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Westport, CT 55+ active adult communities & homes for sale - Page 5

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
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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The Villages NJ 110 HENLEY CT C, FREEHOLD, NJ, 07728, Freehold, NJ 07728
$320,000

2 beds

|

1 baths

|

952 sq ft

|

Ranch

110 HENLEY CT C, FREEHOLD, NJ, 07728
Community: The Villages NJ
Shadow Lake Village 50 HANCOCK CT, RED BANK, NJ, 07701, Red Bank, NJ 07701
$399,000

2 beds

|

2 baths

|

1,235 sq ft

|

Adult Community

50 HANCOCK CT, RED BANK, NJ, 07701
Community: Shadow Lake Village
Heritage Village 331 HERITAGE VLG D, SOUTHBURY, CT, 06488, Southbury, CT 06488
$189,000

2 beds

|

2 baths

|

1,044 sq ft

|

Condo

331 HERITAGE VLG D, SOUTHBURY, CT, 06488
Community: Heritage Village
Shadow Lake Village 8 MANCHESTER CT, RED BANK, NJ, 07701, Red Bank, NJ 07701
$390,000

2 beds

|

1 baths

|

999 sq ft

|

Adult Community

8 MANCHESTER CT, RED BANK, NJ, 07701
Community: Shadow Lake Village
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
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
Winthrop Court 9210 RAVENSCROFT RD 627, CLIFTON, NJ, 07..., Clifton, NJ 07013
$585,000

2 beds

|

2 baths

|

Condo

9210 RAVENSCROFT RD 627, CLIFTON, NJ, 07...
Community: Winthrop Court
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
Oronoque Village 99 SEMINOLE LN A, STRATFORD, CT, 06614, Stratford, CT 06614
$475,000

1 beds

|

3 baths

|

1,426 sq ft

|

Condo

99 SEMINOLE LN A, STRATFORD, CT, 06614
Community: Oronoque Village
The Waterways at Moriches 290 W MIDLAND POND CT 290, BROOKHAVEN, N..., Brookhaven, NY 11955
$629,000

2 beds

|

2 baths

|

1,440 sq ft

|

Condo

290 W MIDLAND POND CT 290, BROOKHAVEN, N...
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
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 196 APACHE LN A, STRATFORD, CT, 06614, Stratford, CT 06614
$365,000

1 beds

|

2 baths

|

1,175 sq ft

|

Condo

196 APACHE LN A, STRATFORD, CT, 06614
Community: Oronoque 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
Equestra at Colts Neck Crossing 21 W BACCIO LN, FARMINGDALE, NJ, 07727, Farmingdale, NJ 07727
$679,000

2 beds

|

2 baths

|

1,632 sq ft

|

House

21 W BACCIO LN, FARMINGDALE, NJ, 07727
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...
Nobility Crest at Ocean 7 CENTRE ST 2101, OCEAN TWP, NJ, 07712, Ocean Twp, NJ 07712
$449,000

1 beds

|

1 baths

|

1,058 sq ft

|

Adult Community

7 CENTRE ST 2101, OCEAN TWP, NJ, 07712
Shadow Lake Village 122 MANCHESTER CT, RED BANK, NJ, 07701, Red Bank, NJ 07701
$465,000

2 beds

|

2 baths

|

952 sq ft

|

Ranch

122 MANCHESTER CT, RED BANK, NJ, 07701
Community: Shadow Lake Village
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
Sunrise Village 93 REVERE DR, ISLIP, NY, 11782, Islip, NY 11782
$499,000

2 beds

|

2 baths

|

1,230 sq ft

|

Condo

93 REVERE DR, ISLIP, NY, 11782
Community: Sunrise Village
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
$240,000
|

1 baths

|

550 sq ft

|

Condo

10 REGENTS PL D, YORKTOWN, NY, 10598
Community: Jefferson Village
Meadowbrooke Pointe East Meadow 137 EMANUEL WAY, HEMPSTEAD, NY, 11554, Hempstead, NY 11554
$839,000

2 beds

|

3 baths

|

1,390 sq ft

|

Condo

137 EMANUEL WAY, HEMPSTEAD, NY, 11554
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 Fishkill 145 REGENCY DR, FISHKILL, NY, 12524, Fishkill, NY 12524
$549,999

2 beds

|

2 baths

|

1,803 sq ft

|

Condo

145 REGENCY DR, FISHKILL, NY, 12524
Community: Regency at Fishkill
Oronoque Village 47 HURON LN A, STRATFORD, CT, 06614, Stratford, CT 06614
$409,000

2 beds

|

2 baths

|

1,360 sq ft

|

Condo

47 HURON LN A, STRATFORD, CT, 06614
Community: Oronoque Village
Leisure Village 279 BERWICK CT B, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$289,999

2 beds

|

1 baths

|

875 sq ft

|

Condo

279 BERWICK CT B, BROOKHAVEN, NY, 11961
Community: Leisure Village
Four Seasons at Colts Farm 2 PASTURE DR, FARMINGDALE, NJ, 07727, Farmingdale, NJ 07727
$999,900

3 beds

|

3 baths

|

2,793 sq ft

|

House

2 PASTURE DR, FARMINGDALE, NJ, 07727
Regency at Prospect 104 CHERRY CIR 104, PROSPECT, CT, 06712, Prospect, CT 06712
$328,417

3 beds

|

2 baths

|

1,500 sq ft

|

Condo

104 CHERRY CIR 104, PROSPECT, CT, 06712
Community: Regency at Prospect
Rivington 131 WINDING RIDGE WAY 131, DANBURY, CT, ..., Danbury, CT 06810
$770,000

3 beds

|

3 baths

|

1,592 sq ft

|

Condo

131 WINDING RIDGE WAY 131, DANBURY, CT, ...
Community: Rivington
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
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
Castle Heights of Cheshire 151 VICTORIA DR, CHESHIRE, CT, 06410, Cheshire, CT 06410
$769,900

2 beds

|

4 baths

|

2,843 sq ft

|

Condo

151 VICTORIA DR, CHESHIRE, CT, 06410
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
The Waterways at Moriches 188 RIVER DR, BROOKHAVEN, NY, 11955, Brookhaven, NY 11955
$775,000

2 beds

|

2 baths

|

2,100 sq ft

|

Condo

188 RIVER DR, BROOKHAVEN, NY, 11955
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.
Glenwood Village 1661 OLD COUNTRY RD 251, RIVERHEAD, NY, ..., Riverhead, NY 11901
$130,000

2 beds

|

1 baths

|

720 sq ft

|

Manufactured Home

1661 OLD COUNTRY RD 251, RIVERHEAD, NY, ...
Community: Glenwood Village
Heritage Village 101 HERITAGE VLG D, SOUTHBURY, CT, 06488, Southbury, CT 06488
$229,000

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
$270,000

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
$270,000

2 beds

|

1 baths

|

949 sq ft

|

Condo

12 LOUISIANA DR D, OLD BRIDGE, NJ, 07747
Community: Cheesequake Village
Heritage Village 29 HERITAGE VLG D, SOUTHBURY, CT, 06488, Southbury, CT 06488
$310,000

2 beds

|

2 baths

|

1,076 sq ft

|

Condo

29 HERITAGE VLG D, SOUTHBURY, CT, 06488
Community: Heritage Village
Equestra at Colts Neck Crossing 29 W DA VINCI WAY, FARMINGDALE, NJ, 0772..., Farmingdale, NJ 07727
$825,000

3 beds

|

3 baths

|

2,172 sq ft

|

House

29 W DA VINCI WAY, FARMINGDALE, NJ, 0772...
Four Seasons at Cedar Grove 1209 HOLLY LN 141, CEDAR GROVE, NJ, 0700..., Cedar Grove, NJ 07009
$750,000

2 beds

|

2 baths

|

Condo

1209 HOLLY LN 141, CEDAR GROVE, NJ, 0700...
Eagles Walk at East Quogue 1504 AERIE WAY 1504, SOUTHAMPTON, NY, 11..., Southampton, NY 11942
$545,000

2 beds

|

2 baths

|

1,341 sq ft

|

House

1504 AERIE WAY 1504, SOUTHAMPTON, NY, 11...
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
The Summit at Bethel 20 GREAT HILL DR 20, BETHEL, CT, 06801, Bethel, CT 06801
$629,000

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
$719,500

2 beds

|

3 baths

|

2,308 sq ft

|

Townhouse

29 VILLAGE DR, EATONTOWN, NJ, 07724
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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