westbury, NY
Resale Only | 55+ age-restricted | Built 2015 - 2016 | 720 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
Leisure Glen
$300ks - $400ks
Leisure Glen, Ridge, NY
Resale Only | 55+ age-restricted | Built 1985 - 2010 | 646 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.
South Pond Village
$300ks - $400ks
South Pond Village, Bloomfield, CT
Resale Only | 55+ age-restricted | Built 1999 - 2005 | 151 homes
Regency at Holmdel
$900ks - $1Ms
Regency at Holmdel, Holmdel, NJ
Resale Only | 55+ age-restricted | Built 2016 - 2019 | 181 homes
The Hollows at Blue Hill
$500ks - $700ks
The Hollows at Blue Hill, Pearl River, NY
Resale Only | 55+ age-restricted | Built 2008 - 2014 | 126 homes
5 rating (1 reviews) Shady Oaks
$200ks - $400ks
Shady Oaks, Red Bank, NJ
Resale Only | 55+ age-restricted | Built 1982 - 1983 | 366 homes
5 rating (1 reviews) Westhampton Pines
$900ks - $1Ms
Westhampton Pines, Westhampton, NY
Resale Only | 55+ age-restricted | Built 2005 - 2013 | 189 homes
Rivington
$300ks - $900ks
Rivington, Danbury, CT
New and Resale | Age-targeted | Built 2006 - present | 1,050 homes
3.5 rating (2 reviews) Foxwood Village
$200ks - $400ks
Foxwood Village, Calverton, NY
Resale Only | 55+ age-restricted | Built 1986 - 2007 | 294 homes
5 rating (1 reviews) Sunken Pond Estates
$400ks
Sunken Pond Estates, Riverhead, NY
Resale Only | 55+ age-restricted | Built 2003 - 2005 | 194 homes
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
Four Seasons at Colts Far...
$600ks - $800ks
Four Seasons at Colts Far..., Farmingdale, NJ
New Construction | 55+ age-restricted | Built 2021 - present | 111 homes
5 rating (1 reviews) Newtown Woods
$300ks - $500ks
Newtown Woods, Newtown, CT
New and Resale | 55+ age-restricted | Built 2011 - present | 178 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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Greenwood Village 54 DOGWOOD LN, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949
$120,000

2 beds

|

2 baths

|

1,134 sq ft

|

Condo

54 DOGWOOD LN, BROOKHAVEN, NY, 11949
Community: Greenwood Village
The Summit at Bethel 12 BRIAR RIDGE DR 12, BETHEL, CT, 06801, Bethel, CT 06801
$619,900

2 beds

|

3 baths

|

2,023 sq ft

|

Condo

12 BRIAR RIDGE DR 12, BETHEL, CT, 06801
Oronoque Village 13 ALGONQUIN LN C, STRATFORD, CT, 06614, Stratford, CT 06614
$389,000

1 beds

|

2 baths

|

1,330 sq ft

|

Condo

13 ALGONQUIN LN C, STRATFORD, CT, 06614
Community: Oronoque Village
Leisure Village 278 BERWICK CT B, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$349,900

2 beds

|

1 baths

|

875 sq ft

|

Condo

278 BERWICK CT B, BROOKHAVEN, NY, 11961
Community: Leisure Village
Heritage Village 405 HERITAGE VLG D, SOUTHBURY, CT, 06488, Southbury, CT 06488
$179,900

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
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
Liberty at Newtown 79 SUZIE DR 79, NEWTOWN, CT, 06470, Newtown, CT 06470
$565,000

2 beds

|

3 baths

|

2,317 sq ft

|

Condo

79 SUZIE DR 79, NEWTOWN, CT, 06470
Community: Liberty at Newtown
The Villages NJ 82 PARKWAY DR B, FREEHOLD, NJ, 07728, Freehold, NJ 07728
$418,500

2 beds

|

2 baths

|

1,168 sq ft

|

Ranch

82 PARKWAY DR B, FREEHOLD, NJ, 07728
Community: The Villages NJ
Leisure Village 274 BERWICK CT A, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$349,999

2 beds

|

1 baths

|

836 sq ft

|

Condo

274 BERWICK CT A, BROOKHAVEN, NY, 11961
Community: Leisure Village
Leisure Village 373 WOODBRIDGE DR B, BROOKHAVEN, NY, 119..., Brookhaven, NY 11961
$399,000

2 beds

|

1 baths

|

1,171 sq ft

|

Condo

373 WOODBRIDGE DR B, BROOKHAVEN, NY, 119...
Community: Leisure 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.
Greenwood Village 164 VILLAGE CIR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949
$129,997

2 beds

|

2 baths

|

938 sq ft

|

Condo

164 VILLAGE CIR, BROOKHAVEN, NY, 11949
Community: Greenwood Village
Eagles Walk at East Quogue 104 AERIE WAY, SOUTHAMPTON, NY, 11942, Southampton, NY 11942
$529,000

2 beds

|

2 baths

|

1,341 sq ft

|

Condo

104 AERIE WAY, SOUTHAMPTON, NY, 11942
The Waterways at Moriches 477 WOODSCREEK CT, BROOKHAVEN, NY, 11955, Brookhaven, NY 11955
$529,000

3 beds

|

2 baths

|

1,839 sq ft

|

Condo

477 WOODSCREEK CT, BROOKHAVEN, NY, 11955
Leisure Village 380 WOODBRIDGE DR D, BROOKHAVEN, NY, 119..., Brookhaven, NY 11961
$434,000

2 beds

|

2 baths

|

1,147 sq ft

|

Condo

380 WOODBRIDGE DR D, BROOKHAVEN, NY, 119...
Community: Leisure Village
Overlook 2042 SUMMIT LOOP 58, CARMEL, NY, 10512, Carmel, NY 10512
$799,000

2 beds

|

4 baths

|

1,957 sq ft

|

Condo

2042 SUMMIT LOOP 58, CARMEL, NY, 10512
Community: Overlook
Overlook 2080 SUMMIT LOOP 75, CARMEL, NY, 10512, Carmel, NY 10512
$979,000

2 beds

|

3 baths

|

2,496 sq ft

|

Condo

2080 SUMMIT LOOP 75, CARMEL, NY, 10512
Community: Overlook
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
The Waterways at Moriches 414 LINDSAY LN, BROOKHAVEN, NY, 11955, Brookhaven, NY 11955
$529,000

2 beds

|

2 baths

|

2,141 sq ft

|

Condo

414 LINDSAY LN, BROOKHAVEN, NY, 11955
Heritage Village 73 HERITAGE VLG C, SOUTHBURY, CT, 06488, Southbury, CT 06488
$199,900

2 beds

|

2 baths

|

1,044 sq ft

|

Condo

73 HERITAGE VLG C, SOUTHBURY, CT, 06488
Community: Heritage Village
Overlook 2086 SUMMIT LOOP 78, CARMEL, NY, 10512, Carmel, NY 10512
$799,000

2 beds

|

3 baths

|

2,126 sq ft

|

Condo

2086 SUMMIT LOOP 78, CARMEL, NY, 10512
Community: Overlook
Kensington Estates 46 PLAINVIEW RD, OYSTER BAY, NY, 11797, Oyster Bay, NY 11797
$2,299,999

6 beds

|

5 baths

|

4,333 sq ft

|

House

46 PLAINVIEW RD, OYSTER BAY, NY, 11797
Community: Kensington Estates
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 Vineyards at Miller Place 48 AVERY LN, BROOKHAVEN, NY, 11764, Brookhaven, NY 11764
$659,900

2 beds

|

3 baths

|

1,486 sq ft

|

Condo

48 AVERY LN, BROOKHAVEN, NY, 11764
Glenwood Village 1661 OLD COUNTRY RD 308, RIVERHEAD, NY, ..., Riverhead, NY 11901
$129,000

2 beds

|

1 baths

|

840 sq ft

|

Mobile Home

1661 OLD COUNTRY RD 308, RIVERHEAD, NY, ...
Community: Glenwood Village
Heritage Village 902 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$379,900

2 beds

|

2 baths

|

1,398 sq ft

|

Condo

902 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Surrey Downs 1 CARNABY CLOSE 1000, FREEHOLD, NJ, 0772..., Freehold, NJ 07728
$395,000

2 beds

|

2 baths

|

1,261 sq ft

|

Ranch

1 CARNABY CLOSE 1000, FREEHOLD, NJ, 0772...
Community: Surrey Downs
Heritage Village 643 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$314,900

2 beds

|

2 baths

|

1,398 sq ft

|

Condo

643 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
The Villages NJ 12 ZACATIN RD A, FREEHOLD, NJ, 07728, Freehold, NJ 07728
$300,000

2 beds

|

1 baths

|

1,008 sq ft

|

Condo

12 ZACATIN RD A, FREEHOLD, NJ, 07728
Community: The Villages NJ
Winthrop Court 8205 HARCOURT RD 8205, CLIFTON, NJ, 0701..., Clifton, NJ 07013
$499,000

2 beds

|

2 baths

|

Condo

8205 HARCOURT RD 8205, CLIFTON, NJ, 0701...
Community: Winthrop Court
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
HarborView 100 HARBOR VIEW DR 423, NORTH HEMPSTEAD,..., North Hempstead, NY 11050
$628,000

1 beds

|

2 baths

|

1,161 sq ft

|

Condo

100 HARBOR VIEW DR 423, NORTH HEMPSTEAD,...
Community: HarborView

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