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Westport, CT 55+ active adult communities & homes for sale - Page 4

167 communities near Westport

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Sonoma Woods
$300Ks
Sonoma Woods, Middletown, CT
Resale Only | 55+ age-restricted | Built 2005 - 2015 | 68 homes
Stoneleigh Woods at Carme...
$400Ks
Stoneleigh Woods at Carme..., Carmel, NY
Resale Only | 55+ age-restricted | Built 2012 - 2017 | 68 homes
Eagles Walk at East Quogu...
$500Ks
Eagles Walk at East Quogu..., East Quogue, NY
Resale Only | 55+ age-restricted | Built 2004 - 2014 | 67 homes
Hopmeadow Place
$200Ks - $300Ks
Hopmeadow Place, Simsbury, CT
Resale Only | 55+ age-restricted | Built 2005 - 2005 | 66 homes
Parker Village Estates
$700Ks
Parker Village Estates, Eatontown, NJ
Resale Only | 55+ age-restricted | Built 2002 - 2002 | 66 homes
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Enclave at Shrewsbury
$600Ks - $800Ks
Enclave at Shrewsbury, Shrewsbury, NJ
Resale Only | 55+ age-restricted | Built 2011 - 2014 | 66 homes
Glassbury Court at Hunter...
$500Ks - $700Ks
Glassbury Court at Hunter..., Cortlandt, NY
Resale Only | 55+ age-restricted | Built 2007 - 2014 | 64 homes
RiverWalk
$500Ks - $600Ks
RiverWalk, Branford, CT
New and Resale | 55+ age-restricted | Built 2007 - present | 60 homes
Woodcrest at Jacobs Hill
$300Ks
Woodcrest at Jacobs Hill, Cortlandt, NY
Resale Only | 55+ age-restricted | Built 2005 - 2006 | 58 homes
Autumn Fields
$200Ks - $300Ks
Autumn Fields, Enfield, CT
Resale Only | 55+ age-restricted | Built 2004 - 2006 | 56 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 Atrium of Portland
<$100k
The Atrium of Portland, Portland, CT
Resale Only | 55+ age-restricted | Built 2004 - 2004 | 56 homes
The Views at Pomona
$200Ks - $400Ks
The Views at Pomona, Pomona, NY
Resale Only | 55+ age-restricted | Built 2011 - 2011 | 56 homes
The Village at Buckingham
$500Ks - $600Ks
The Village at Buckingham, Avon, CT
Resale Only | 55+ age-restricted | Built 2002 - 2006 | 56 homes
77 Sunset Lane
$400Ks - $700Ks
77 Sunset Lane, Ridgefield, CT
Resale Only | 55+ age-restricted | Built 2016 - 2018 | 54 homes
Evergreen
$500Ks
Evergreen, Cromwell, CT
New and Resale | 55+ age-restricted | Built 2005 - present | 52 homes
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
Regency Meadows
$500Ks
Regency Meadows, Trumbull, CT
Resale Only | 55+ age-restricted | Built 2003 - 2005 | 51 homes
Gloria Commons
$400Ks
Gloria Commons, Milford, CT
Resale Only | 55+ age-restricted | Built 2007 - 2015 | 50 homes
Eastport Meadows
$400Ks
Eastport Meadows, Eastport, NY
Resale Only | 55+ age-restricted | Built 2009 - 2016 | 50 homes
Villas at Seminary Hill
$400Ks
Villas at Seminary Hill, Carmel, NY
New Construction | 55+ age-restricted | Built 2018 - present | 50 homes
The Residences at Butterf...
$500Ks - $600Ks
The Residences at Butterf..., Cold Spring, NY
Resale Only | 55+ age-restricted | Built 2018 - 2023 | 49 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.
Bramble Ridge
$400Ks - $500Ks
Bramble Ridge, Suffield, CT
Resale Only | 55+ age-restricted | Built 2005 - 2015 | 47 homes
Chimney Hill
$500Ks - $700Ks
Chimney Hill, Farmington, CT
Resale Only | 55+ age-restricted | Built 2006 - 2013 | 44 homes
Enclave at Shark River
$500Ks
Enclave at Shark River, Tinton Falls, NJ
Resale Only | 55+ age-restricted | Built 2015 - 2018 | 44 homes
Cheshire Square
$600Ks - $700Ks
Cheshire Square, Little Silver, NJ
Resale Only | 55+ age-restricted | Built 1974 - 1974 | 44 homes
Wolfe Landing
$500Ks - $600Ks
Wolfe Landing, Clarkstown, NY
Resale Only | 55+ age-restricted | Built 2015 - 2016 | 43 homes
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
Village Vistas
$800Ks - $1Ms
Village Vistas, Port Jefferson, NY
Resale Only | 55+ age-restricted | Built 2013 - 2017 | 43 homes
Harbor View Estates
$400Ks - $600Ks
Harbor View Estates, Copiague, NY
New Construction | 55+ age-restricted | Built 2017 - 2018 | 40 homes
Forest Mews
$300Ks - $400Ks
Forest Mews, Avon, CT
Resale Only | 55+ age-restricted | Built 2001 - 2004 | 40 homes
Clockmaker's Hill
$100Ks
Clockmaker's Hill, Winsted, CT
Resale Only | 55+ age-restricted | Built 2005 - 2014 | 38 homes
Hidden Harbor Estates
$500Ks - $600Ks
Hidden Harbor Estates, Copiague, NY
Resale Only | 55+ age-restricted | Built 2010 - 2015 | 38 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.
Billingsgate
$400Ks - $600Ks
Billingsgate, Simsbury, CT
Resale Only | 55+ age-restricted | Built 2003 - 2006 | 37 homes
Stratford Park
$900Ks
Stratford Park, Melville, NY
Resale Only | 55+ age-restricted | Built 2011 - 2013 | 36 homes
Boulder Brook
$200Ks
Boulder Brook, Prospect, CT
Resale Only | 55+ age-restricted | Built 2004 - 2006 | 35 homes
Eden Park
$500Ks - $600Ks
Eden Park, Clarkstown, NY
Resale Only | 55+ age-restricted | Built 2011 - 2011 | 34 homes
The Woods at Dunham Pond
$400Ks - $500Ks
The Woods at Dunham Pond, New Fairfield, CT
Resale Only | 55+ age-restricted | Built 2004 - 2015 | 33 homes
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
Knickerbocker Bay Club
$700Ks - $3Ms
Knickerbocker Bay Club, Port Washington, NY
New and Resale | 55+ age-restricted | Built 2014 - present | 32 homes
Jessup's Landing
$1Ms
Jessup's Landing, Quogue, NY
New and Resale | 55+ age-restricted | Built 2009 - 2016 | 31 homes
Oak Meadow Estates
$200Ks - $400Ks
Oak Meadow Estates, Torrington, CT
New and Resale | 55+ age-restricted | Built 2013 - present | 31 homes
Autumn Estates
$500Ks - $600Ks
Autumn Estates, Farmington, CT
Resale Only | 55+ age-restricted | Built 2011 - 2017 | 30 homes
The Coach Homes at Ridgef...
$200Ks - $500Ks
The Coach Homes at Ridgef..., Ridgefield, CT
New Construction | 55+ age-restricted | Built 2019 - present | 30 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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