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

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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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
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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New Heritage Village 110 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$399,999

3 beds

|

2 baths

|

1,716 sq ft

|

Condo

110 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Shadow Lake Village 18 LEXINGTON CT, RED BANK, NJ, 07701, Red Bank, NJ 07701
$279,900

1 beds

|

1 baths

|

1,021 sq ft

|

Adult Community

18 LEXINGTON CT, RED BANK, NJ, 07701
Community: Shadow Lake Village
Shadow Lake Village 42 MEDFORD CT, RED BANK, NJ, 07701, Red Bank, NJ 07701
$400,000

2 beds

|

2 baths

|

1,210 sq ft

|

Adult Community

42 MEDFORD CT, RED BANK, NJ, 07701
Community: Shadow Lake Village
Glassbury Court at Hunterbrook 2272 DALTON DR, CORTLANDT, NY, 10567, Cortlandt, NY 10567
$944,500

2 beds

|

3 baths

|

2,265 sq ft

|

Condo

2272 DALTON DR, CORTLANDT, NY, 10567
Surrey Downs 23 DATCHET CLOSE 1000, FREEHOLD, NJ, 077..., Freehold, NJ 07728
$299,999

2 beds

|

1 baths

|

896 sq ft

|

Ranch

23 DATCHET CLOSE 1000, FREEHOLD, NJ, 077...
Community: Surrey Downs
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
The Greens at Half Hollow 259 ALTESSA BLVD, HUNTINGTON, NY, 11747, Huntington, NY 11747
$1,399,999

3 beds

|

3 baths

|

3,200 sq ft

|

Condo

259 ALTESSA BLVD, HUNTINGTON, NY, 11747
Setauket Meadows 113 BRIANNA DR, BROOKHAVEN, NY, 11733, Brookhaven, NY 11733
$779,000

2 beds

|

3 baths

|

1,842 sq ft

|

Condo

113 BRIANNA DR, BROOKHAVEN, NY, 11733
Community: Setauket Meadows
Regency at Prospect 28 TAMARACK CT 28, PROSPECT, CT, 06712, Prospect, CT 06712
$635,000

2 beds

|

3 baths

|

2,005 sq ft

|

Condo

28 TAMARACK CT 28, PROSPECT, CT, 06712
Community: Regency at Prospect
Rosemont Estates 23 HULSART CT, MARLBORO, NJ, 07746, Marlboro, NJ 07746
$939,000

3 beds

|

3 baths

|

2,528 sq ft

|

House

23 HULSART CT, MARLBORO, NJ, 07746
Community: Rosemont Estates
Setauket Meadows 58 BLAIR RD 58, BROOKHAVEN, NY, 11733, Brookhaven, NY 11733
$849,999

2 beds

|

4 baths

|

1,773 sq ft

|

House

58 BLAIR RD 58, BROOKHAVEN, NY, 11733
Community: Setauket Meadows
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.
Cedar Village at Holmdel 35 CHESAPEAKE DR, HOLMDEL, NJ, 07733, Holmdel, NJ 07733
$815,000

2 beds

|

2 baths

|

1,843 sq ft

35 CHESAPEAKE DR, HOLMDEL, NJ, 07733
Newbury Village 46 GREAT HERON LN 46, BROOKFIELD, CT, 06..., Brookfield, CT 06804
$725,000

2 beds

|

4 baths

|

2,560 sq ft

|

Condo

46 GREAT HERON LN 46, BROOKFIELD, CT, 06...
Community: Newbury Village
Breton Hills 704 BRETON WAY 704, GLEN COVE, NY, 11542, Glen Cove, NY 11542
$669,000

2 beds

|

2 baths

|

1,449 sq ft

|

Condo

704 BRETON WAY 704, GLEN COVE, NY, 11542
Community: Breton Hills
Leisure Village 150 EASTBOURNE CT B, BROOKHAVEN, NY, 119..., Brookhaven, NY 11961
$419,000

2 beds

|

2 baths

|

1,515 sq ft

|

Condo

150 EASTBOURNE CT B, BROOKHAVEN, NY, 119...
Community: Leisure Village
Heritage Village 32 HERITAGE VLG C, SOUTHBURY, CT, 06488, Southbury, CT 06488
$289,900

2 beds

|

2 baths

|

1,032 sq ft

|

Condo

32 HERITAGE VLG C, SOUTHBURY, CT, 06488
Community: Heritage Village
Shadow Lake Village 61 HANCOCK CT, RED BANK, NJ, 07701, Red Bank, NJ 07701
$315,000

2 beds

|

1 baths

|

1,007 sq ft

|

Adult Community

61 HANCOCK 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
Heritage Village 12 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$239,900

1 beds

|

1 baths

|

928 sq ft

|

Condo

12 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Hills 342 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589
$675,000

2 beds

|

2 baths

|

1,484 sq ft

|

Condo

342 HERITAGE HLS B, SOMERS, NY, 10589
Community: Heritage Hills
Foxwood Village 1407 MIDDLE RD 265, RIVERHEAD, NY, 11933, Riverhead, NY 11933
$469,000

3 beds

|

2 baths

|

1,792 sq ft

|

Manufactured Home

1407 MIDDLE RD 265, RIVERHEAD, NY, 11933
Community: Foxwood Village
Meadowbrook Pointe Athletic Club & Spa 477 PACING WAY, HEMPSTEAD, NY, 11590, Hempstead, NY 11590
$1,150,000

2 beds

|

3 baths

|

2,628 sq ft

|

Condo

477 PACING WAY, HEMPSTEAD, NY, 11590
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 45 DATCHET CLOSE, FREEHOLD, NJ, 07728, Freehold, NJ 07728
$415,000

2 beds

|

2 baths

|

1,261 sq ft

|

Ranch

45 DATCHET CLOSE, FREEHOLD, NJ, 07728
Community: Surrey Downs
The Coves at Melville 80 MORLEY CIR, HUNTINGTON, NY, 11747, Huntington, NY 11747
$589,999

2 beds

|

2 baths

|

1,169 sq ft

|

Condo

80 MORLEY CIR, HUNTINGTON, NY, 11747
Heritage Hills 599 HERITAGE HILLS DR A, SOMERS, NY, 105..., Somers, NY 10589
$639,000

2 beds

|

2 baths

|

1,483 sq ft

|

Condo

599 HERITAGE HILLS DR A, SOMERS, NY, 105...
Community: Heritage Hills
Rivington 524 CENTER MEADOW LN 524, DANBURY, CT, 0..., Danbury, CT 06810
$519,000

2 beds

|

2 baths

|

1,258 sq ft

|

Condo

524 CENTER MEADOW LN 524, DANBURY, CT, 0...
Community: Rivington
Heritage Hills 958 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589
$594,000

2 beds

|

2 baths

|

1,265 sq ft

|

Condo

958 HERITAGE HLS B, SOMERS, NY, 10589
Community: Heritage Hills
Leisure Glen 82 GLEN DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$469,000

2 beds

|

2 baths

|

1,312 sq ft

|

Condo

82 GLEN DR, BROOKHAVEN, NY, 11961
Community: Leisure Glen
Leisure Knoll 259 EDINBURGH DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$445,000

2 beds

|

2 baths

|

1,135 sq ft

|

Condo

259 EDINBURGH DR, BROOKHAVEN, NY, 11961
Community: Leisure Knoll
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
Strathmore Gate East 55 FORGE LN, BROOKHAVEN, NY, 11727, Brookhaven, NY 11727
$420,000

2 beds

|

1 baths

|

964 sq ft

|

Condo

55 FORGE LN, BROOKHAVEN, NY, 11727
Heritage Hills 412 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589
$875,000

3 beds

|

2 baths

|

1,909 sq ft

|

Condo

412 HERITAGE HLS A, SOMERS, NY, 10589
Community: Heritage Hills
Rivington 78 WARRINGTON ROUND 78, DANBURY, CT, 068..., Danbury, CT 06810
$625,000

3 beds

|

3 baths

|

1,600 sq ft

|

Condo

78 WARRINGTON ROUND 78, DANBURY, CT, 068...
Community: Rivington
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 7 KANSAS CT, OLD BRIDGE TWP., NJ, 07747, Old Bridge Twp., NJ 07747
$319,000

2 beds

|

2 baths

7 KANSAS CT, OLD BRIDGE TWP., NJ, 07747
Community: Cheesequake Village
Four Seasons at Cedar Grove 706 HOLLY LN, CEDAR GROVE TWP., NJ, 0700..., Cedar Grove Twp., NJ 07009
$749,900

2 beds

|

2 baths

706 HOLLY LN, CEDAR GROVE TWP., NJ, 0700...
Cheesequake Village 7 KANSAS CT, OLD BRIDGE, NJ, 07747, Old Bridge, NJ 07747
$319,000

2 beds

|

2 baths

|

976 sq ft

|

Townhouse,Condominium

7 KANSAS CT, OLD BRIDGE, NJ, 07747
Community: Cheesequake Village
Oronoque Village 377 PIUTE LN A, STRATFORD, CT, 06614, Stratford, CT 06614
$499,000

1 beds

|

3 baths

|

2,025 sq ft

|

Condo

377 PIUTE LN A, STRATFORD, CT, 06614
Community: Oronoque Village
Knickerbocker Bay Club 433 MAIN ST 212, NORTH HEMPSTEAD, NY, 11..., North Hempstead, NY 11050
$2,300,000

3 beds

|

3 baths

|

2,544 sq ft

|

Condo

433 MAIN ST 212, NORTH HEMPSTEAD, NY, 11...
Leisure Glen 12 BALDWIN CT, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$469,990

2 beds

|

2 baths

|

1,542 sq ft

|

Condo

12 BALDWIN CT, BROOKHAVEN, NY, 11961
Community: Leisure Glen
The Villages at Mount Sinai Park 16 OAKHURST CT, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766
$789,000

2 beds

|

2 baths

|

1,929 sq ft

|

House

16 OAKHURST CT, BROOKHAVEN, NY, 11766
The Villages NJ 24 CALLE DE ELVIRA B, FREEHOLD, NJ, 0772..., Freehold, NJ 07728
$415,000

2 beds

|

2 baths

|

1,144 sq ft

|

House

24 CALLE DE ELVIRA B, FREEHOLD, NJ, 0772...
Community: The Villages NJ
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
The Waterways at Moriches 485 WOODSCREEK CT, BROOKHAVEN, NY, 11955, Brookhaven, NY 11955
$778,000

2 beds

|

3 baths

|

1,854 sq ft

|

Condo

485 WOODSCREEK CT, BROOKHAVEN, NY, 11955
Leisure Village 404 WOODBRIDGE RD B, BROOKHAVEN, NY, 119..., Brookhaven, NY 11961
$359,900

2 beds

|

1 baths

|

907 sq ft

|

Condo

404 WOODBRIDGE RD B, BROOKHAVEN, NY, 119...
Community: Leisure 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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