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

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
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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
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
Want to learn more about 55+ communities in Westport? 55places can help!
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 930 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$449,900

2 beds

|

2 baths

|

1,398 sq ft

|

Condo

930 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Paris Square 2310 RIO VISTA LN 2310, NORTHVALE, NJ, 0..., Northvale, NJ 07647
$750,000

3 beds

|

2 baths

|

Condo

2310 RIO VISTA LN 2310, NORTHVALE, NJ, 0...
Community: Paris Square
The Manors at The Colony Preserve 15 CRICKET CT, BROOKHAVEN, NY, 11967, Brookhaven, NY 11967
$499,999

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
$849,900

3 beds

|

3 baths

|

2,777 sq ft

|

House

17 E SAGAMORE DR, FARMINGDALE, NJ, 07727
The Villas at Jumping Brook 3 DORAL WAY, NEPTUNE TOWNSHIP, NJ, 07753, Neptune Township, NJ 07753
$724,900

2 beds

|

2 baths

|

1,742 sq ft

|

Ranch

3 DORAL WAY, NEPTUNE TOWNSHIP, NJ, 07753
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
$139,999

2 beds

|

2 baths

|

1,032 sq ft

|

Condo

191 VILLAGE CIR, BROOKHAVEN, NY, 11949
Community: Greenwood Village
Leisure Village 375 WOODBRIDGE DR C, BROOKHAVEN, NY, 119..., Brookhaven, NY 11961
$379,000

2 beds

|

1 baths

|

1,171 sq ft

|

Condo

375 WOODBRIDGE DR C, BROOKHAVEN, NY, 119...
Community: Leisure 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
South Pond Village 78 SILO WAY 78, BLOOMFIELD, CT, 06002, Bloomfield, CT 06002
$289,900

3 beds

|

3 baths

|

1,639 sq ft

|

Condo

78 SILO WAY 78, BLOOMFIELD, CT, 06002
Community: South Pond Village
Cheesequake Village 11 ALABAMA CT 835, MATAWAN, NJ, 07747, Matawan, NJ 07747
$369,000

2 beds

|

2 baths

|

976 sq ft

|

Adult Community

11 ALABAMA CT 835, 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.
Cheesequake Village 11 ALABAMA CT, OLD BRIDGE, NJ, 07747, Old Bridge, NJ 07747
$369,000

2 beds

|

2 baths

|

976 sq ft

|

Condo

11 ALABAMA CT, OLD BRIDGE, NJ, 07747
Community: Cheesequake Village
Jefferson Village 119 VILLAGE RD H, YORKTOWN, NY, 10598, Yorktown, NY 10598
$417,000

2 beds

|

2 baths

|

1,100 sq ft

|

Condo

119 VILLAGE RD H, YORKTOWN, NY, 10598
Community: Jefferson Village
Rosemont Estates 329 VAN DUSEN DR, MARLBORO, NJ, 07746, Marlboro, NJ 07746
$959,900

3 beds

|

4 baths

|

2,885 sq ft

|

House

329 VAN DUSEN DR, MARLBORO, NJ, 07746
Community: Rosemont Estates
Heritage Village 4 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$249,000

1 beds

|

1 baths

|

928 sq ft

|

Condo

4 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Fairview at Oxford Greens 1077 AUGUSTA DR 1077, OXFORD, CT, 06478, Oxford, CT 06478
$619,900

3 beds

|

3 baths

|

2,256 sq ft

|

Condo

1077 AUGUSTA DR 1077, OXFORD, CT, 06478
The Village at Oxford Greens 1077 AUGUSTA DR 1077, OXFORD, CT, 06478, Oxford, CT 06478
$619,900

3 beds

|

3 baths

|

2,256 sq ft

|

Condo

1077 AUGUSTA DR 1077, OXFORD, CT, 06478
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
Glenwood Village 1661 OLD COUNTRY RD 62, RIVERHEAD, NY, 1..., Riverhead, NY 11901
$409,900

3 beds

|

2 baths

|

1,680 sq ft

|

Manufactured Home

1661 OLD COUNTRY RD 62, RIVERHEAD, NY, 1...
Community: Glenwood Village
Winthrop Court 1107 WICKHAM TER 374, CLIFTON, NJ, 07013, Clifton, NJ 07013
$559,000

2 beds

|

2 baths

|

Condo

1107 WICKHAM TER 374, CLIFTON, NJ, 07013
Community: Winthrop Court
The Villages NJ 110 HENLEY CT C, FREEHOLD, NJ, 07728, Freehold, NJ 07728
$295,900

2 beds

|

1 baths

|

952 sq ft

|

Ranch

110 HENLEY CT C, FREEHOLD, NJ, 07728
Community: The Villages NJ
Cheesequake Village 10 HAVEN DR A, OLD BRIDGE, NJ, 07747, Old Bridge, NJ 07747
$250,000

1 beds

|

1 baths

|

748 sq ft

|

Condo

10 HAVEN DR A, OLD BRIDGE, 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.
Country Pointe Preserve 118 JUNIPER LN 31, BROOKHAVEN, NY, 11980, Brookhaven, NY 11980
$865,000

2 beds

|

3 baths

|

1,998 sq ft

|

Condo

118 JUNIPER LN 31, BROOKHAVEN, NY, 11980
Heritage Village 53 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$269,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

53 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Breton Hills 401 BRETON WAY, GLEN COVE, NY, 11542, Glen Cove, NY 11542
$699,999

2 beds

|

2 baths

|

1,300 sq ft

|

Condo

401 BRETON WAY, GLEN COVE, NY, 11542
Community: Breton Hills
Enclave at Shrewsbury 188 CAMPBELL CT, SHREWSBURY BORO, NJ, 07..., Shrewsbury Boro, NJ 07702
$1,249,000

3 beds

|

3 baths

|

2,777 sq ft

|

House

188 CAMPBELL CT, SHREWSBURY BORO, NJ, 07...
Surrey Downs 53 FARNWORTH CLOSE, FREEHOLD, NJ, 07728, Freehold, NJ 07728
$379,900

2 beds

|

2 baths

|

Ranch

53 FARNWORTH CLOSE, FREEHOLD, NJ, 07728
Community: Surrey Downs
Jefferson Village 10 REGENTS PL D, YORKTOWN, NY, 10598, Yorktown, NY 10598
$235,000
|

1 baths

|

550 sq ft

|

Condo

10 REGENTS PL D, YORKTOWN, NY, 10598
Community: Jefferson Village
Leisure Village 279 BERWICK CT B, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$275,000

2 beds

|

1 baths

|

875 sq ft

|

Condo

279 BERWICK CT B, BROOKHAVEN, NY, 11961
Community: Leisure Village
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
Regency at Prospect 11 POPLAR DR 11, PROSPECT, CT, 06712, Prospect, CT 06712
$549,000

3 beds

|

3 baths

|

2,058 sq ft

|

Condo

11 POPLAR DR 11, PROSPECT, CT, 06712
Community: Regency at Prospect
Regency at Woodbridge 27 HERITAGE LN, WOODBRIDGE, CT, 06525, Woodbridge, CT 06525
$599,900

3 beds

|

3 baths

|

Condo

27 HERITAGE LN, WOODBRIDGE, CT, 06525
Apple Ridge 37 NIAGARA DR 37, MAHWAH, NJ, 07430, Mahwah, NJ 07430
$760,000

2 beds

|

3 baths

|

Townhouse

37 NIAGARA DR 37, MAHWAH, NJ, 07430
Community: Apple Ridge
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 101 HERITAGE VLG D, SOUTHBURY, CT, 06488, Southbury, CT 06488
$215,000

2 beds

|

2 baths

|

1,076 sq ft

|

Condo

101 HERITAGE VLG D, SOUTHBURY, CT, 06488
Community: Heritage Village
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
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
The Summit at Bethel 20 GREAT HILL DR 20, BETHEL, CT, 06801, Bethel, CT 06801
$619,000

3 beds

|

3 baths

|

2,159 sq ft

|

Condo

20 GREAT HILL DR 20, BETHEL, CT, 06801
Parker Village Estates 29 VILLAGE DR, EATONTOWN, NJ, 07724, Eatontown, NJ 07724
$699,995

2 beds

|

3 baths

|

2,308 sq ft

|

Townhouse

29 VILLAGE DR, EATONTOWN, NJ, 07724
Jefferson Village 59 KIRBY CLOSE D, YORKTOWN, NY, 10598, Yorktown, NY 10598
$375,000

2 beds

|

2 baths

|

910 sq ft

|

Condo

59 KIRBY CLOSE D, YORKTOWN, NY, 10598
Community: Jefferson Village
Heritage Village 401 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$339,900

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

401 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Hills 415 HERITAGE HILLS DR D, SOMERS, NY, 105..., Somers, NY 10589
$875,000

2 beds

|

2 baths

|

1,663 sq ft

|

Condo

415 HERITAGE HILLS DR D, SOMERS, NY, 105...
Community: Heritage Hills
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
Sunken Pond Estates 3006 AMEN COR, RIVERHEAD, NY, 11901, Riverhead, NY 11901
$475,000

2 beds

|

2 baths

|

1,587 sq ft

|

Condo

3006 AMEN COR, RIVERHEAD, NY, 11901
Community: Sunken Pond Estates
Heritage Village 1016 HERITAGE VLG B, SOUTHBURY, CT, 0648..., Southbury, CT 06488
$225,000

1 beds

|

1 baths

|

928 sq ft

|

Condo

1016 HERITAGE VLG B, SOUTHBURY, CT, 0648...
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.

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