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

170 communities near Westport

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Beckley Farms
$300ks - $400ks
Beckley Farms, Berlin, CT
New and Resale | 55+ age-restricted | Built 2010 - present | 170 homes
Castle Heights of Cheshir...
$500ks - $600ks
Castle Heights of Cheshir..., Cheshire, CT
Resale Only | 55+ age-restricted | Built 2007 - 2022 | 88 homes
4.9 rating (14 reviews) Chatfield Farms
$400ks - $700ks
Chatfield Farms, Beacon Falls, CT
New Construction | 55+ age-restricted | Built 2014 - present | 231 homes
Chimney Hill
$500ks - $700ks
Chimney Hill, Farmington, CT
Resale Only | 55+ age-restricted | Built 2006 - 2013 | 44 homes
RiverWalk
$500ks - $600ks
RiverWalk, Branford, CT
New and Resale | 55+ age-restricted | Built 2007 - present | 60 homes
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
Newington Ridge Preserve
$300ks - $400ks
Newington Ridge Preserve, Newington, CT
New Construction | 55+ age-restricted | Built 2014 - present | 16 homes
Baldwin Station
$400ks
Baldwin Station, Milford, CT
Resale Only | 55+ age-restricted | Built 2001 - 2003 | 82 homes
5 rating (3 reviews) Founders Ridge
$300ks - $400ks
Founders Ridge, Middletown, CT
New Construction | 55+ age-restricted | Built 2017 - present | 75 homes
77 Sunset Lane
$400ks - $700ks
77 Sunset Lane, Ridgefield, CT
Resale Only | 55+ age-restricted | Built 2016 - 2018 | 54 homes
Bartlett Hollow
$200ks - $400ks
Bartlett Hollow, Middletown, CT
New Construction | 55+ age-restricted | Built 2015 - present | 25 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.
Autumn Estates
$500ks - $600ks
Autumn Estates, Farmington, CT
Resale Only | 55+ age-restricted | Built 2011 - 2017 | 30 homes
The Atrium of Portland
<$100k
The Atrium of Portland, Portland, CT
Resale Only | 55+ age-restricted | Built 2004 - 2004 | 56 homes
Billingsgate
$400ks - $600ks
Billingsgate, Simsbury, CT
Resale Only | 55+ age-restricted | Built 2003 - 2006 | 37 homes
Boulder Brook
$200ks
Boulder Brook, Prospect, CT
Resale Only | 55+ age-restricted | Built 2004 - 2006 | 35 homes
Gloria Commons
$200ks - $300ks
Gloria Commons, Milford, CT
Resale Only | 55+ age-restricted | Built 2007 - 2015 | 50 homes
Hopmeadow Place
$200ks - $300ks
Hopmeadow Place, Simsbury, CT
Resale Only | 55+ age-restricted | Built 2005 - 2005 | 66 homes
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
Long Hill Village
$300ks - $400ks
Long Hill Village, Trumbull, CT
Resale Only | 55+ age-restricted | Built 1997 - 1999 | 71 homes
Oak Meadow Estates
$200ks - $300ks
Oak Meadow Estates, Torrington, CT
New and Resale | 55+ age-restricted | Built 2013 - present | 31 homes
Park Glen
$300ks - $500ks
Park Glen, New Milford, CT
Resale Only | 55+ age-restricted | Built 2006 - 2015 | 17 homes
RiverBend Estates
$400ks
RiverBend Estates, Oxford, CT
New and Resale | 55+ age-restricted | Built 2012 - present | 25 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.
Summer Wind Estates
$300ks - $400ks
Summer Wind Estates, North Haven, CT
New Construction | 55+ age-restricted | Built 2015 - present | 18 homes
The Woods at Dunham Pond
$200ks - $400ks
The Woods at Dunham Pond, New Fairfield, CT
Resale Only | 55+ age-restricted | Built 2004 - 2015 | 33 homes
Forest Mews
$300ks - $400ks
Forest Mews, Avon, CT
Resale Only | 55+ age-restricted | Built 2001 - 2004 | 40 homes
The Village at Hunt Glen
$300ks
The Village at Hunt Glen, Granby, CT
Resale Only | 55+ age-restricted | Built 2003 - 2006 | 69 homes
O'Meara Farm
$400ks
O'Meara Farm, Farmington, CT
Resale Only | 55+ age-restricted | Built 1998 - 2005 | 104 homes
The Coach Homes at Ridgef...
$300ks - $400ks
The Coach Homes at Ridgef..., Ridgefield, CT
New Construction | 55+ age-restricted | Built 2019 - present | 30 homes
Evergreen
$400ks - $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
Whitney Glen
$500ks - $600ks
Whitney Glen, Westport, CT
Resale Only | 55+ age-restricted | Built 1982 - 1982 | 62 homes
Shaker Heights
$400ks - $500ks
Shaker Heights, Enfield, CT
New Construction | 55+ age-restricted | Built 2018 - present | 77 homes
Bramble Ridge
$300ks
Bramble Ridge, Suffield, CT
Resale Only | 55+ age-restricted | Built 2005 - 2015 | 47 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.
Autumn Fields
$200ks - $300ks
Autumn Fields, Enfield, CT
Resale Only | 55+ age-restricted | Built 2004 - 2006 | 56 homes
Vineyards at Moriches
$500ks - $600ks
Vineyards at Moriches, Center Moriches, NY
Resale Only | 55+ age-restricted | Built 2008 - 2014 | 92 homes
The Retreat at Carmel
$300ks - $800ks
The Retreat at Carmel, Carmel, NY
Resale Only | 55+ age-restricted | Built 2008 - 2018 | 312 homes
Eastport Meadows
$400ks
Eastport Meadows, Eastport, NY
Resale Only | 55+ age-restricted | Built 2009 - 2016 | 50 homes
Stoneleigh Woods at Carme...
$400ks
Stoneleigh Woods at Carme..., Carmel, NY
Resale Only | 55+ age-restricted | Built 2012 - 2017 | 68 homes
Saddle Lakes
$400ks - $500ks
Saddle Lakes, Riverhead, NY
Resale Only | 55+ age-restricted | Built 2000 - 2002 | 196 homes
The Seasons at Plainview
$500ks - $600ks
The Seasons at Plainview, Plainview, NY
Resale Only | 55+ age-restricted | Built 2006 - 2007 | 134 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
Woodcrest at Jacobs Hill
$200ks - $300ks
Woodcrest at Jacobs Hill, Cortlandt, NY
Resale Only | 55+ age-restricted | Built 2005 - 2006 | 58 homes
Strathmore Gate East
$300ks
Strathmore Gate East, Coram, NY
Resale Only | 55+ age-restricted | Built 1970 - 1975 | 174 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.
Heritage Hills 567 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589
$469,900

1 beds

|

2 baths

|

967 sq ft

|

Condo

567 HERITAGE HLS B, SOMERS, NY, 10589
Community: Heritage Hills
Greenwood Village 19 DOGWOOD LN, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949
$105,900

2 beds

|

2 baths

|

871 sq ft

|

Condo

19 DOGWOOD LN, BROOKHAVEN, NY, 11949
Community: Greenwood Village
New The Village at Oxford Greens 527 PUTTING GREEN LN 527, OXFORD, CT, 06..., Oxford, CT 06478
$699,000

3 beds

|

3 baths

|

2,008 sq ft

|

Condo

527 PUTTING GREEN LN 527, OXFORD, CT, 06...
New Heritage Hills 758 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589
$875,000

3 beds

|

2 baths

|

2,030 sq ft

|

Condo

758 HERITAGE HLS B, SOMERS, NY, 10589
Community: Heritage Hills
New The Greens at Half Hollow 698 BALFOUR PL, HUNTINGTON, NY, 11747, Huntington, NY 11747
$1,099,000

2 beds

|

3 baths

|

1,941 sq ft

|

Condo

698 BALFOUR PL, HUNTINGTON, NY, 11747
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
New The Greens at Half Hollow 1165 SAVOY DR, HUNTINGTON, NY, 11747, Huntington, NY 11747
$749,000

2 beds

|

2 baths

|

1,159 sq ft

|

Condo

1165 SAVOY DR, HUNTINGTON, NY, 11747
New Regency at Prospect 10 ASH LN 10, PROSPECT, CT, 06712, Prospect, CT 06712
$539,000

2 beds

|

3 baths

|

1,928 sq ft

|

Condo

10 ASH LN 10, PROSPECT, CT, 06712
Community: Regency at Prospect
New Oronoque Village 493 PAWNEE LN B, STRATFORD, CT, 06614, Stratford, CT 06614
$425,000

1 beds

|

3 baths

|

1,175 sq ft

|

Condo

493 PAWNEE LN B, STRATFORD, CT, 06614
Community: Oronoque Village
New Regency at Fishkill 811 REGENCY DR 802, FISHKILL, NY, 12524, Fishkill, NY 12524
$161,450

2 beds

|

2 baths

|

1,100 sq ft

|

Condo

811 REGENCY DR 802, FISHKILL, NY, 12524
Community: Regency at Fishkill
New Newtown Woods 1011 BROOKSIDE CT 1011, NEWTOWN, CT, 064..., Newtown, CT 06470
$500,000

2 beds

|

2 baths

|

1,483 sq ft

|

Condo

1011 BROOKSIDE CT 1011, NEWTOWN, CT, 064...
Community: Newtown Woods
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.
New Kensington Estates 238 COACH DR 56, OYSTER BAY, NY, 11797, Oyster Bay, NY 11797
$2,100,000

3 beds

|

4 baths

|

2,662 sq ft

|

Condo

238 COACH DR 56, OYSTER BAY, NY, 11797
Community: Kensington Estates
New Cheesequake Village 21 IOWA CT, OLD BRIDGE, NJ, 07747, Old Bridge, NJ 07747
$250,000

2 beds

|

2 baths

|

976 sq ft

|

Townhouse,Condominium

21 IOWA CT, OLD BRIDGE, NJ, 07747
Community: Cheesequake Village
New Glassbury Court at Cold Spring 28 YESTERDAY DR, PHILIPSTOWN, NY, 10516, Philipstown, NY 10516
$690,000

2 beds

|

2 baths

|

2,071 sq ft

|

House

28 YESTERDAY DR, PHILIPSTOWN, NY, 10516
New Four Seasons at Great Notch Spa and Club 5 SLATE CT A3, WOODLAND PARK, NJ, 07424, Woodland Park, NJ 07424
$615,000

2 beds

|

2 baths

|

Condo

5 SLATE CT A3, WOODLAND PARK, NJ, 07424
New Heritage Village 18 HERITAGE CRST D, SOUTHBURY, CT, 06488, Southbury, CT 06488
$474,981

3 beds

|

2 baths

|

1,735 sq ft

|

Condo

18 HERITAGE CRST D, SOUTHBURY, CT, 06488
Community: Heritage Village
New Fairview at Oxford Greens 1131 ST ANDREWS DR 50, OXFORD, CT, 06478, Oxford, CT 06478
$713,775

2 beds

|

3 baths

|

2,536 sq ft

|

Condo

1131 ST ANDREWS DR 50, OXFORD, CT, 06478
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
New The Village at Oxford Greens 1131 ST ANDREWS DR 50, OXFORD, CT, 06478, Oxford, CT 06478
$713,775

2 beds

|

3 baths

|

2,536 sq ft

|

Condo

1131 ST ANDREWS DR 50, OXFORD, CT, 06478
New Country Village Estates 114 THEODORE DR, BROOKHAVEN, NY, 11727, Brookhaven, NY 11727
$449,000

2 beds

|

2 baths

|

1,198 sq ft

|

Condo

114 THEODORE DR, BROOKHAVEN, NY, 11727
New The Seasons at Seaford 54 SPRING DR, HEMPSTEAD, NY, 11783, Hempstead, NY 11783
$819,000

2 beds

|

2 baths

|

1,034 sq ft

|

Condo

54 SPRING DR, HEMPSTEAD, NY, 11783
New Heritage Village 28 HERITAGE CRST E, SOUTHBURY, CT, 06488, Southbury, CT 06488
$615,000

3 beds

|

2 baths

|

1,735 sq ft

|

Condo

28 HERITAGE CRST E, 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.
New Sunken Pond Estates 2201 PEBBLE BEACH PATH 2201, RIVERHEAD, ..., Riverhead, NY 11901
$549,900

2 beds

|

2 baths

|

1,258 sq ft

|

Condo

2201 PEBBLE BEACH PATH 2201, RIVERHEAD, ...
Community: Sunken Pond Estates
New Encore Atlantic Shores 177 MELODY CT, BROOKHAVEN, NY, 11941, Brookhaven, NY 11941
$765,000

2 beds

|

2 baths

|

2,150 sq ft

|

Condo

177 MELODY CT, BROOKHAVEN, NY, 11941
New The Village Grande at Holmdel 22 HYACINTH CT, HOLMDEL, NJ, 07733, Holmdel, NJ 07733
$925,000

2 beds

|

3 baths

|

2,273 sq ft

|

House

22 HYACINTH CT, HOLMDEL, NJ, 07733
New Paris Square 1302 RIO VISTA LN, NORTHVALE, NJ, 07647, Northvale, NJ 07647
$750,000

3 beds

|

2 baths

|

Condo

1302 RIO VISTA LN, NORTHVALE, NJ, 07647
Community: Paris Square
New Shadow Lake Village 46 FRIENDSHIP CT, RED BANK, NJ, 07701, Red Bank, NJ 07701
$599,000

2 beds

|

2 baths

|

1,108 sq ft

|

House

46 FRIENDSHIP CT, RED BANK, NJ, 07701
Community: Shadow Lake Village
New The Seasons at East Meadow 115 SPRING DR, HEMPSTEAD, NY, 11554, Hempstead, NY 11554
$615,000

2 beds

|

2 baths

|

1,367 sq ft

|

Condo

115 SPRING DR, HEMPSTEAD, NY, 11554
The Waterways at Moriches 376 QUARRY POND CT, BROOKHAVEN, NY, 1195..., Brookhaven, NY 11955
$519,000

2 beds

|

2 baths

|

1,440 sq ft

|

Condo

376 QUARRY POND CT, BROOKHAVEN, NY, 1195...
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
Meadowbrook Pointe Athletic Club & Spa 236 ROOSEVELT WAY 3306, HEMPSTEAD, NY, 1..., Hempstead, NY 11590
$910,000

2 beds

|

2 baths

|

1,349 sq ft

|

Condo

236 ROOSEVELT WAY 3306, HEMPSTEAD, NY, 1...
Cheesequake Village 67 GALEWOOD DR B, OLD BRIDGE, NJ, 07747, Old Bridge, NJ 07747
$330,000

2 beds

|

1 baths

|

Condo

67 GALEWOOD DR B, OLD BRIDGE, NJ, 07747
Community: Cheesequake Village
The Waterways at Moriches 519 HIGHLAND CT, BROOKHAVEN, NY, 11955, Brookhaven, NY 11955
$610,000

2 beds

|

2 baths

|

1,497 sq ft

|

Condo

519 HIGHLAND CT, 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.
Fairfield at St. James 409 ELTON CT, SMITHTOWN, NY, 11780, Smithtown, NY 11780
$649,000

3 beds

|

3 baths

|

1,733 sq ft

|

Condo

409 ELTON CT, SMITHTOWN, NY, 11780
Winthrop Court 9104 RAVENSCROFT RD, CLIFTON CITY, NJ, 0..., Clifton City, NJ 07013
$525,000

2 beds

|

2 baths

9104 RAVENSCROFT RD, CLIFTON CITY, NJ, 0...
Community: Winthrop Court
Country Pointe Plainview 15103 ASPENWOOD DR, OYSTER BAY, NY, 1180..., Oyster Bay, NY 11803
$1,075,000

2 beds

|

2 baths

|

1,335 sq ft

|

Condo

15103 ASPENWOOD DR, OYSTER BAY, NY, 1180...
Jefferson Village 51 JEFFERSON OVAL E, YORKTOWN, NY, 10598, Yorktown, NY 10598
$455,000

2 beds

|

2 baths

|

1,100 sq ft

|

Condo

51 JEFFERSON OVAL E, YORKTOWN, NY, 10598
Community: Jefferson Village
Oronoque Village 44 BUCKSKIN LN A, STRATFORD, CT, 06614, Stratford, CT 06614
$599,000

2 beds

|

2 baths

|

1,400 sq ft

|

Condo

44 BUCKSKIN LN A, STRATFORD, CT, 06614
Community: Oronoque Village
Cheesequake Village 67 GALEWOOD DR B, MATAWAN, NJ, 07747, Matawan, NJ 07747
$330,000

2 beds

|

1 baths

|

914 sq ft

|

Adult Community

67 GALEWOOD DR B, MATAWAN, NJ, 07747
Community: Cheesequake Village
The Vineyards at Mount Sinai 51 FARM ACRE CIR, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766
$1,085,000

2 beds

|

3 baths

|

3,214 sq ft

|

Condo

51 FARM ACRE CIR, BROOKHAVEN, NY, 11766
Heritage Village 29 HERITAGE VLG D, SOUTHBURY, CT, 06488, Southbury, CT 06488
$315,000

2 beds

|

2 baths

|

1,076 sq ft

|

Condo

29 HERITAGE VLG D, SOUTHBURY, CT, 06488
Community: Heritage Village
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
Oronoque Village 513 OPA LN A, STRATFORD, CT, 06614, Stratford, CT 06614
$584,900

2 beds

|

3 baths

|

1,620 sq ft

|

Condo

513 OPA LN A, STRATFORD, CT, 06614
Community: Oronoque Village
Heritage Hills 900 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589
$742,000

2 beds

|

3 baths

|

1,552 sq ft

|

Condo

900 HERITAGE HLS B, SOMERS, NY, 10589
Community: Heritage Hills
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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