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Westport, CT 55+ active adult communities & homes for sale - Page 8

369 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
Oronoque Village
$200ks - $400ks
Oronoque Village, Stratford, CT
Resale Only | 55+ age-restricted | Built 1971 - 1977 | 929 homes
3 rating (2 reviews) Heritage Hills
$400ks - $800ks
Heritage Hills, Somers, NY
Resale Only | Age-targeted | Built 1974 - 2006 | 2,600 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
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4 rating (1 reviews) Jefferson Village
$100ks - $500ks
Jefferson Village, Yorktown Heights, NY
Resale Only | 55+ age-restricted | Built 1967 - 1982 | 1,000 homes
Overlook
$600ks - $900ks
Overlook, Carmel, NY
New Construction | 55+ age-restricted | 300 homes
The Waterways at Moriches
$300ks - $600ks
The Waterways at Moriches, Moriches, NY
Resale Only | 55+ age-restricted | Built 1985 - 1999 | 343 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
Country Pointe Plainview
$700ks - $1Ms
Country Pointe Plainview, Plainview, NY
New Construction | 55+ age-restricted | Built 2017 - present | 660 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 (2 reviews) Shadow Lake Village
$200ks - $500ks
Shadow Lake Village, Red Bank, NJ
Resale Only | 55+ age-restricted | Built 1972 - 1980 | 952 homes
3.7 rating (3 reviews) Greenwood Village
$100ks
Greenwood Village, Manorville, NY
Resale Only | 55+ age-restricted | Built 1980 - 2000 | 512 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
4.2 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
4 rating (8 reviews) Glenwood Village
$100ks - $200ks
Glenwood Village, Riverhead, NY
New and Resale | 55+ age-restricted | Built 1959 - present | 588 homes
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Questions? Call us: (475) 471-1908
The Manors at The Colony ...
$300ks - $400ks
The Manors at The Colony ..., Shirley, NY
New Construction | 55+ age-restricted | Built 2013 - present | 150 homes
Dutchgate
$300ks - $500ks
Dutchgate, Valley Stream, NY
Resale Only | 55+ age-restricted | Built 2009 - 2015 | 348 homes
Fairview at Oxford Greens
$400ks - $600ks
Fairview at Oxford Greens, Oxford, CT
New and Resale | 55+ age-restricted | Built 2019 - present | 125 homes
Rolling Meadows at Waysid...
$500ks - $600ks
Rolling Meadows at Waysid..., Ocean Township, NJ
Resale Only | 55+ age-restricted | Built 2002 - 2007 | 328 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
Regency at Fishkill
$300ks - $400ks
Regency at Fishkill, Fishkill, NY
Resale Only | 55+ age-restricted | Built 2008 - 2020 | 164 homes
Stoneleigh Woods at River...
$500ks
Stoneleigh Woods at River..., Riverhead, NY
Resale Only | 55+ age-restricted | Built 2007 - 2016 | 176 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
Liberty at Newtown
$300ks - $400ks
Liberty at Newtown, Newtown, CT
Resale Only | 55+ age-restricted | Built 2003 - 2007 | 96 homes
Leisure Glen
$300ks - $400ks
Leisure Glen, Ridge, NY
Resale Only | 55+ age-restricted | Built 1985 - 2010 | 646 homes
5 rating (1 reviews) Newtown Woods
$300ks - $500ks
Newtown Woods, Newtown, CT
New and Resale | 55+ age-restricted | Built 2011 - present | 178 homes
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Questions? Call us: (475) 471-1908
Woodridge Strathmore Terr...
$200ks - $300ks
Woodridge Strathmore Terr..., Mount Sinai, NY
Resale Only | 55+ age-restricted | Built 1974 - 1985 | 226 homes
Village Estates
$300ks - $400ks
Village Estates, Amityville, NY
Resale Only | 55+ age-restricted | Built 2006 - 2008 | 138 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
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.
Vineyards at Moriches
$500ks - $600ks
Vineyards at Moriches, Center Moriches, NY
Resale Only | 55+ age-restricted | Built 2008 - 2014 | 92 homes
5 rating (1 reviews) The Villas at Jumping Bro...
$300ks - $500ks
The Villas at Jumping Bro..., Neptune Township, NJ
Resale Only | 55+ age-restricted | Built 2001 - 2003 | 168 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
HarborView
$800ks - $1Ms
HarborView, Port Washington, NY
Resale Only | 55+ age-restricted | Built 2002 - 2004 | 270 homes
5 rating (1 reviews) Sunken Pond Estates
$400ks
Sunken Pond Estates, Riverhead, NY
Resale Only | 55+ age-restricted | Built 2003 - 2005 | 194 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
3.5 rating (2 reviews) Foxwood Village
$200ks - $400ks
Foxwood Village, Calverton, NY
Resale Only | 55+ age-restricted | Built 1986 - 2007 | 294 homes
Winthrop Court
$400ks - $600ks
Winthrop Court, Clifton, NJ
Resale Only | 55+ age-restricted | Built 2000 - 2010 | 270 homes
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
5 rating (1 reviews) Westhampton Pines
$900ks - $1Ms
Westhampton Pines, Westhampton, NY
Resale Only | 55+ age-restricted | Built 2005 - 2013 | 189 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
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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Surrey Downs 20 JAFFREYTON CLOSE, FREEHOLD, NJ, 07728, Freehold, NJ 07728
$434,900

2 beds

|

2 baths

|

1,146 sq ft

|

Ranch

20 JAFFREYTON CLOSE, FREEHOLD, NJ, 07728
Community: Surrey Downs
The Villages at Mount Sinai Park 54 LOUDEN LOOP, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766
$899,000

3 beds

|

3 baths

|

2,816 sq ft

|

House

54 LOUDEN LOOP, BROOKHAVEN, NY, 11766
The Villages NJ 93 HALLS CROFT RD C, FREEHOLD, NJ, 07728, Freehold, NJ 07728
$259,900

2 beds

|

1 baths

|

1,082 sq ft

|

Ranch

93 HALLS CROFT RD C, FREEHOLD, NJ, 07728
Community: The Villages NJ
Regency at Holmdel 17 SPALDING DR 331, HOLMDEL, NJ, 07733, Holmdel, NJ 07733
$1,333,000

3 beds

|

4 baths

|

3,490 sq ft

|

Townhouse

17 SPALDING DR 331, HOLMDEL, NJ, 07733
Community: Regency at Holmdel
The Village at Oxford Greens 505 TRADITIONS CT 505, OXFORD, CT, 06478, Oxford, CT 06478
$755,000

3 beds

|

3 baths

|

2,652 sq ft

|

Condo

505 TRADITIONS CT 505, OXFORD, CT, 06478
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
Stoneleigh Woods at Riverhead 47 STONELEIGH DR, RIVERHEAD, NY, 11901, Riverhead, NY 11901
$659,000

2 beds

|

3 baths

|

1,942 sq ft

|

Condo

47 STONELEIGH DR, RIVERHEAD, NY, 11901
The Greens at Half Hollow 398 ALTESSA BLVD, HUNTINGTON, NY, 11747, Huntington, NY 11747
$1,599,999

2 beds

|

2 baths

|

2,525 sq ft

|

Condo

398 ALTESSA BLVD, HUNTINGTON, NY, 11747
Heritage Village 916 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$379,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

916 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Oronoque Village 315 NAVAJO LN A, STRATFORD, CT, 06614, Stratford, CT 06614
$499,000

2 beds

|

3 baths

|

1,434 sq ft

|

Condo

315 NAVAJO LN A, STRATFORD, CT, 06614
Community: Oronoque Village
Heritage Village 14 HERITAGE CIR B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$269,000

2 beds

|

2 baths

|

1,000 sq ft

|

Condo

14 HERITAGE CIR 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 17 GREENTREE CT, BROOKHAVEN, NY, 11967, Brookhaven, NY 11967
$559,000

2 beds

|

2 baths

|

1,557 sq ft

|

Condo

17 GREENTREE CT, BROOKHAVEN, NY, 11967
Cheesequake Village 12 LOUISIANA DR D, OLD BRIDGE TWP., NJ, ..., Old Bridge Twp., NJ 07747
$265,000

2 beds

|

1 baths

|

949 sq ft

12 LOUISIANA DR D, OLD BRIDGE TWP., NJ, ...
Community: Cheesequake Village
Cheesequake Village 12 UTAH DR A, OLD BRIDGE, NJ, 07747, Old Bridge, NJ 07747
$300,000

2 beds

|

1 baths

|

Condo

12 UTAH DR A, OLD BRIDGE, NJ, 07747
Community: Cheesequake Village
Apple Ridge 134 FISHER RD, MAHWAH, NJ, 07430, Mahwah, NJ 07430
$950,000

4 beds

|

4 baths

|

Townhouse

134 FISHER RD, MAHWAH, NJ, 07430
Community: Apple Ridge
Heritage Village 551 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$239,000

1 beds

|

1 baths

|

928 sq ft

|

Condo

551 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 149 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$219,000

1 beds

|

1 baths

|

928 sq ft

|

Condo

149 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
Heritage Village 59 HERITAGE VLG F, SOUTHBURY, CT, 06488, Southbury, CT 06488
$219,900

2 beds

|

2 baths

|

1,308 sq ft

|

Condo

59 HERITAGE VLG F, SOUTHBURY, CT, 06488
Community: Heritage Village
Oronoque Village 619 ERIE LN B, STRATFORD, CT, 06614, Stratford, CT 06614
$635,000

1 beds

|

3 baths

|

1,583 sq ft

|

Condo

619 ERIE LN B, STRATFORD, CT, 06614
Community: Oronoque Village
The Hollows at Blue Hill 4105 FRED ILL JR CT, ORANGETOWN, NY, 109..., Orangetown, NY 10965
$739,900

2 beds

|

2 baths

|

1,420 sq ft

|

Condo

4105 FRED ILL JR CT, ORANGETOWN, NY, 109...
Fairview at Oxford Greens 1126 ST ANDREWS DR 96, OXFORD, CT, 06478, Oxford, CT 06478
$801,070

2 beds

|

3 baths

|

1,955 sq ft

|

Condo

1126 ST ANDREWS DR 96, 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.
The Village at Oxford Greens 1126 ST ANDREWS DR 96, OXFORD, CT, 06478, Oxford, CT 06478
$801,070

2 beds

|

3 baths

|

1,955 sq ft

|

Condo

1126 ST ANDREWS DR 96, OXFORD, CT, 06478
Heritage Village 953 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$250,000

1 beds

|

1 baths

|

928 sq ft

|

Condo

953 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
The Villages NJ 71 PATRICK HENRY SQ A, FREEHOLD, NJ, 077..., Freehold, NJ 07728
$349,900

2 beds

|

1 baths

|

1,144 sq ft

|

Ranch

71 PATRICK HENRY SQ A, FREEHOLD, NJ, 077...
Community: The Villages NJ
Regency at Fishkill 734 REGENCY DR, FISHKILL, NY, 12524, Fishkill, NY 12524
$538,500

2 beds

|

2 baths

|

1,499 sq ft

|

Condo

734 REGENCY DR, FISHKILL, NY, 12524
Community: Regency at Fishkill
Stoneleigh Woods at Riverhead 156 STONELEIGH DR, RIVERHEAD, NY, 11901, Riverhead, NY 11901
$649,000

2 beds

|

3 baths

|

1,942 sq ft

|

Condo

156 STONELEIGH DR, RIVERHEAD, NY, 11901
Overlook 2052 SUMMIT LOOP 62, CARMEL, NY, 10512, Carmel, NY 10512
$869,000

2 beds

|

2 baths

|

2,102 sq ft

|

Condo

2052 SUMMIT LOOP 62, CARMEL, NY, 10512
Community: Overlook
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
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
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
Heritage Village 12 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$239,900

1 beds

|

1 baths

|

928 sq ft

|

Condo

12 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
The Coves at Melville 80 MORLEY CIR, HUNTINGTON, NY, 11747, Huntington, NY 11747
$569,999

2 beds

|

2 baths

|

1,169 sq ft

|

Condo

80 MORLEY CIR, HUNTINGTON, 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.
The Greens at Half Hollow 420 FLORENCIA PL, HUNTINGTON, NY, 11747, Huntington, NY 11747
$1,149,000

3 beds

|

3 baths

|

2,500 sq ft

|

Condo

420 FLORENCIA PL, 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
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
$329,000

2 beds

|

2 baths

|

1,344 sq ft

|

Manufactured Home

1661 OLD COUNTRY RD 417, RIVERHEAD, NY, ...
Community: Glenwood Village
Heritage Village 930 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$439,900

2 beds

|

2 baths

|

1,398 sq ft

|

Condo

930 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
The Manors at The Colony Preserve 15 CRICKET CT, BROOKHAVEN, NY, 11967, Brookhaven, NY 11967
$489,900

2 beds

|

2 baths

|

1,322 sq ft

|

Condo

15 CRICKET CT, BROOKHAVEN, NY, 11967
Equestra at Colts Neck Crossing 17 E SAGAMORE DR, FARMINGDALE, NJ, 07727, Farmingdale, NJ 07727
$749,999

3 beds

|

3 baths

|

2,777 sq ft

|

House

17 E SAGAMORE DR, FARMINGDALE, NJ, 07727
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
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
$325,000

2 beds

|

1 baths

|

949 sq ft

|

Adult Community

10 MAINE CT 734, MATAWAN, NJ, 07747
Community: Cheesequake 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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