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Westport, CT 55+ active adult communities & homes for sale - Page 10

393 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
4 rating (1 reviews) Jefferson Village
$100ks - $500ks
Jefferson Village, Yorktown Heights, NY
Resale Only | 55+ age-restricted | Built 1967 - 1982 | 1,000 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
5 rating (2 reviews) Oronoque Village
$200ks - $400ks
Oronoque Village, Stratford, CT
Resale Only | 55+ age-restricted | Built 1971 - 1977 | 929 homes
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
3 rating (2 reviews) Heritage Hills
$400ks - $800ks
Heritage Hills, Somers, NY
Resale Only | Age-targeted | Built 1974 - 2006 | 2,600 homes
3.7 rating (3 reviews) Greenwood Village
$100ks
Greenwood Village, Manorville, NY
Resale Only | 55+ age-restricted | Built 1980 - 2000 | 512 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) Shadow Lake Village
$200ks - $500ks
Shadow Lake Village, Red Bank, NJ
Resale Only | 55+ age-restricted | Built 1972 - 1980 | 952 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
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 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
Leisure Village
$100ks - $300ks
Leisure Village, Ridge, NY
Resale Only | 55+ age-restricted | Built 1969 - 1986 | 1,500 homes
Country Pointe Plainview
$700ks - $1Ms
Country Pointe Plainview, Plainview, NY
New Construction | 55+ age-restricted | Built 2017 - present | 660 homes
Leisure Glen
$300ks - $400ks
Leisure Glen, Ridge, NY
Resale Only | 55+ age-restricted | Built 1985 - 2010 | 646 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
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
Rivington
$300ks - $900ks
Rivington, Danbury, CT
New and Resale | Age-targeted | Built 2006 - present | 1,050 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
HarborView
$600ks - $1Ms
HarborView, Port Washington, NY
Resale Only | 55+ age-restricted | Built 2002 - 2004 | 270 homes
Leisure Knoll
$200ks - $400ks
Leisure Knoll, Ridge, NY
Resale Only | 55+ age-restricted | Built 1972 - 1982 | 701 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.
Rolling Meadows at Waysid...
$500ks - $600ks
Rolling Meadows at Waysid..., Ocean Township, NJ
Resale Only | 55+ age-restricted | Built 2002 - 2007 | 328 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
Apple Ridge
$500ks - $1Ms
Apple Ridge, Mahwah, NJ
Resale Only | Age-targeted | Built 1977 - 1991 | 276 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
Regency at Fishkill
$300ks - $400ks
Regency at Fishkill, Fishkill, NY
Resale Only | 55+ age-restricted | Built 2008 - 2020 | 164 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
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
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
Woodridge Strathmore Terr...
$200ks - $300ks
Woodridge Strathmore Terr..., Mount Sinai, NY
Resale Only | 55+ age-restricted | Built 1974 - 1985 | 226 homes
Snug Harbor
$600ks - $700ks
Snug Harbor, Amityville, NY
Resale Only | 55+ age-restricted | Built 1970 - 1974 | 176 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.
Dutchgate
$300ks - $500ks
Dutchgate, Valley Stream, NY
Resale Only | 55+ age-restricted | Built 2009 - 2015 | 348 homes
Stoneleigh Woods at River...
$500ks
Stoneleigh Woods at River..., Riverhead, NY
Resale Only | 55+ age-restricted | Built 2007 - 2016 | 176 homes
Meadowbrook Pointe Athlet...
$700ks - $1Ms
Meadowbrook Pointe Athlet..., Westbury, NY
Resale Only | 55+ age-restricted | Built 2015 - 2016 | 720 homes
5 rating (1 reviews) Westhampton Pines
$900ks - $1Ms
Westhampton Pines, Westhampton, NY
Resale Only | 55+ age-restricted | Built 2005 - 2013 | 189 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
Chelsea Square
$300ks - $400ks
Chelsea Square, Morganville, NJ
New and Resale | 55+ age-restricted | Built 2007 - present | 225 homes
The Seasons at East Meado...
$400ks - $600ks
The Seasons at East Meado..., East Meadow, NY
Resale Only | 55+ age-restricted | Built 2009 - 2012 | 404 homes
Vineyards at Moriches
$500ks - $600ks
Vineyards at Moriches, Center Moriches, NY
Resale Only | 55+ age-restricted | Built 2008 - 2014 | 92 homes
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
Stone Ridge Estates
$500ks - $600ks
Stone Ridge Estates, Dix Hills, NY
Resale Only | 55+ age-restricted | Built 2004 - 2013 | 76 homes
Country Pointe Preserve
$600ks - $900ks
Country Pointe PreserveYaphank, NY
New Construction | 55+ age-restricted | Built 2024 - present | 152 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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Stoneleigh Woods at Riverhead 156 STONELEIGH DR, RIVERHEAD, NY, 11901, Riverhead, NY 11901
$639,000

2 beds

|

3 baths

|

1,942 sq ft

|

Condo

156 STONELEIGH DR, RIVERHEAD, NY, 11901
Oronoque Village 638A ONONDAGA LN, STRATFORD, CT, 06614, Stratford, CT 06614
$510,000

1 beds

|

3 baths

|

1,175 sq ft

|

Condo

638A ONONDAGA LN, STRATFORD, CT, 06614
Community: Oronoque Village
The Greens at Half Hollow 381 ALTESSA BLVD, HUNTINGTON, NY, 11747, Huntington, NY 11747
$1,399,999

2 beds

|

2 baths

|

2,575 sq ft

|

Condo

381 ALTESSA BLVD, HUNTINGTON, NY, 11747
The Coves at Melville 80 MORLEY CIR, HUNTINGTON, NY, 11747, Huntington, NY 11747
$549,999

2 beds

|

2 baths

|

1,169 sq ft

|

Condo

80 MORLEY CIR, HUNTINGTON, NY, 11747
Oronoque Village 377 PIUTE LN A, STRATFORD, CT, 06614, Stratford, CT 06614
$465,000

1 beds

|

3 baths

|

2,025 sq ft

|

Condo

377 PIUTE LN A, STRATFORD, CT, 06614
Community: Oronoque Village
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
The Villages at Mount Sinai Park 16 OAKHURST CT, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766
$789,000

2 beds

|

2 baths

|

1,929 sq ft

|

House

16 OAKHURST CT, BROOKHAVEN, NY, 11766
The Villages NJ 24 CALLE DE ELVIRA B, FREEHOLD, NJ, 0772..., Freehold, NJ 07728
$395,500

2 beds

|

2 baths

|

1,144 sq ft

|

House

24 CALLE DE ELVIRA B, FREEHOLD, NJ, 0772...
Community: The Villages NJ
Glenwood Village 1661 OLD COUNTRY RD 417, RIVERHEAD, NY, ..., Riverhead, NY 11901
$299,999

2 beds

|

2 baths

|

1,344 sq ft

|

Manufactured Home

1661 OLD COUNTRY RD 417, RIVERHEAD, NY, ...
Community: Glenwood Village
Jefferson Village 51 JEFFERSON OVAL F, YORKTOWN, NY, 10598, Yorktown, NY 10598
$419,000

2 beds

|

2 baths

|

1,100 sq ft

|

Condo

51 JEFFERSON OVAL F, YORKTOWN, NY, 10598
Community: Jefferson Village
Heritage Village 930 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$419,900

2 beds

|

2 baths

|

1,398 sq ft

|

Condo

930 HERITAGE VLG B, 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 Manors at The Colony Preserve 15 CRICKET CT, BROOKHAVEN, NY, 11967, Brookhaven, NY 11967
$479,000

2 beds

|

2 baths

|

1,322 sq ft

|

Condo

15 CRICKET CT, BROOKHAVEN, NY, 11967
Greenwood Village 191 VILLAGE CIR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949
$125,999

2 beds

|

2 baths

|

1,032 sq ft

|

Condo

191 VILLAGE CIR, BROOKHAVEN, NY, 11949
Community: Greenwood Village
Cheesequake Village 10 MAINE CT 734, MATAWAN, NJ, 07747, Matawan, NJ 07747
$290,000

2 beds

|

1 baths

|

949 sq ft

|

Adult Community

10 MAINE CT 734, MATAWAN, NJ, 07747
Community: Cheesequake Village
Cheesequake Village 10 HAVEN DR A, OLD BRIDGE, NJ, 07747, Old Bridge, NJ 07747
$225,000

1 beds

|

1 baths

|

748 sq ft

|

Condo

10 HAVEN DR A, OLD BRIDGE, NJ, 07747
Community: Cheesequake Village
Enclave at Shrewsbury 188 CAMPBELL CT, SHREWSBURY BORO, NJ, 07..., Shrewsbury Boro, NJ 07702
$1,099,000

3 beds

|

3 baths

|

2,777 sq ft

|

House

188 CAMPBELL CT, SHREWSBURY BORO, NJ, 07...
Cheesequake Village 12 LOUISIANA DR D, MATAWAN, NJ, 07747, Matawan, NJ 07747
$265,000

2 beds

|

1 baths

|

949 sq ft

|

Adult Community

12 LOUISIANA DR D, MATAWAN, NJ, 07747
Community: Cheesequake Village
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
Cheesequake Village 12 LOUISIANA DR D, OLD BRIDGE, NJ, 07747, Old Bridge, NJ 07747
$265,000

2 beds

|

1 baths

|

949 sq ft

|

Condo

12 LOUISIANA DR D, OLD BRIDGE, NJ, 07747
Community: Cheesequake Village
Jefferson Village 59 KIRBY CLOSE D, YORKTOWN, NY, 10598, Yorktown, NY 10598
$370,000

2 beds

|

2 baths

|

910 sq ft

|

Condo

59 KIRBY CLOSE D, YORKTOWN, NY, 10598
Community: Jefferson Village
The Waterways at Moriches 548 HIGHLAND CT, BROOKHAVEN, NY, 11955, Brookhaven, NY 11955
$479,000

2 beds

|

2 baths

|

1,771 sq ft

|

Condo

548 HIGHLAND CT, BROOKHAVEN, NY, 11955
Cheshire Square 55 CHESHIRE SQ, LITTLE SILVER, NJ, 07739, Little Silver, NJ 07739
$670,000

2 beds

|

3 baths

|

Townhouse

55 CHESHIRE SQ, LITTLE SILVER, NJ, 07739
Community: Cheshire Square
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.
Jefferson Village 41 JEFFERSON OVAL G, YORKTOWN, NY, 10598, Yorktown, NY 10598
$469,000

2 beds

|

2 baths

|

1,100 sq ft

|

Condo

41 JEFFERSON OVAL G, YORKTOWN, NY, 10598
Community: Jefferson Village
Shadow Lake Village 80 MANCHESTER CT, RED BANK, NJ, 07701, Red Bank, NJ 07701
$299,999

2 beds

|

1 baths

|

1,142 sq ft

|

Adult Community

80 MANCHESTER CT, RED BANK, NJ, 07701
Community: Shadow Lake Village
The Villages NJ 139 WEIN MARKET F, FREEHOLD, NJ, 07728, Freehold, NJ 07728
$339,000

2 beds

|

2 baths

|

1,244 sq ft

|

Ranch

139 WEIN MARKET F, FREEHOLD, NJ, 07728
Community: The Villages NJ
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
Oronoque Village 446 HAMMERSTONE LN B, STRATFORD, CT, 066..., Stratford, CT 06614
$605,000

3 beds

|

3 baths

|

1,426 sq ft

|

Condo

446 HAMMERSTONE LN B, STRATFORD, CT, 066...
Community: Oronoque Village
The Villages NJ 82 PARKWAY DR B, FREEHOLD, NJ, 07728, Freehold, NJ 07728
$408,000

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
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
Overlook 2042 SUMMIT LOOP 58, CARMEL, NY, 10512, Carmel, NY 10512
$829,000

2 beds

|

4 baths

|

1,957 sq ft

|

Condo

2042 SUMMIT LOOP 58, CARMEL, NY, 10512
Community: Overlook
Overlook 2069 SUMMIT LOOP 98, CARMEL, NY, 10512, Carmel, NY 10512
$899,000

2 beds

|

2 baths

|

2,850 sq ft

|

Condo

2069 SUMMIT LOOP 98, CARMEL, NY, 10512
Community: Overlook
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
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 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
The Vineyards at Miller Place 48 AVERY LN, BROOKHAVEN, NY, 11764, Brookhaven, NY 11764
$649,900

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
$99,000

2 beds

|

1 baths

|

840 sq ft

|

Mobile Home

1661 OLD COUNTRY RD 308, RIVERHEAD, NY, ...
Community: Glenwood Village

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