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Westport, CT 55+ active adult communities & homes for sale - Page 2

167 communities near Westport

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The Seasons at Elwood
$800Ks - $900Ks
The Seasons at Elwood, East Northport, NY
Resale Only | 55+ age-restricted | Built 2018 - 2020 | 256 homes
Meadow Brook Estates
$500Ks
Meadow Brook Estates, Oxford, CT
Resale Only | 55+ age-restricted | Built 2003 - 2020 | 246 homes
3.7 rating (3 reviews) Rosemont Estates
$700Ks - $800Ks
Rosemont Estates, Marlboro, NJ
Resale Only | 55+ age-restricted | Built 2004 - 2014 | 242 homes
5 rating (1 reviews) Encore Atlantic Shores
$700Ks - $800Ks
Encore Atlantic Shores, Eastport, NY
Resale Only | 55+ age-restricted | Built 2004 - 2011 | 240 homes
The Summit at Bethel
$600Ks
The Summit at Bethel, Bethel, CT
Resale Only | 55+ age-restricted | Built 2010 - 2021 | 235 homes
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4.9 rating (14 reviews) Chatfield Farms
$500Ks - $600Ks
Chatfield Farms, Beacon Falls, CT
New Construction | 55+ age-restricted | Built 2014 - present | 231 homes
Four Seasons at Wayne
$500Ks
Four Seasons at Wayne, Wayne, NJ
Resale Only | 55+ age-restricted | Built 1999 - 2001 | 230 homes
5 rating (1 reviews) Encore at Lake Grove
$600Ks - $800Ks
Encore at Lake Grove, Lake Grove, NY
Resale Only | 55+ age-restricted | Built 2006 - 2007 | 228 homes
Woodridge Strathmore Terr...
$400Ks
Woodridge Strathmore Terr..., Mount Sinai, NY
Resale Only | 55+ age-restricted | Built 1974 - 1985 | 226 homes
Regency at Wappinger
$600Ks - $700Ks
Regency at Wappinger, Wappingers Falls, NY
Resale Only | 55+ age-restricted | Built 2014 - 2020 | 225 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.
Chelsea Square
$400Ks - $500Ks
Chelsea Square, Morganville, NJ
New and Resale | 55+ age-restricted | Built 2007 - present | 225 homes
5 rating (1 reviews) Sunrise Village
$400Ks - $500Ks
Sunrise Village, Sayville, NY
Resale Only | 55+ age-restricted | Built 1985 - 1990 | 213 homes
3.7 rating (3 reviews) Nobility Crest at Ocean
$500Ks
Nobility Crest at Ocean, Ocean Township, NJ
New and Resale | 55+ age-restricted | Built 2006 - present | 198 homes
Saddle Lakes
$400Ks
Saddle Lakes, Riverhead, NY
Resale Only | 55+ age-restricted | Built 2000 - 2002 | 196 homes
Country Village Estates
$400Ks
Country Village Estates, Coram, NY
Resale Only | 55+ age-restricted | Built 1993 - 2001 | 195 homes
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Questions? Call us: (475) 471-1908
5 rating (1 reviews) Sunken Pond Estates
$400Ks - $500Ks
Sunken Pond Estates, Riverhead, NY
Resale Only | 55+ age-restricted | Built 2003 - 2005 | 194 homes
The Seasons at East North...
$700Ks
The Seasons at East North..., East Northport, NY
New Construction | 55+ age-restricted | Built 2023 - present | 190 homes
5 rating (1 reviews) Westhampton Pines
$900Ks - $1Ms
Westhampton Pines, Westhampton, NY
Resale Only | 55+ age-restricted | Built 2005 - 2013 | 189 homes
5 rating (1 reviews) The Villages at Mount Sin...
$500Ks - $700Ks
The Villages at Mount Sin..., Mount Sinai, NY
Resale Only | 55+ age-restricted | Built 2005 - 2007 | 185 homes
The Powder Forest Homes
$600Ks - $700Ks
The Powder Forest Homes, Simsbury, CT
Resale Only | 55+ age-restricted | Built 2006 - 2016 | 182 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 (1 reviews) Regency at Trotters Point...
$700Ks - $800Ks
Regency at Trotters Point..., Tinton Falls, NJ
Resale Only | 55+ age-restricted | Built 2014 - 2021 | 181 homes
Regency at Holmdel
$1Ms
Regency at Holmdel, Holmdel, NJ
Resale Only | 55+ age-restricted | Built 2016 - 2019 | 181 homes
5 rating (1 reviews) Newtown Woods
$400Ks - $500Ks
Newtown Woods, Newtown, CT
New and Resale | 55+ age-restricted | Built 2011 - present | 178 homes
Stoneleigh Woods at River...
$500Ks - $600Ks
Stoneleigh Woods at River..., Riverhead, NY
Resale Only | 55+ age-restricted | Built 2007 - 2016 | 176 homes
Snug Harbor
$600Ks - $700Ks
Snug Harbor, Amityville, NY
Resale Only | 55+ age-restricted | Built 1970 - 1974 | 176 homes
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Questions? Call us: (475) 471-1908
The Coves at Melville
$500Ks
The Coves at Melville, Melville, NY
Resale Only | 62+ age-restricted | Built 2004 - 2005 | 175 homes
Strathmore Gate East
$300Ks - $400Ks
Strathmore Gate East, Coram, NY
Resale Only | 55+ age-restricted | Built 1970 - 1975 | 174 homes
Beckley Farms
$300Ks - $400Ks
Beckley Farms, Berlin, CT
New and Resale | 55+ age-restricted | Built 2010 - present | 170 homes
Greenbriar Falls
$900Ks - $1Ms
Greenbriar Falls, Tinton Falls, NJ
New and Resale | 55+ age-restricted | Built 2006 - present | 168 homes
5 rating (1 reviews) The Villas at Jumping Bro...
$700Ks
The Villas at Jumping Bro..., Neptune Township, NJ
Resale Only | 55+ age-restricted | Built 2001 - 2003 | 168 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.
Regency at Fishkill
$400Ks - $500Ks
Regency at Fishkill, Fishkill, NY
Resale Only | 55+ age-restricted | Built 2008 - 2020 | 164 homes
Cedar Village at Holmdel
$700Ks
Cedar Village at Holmdel, Holmdel Township, NJ
Resale Only | 55+ age-restricted | Built 1997 - 2005 | 158 homes
Four Seasons at Cedar Gro...
$700Ks
Four Seasons at Cedar Gro..., Cedar Grove, NJ
Resale Only | 55+ age-restricted | Built 2000 - 2005 | 156 homes
South Pond Village
$100Ks - $200Ks
South Pond Village, Bloomfield, CT
Resale Only | 55+ age-restricted | Built 1999 - 2005 | 151 homes
The Manors at The Colony ...
$400Ks - $500Ks
The Manors at The Colony ..., Shirley, NY
New Construction | 55+ age-restricted | Built 2013 - present | 150 homes
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
Setauket Meadows
$600Ks - $700Ks
Setauket Meadows, Setauket, NY
Resale Only | 55+ age-restricted | Built 2005 - 2007 | 150 homes
Vineyards at Brookfield
$700Ks
Vineyards at Brookfield, Center Moriches, NY
New Construction | 55+ age-restricted | Built 2019 - present | 146 homes
Fieldstone Village
$500Ks - $800Ks
Fieldstone Village, Orange, CT
Resale Only | 55+ age-restricted | Built 2010 - 2018 | 142 homes
Village Estates
$500Ks
Village Estates, Amityville, NY
Resale Only | 55+ age-restricted | Built 2006 - 2008 | 138 homes
The Villas at Narraganset...
$600Ks
The Villas at Narraganset..., Lindenhurst, NY
Resale Only | 55+ age-restricted | Built 2004 - 2005 | 138 homes
The Villages NJ 120 MUHLEN PLATZ D, FREEHOLD, NJ, 07728, Freehold, NJ 07728
$339,000

2 beds

|

1 baths

|

1,262 sq ft

|

Adult Community

120 MUHLEN PLATZ D, FREEHOLD, NJ, 07728
Community: The Villages NJ
Shadow Lake Village 126 MANCHESTER CT, RED BANK, NJ, 07701, Red Bank, NJ 07701
$425,000

1 beds

|

1 baths

|

999 sq ft

|

Adult Community

126 MANCHESTER CT, RED BANK, NJ, 07701
Community: Shadow Lake Village
New Shadow Lake Village 60 FALMOUTH CT, RED BANK, NJ, 07701, Red Bank, NJ 07701
$499,999

2 beds

|

2 baths

|

1,132 sq ft

|

House

60 FALMOUTH CT, RED BANK, NJ, 07701
Community: Shadow Lake Village
Cheesequake Village 4 HAWAII CT # 1003, MATAWAN, NJ, 07747, Matawan, NJ 07747
$285,000

1 beds

|

1 baths

|

708 sq ft

|

Adult Community

4 HAWAII CT # 1003, MATAWAN, NJ, 07747
Community: Cheesequake Village
Rolling Meadows at Wayside 106 ROLLING MEADOWS BLVD, ASBURY PARK, N..., Asbury Park, NJ 07712
$739,000

2 beds

|

2 baths

|

Ranch

106 ROLLING MEADOWS BLVD, ASBURY PARK, N...
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
Surrey Downs 55 FARNWORTH CLOSE # 1000, FREEHOLD, NJ,..., Freehold, NJ 07728
$419,000

2 beds

|

2 baths

|

1,295 sq ft

|

House

55 FARNWORTH CLOSE # 1000, FREEHOLD, NJ,...
Community: Surrey Downs
Cheesequake Village 9 VALERY RD, MATAWAN, NJ, 07747, Matawan, NJ 07747
$259,900

1 beds

|

1 baths

|

758 sq ft

|

House

9 VALERY RD, MATAWAN, NJ, 07747
Community: Cheesequake Village
Four Seasons at Cedar Grove 911 HOLLY LN # 11, CEDAR GROVE, NJ, 0700..., Cedar Grove, NJ 07009
$775,000

2 beds

|

2 baths

911 HOLLY LN # 11, CEDAR GROVE, NJ, 0700...
Four Seasons at Cedar Grove 911 HOLLY LN, CEDAR GROVE, NJ, 07009, Cedar Grove, NJ 07009
$775,000

2 beds

|

2 baths

|

Condo

911 HOLLY LN, CEDAR GROVE, NJ, 07009
Cheesequake Village 56 GALEWOOD DR A, MATAWAN, NJ, 07747, Matawan, NJ 07747
$315,000

2 beds

|

1 baths

|

914 sq ft

|

Condo

56 GALEWOOD DR A, 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.
Rolling Meadows at Wayside 16 ROLLING MEADOWS BLVD, ASBURY PARK, NJ..., Asbury Park, NJ 07712
$839,900

2 beds

|

3 baths

|

2,288 sq ft

|

House

16 ROLLING MEADOWS BLVD, ASBURY PARK, NJ...
The Villages NJ 138 WEIN MARKET C, FREEHOLD, NJ, 07728, Freehold, NJ 07728
$359,900

2 beds

|

2 baths

|

1,262 sq ft

|

Adult Community

138 WEIN MARKET C, FREEHOLD, NJ, 07728
Community: The Villages NJ
Cheesequake Village 9 NEBRASKA DR, MATAWAN, NJ, 07747, Matawan, NJ 07747
$329,900

2 beds

|

1 baths

|

Ranch

9 NEBRASKA DR, MATAWAN, NJ, 07747
Community: Cheesequake Village
Cheesequake Village 10 CALIFORNIA CT A, MATAWAN, NJ, 07747, Matawan, NJ 07747
$290,000

2 beds

|

1 baths

|

914 sq ft

|

Condo

10 CALIFORNIA CT A, MATAWAN, NJ, 07747
Community: Cheesequake Village
Shadow Lake Village 12 ELLSWORTH CT, RED BANK, NJ, 07701, Red Bank, NJ 07701
$599,000

2 beds

|

2 baths

|

Ranch

12 ELLSWORTH 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
Cheesequake Village 4 HAWAII CT B, MATAWAN, NJ, 07747, Matawan, NJ 07747
$285,000

1 beds

|

1 baths

|

Condo

4 HAWAII CT B, MATAWAN, NJ, 07747
Community: Cheesequake Village
Shadow Lake Village 19 MANCHESTER CT, RED BANK, NJ, 07701, Red Bank, NJ 07701
$429,900

2 beds

|

1 baths

|

952 sq ft

|

Ranch

19 MANCHESTER CT, RED BANK, NJ, 07701
Community: Shadow Lake Village
Rolling Meadows at Wayside 11 ROLLING MEADOWS BLVD, ASBURY PARK, NJ..., Asbury Park, NJ 07712
$829,900

3 beds

|

3 baths

|

2,288 sq ft

|

House

11 ROLLING MEADOWS BLVD, ASBURY PARK, NJ...
Cheesequake Village 5 INDIANA CT A, MATAWAN, NJ, 07747, Matawan, NJ 07747
$350,000

2 beds

|

1 baths

|

914 sq ft

|

Ranch

5 INDIANA CT A, MATAWAN, NJ, 07747
Community: Cheesequake Village
The Villages NJ 160 RUE DE ST GERMAINE C, FREEHOLD, NJ, ..., Freehold, NJ 07728
$263,000

2 beds

|

1 baths

|

1,008 sq ft

|

Ranch

160 RUE DE ST GERMAINE C, FREEHOLD, NJ, ...
Community: The Villages NJ
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 NJ 84 PARKWAY DR B, FREEHOLD, NJ, 07728, Freehold, NJ 07728
$337,000

2 beds

|

1 baths

|

1,008 sq ft

84 PARKWAY DR B, FREEHOLD, NJ, 07728
Community: The Villages NJ
Shadow Lake Village 109 LEXINGTON CT, RED BANK, NJ, 07701, Red Bank, NJ 07701
$399,000

2 beds

|

1 baths

|

Ranch

109 LEXINGTON CT, RED BANK, NJ, 07701
Community: Shadow Lake Village
Surrey Downs 5 JAFFREYTON CLOSE, FREEHOLD, NJ, 07728, Freehold, NJ 07728
$385,000

2 beds

|

2 baths

|

1,144 sq ft

|

Ranch

5 JAFFREYTON CLOSE, FREEHOLD, NJ, 07728
Community: Surrey Downs
The Villages NJ 56 LARGO SAN NICOLA A, FREEHOLD, NJ, 077..., Freehold, NJ 07728
$365,000

2 beds

|

1 baths

|

1,144 sq ft

|

Ranch

56 LARGO SAN NICOLA A, FREEHOLD, NJ, 077...
Community: The Villages NJ
Shadow Lake Village 11 MANCHESTER CT, RED BANK, NJ, 07701, Red Bank, NJ 07701
$385,000

2 beds

|

1 baths

|

999 sq ft

|

Adult Community

11 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
Cheesequake Village 48 HAVEN DR, OLD BRIDGE, NJ, 07747, Old Bridge, NJ 07747
$349,900

2 beds

|

1 baths

|

House

48 HAVEN DR, OLD BRIDGE, NJ, 07747
Community: Cheesequake Village
Regency at Holmdel 17 SPALDING DR, HOLMDEL, NJ, 07733, Holmdel, NJ 07733
$1,350,000

3 beds

|

4 baths

|

3,417 sq ft

|

Adult Community

17 SPALDING DR, HOLMDEL, NJ, 07733
Community: Regency at Holmdel
Surrey Downs 53 FARNWORTH CLOSE, FREEHOLD, NJ, 07728, Freehold, NJ 07728
$399,900

2 beds

|

2 baths

|

Ranch

53 FARNWORTH CLOSE, FREEHOLD, NJ, 07728
Community: Surrey Downs
Four Seasons at Wayne 801 FOUR SEASONS DR, WAYNE, NJ, 07470, Wayne, NJ 07470
$542,000

2 beds

|

2 baths

|

Condo

801 FOUR SEASONS DR, WAYNE, NJ, 07470
Cheesequake Village 1 HAWAII CT A, MATAWAN, NJ, 07747, Matawan, NJ 07747
$195,000

2 beds

|

1 baths

|

914 sq ft

|

Adult Community

1 HAWAII CT A, 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.
Surrey Downs 1 LINTON CLOSE, FREEHOLD, NJ, 07728, Freehold, NJ 07728
$340,000

2 beds

|

1 baths

|

942 sq ft

|

Ranch

1 LINTON CLOSE, FREEHOLD, NJ, 07728
Community: Surrey Downs
Rosemont Estates 211 BRADWICK WAY, MARLBORO, NJ, 07746, Marlboro, NJ 07746
$799,900

2 beds

|

3 baths

|

2,452 sq ft

|

House

211 BRADWICK WAY, MARLBORO, NJ, 07746
Community: Rosemont Estates
Shadow Lake Village 40 ELLSWORTH CT, RED BANK, NJ, 07701, Red Bank, NJ 07701
$549,900

2 beds

|

2 baths

|

1,132 sq ft

|

Ranch

40 ELLSWORTH CT, RED BANK, NJ, 07701
Community: Shadow Lake Village
Cheesequake Village 14 CONNECTICUT CT D, MATAWAN, NJ, 07747, Matawan, NJ 07747
$279,999

2 beds

|

1 baths

|

Adult Community

14 CONNECTICUT CT D, MATAWAN, NJ, 07747
Community: Cheesequake Village
Cheesequake Village 11 ALABAMA CT, MATAWAN, NJ, 07747, Matawan, NJ 07747
$250,000

2 beds

|

2 baths

|

976 sq ft

|

Townhouse,Condominium

11 ALABAMA CT, MATAWAN, NJ, 07747
Community: Cheesequake Village
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
Regency at Allaire 106 GRANDVIEW CIR, FARMINGDALE, NJ, 0772..., Farmingdale, NJ 07727
$1,350,000

4 beds

|

3 baths

|

2,928 sq ft

|

House

106 GRANDVIEW CIR, FARMINGDALE, NJ, 0772...
Community: Regency at Allaire
Enclave at Ocean 1218 W PARK AVE, OCEAN, NJ, 07712, Ocean, NJ 07712
$1,500,000

5 beds

|

7 baths

|

3,953 sq ft

|

House

1218 W PARK AVE, OCEAN, NJ, 07712
Community: Enclave at Ocean
Surrey Downs 32 CARNABY CLOSE, FREEHOLD, NJ, 07728, Freehold, NJ 07728
$339,000

2 beds

|

1 baths

|

Ranch

32 CARNABY CLOSE, FREEHOLD, NJ, 07728
Community: Surrey Downs
Winthrop Court 6102 HARCOURT RD # 519, CLIFTON, NJ, 070..., Clifton, NJ 07013
$515,000

2 beds

|

2 baths

|

Condo

6102 HARCOURT RD # 519, CLIFTON, NJ, 070...
Community: Winthrop Court
The Villages NJ 32 PLAZA DE LAS LOBOS C, FREEHOLD, NJ, 0..., Freehold, NJ 07728
$389,000

2 beds

|

2 baths

|

Adult Community

32 PLAZA DE LAS LOBOS C, FREEHOLD, NJ, 0...
Community: The Villages NJ
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167 communities near Westport
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