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

393 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
4 rating (1 reviews) Jefferson Village
$100ks - $500ks
Jefferson Village, Yorktown Heights, NY
Resale Only | 55+ age-restricted | Built 1967 - 1982 | 1,000 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
5 rating (2 reviews) 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
3 rating (2 reviews) Heritage Hills
$400ks - $800ks
Heritage Hills, Somers, NY
Resale Only | Age-targeted | Built 1974 - 2006 | 2,600 homes
3.7 rating (3 reviews) Greenwood Village
$100ks
Greenwood Village, Manorville, NY
Resale Only | 55+ age-restricted | Built 1980 - 2000 | 512 homes
4 rating (8 reviews) Glenwood Village
$100ks - $200ks
Glenwood Village, Riverhead, NY
New and Resale | 55+ age-restricted | Built 1959 - present | 588 homes
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
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
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 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
Leisure Village
$100ks - $300ks
Leisure Village, Ridge, NY
Resale Only | 55+ age-restricted | Built 1969 - 1986 | 1,500 homes
Country Pointe Plainview
$700ks - $1Ms
Country Pointe Plainview, Plainview, NY
New Construction | 55+ age-restricted | Built 2017 - present | 660 homes
Leisure Glen
$300ks - $400ks
Leisure Glen, Ridge, NY
Resale Only | 55+ age-restricted | Built 1985 - 2010 | 646 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
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
Rivington
$300ks - $900ks
Rivington, Danbury, CT
New and Resale | Age-targeted | Built 2006 - present | 1,050 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
HarborView
$600ks - $1Ms
HarborView, Port Washington, NY
Resale Only | 55+ age-restricted | Built 2002 - 2004 | 270 homes
Leisure Knoll
$200ks - $400ks
Leisure Knoll, Ridge, NY
Resale Only | 55+ age-restricted | Built 1972 - 1982 | 701 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.
Rolling Meadows at Waysid...
$500ks - $600ks
Rolling Meadows at Waysid..., Ocean Township, NJ
Resale Only | 55+ age-restricted | Built 2002 - 2007 | 328 homes
Overlook
$600ks - $900ks
Overlook, Carmel, NY
New Construction | 55+ age-restricted | 300 homes
Fairview at Oxford Greens
$400ks - $600ks
Fairview at Oxford Greens, Oxford, CT
New and Resale | 55+ age-restricted | Built 2019 - present | 125 homes
Apple Ridge
$500ks - $1Ms
Apple Ridge, Mahwah, NJ
Resale Only | Age-targeted | Built 1977 - 1991 | 276 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
Regency at Fishkill
$300ks - $400ks
Regency at Fishkill, Fishkill, NY
Resale Only | 55+ age-restricted | Built 2008 - 2020 | 164 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
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Questions? Call us: (475) 471-1908
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
Woodridge Strathmore Terr...
$200ks - $300ks
Woodridge Strathmore Terr..., Mount Sinai, NY
Resale Only | 55+ age-restricted | Built 1974 - 1985 | 226 homes
Snug Harbor
$600ks - $700ks
Snug Harbor, Amityville, NY
Resale Only | 55+ age-restricted | Built 1970 - 1974 | 176 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.
Dutchgate
$300ks - $500ks
Dutchgate, Valley Stream, NY
Resale Only | 55+ age-restricted | Built 2009 - 2015 | 348 homes
Stoneleigh Woods at River...
$500ks
Stoneleigh Woods at River..., Riverhead, NY
Resale Only | 55+ age-restricted | Built 2007 - 2016 | 176 homes
Meadowbrook Pointe Athlet...
$700ks - $1Ms
Meadowbrook Pointe Athlet..., Westbury, NY
Resale Only | 55+ age-restricted | Built 2015 - 2016 | 720 homes
5 rating (1 reviews) Westhampton Pines
$900ks - $1Ms
Westhampton Pines, Westhampton, NY
Resale Only | 55+ age-restricted | Built 2005 - 2013 | 189 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
Chelsea Square
$300ks - $400ks
Chelsea Square, Morganville, NJ
New and Resale | 55+ age-restricted | Built 2007 - present | 225 homes
The Seasons at East Meado...
$400ks - $600ks
The Seasons at East Meado..., East Meadow, NY
Resale Only | 55+ age-restricted | Built 2009 - 2012 | 404 homes
Vineyards at Moriches
$500ks - $600ks
Vineyards at Moriches, Center Moriches, NY
Resale Only | 55+ age-restricted | Built 2008 - 2014 | 92 homes
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
Stone Ridge Estates
$500ks - $600ks
Stone Ridge Estates, Dix Hills, NY
Resale Only | 55+ age-restricted | Built 2004 - 2013 | 76 homes
Country Pointe Preserve
$600ks - $900ks
Country Pointe PreserveYaphank, NY
New Construction | 55+ age-restricted | Built 2024 - present | 152 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 Waterways at Moriches 632 WATER WAY 32, BROOKHAVEN, NY, 11955, Brookhaven, NY 11955
$799,000

2 beds

|

3 baths

|

1,874 sq ft

|

Condo

632 WATER WAY 32, BROOKHAVEN, NY, 11955
The Seasons at Elwood 178 SUMMER CIR, HUNTINGTON, NY, 11731, Huntington, NY 11731
$1,599,000

2 beds

|

3 baths

|

2,900 sq ft

|

Condo

178 SUMMER CIR, HUNTINGTON, NY, 11731
Greenwood Village 5131 VILLAGE CIR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949
$115,000

2 beds

|

2 baths

|

987 sq ft

|

House

5131 VILLAGE CIR, BROOKHAVEN, NY, 11949
Community: Greenwood Village
Fairfield at St. James 1205 GOTHAM DR, SMITHTOWN, NY, 11780, Smithtown, NY 11780
$649,000

2 beds

|

2 baths

|

948 sq ft

|

Condo

1205 GOTHAM DR, SMITHTOWN, NY, 11780
Cheesequake Village 1 ALABAMA CT 820, MATAWAN, NJ, 07747, Matawan, NJ 07747
$265,000

2 beds

|

1 baths

|

949 sq ft

|

Adult Community

1 ALABAMA CT 820, MATAWAN, NJ, 07747
Community: Cheesequake Village
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
Cheesequake Village 1-D ALABAMA CT D, OLD BRIDGE, NJ, 07747, Old Bridge, NJ 07747
$265,000

2 beds

|

1 baths

|

949 sq ft

|

Condo

1-D ALABAMA CT D, OLD BRIDGE, NJ, 07747
Community: Cheesequake Village
Oronoque Village 46 BUCKSKIN LN A, STRATFORD, CT, 06614, Stratford, CT 06614
$559,900

1 beds

|

2 baths

|

1,375 sq ft

|

Condo

46 BUCKSKIN LN A, STRATFORD, CT, 06614
Community: Oronoque Village
Heritage Hills 156 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589
$649,000

3 beds

|

2 baths

|

1,689 sq ft

|

Condo

156 HERITAGE HLS A, SOMERS, NY, 10589
Community: Heritage Hills
Surrey Downs 13 GATLEY CLOSE, FREEHOLD, NJ, 07728, Freehold, NJ 07728
$475,000

2 beds

|

2 baths

|

1,261 sq ft

|

Ranch

13 GATLEY CLOSE, FREEHOLD, NJ, 07728
Community: Surrey Downs
Heritage Village 701 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$392,000

2 beds

|

2 baths

|

1,398 sq ft

|

Condo

701 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.
Heritage Village 191 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$579,900

3 beds

|

2 baths

|

1,716 sq ft

|

Condo

191 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Surrey Downs 7 KINGSTON CLOSE 1000, FREEHOLD, NJ, 077..., Freehold, NJ 07728
$399,000

2 beds

|

2 baths

|

1,261 sq ft

|

Ranch

7 KINGSTON CLOSE 1000, FREEHOLD, NJ, 077...
Community: Surrey Downs
Dutchgate 1120 WILLOW LN, HEMPSTEAD, NY, 11580, Hempstead, NY 11580
$510,000

2 beds

|

2 baths

|

941 sq ft

|

Condo

1120 WILLOW LN, HEMPSTEAD, NY, 11580
Community: Dutchgate
The Cottages at Wire Mill 16 WIRE MILL RD A, STAMFORD, CT, 06903, Stamford, CT 06903
$1,495,000

3 beds

|

4 baths

|

3,244 sq ft

16 WIRE MILL RD A, STAMFORD, CT, 06903
Heritage Village 24-B HERITAGE CRST B, SOUTHBURY, CT, 064..., Southbury, CT 06488
$398,500

2 beds

|

2 baths

|

1,217 sq ft

|

Condo

24-B HERITAGE CRST B, SOUTHBURY, CT, 064...
Community: Heritage Village
Heritage Village 147 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$215,000

2 beds

|

2 baths

|

1,076 sq ft

|

Condo

147 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
Greenwood Village 130 VILLAGE CIR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949
$105,000

2 beds

|

2 baths

|

1,177 sq ft

|

Condo

130 VILLAGE CIR, BROOKHAVEN, NY, 11949
Community: Greenwood Village
Jefferson Village 5 DEVON CT B, YORKTOWN, NY, 10598, Yorktown, NY 10598
$366,750

2 beds

|

1 baths

|

989 sq ft

|

Condo

5 DEVON CT B, YORKTOWN, NY, 10598
Community: Jefferson Village
The Villages NJ 128 KORN MARKET A, FREEHOLD, NJ, 07728, Freehold, NJ 07728
$365,000

2 beds

|

1 baths

|

1,088 sq ft

|

Ranch

128 KORN MARKET A, FREEHOLD, NJ, 07728
Community: The Villages NJ
Country Pointe Plainview 17101 ASPENWOOD DR, OYSTER BAY, NY, 1180..., Oyster Bay, NY 11803
$1,100,000

2 beds

|

2 baths

|

1,400 sq ft

|

Condo

17101 ASPENWOOD DR, OYSTER BAY, NY, 1180...
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.
Jefferson Village 27 WALDEN CT J, YORKTOWN, NY, 10598, Yorktown, NY 10598
$349,900

1 beds

|

1 baths

|

800 sq ft

|

Condo

27 WALDEN CT J, YORKTOWN, NY, 10598
Community: Jefferson Village
Billingsgate 14 BILLINGSGATE DR 14, SIMSBURY, CT, 060..., Simsbury, CT 06070
$750,000

2 beds

|

3 baths

|

2,729 sq ft

|

Condo

14 BILLINGSGATE DR 14, SIMSBURY, CT, 060...
Community: Billingsgate
Heritage Village 184 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$199,900

1 beds

|

1 baths

|

928 sq ft

|

Condo

184 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
The Manors at The Colony Preserve 22 CRICKET CT, BROOKHAVEN, NY, 11967, Brookhaven, NY 11967
$425,000

2 beds

|

2 baths

|

1,500 sq ft

|

Condo

22 CRICKET CT, BROOKHAVEN, NY, 11967
Heritage Village 333 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$315,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

333 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Hills 103 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589
$780,000

3 beds

|

2 baths

|

1,780 sq ft

|

Condo

103 HERITAGE HLS B, SOMERS, NY, 10589
Community: Heritage Hills
Greenbriar Falls 26 MAJESTIC DR, TINTON FALLS, NJ, 07724, Tinton Falls, NJ 07724
$1,199,000

3 beds

|

4 baths

|

Townhouse

26 MAJESTIC DR, TINTON FALLS, NJ, 07724
Community: Greenbriar Falls
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
The Bel Aire at East Meadow 50 MERRICK AVE 415, HEMPSTEAD, NY, 11554, Hempstead, NY 11554
$500,000

2 beds

|

2 baths

|

1,000 sq ft

|

Condo

50 MERRICK AVE 415, HEMPSTEAD, NY, 11554
HarborView 100 HARBOR VIEW DR 251, NORTH HEMPSTEAD,..., North Hempstead, NY 11050
$829,000

2 beds

|

3 baths

|

Condo

100 HARBOR VIEW DR 251, NORTH HEMPSTEAD,...
Community: HarborView
Saddle Lakes 174 ADELE CT, RIVERHEAD, NY, 11901, Riverhead, NY 11901
$619,000

2 beds

|

2 baths

|

1,631 sq ft

|

Condo

174 ADELE CT, RIVERHEAD, NY, 11901
Community: Saddle Lakes
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.
Newtown Woods 832 BROOKSIDE CT 832, NEWTOWN, CT, 06470, Newtown, CT 06470
$585,000

2 beds

|

2 baths

|

1,807 sq ft

|

Condo

832 BROOKSIDE CT 832, NEWTOWN, CT, 06470
Community: Newtown Woods
Westhampton Pines 171 JONATHAN LN, SOUTHAMPTON, NY, 11977, Southampton, NY 11977
$1,345,000

3 beds

|

3 baths

|

2,310 sq ft

|

Condo

171 JONATHAN LN, SOUTHAMPTON, NY, 11977
Community: Westhampton Pines
Meadowbrook Pointe Links & Spa 163 AUGUSTA DR 163, BROOKHAVEN, NY, 1176..., Brookhaven, NY 11763
$699,990

2 beds

|

3 baths

|

1,558 sq ft

|

Condo

163 AUGUSTA DR 163, BROOKHAVEN, NY, 1176...
Dutchgate 212 WILLOW LN, HEMPSTEAD, NY, 11580, Hempstead, NY 11580
$515,000

2 beds

|

2 baths

|

941 sq ft

|

Condo

212 WILLOW LN, HEMPSTEAD, NY, 11580
Community: Dutchgate
Stone Ridge Estates 160 CHRISTINE DR, HUNTINGTON, NY, 11746, Huntington, NY 11746
$770,000

2 beds

|

2 baths

|

Condo

160 CHRISTINE DR, HUNTINGTON, NY, 11746
Community: Stone Ridge Estates
The Powder Forest Homes 15 BANTRY RD 15, SIMSBURY, CT, 06070, Simsbury, CT 06070
$899,000

4 beds

|

3 baths

|

1,878 sq ft

15 BANTRY RD 15, SIMSBURY, CT, 06070
Oronoque Village 283 AGAWAM DR A, STRATFORD, CT, 06614, Stratford, CT 06614
$625,000

2 beds

|

3 baths

|

1,415 sq ft

|

Condo

283 AGAWAM DR A, STRATFORD, CT, 06614
Community: Oronoque Village
Cheesequake Village 5 PENNSYLVANIA DR 454, OLD BRIDGE, NJ, 0..., Old Bridge, NJ 07747
$299,500

2 beds

|

1 baths

|

Condo

5 PENNSYLVANIA DR 454, OLD BRIDGE, NJ, 0...
Community: Cheesequake Village
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
Heritage Village 10 HERITAGE CIR A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$353,900

3 beds

|

2 baths

|

1,716 sq ft

|

Condo

10 HERITAGE CIR A, SOUTHBURY, CT, 06488
Community: Heritage Village
Liberty at Newtown 49 JO AL CT 49, NEWTOWN, CT, 06470, Newtown, CT 06470
$619,000

2 beds

|

3 baths

|

2,341 sq ft

|

Condo

49 JO AL CT 49, NEWTOWN, CT, 06470
Community: Liberty at Newtown
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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