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Westport, CT 55+ active adult communities & homes for sale - Page 3

170 communities near Westport

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Eagles Walk at East Quogu...
$300ks - $400ks
Eagles Walk at East Quogu..., East Quogue, NY
Resale Only | 55+ age-restricted | Built 2004 - 2014 | 67 homes
The Seasons at Elwood
$800ks - $900ks
The Seasons at Elwood, East Northport, NY
Resale Only | 55+ age-restricted | Built 2018 - 2020 | 256 homes
Vineyards at Brookfield
$400ks - $500ks
Vineyards at Brookfield, Center Moriches, NY
New Construction | 55+ age-restricted | Built 2019 - present | 146 homes
The Vineyards at Mount Si...
$800ks - $1Ms
The Vineyards at Mount Si..., Mount Sinai, NY
New Construction | 55+ age-restricted | Built 2020 - present | 91 homes
Regency at Prospect
$300ks - $400ks
Regency at Prospect, Prospect, CT
Resale Only | 55+ age-restricted | Built 2006 - 2020 | 379 homes
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
The Summit at Bethel
$500ks - $700ks
The Summit at Bethel, Bethel, CT
Resale Only | 55+ age-restricted | Built 2010 - 2021 | 235 homes
Bartlett Hill
$300ks - $400ks
Bartlett Hill, Portland, CT
Resale Only | 55+ age-restricted | Built 2005 - 2011 | 82 homes
Pond Spring Village
$300ks
Pond Spring Village, Beacon Falls, CT
New and Resale | 55+ age-restricted | Built 2005 - present | 92 homes
Baldwin Station
$400ks
Baldwin Station, Milford, CT
Resale Only | 55+ age-restricted | Built 2001 - 2003 | 82 homes
Oak Meadow Estates
$200ks - $300ks
Oak Meadow Estates, Torrington, CT
New and Resale | 55+ age-restricted | Built 2013 - present | 31 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 Meadows
$500ks
Regency Meadows, Trumbull, CT
Resale Only | 55+ age-restricted | Built 2003 - 2005 | 51 homes
South Pond Village
$300ks - $400ks
South Pond Village, Bloomfield, CT
Resale Only | 55+ age-restricted | Built 1999 - 2005 | 151 homes
The Powder Forest Homes
$500ks - $700ks
The Powder Forest Homes, Simsbury, CT
Resale Only | 55+ age-restricted | Built 2006 - 2016 | 182 homes
Billingsgate
$400ks - $600ks
Billingsgate, Simsbury, CT
Resale Only | 55+ age-restricted | Built 2003 - 2006 | 37 homes
Windcrest East
$400ks - $500ks
Windcrest East, Calverton, NY
Resale Only | 55+ age-restricted | Built 2004 - 2005 | 126 homes
Park Glen
$300ks - $500ks
Park Glen, New Milford, CT
Resale Only | 55+ age-restricted | Built 2006 - 2015 | 17 homes
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
RiverBend Estates
$400ks
RiverBend Estates, Oxford, CT
New and Resale | 55+ age-restricted | Built 2012 - present | 25 homes
Summer Wind Estates
$300ks - $400ks
Summer Wind Estates, North Haven, CT
New Construction | 55+ age-restricted | Built 2015 - present | 18 homes
5 rating (1 reviews) Enclave at Ocean
$900ks
Enclave at Ocean, Tinton Falls, NJ
Resale Only | 55+ age-restricted | Built 2017 - 2022 | 75 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
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 Club at Melville
$500ks
The Club at Melville, Melville, NY
Resale Only | 55+ age-restricted | Built 2015 - 2017 | 261 homes
The Seasons at Seaford
$600ks
The Seasons at Seaford, Seaford, NY
Resale Only | 55+ age-restricted | Built 2015 - 2017 | 112 homes
The Village at Hunt Glen
$300ks
The Village at Hunt Glen, Granby, CT
Resale Only | 55+ age-restricted | Built 2003 - 2006 | 69 homes
Shaker Heights
$400ks - $500ks
Shaker Heights, Enfield, CT
New Construction | 55+ age-restricted | Built 2018 - present | 77 homes
3.5 rating (2 reviews) Harvest Pointe
$800ks - $3Ms
Harvest Pointe, Cutchogue, NY
New Construction | 55+ age-restricted | Built 2017 - present | 124 homes
Forest Mews
$300ks - $400ks
Forest Mews, Avon, CT
Resale Only | 55+ age-restricted | Built 2001 - 2004 | 40 homes
Kensington Estates
$1Ms
Kensington Estates, Woodbury, NY
New Construction | 55+ age-restricted | Built 2019 - 2021 | 80 homes
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
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
Jessup's Landing
$1Ms
Jessup's Landing, Quogue, NY
New and Resale | 55+ age-restricted | Built 2009 - 2016 | 31 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.
Hidden Harbor Estates
$500ks - $600ks
Hidden Harbor Estates, Copiague, NY
Resale Only | 55+ age-restricted | Built 2010 - 2015 | 38 homes
5 rating (1 reviews) Paris Square
$500ks - $700ks
Paris Square, Northvale, NJ
New and Resale | 55+ age-restricted | Built 2000 - present | 88 homes
Evergreen
$400ks - $500ks
Evergreen, Cromwell, CT
New and Resale | 55+ age-restricted | Built 2005 - present | 52 homes
The Pines at Bohemia
$400ks - $500ks
The Pines at Bohemia, Bohemia, NY
New Construction | 55+ age-restricted | Built 2019 - present | 20 homes
The Polo Club at Islandia
$600ks - $700ks
The Polo Club at Islandia, Islandia, NY
New Construction | 55+ age-restricted | Built 2019 - present | 72 homes
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
Stratford Park
$600ks - $800ks
Stratford Park, Melville, NY
Resale Only | 55+ age-restricted | Built 2011 - 2013 | 36 homes
Bear's Cove
$800ks - $900ks
Bear's Cove, Ramsey, NJ
Resale Only | 55+ age-restricted | Built 2006 - 2014 | 104 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
5 rating (2 reviews) Benson Woods
$400ks - $600ks
Benson Woods, Middlebury, CT
New and Resale | 55+ age-restricted | Built 2004 - present | 79 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.
New Greenwood Village 105 W VILLAGE CIR 105, BROOKHAVEN, NY, 1..., Brookhaven, NY 11949
$245,000

2 beds

|

2 baths

|

1,130 sq ft

|

Condo

105 W VILLAGE CIR 105, BROOKHAVEN, NY, 1...
Community: Greenwood Village
The Villages NJ 41 PIAZZA SAN PAOLA C, FREEHOLD, NJ, 077..., Freehold, NJ 07728
$410,000

2 beds

|

2 baths

|

1,008 sq ft

|

Ranch

41 PIAZZA SAN PAOLA C, FREEHOLD, NJ, 077...
Community: The Villages NJ
Glenwood Village 1661 OLD COUNTRY RD 516, RIVERHEAD, NY, ..., Riverhead, NY 11901
$419,000

2 beds

|

2 baths

|

1,624 sq ft

|

Manufactured Home

1661 OLD COUNTRY RD 516, RIVERHEAD, NY, ...
Community: Glenwood Village
New Village Estates 130 FRANCESCA WAY, BABYLON, NY, 11701, Babylon, NY 11701
$639,000

2 beds

|

2 baths

|

1,243 sq ft

|

Condo

130 FRANCESCA WAY, BABYLON, NY, 11701
Community: Village Estates
New Jefferson Village 90 MOLLY PITCHER LN F, YORKTOWN, NY, 105..., Yorktown, NY 10598
$359,900

1 beds

|

1 baths

|

800 sq ft

|

Condo

90 MOLLY PITCHER LN F, YORKTOWN, NY, 105...
Community: Jefferson Village
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
New Eagles Walk at East Quogue 1204 AERIE WAY 1204, SOUTHAMPTON, NY, 11..., Southampton, NY 11942
$565,000

2 beds

|

2 baths

|

1,341 sq ft

|

Condo

1204 AERIE WAY 1204, SOUTHAMPTON, NY, 11...
New Cheesequake Village 10 HAVEN DR B, MATAWAN, NJ, 07747, Matawan, NJ 07747
$283,000

1 beds

|

1 baths

|

664 sq ft

|

Adult Community

10 HAVEN DR B, MATAWAN, NJ, 07747
Community: Cheesequake Village
New Woodridge Strathmore Terrace 89 STANDISH DR, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766
$500,000

2 beds

|

2 baths

|

1,240 sq ft

|

House

89 STANDISH DR, BROOKHAVEN, NY, 11766
New Jefferson Village 149 FLINTLOCK WAY E, YORKTOWN, NY, 10598, Yorktown, NY 10598
$375,000

1 beds

|

1 baths

|

853 sq ft

|

Condo

149 FLINTLOCK WAY E, YORKTOWN, NY, 10598
Community: Jefferson Village
New Leisure Village 231 BLACKPOOL CT, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$299,000

2 beds

|

1 baths

|

836 sq ft

|

Condo

231 BLACKPOOL CT, BROOKHAVEN, NY, 11961
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.
New The Greens at Half Hollow 742 VERONA DR, HUNTINGTON, NY, 11747, Huntington, NY 11747
$1,099,000

2 beds

|

3 baths

|

1,940 sq ft

|

Condo

742 VERONA DR, HUNTINGTON, NY, 11747
New Dutchgate 301 WILLOW LN, HEMPSTEAD, NY, 11580, Hempstead, NY 11580
$510,000

2 beds

|

2 baths

|

941 sq ft

|

Condo

301 WILLOW LN, HEMPSTEAD, NY, 11580
Community: Dutchgate
New Overlook 4095 FAIRWAYS DR 148, CARMEL, NY, 10512, Carmel, NY 10512
$699,000

3 beds

|

3 baths

|

1,914 sq ft

|

Condo

4095 FAIRWAYS DR 148, CARMEL, NY, 10512
Community: Overlook
New Heritage Hills 241 HERITAGE HLS D, SOMERS, NY, 10589, Somers, NY 10589
$499,900

2 beds

|

2 baths

|

1,138 sq ft

|

Condo

241 HERITAGE HLS D, SOMERS, NY, 10589
Community: Heritage Hills
New Four Seasons at Great Notch Spa and Club 8 PEBBLE RD C2, WOODLAND PARK, NJ, 07424, Woodland Park, NJ 07424
$699,900

2 beds

|

2 baths

|

Townhouse

8 PEBBLE RD C2, WOODLAND PARK, NJ, 07424
New Country Pointe Plainview 52102 BEECH TREE LN, OYSTER BAY, NY, 118..., Oyster Bay, NY 11803
$1,649,990

2 beds

|

3 baths

|

1,750 sq ft

|

Condo

52102 BEECH TREE LN, OYSTER BAY, NY, 118...
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
New Encore Atlantic Shores 216 SONATA CT, BROOKHAVEN, NY, 11941, Brookhaven, NY 11941
$899,000

2 beds

|

3 baths

|

2,439 sq ft

|

Condo

216 SONATA CT, BROOKHAVEN, NY, 11941
New The Waterways at Moriches 132 CAPTAINS CT, BROOKHAVEN, NY, 11955, Brookhaven, NY 11955
$550,000

2 beds

|

2 baths

|

1,544 sq ft

|

Condo

132 CAPTAINS CT, BROOKHAVEN, NY, 11955
New Vineyards at Blue Point 37 HALLEY DR 17, BROOKHAVEN, NY, 11772, Brookhaven, NY 11772
$660,000

2 beds

|

2 baths

|

1,220 sq ft

|

Condo

37 HALLEY DR 17, BROOKHAVEN, NY, 11772
New Surrey Downs 39 DATCHET CLOSE, FREEHOLD, NJ, 07728, Freehold, NJ 07728
$445,000

2 beds

|

2 baths

|

1,146 sq ft

|

Ranch

39 DATCHET CLOSE, FREEHOLD, NJ, 07728
Community: Surrey Downs
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.
Woodridge Strathmore Terrace 32 CHIPPENDALE DR, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766
$579,999

2 beds

|

2 baths

|

1,501 sq ft

|

Condo

32 CHIPPENDALE DR, BROOKHAVEN, NY, 11766
Heritage Village 786 HERITAGE VLG C, SOUTHBURY, CT, 06488, Southbury, CT 06488
$200,000

2 beds

|

2 baths

|

1,000 sq ft

|

Condo

786 HERITAGE VLG C, SOUTHBURY, CT, 06488
Community: Heritage Village
Newtown Woods 1227 BROOKSIDE CT 1227, NEWTOWN, CT, 064..., Newtown, CT 06470
$500,000

2 beds

|

2 baths

|

1,483 sq ft

|

Condo

1227 BROOKSIDE CT 1227, NEWTOWN, CT, 064...
Community: Newtown Woods
Newtown Woods 23 WOODS LN 23, NEWTOWN, CT, 06470, Newtown, CT 06470
$600,000

2 beds

|

3 baths

|

2,073 sq ft

|

Condo

23 WOODS LN 23, NEWTOWN, CT, 06470
Community: Newtown Woods
Greenwood Village 5127 VILLAGE CIR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949
$227,000

2 beds

|

2 baths

|

1,291 sq ft

|

Condo

5127 VILLAGE CIR, BROOKHAVEN, NY, 11949
Community: Greenwood Village
HarborView 100 HARBOR VIEW DR 335, NORTH HEMPSTEAD,..., North Hempstead, NY 11050
$1,199,000

3 beds

|

3 baths

|

2,216 sq ft

|

Condo

100 HARBOR VIEW DR 335, NORTH HEMPSTEAD,...
Community: HarborView
HarborView 123 LINKS CT, NORTH HEMPSTEAD, NY, 11050, North Hempstead, NY 11050
$1,299,000

3 beds

|

3 baths

|

2,160 sq ft

|

Condo

123 LINKS CT, NORTH HEMPSTEAD, NY, 11050
Community: HarborView
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
Heritage Village 581 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$350,000

2 beds

|

2 baths

|

1,398 sq ft

|

Condo

581 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Rosemont Estates 207 BRADWICK WAY, MARLBORO, NJ, 07746, Marlboro, NJ 07746
$960,000

2 beds

|

3 baths

|

2,551 sq ft

|

House

207 BRADWICK WAY, MARLBORO, NJ, 07746
Community: Rosemont Estates
Jefferson Village 56 KIRBY CLOSE B, YORKTOWN, NY, 10598, Yorktown, NY 10598
$489,500

2 beds

|

2 baths

|

970 sq ft

|

Condo

56 KIRBY CLOSE B, YORKTOWN, NY, 10598
Community: Jefferson 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.
Cheesequake Village 11 ALABAMA CT, OLD BRIDGE, NJ, 07747, Old Bridge, NJ 07747
$335,000

2 beds

|

2 baths

|

Townhouse,Condominium

11 ALABAMA CT, OLD BRIDGE, NJ, 07747
Community: Cheesequake Village
Cheesequake Village 11 ALABAMA CT 835, MATAWAN, NJ, 07747, Matawan, NJ 07747
$335,000

2 beds

|

2 baths

|

976 sq ft

|

Adult Community

11 ALABAMA CT 835, MATAWAN, NJ, 07747
Community: Cheesequake Village
Cheesequake Village 72 HAVEN DR D, MATAWAN, NJ, 07747, Matawan, NJ 07747
$310,000

2 beds

|

1 baths

|

949 sq ft

|

Adult Community

72 HAVEN DR D, MATAWAN, NJ, 07747
Community: Cheesequake Village
Cheesequake Village 72-D HAVEN DR 500, OLD BRIDGE, NJ, 07747, Old Bridge, NJ 07747
$310,000

2 beds

|

1 baths

|

Condo

72-D HAVEN DR 500, OLD BRIDGE, NJ, 07747
Community: Cheesequake Village
Heritage Hills 828 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589
$650,000

2 beds

|

2 baths

|

1,296 sq ft

|

Condo

828 HERITAGE HLS B, SOMERS, NY, 10589
Community: Heritage Hills
Windcrest East 5 GREEN ASH ST, RIVERHEAD, NY, 11933, Riverhead, NY 11933
$775,000

3 beds

|

3 baths

|

2,449 sq ft

|

House

5 GREEN ASH ST, RIVERHEAD, NY, 11933
Community: Windcrest East
Oronoque Village 212 AGAWAM DR B, STRATFORD, CT, 06614, Stratford, CT 06614
$319,000

1 beds

|

2 baths

|

1,426 sq ft

|

Condo

212 AGAWAM DR B, STRATFORD, CT, 06614
Community: Oronoque Village
The Views at Pomona 2202 VIEWS WAY, RAMAPO, NY, 10970, Ramapo, NY 10970
$469,000

2 beds

|

2 baths

|

1,360 sq ft

|

Condo

2202 VIEWS WAY, RAMAPO, NY, 10970
Community: The Views at Pomona
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
Oronoque Village 383 SEQUOIA LN B, STRATFORD, CT, 06614, Stratford, CT 06614
$485,000

1 beds

|

3 baths

|

1,360 sq ft

|

Condo

383 SEQUOIA LN B, STRATFORD, CT, 06614
Community: Oronoque Village
Glassbury Court at Cold Spring 1 MAGGIE MAY WAY, PHILIPSTOWN, NY, 10516, Philipstown, NY 10516
$715,000

2 beds

|

2 baths

|

1,974 sq ft

|

House

1 MAGGIE MAY WAY, PHILIPSTOWN, NY, 10516
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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