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Westport, CT 55+ active adult communities & homes for sale - Page 6

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
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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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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
$639,000

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
$769,900

2 beds

|

2 baths

|

1,420 sq ft

|

Condo

4105 FRED ILL JR CT, ORANGETOWN, NY, 109...
The Village at Oxford Greens 1126 ST ANDREWS DR 96, OXFORD, CT, 06478, Oxford, CT 06478
$761,150

2 beds

|

3 baths

|

1,955 sq ft

|

Condo

1126 ST ANDREWS DR 96, OXFORD, CT, 06478
Fairview at Oxford Greens 1126 ST ANDREWS DR 96, OXFORD, CT, 06478, Oxford, CT 06478
$761,150

2 beds

|

3 baths

|

1,955 sq ft

|

Condo

1126 ST ANDREWS DR 96, OXFORD, CT, 06478
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
Leisure Village 323 A WOODBRIDGE DR, BROOKHAVEN, NY, 119..., Brookhaven, NY 11961
$425,000

2 beds

|

2 baths

|

1,278 sq ft

|

Condo

323 A WOODBRIDGE DR, BROOKHAVEN, NY, 119...
Community: Leisure Village
Heritage Village 953 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$264,000

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
$369,900

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
$539,000

2 beds

|

2 baths

|

1,499 sq ft

|

Condo

734 REGENCY DR, FISHKILL, NY, 12524
Community: Regency at Fishkill
Country Pointe Preserve 3 JUNIPER LN 94, BROOKHAVEN, NY, 11980, Brookhaven, NY 11980
$965,000

2 beds

|

3 baths

|

2,389 sq ft

|

Condo

3 JUNIPER LN 94, BROOKHAVEN, NY, 11980
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.
Cheesequake Village 5 MISSOURI CT, OLD BRIDGE, NJ, 07747, Old Bridge, NJ 07747
$315,000

2 beds

|

1 baths

|

Condo

5 MISSOURI CT, OLD BRIDGE, NJ, 07747
Community: Cheesequake Village
Stoneleigh Woods at Riverhead 156 STONELEIGH DR, RIVERHEAD, NY, 11901, Riverhead, NY 11901
$659,000

2 beds

|

3 baths

|

1,942 sq ft

|

Condo

156 STONELEIGH DR, RIVERHEAD, NY, 11901
Cheesequake Village 52 GALEWOOD DR 52, OLD BRIDGE, NJ, 07747, Old Bridge, NJ 07747
$359,000

2 beds

|

2 baths

|

Condo

52 GALEWOOD DR 52, OLD BRIDGE, NJ, 07747
Community: Cheesequake Village
Overlook 2052 SUMMIT LOOP 62, CARMEL, NY, 10512, Carmel, NY 10512
$954,000

2 beds

|

2 baths

|

2,102 sq ft

|

Condo

2052 SUMMIT LOOP 62, CARMEL, NY, 10512
Community: Overlook
Oronoque Village 564 PEQUOT LN A, STRATFORD, CT, 06614, Stratford, CT 06614
$599,900

2 beds

|

2 baths

|

1,438 sq ft

|

Condo

564 PEQUOT LN A, STRATFORD, CT, 06614
Community: Oronoque Village
Oronoque Village 638A ONONDAGA LN, STRATFORD, CT, 06614, Stratford, CT 06614
$525,000

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
Encore Atlantic Shores 11 OVATION PL, BROOKHAVEN, NY, 11941, Brookhaven, NY 11941
$925,000

2 beds

|

3 baths

|

3,037 sq ft

|

House

11 OVATION PL, BROOKHAVEN, NY, 11941
Heritage Village 44 HERITAGE VLG F, SOUTHBURY, CT, 06488, Southbury, CT 06488
$205,000

2 beds

|

2 baths

|

1,308 sq ft

|

Condo

44 HERITAGE VLG F, SOUTHBURY, CT, 06488
Community: Heritage Village
Rivington 80 WINDING RIDGE WAY 80, DANBURY, CT, 06..., Danbury, CT 06810
$775,000

3 beds

|

3 baths

|

2,204 sq ft

|

Condo

80 WINDING RIDGE WAY 80, DANBURY, CT, 06...
Community: Rivington
The Greens at Half Hollow 381 ALTESSA BLVD, HUNTINGTON, NY, 11747, Huntington, NY 11747
$1,449,999

2 beds

|

2 baths

|

2,575 sq ft

|

Condo

381 ALTESSA BLVD, 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.
Heritage Village 110 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$399,999

3 beds

|

2 baths

|

1,716 sq ft

|

Condo

110 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Shadow Lake Village 42 MEDFORD CT, RED BANK, NJ, 07701, Red Bank, NJ 07701
$375,000

2 beds

|

2 baths

|

1,210 sq ft

|

Adult Community

42 MEDFORD CT, RED BANK, NJ, 07701
Community: Shadow Lake Village
Surrey Downs 23 DATCHET CLOSE 1000, FREEHOLD, NJ, 077..., Freehold, NJ 07728
$299,999

2 beds

|

1 baths

|

896 sq ft

|

Ranch

23 DATCHET CLOSE 1000, FREEHOLD, NJ, 077...
Community: Surrey Downs
Breton Hills 704 BRETON WAY 704, GLEN COVE, NY, 11542, Glen Cove, NY 11542
$669,000

2 beds

|

2 baths

|

1,449 sq ft

|

Condo

704 BRETON WAY 704, GLEN COVE, NY, 11542
Community: Breton Hills
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
Heritage Hills 342 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589
$650,000

2 beds

|

2 baths

|

1,484 sq ft

|

Condo

342 HERITAGE HLS B, SOMERS, NY, 10589
Community: Heritage Hills
Foxwood Village 1407 MIDDLE RD 265, RIVERHEAD, NY, 11933, Riverhead, NY 11933
$469,000

3 beds

|

2 baths

|

1,792 sq ft

|

Manufactured Home

1407 MIDDLE RD 265, RIVERHEAD, NY, 11933
Community: Foxwood Village
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
The Coves at Melville 80 MORLEY CIR, HUNTINGTON, NY, 11747, Huntington, NY 11747
$579,999

2 beds

|

2 baths

|

1,169 sq ft

|

Condo

80 MORLEY CIR, HUNTINGTON, NY, 11747
Leisure Glen 82 GLEN DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$469,000

2 beds

|

2 baths

|

1,312 sq ft

|

Condo

82 GLEN DR, BROOKHAVEN, NY, 11961
Community: Leisure Glen
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
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 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
$405,000

2 beds

|

2 baths

|

1,144 sq ft

|

House

24 CALLE DE ELVIRA B, FREEHOLD, NJ, 0772...
Community: The Villages NJ
The Waterways at Moriches 485 WOODSCREEK CT, BROOKHAVEN, NY, 11955, Brookhaven, NY 11955
$778,000

2 beds

|

3 baths

|

1,854 sq ft

|

Condo

485 WOODSCREEK CT, BROOKHAVEN, NY, 11955
Paris Square 2303 RIO VISTA LN, NORTHVALE, NJ, 07647, Northvale, NJ 07647
$575,000

2 beds

|

2 baths

|

Condo

2303 RIO VISTA LN, NORTHVALE, NJ, 07647
Community: Paris Square
Beckley Farms 13 CONCORD DR 13, BERLIN, CT, 06037, Berlin, CT 06037
$599,900

3 beds

|

3 baths

|

2,030 sq ft

|

Condo

13 CONCORD DR 13, BERLIN, CT, 06037
Community: Beckley Farms
Rosemont Estates 202 SCARBOROUGH WAY, MARLBORO, NJ, 07746, Marlboro, NJ 07746
$925,000

3 beds

|

4 baths

|

2,885 sq ft

|

Adult Community

202 SCARBOROUGH WAY, MARLBORO, NJ, 07746
Community: Rosemont Estates
Meadow Brook Estates 521 HEATHERWOOD CT 521, OXFORD, CT, 0647..., Oxford, CT 06478
$599,900

2 beds

|

3 baths

|

1,866 sq ft

|

Condo

521 HEATHERWOOD CT 521, OXFORD, CT, 0647...
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
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
The Village at Oxford Greens 114 COUNTRY CLUB DR 114, OXFORD, CT, 064..., Oxford, CT 06478
$550,000

2 beds

|

2 baths

|

1,590 sq ft

114 COUNTRY CLUB DR 114, OXFORD, CT, 064...
Leisure Knoll 204 BELFAST LN, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$439,000

2 beds

|

2 baths

|

970 sq ft

|

House

204 BELFAST LN, BROOKHAVEN, NY, 11961
Community: Leisure Knoll
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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