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Westport, CT 55+ active adult communities & homes for sale - Page 7

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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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
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
Want to learn more about 55+ communities in Westport? 55places can help!
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
Want to learn more about 55+ communities in Westport? 55places can help!
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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Leisure Village 421 WEYMOUTH CT D, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$349,000

2 beds

|

1 baths

|

875 sq ft

|

Condo

421 WEYMOUTH CT D, BROOKHAVEN, NY, 11961
Community: Leisure Village
Leisure Knoll 151 LAURANCE LN, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$489,000

2 beds

|

1 baths

|

1,000 sq ft

|

Condo

151 LAURANCE LN, BROOKHAVEN, NY, 11961
Community: Leisure Knoll
Heritage Village 665 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$509,000

3 beds

|

2 baths

|

1,716 sq ft

|

Condo

665 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Four Seasons at Great Notch Spa and Club 7 GRAPHITE DR, LITTLE FALLS, NJ, 07424, Little Falls, NJ 07424
$849,900

2 beds

|

3 baths

7 GRAPHITE DR, LITTLE FALLS, NJ, 07424
Newtown Woods 433 BROOKSIDE CT 433, NEWTOWN, CT, 06470, Newtown, CT 06470
$485,000

2 beds

|

2 baths

|

1,504 sq ft

|

Condo

433 BROOKSIDE CT 433, NEWTOWN, CT, 06470
Community: Newtown Woods
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
Glenwood Village 1661 OLD COUNTRY RD 69, RIVERHEAD, NY, 1..., Riverhead, NY 11901
$249,999

2 beds

|

2 baths

|

924 sq ft

|

Manufactured Home

1661 OLD COUNTRY RD 69, RIVERHEAD, NY, 1...
Community: Glenwood Village
Oronoque Village 261 AGAWAM DR A, STRATFORD, CT, 06614, Stratford, CT 06614
$575,000

2 beds

|

3 baths

|

1,620 sq ft

|

Condo

261 AGAWAM DR A, STRATFORD, CT, 06614
Community: Oronoque Village
The Waterways at Moriches 548 HIGHLAND CT, BROOKHAVEN, NY, 11955, Brookhaven, NY 11955
$525,000

2 beds

|

2 baths

|

1,771 sq ft

|

Condo

548 HIGHLAND CT, BROOKHAVEN, NY, 11955
The Village at Oxford Greens 1125 ST ANDREWS DR 47, OXFORD, CT, 06478, Oxford, CT 06478
$689,900

2 beds

|

3 baths

|

2,454 sq ft

|

Condo

1125 ST ANDREWS DR 47, OXFORD, CT, 06478
Fairview at Oxford Greens 1125 ST ANDREWS DR 47, OXFORD, CT, 06478, Oxford, CT 06478
$689,900

2 beds

|

3 baths

|

2,454 sq ft

|

Condo

1125 ST ANDREWS DR 47, 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.
Fairview at Oxford Greens 1093 ST ANDREWS DR 7, OXFORD, CT, 06478, Oxford, CT 06478
$689,900

2 beds

|

3 baths

|

2,454 sq ft

|

Condo

1093 ST ANDREWS DR 7, OXFORD, CT, 06478
The Village at Oxford Greens 1093 ST ANDREWS DR 7, OXFORD, CT, 06478, Oxford, CT 06478
$689,900

2 beds

|

3 baths

|

2,454 sq ft

|

Condo

1093 ST ANDREWS DR 7, OXFORD, CT, 06478
Fairview at Oxford Greens 1091 ST ANDREWS DR 6, OXFORD, CT, 06478, Oxford, CT 06478
$739,900

2 beds

|

3 baths

|

2,536 sq ft

|

Condo

1091 ST ANDREWS DR 6, OXFORD, CT, 06478
The Village at Oxford Greens 1091 ST ANDREWS DR 6, OXFORD, CT, 06478, Oxford, CT 06478
$739,900

2 beds

|

3 baths

|

2,536 sq ft

|

Condo

1091 ST ANDREWS DR 6, OXFORD, CT, 06478
Heritage Village 103 HERITAGE VLG D, SOUTHBURY, CT, 06488, Southbury, CT 06488
$279,900

2 beds

|

2 baths

|

1,044 sq ft

|

Condo

103 HERITAGE VLG D, SOUTHBURY, CT, 06488
Community: Heritage Village
Oronoque Village 546 N TRL B, STRATFORD, CT, 06614, Stratford, CT 06614
$679,000

2 beds

|

3 baths

|

1,434 sq ft

|

Condo

546 N TRL B, STRATFORD, CT, 06614
Community: Oronoque Village
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
Heritage Hills 228 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589
$689,900

3 beds

|

3 baths

|

1,700 sq ft

|

Condo

228 HERITAGE HLS A, SOMERS, NY, 10589
Community: Heritage Hills
Oronoque Village 383 SEQUOIA LN A, STRATFORD, CT, 06614, Stratford, CT 06614
$635,000

1 beds

|

2 baths

|

1,360 sq ft

|

Condo

383 SEQUOIA LN A, STRATFORD, CT, 06614
Community: Oronoque Village
The Manors at The Colony Preserve 41 GREENTREE CT, BROOKHAVEN, NY, 11967, Brookhaven, NY 11967
$515,000

2 beds

|

2 baths

|

1,557 sq ft

|

Condo

41 GREENTREE CT, BROOKHAVEN, NY, 11967
Cheshire Square 55 CHESHIRE SQ, LITTLE SILVER, NJ, 07739, Little Silver, NJ 07739
$699,000

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.
Regency at Wappinger 27 DUTCH CT, WAPPINGER, NY, 12590, Wappinger, NY 12590
$749,000

2 beds

|

4 baths

|

3,362 sq ft

|

Condo

27 DUTCH CT, WAPPINGER, NY, 12590
Heritage Village 191 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$599,900

3 beds

|

2 baths

|

1,716 sq ft

|

Condo

191 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
The Manors at The Colony Preserve 21 GREENTREE CT, BROOKHAVEN, NY, 11967, Brookhaven, NY 11967
$499,999

2 beds

|

2 baths

|

1,557 sq ft

|

Condo

21 GREENTREE CT, BROOKHAVEN, NY, 11967
Heritage Village 865 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$349,900

2 beds

|

2 baths

|

1,398 sq ft

|

Condo

865 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 1041 HERITAGE VLG A, SOUTHBURY, CT, 0648..., Southbury, CT 06488
$279,900

2 beds

|

2 baths

|

1,000 sq ft

|

Condo

1041 HERITAGE VLG A, SOUTHBURY, CT, 0648...
Community: Heritage Village
The Seasons at Seaford 28 SPRING DR, SEAFORD, NY, 11783, Seaford, NY 11783
$829,000

2 beds

|

2 baths

|

1,034 sq ft

|

Condo

28 SPRING DR, SEAFORD, NY, 11783
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
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
Four Seasons at Great Notch Spa and Club 12 QUARTZ WAY, WOODLAND PARK, NJ, 07424, Woodland Park, NJ 07424
$749,900

2 beds

|

2 baths

|

Townhouse

12 QUARTZ WAY, WOODLAND PARK, NJ, 07424
Jefferson Village 113 VILLAGE RD B, YORKTOWN, NY, 10598, Yorktown, NY 10598
$459,999

2 beds

|

2 baths

|

1,200 sq ft

|

Condo

113 VILLAGE RD B, YORKTOWN, NY, 10598
Community: Jefferson Village
Spring Lake Village 6 LAKEVIEW DR 6, SOUTHINGTON, CT, 06489, Southington, CT 06489
$315,000

3 beds

|

3 baths

|

1,471 sq ft

|

Condo

6 LAKEVIEW DR 6, SOUTHINGTON, CT, 06489
Community: Spring Lake 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.
Oronoque Village 488 COMMANCHE LN A, STRATFORD, CT, 06614, Stratford, CT 06614
$599,000

1 beds

|

3 baths

|

2,199 sq ft

|

Condo

488 COMMANCHE LN A, STRATFORD, CT, 06614
Community: Oronoque Village
Heritage Village 170 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$349,900

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

170 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Glassbury Court at Cold Spring 15 REVOLUTION RD, PHILIPSTOWN, NY, 10516, Philipstown, NY 10516
$556,904

2 beds

|

3 baths

|

1,785 sq ft

|

Condo

15 REVOLUTION RD, PHILIPSTOWN, NY, 10516
The Villages NJ 93 HALLS CROFT RD C, FREEHOLD, NJ, 07728, Freehold, NJ 07728
$279,000

2 beds

|

1 baths

|

1,082 sq ft

|

Ranch

93 HALLS CROFT RD C, FREEHOLD, NJ, 07728
Community: The Villages NJ
Leisure Glen 530 LEISURE DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$579,000

2 beds

|

2 baths

|

1,434 sq ft

|

Condo

530 LEISURE DR, BROOKHAVEN, NY, 11961
Community: Leisure Glen
Heritage Hills 40 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589
$615,000

2 beds

|

2 baths

|

1,139 sq ft

|

Condo

40 HERITAGE HLS A, SOMERS, NY, 10589
Community: Heritage Hills
Heritage Village 575 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$399,000

3 beds

|

2 baths

|

1,716 sq ft

|

Condo

575 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
The Coves at Melville 54 MORLEY CIR, HUNTINGTON, NY, 11747, Huntington, NY 11747
$549,000

2 beds

|

2 baths

|

1,162 sq ft

|

Condo

54 MORLEY CIR, HUNTINGTON, NY, 11747
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
Heritage Hills 243 HERITAGE HILLS DR B, SOMERS, NY, 105..., Somers, NY 10589
$699,999

3 beds

|

2 baths

|

1,689 sq ft

|

Condo

243 HERITAGE HILLS DR B, SOMERS, NY, 105...
Community: Heritage Hills
Oronoque Village 133 BANNOCK LN B, STRATFORD, CT, 06614, Stratford, CT 06614
$635,000

2 beds

|

3 baths

|

2,038 sq ft

|

Condo

133 BANNOCK LN B, STRATFORD, CT, 06614
Community: Oronoque 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.

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