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

363 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
Leisure Village
$100ks - $300ks
Leisure Village, Ridge, NY
Resale Only | 55+ age-restricted | Built 1969 - 1986 | 1,500 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
3 rating (2 reviews) Heritage Hills
- $900ks
Heritage Hills, Somers, NY
Resale Only | Age-targeted | Built 1974 - 2006 | 2,600 homes
Oronoque Village
$200ks - $400ks
Oronoque Village, Stratford, CT
Resale Only | 55+ age-restricted | Built 1971 - 1977 | 929 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
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
The Waterways at Moriches
$300ks - $600ks
The Waterways at Moriches, Moriches, NY
Resale Only | 55+ age-restricted | Built 1985 - 1999 | 343 homes
3.7 rating (3 reviews) Greenwood Village
$100ks
Greenwood Village, Manorville, NY
Resale Only | 55+ age-restricted | Built 1980 - 2000 | 512 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 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
4 rating (8 reviews) Glenwood Village
$100ks - $200ks
Glenwood Village, Riverhead, NY
New and Resale | 55+ age-restricted | Built 1959 - present | 588 homes
3.7 rating (3 reviews) Rosemont Estates
$500ks - $700ks
Rosemont Estates, Marlboro, NJ
Resale Only | 55+ age-restricted | Built 2004 - 2014 | 242 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
Leisure Knoll
$200ks - $400ks
Leisure Knoll, Ridge, NY
Resale Only | 55+ age-restricted | Built 1972 - 1982 | 701 homes
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Questions? Call us: (475) 471-1908
4.2 rating (12 reviews) Surrey Downs
$200ks - $300ks
Surrey Downs, Freehold, NJ
Resale Only | 55+ age-restricted | Built 1986 - 1997 | 443 homes
Fairview at Oxford Greens
$400ks - $600ks
Fairview at Oxford Greens, Oxford, CT
New and Resale | 55+ age-restricted | Built 2019 - present | 125 homes
Leisure Glen
$300ks - $400ks
Leisure Glen, Ridge, NY
Resale Only | 55+ age-restricted | Built 1985 - 2010 | 646 homes
HarborView
$600ks - $1Ms
HarborView, Port Washington, NY
Resale Only | 55+ age-restricted | Built 2002 - 2004 | 270 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
Equestra at Colts Neck Cr...
$600ks - $700ks
Equestra at Colts Neck Cr..., Farmingdale, NJ
Resale Only | 55+ age-restricted | Built 2007 - 2018 | 483 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
The Coves at Melville
$500ks
The Coves at Melville, Melville, NY
Resale Only | 62+ age-restricted | Built 2004 - 2005 | 175 homes
The Retreat at Carmel
$300ks - $800ks
The Retreat at Carmel, Carmel, NY
Resale Only | 55+ age-restricted | Built 2008 - 2018 | 312 homes
5 rating (1 reviews) Newtown Woods
$300ks - $500ks
Newtown Woods, Newtown, CT
New and Resale | 55+ age-restricted | Built 2011 - present | 178 homes
5 rating (1 reviews) Sunrise Village
$400ks
Sunrise Village, Sayville, NY
Resale Only | 55+ age-restricted | Built 1985 - 1990 | 213 homes
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Questions? Call us: (475) 471-1908
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
Setauket Meadows
$500ks - $600ks
Setauket Meadows, Setauket, NY
Resale Only | 55+ age-restricted | Built 2005 - 2007 | 150 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.
Meadowbrook Pointe Athlet...
$700ks - $1Ms
Meadowbrook Pointe Athlet..., Westbury, NY
Resale Only | 55+ age-restricted | Built 2015 - 2016 | 720 homes
Kensington Estates
$1Ms
Kensington Estates, Woodbury, NY
New Construction | 55+ age-restricted | Built 2019 - 2021 | 80 homes
Village Estates
$300ks - $400ks
Village Estates, Amityville, NY
Resale Only | 55+ age-restricted | Built 2006 - 2008 | 138 homes
Winthrop Court
$400ks - $600ks
Winthrop Court, Clifton, NJ
Resale Only | 55+ age-restricted | Built 2000 - 2010 | 270 homes
Liberty at Newtown
$300ks - $400ks
Liberty at Newtown, Newtown, CT
Resale Only | 55+ age-restricted | Built 2003 - 2007 | 96 homes
Regency at Wappinger
$500ks
Regency at Wappinger, Wappingers Falls, NY
Resale Only | 55+ age-restricted | Built 2014 - 2020 | 225 homes
Parker Village Estates
$500ks - $600ks
Parker Village Estates, Eatontown, NJ
Resale Only | 55+ age-restricted | Built 2002 - 2002 | 66 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
Spring Lake Village
$100ks - $200ks
Spring Lake Village, Southington, CT
Resale Only | 55+ age-restricted | Built 1970 - 2004 | 640 homes
Breton Hills
$500ks
Breton Hills, Glen Cove, NY
New Construction | 55+ age-restricted | Built 2019 - present | 72 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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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
Leisure Village 432A FALMOUTH CT # 432A, RIDGE, NY, 1196..., Ridge, NY 11961
$389,000

2 beds

|

1 baths

|

1,074 sq ft

|

Condo

432A FALMOUTH CT # 432A, RIDGE, NY, 1196...
Community: Leisure Village
Greenwood Village 164 VILLAGE CIR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949
$142,997

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
Baldwin Station 7 FIRE THORN LN 7, MILFORD, CT, 06461, Milford, CT 06461
$679,950

2 beds

|

3 baths

|

2,331 sq ft

|

Condo

7 FIRE THORN LN 7, MILFORD, CT, 06461
Community: Baldwin Station
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
The Waterways at Moriches 477 WOODSCREEK CT, BROOKHAVEN, NY, 11955, Brookhaven, NY 11955
$565,000

3 beds

|

2 baths

|

1,839 sq ft

|

Condo

477 WOODSCREEK CT, BROOKHAVEN, NY, 11955
The Greens at Half Hollow 910 ALTESSA BLVD, HUNTINGTON, NY, 11747, Huntington, NY 11747
$779,000

2 beds

|

2 baths

|

1,120 sq ft

|

Condo

910 ALTESSA BLVD, HUNTINGTON, NY, 11747
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
The Villages NJ 93 HALLS CROFT RD D, FREEHOLD, NJ, 07728, Freehold, NJ 07728
$309,000

2 beds

|

2 baths

|

1,008 sq ft

|

Ranch

93 HALLS CROFT RD D, FREEHOLD, NJ, 07728
Community: The Villages NJ
The Villas at Narragansett 512 NARRAGANSETT VILLAS DR, BABYLON, NY,..., Babylon, NY 11757
$555,000

2 beds

|

2 baths

|

1,227 sq ft

|

Condo

512 NARRAGANSETT VILLAS DR, BABYLON, NY,...
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 177 MELODY CT, BROOKHAVEN, NY, 11941, Brookhaven, NY 11941
$795,000

2 beds

|

2 baths

|

2,150 sq ft

|

Condo

177 MELODY CT, BROOKHAVEN, NY, 11941
Overlook 2042 SUMMIT LOOP 58, CARMEL, NY, 10512, Carmel, NY 10512
$849,000

2 beds

|

4 baths

|

1,957 sq ft

|

Condo

2042 SUMMIT LOOP 58, CARMEL, NY, 10512
Community: Overlook
Overlook 2090 SUMMIT LOOP 80, CARMEL, NY, 10512, Carmel, NY 10512
$898,000

2 beds

|

3 baths

|

2,496 sq ft

|

Condo

2090 SUMMIT LOOP 80, CARMEL, NY, 10512
Community: Overlook
Rivington 1 RIVINGTON WAY 201, DANBURY, CT, 06810, Danbury, CT 06810
$479,900

2 beds

|

2 baths

|

1,229 sq ft

|

Condo

1 RIVINGTON WAY 201, DANBURY, CT, 06810
Community: Rivington
The Villages NJ 56 LARGO SAN NICOLA A, FREEHOLD, NJ, 077..., Freehold, NJ 07728
$350,000

2 beds

|

1 baths

|

1,144 sq ft

|

Ranch

56 LARGO SAN NICOLA A, FREEHOLD, NJ, 077...
Community: The Villages NJ
Greenwood Village 91 VILLAGE CIR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949
$139,999

2 beds

|

2 baths

|

938 sq ft

|

Condo

91 VILLAGE CIR, BROOKHAVEN, NY, 11949
Community: Greenwood Village
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
Greenwood Village 19 DOGWOOD LN, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949
$119,900

2 beds

|

2 baths

|

871 sq ft

|

Condo

19 DOGWOOD LN, BROOKHAVEN, NY, 11949
Community: Greenwood Village
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 98 HERITAGE VLG D, SOUTHBURY, CT, 06488, Southbury, CT 06488
$279,900

2 beds

|

2 baths

|

1,044 sq ft

|

Condo

98 HERITAGE VLG D, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 73 HERITAGE VLG C, SOUTHBURY, CT, 06488, Southbury, CT 06488
$214,900

2 beds

|

2 baths

|

1,044 sq ft

|

Condo

73 HERITAGE VLG C, 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.
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
Heritage Hills 356 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589
$750,000

2 beds

|

2 baths

|

1,435 sq ft

|

Condo

356 HERITAGE HLS A, SOMERS, NY, 10589
Community: Heritage Hills
Evergreen 34 WOODSBORO CIR 34, CROMWELL, CT, 06416, Cromwell, CT 06416
$499,000

2 beds

|

2 baths

|

1,758 sq ft

|

Condo

34 WOODSBORO CIR 34, CROMWELL, CT, 06416
Community: Evergreen
Kensington Estates 46 PLAINVIEW RD, WOODBURY, NY, 11797, Woodbury, NY 11797
$2,299,999

6 beds

|

5 baths

|

4,333 sq ft

|

House

46 PLAINVIEW RD, WOODBURY, NY, 11797
Community: Kensington Estates
Heritage Village 862 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$469,900

3 beds

|

2 baths

|

1,716 sq ft

|

Condo

862 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
The Waterways at Moriches 244 RIVER DR, BROOKHAVEN, NY, 11955, Brookhaven, NY 11955
$625,000

2 beds

|

2 baths

|

1,960 sq ft

|

Condo

244 RIVER DR, BROOKHAVEN, NY, 11955
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
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
Cheesequake Village 9 VALERY RD, OLD BRIDGE, NJ, 07747, Old Bridge, NJ 07747
$259,900

1 beds

|

1 baths

|

758 sq ft

|

House

9 VALERY RD, OLD BRIDGE, NJ, 07747
Community: Cheesequake Village
Greenwood Village 2 LIMETREE DR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949
$250,000

2 beds

|

2 baths

|

1,242 sq ft

|

House

2 LIMETREE DR, BROOKHAVEN, NY, 11949
Community: Greenwood Village
Glenwood Village 1661 OLD COUNTRY RD 308, RIVERHEAD, NY, ..., Riverhead, NY 11901
$149,000

2 beds

|

1 baths

|

840 sq ft

|

Mobile Home

1661 OLD COUNTRY RD 308, RIVERHEAD, NY, ...
Community: Glenwood 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.
Leisure Village 405 WOODBRIDGE DR D, BROOKHAVEN, NY, 119..., Brookhaven, NY 11961
$290,000

2 beds

|

1 baths

|

874 sq ft

|

Condo

405 WOODBRIDGE DR D, BROOKHAVEN, NY, 119...
Community: Leisure 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
Westhampton Pines 112 ASHLEY DR, SOUTHAMPTON, NY, 11977, Southampton, NY 11977
$1,295,000

3 beds

|

3 baths

|

2,306 sq ft

|

Condo

112 ASHLEY DR, SOUTHAMPTON, NY, 11977
Community: Westhampton Pines
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
Rosemont Estates 211 BRADWICK WAY, MARLBORO, NJ, 07746, Marlboro, NJ 07746
$774,900

2 beds

|

3 baths

|

2,452 sq ft

|

House

211 BRADWICK WAY, MARLBORO, NJ, 07746
Community: Rosemont Estates
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
Heritage Village 740 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$409,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

740 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
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
The Village at Oxford Greens 1097 ST ANDREWS DR 9, OXFORD, CT, 06478, Oxford, CT 06478
$780,580

2 beds

|

3 baths

|

2,536 sq ft

|

Condo

1097 ST ANDREWS DR 9, OXFORD, CT, 06478
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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