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

393 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
2.8 rating (4 reviews) Cheesequake Village
$100ks - $200ks
Cheesequake Village, Old Bridge, NJ
Resale Only | 55+ age-restricted | Built 1965 - 1971 | 713 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
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
5 rating (2 reviews) Oronoque Village
$200ks - $400ks
Oronoque Village, Stratford, CT
Resale Only | 55+ age-restricted | Built 1971 - 1977 | 929 homes
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
3 rating (2 reviews) Heritage Hills
$400ks - $800ks
Heritage Hills, Somers, NY
Resale Only | Age-targeted | Built 1974 - 2006 | 2,600 homes
3.7 rating (3 reviews) Greenwood Village
$100ks
Greenwood Village, Manorville, NY
Resale Only | 55+ age-restricted | Built 1980 - 2000 | 512 homes
4 rating (8 reviews) Glenwood Village
$100ks - $200ks
Glenwood Village, Riverhead, NY
New and Resale | 55+ age-restricted | Built 1959 - present | 588 homes
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
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
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 Waterways at Moriches
$300ks - $600ks
The Waterways at Moriches, Moriches, NY
Resale Only | 55+ age-restricted | Built 1985 - 1999 | 343 homes
4.2 rating (12 reviews) Surrey Downs
$200ks - $300ks
Surrey Downs, Freehold, NJ
Resale Only | 55+ age-restricted | Built 1986 - 1997 | 443 homes
Leisure Village
$100ks - $300ks
Leisure Village, Ridge, NY
Resale Only | 55+ age-restricted | Built 1969 - 1986 | 1,500 homes
Country Pointe Plainview
$700ks - $1Ms
Country Pointe Plainview, Plainview, NY
New Construction | 55+ age-restricted | Built 2017 - present | 660 homes
Leisure Glen
$300ks - $400ks
Leisure Glen, Ridge, NY
Resale Only | 55+ age-restricted | Built 1985 - 2010 | 646 homes
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
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
Rivington
$300ks - $900ks
Rivington, Danbury, CT
New and Resale | Age-targeted | Built 2006 - present | 1,050 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
HarborView
$600ks - $1Ms
HarborView, Port Washington, NY
Resale Only | 55+ age-restricted | Built 2002 - 2004 | 270 homes
Leisure Knoll
$200ks - $400ks
Leisure Knoll, Ridge, NY
Resale Only | 55+ age-restricted | Built 1972 - 1982 | 701 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.
Rolling Meadows at Waysid...
$500ks - $600ks
Rolling Meadows at Waysid..., Ocean Township, NJ
Resale Only | 55+ age-restricted | Built 2002 - 2007 | 328 homes
Overlook
$600ks - $900ks
Overlook, Carmel, NY
New Construction | 55+ age-restricted | 300 homes
Fairview at Oxford Greens
$400ks - $600ks
Fairview at Oxford Greens, Oxford, CT
New and Resale | 55+ age-restricted | Built 2019 - present | 125 homes
Apple Ridge
$500ks - $1Ms
Apple Ridge, Mahwah, NJ
Resale Only | Age-targeted | Built 1977 - 1991 | 276 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
Regency at Fishkill
$300ks - $400ks
Regency at Fishkill, Fishkill, NY
Resale Only | 55+ age-restricted | Built 2008 - 2020 | 164 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
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Questions? Call us: (475) 471-1908
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
Woodridge Strathmore Terr...
$200ks - $300ks
Woodridge Strathmore Terr..., Mount Sinai, NY
Resale Only | 55+ age-restricted | Built 1974 - 1985 | 226 homes
Snug Harbor
$600ks - $700ks
Snug Harbor, Amityville, NY
Resale Only | 55+ age-restricted | Built 1970 - 1974 | 176 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.
Dutchgate
$300ks - $500ks
Dutchgate, Valley Stream, NY
Resale Only | 55+ age-restricted | Built 2009 - 2015 | 348 homes
Stoneleigh Woods at River...
$500ks
Stoneleigh Woods at River..., Riverhead, NY
Resale Only | 55+ age-restricted | Built 2007 - 2016 | 176 homes
Meadowbrook Pointe Athlet...
$700ks - $1Ms
Meadowbrook Pointe Athlet..., Westbury, NY
Resale Only | 55+ age-restricted | Built 2015 - 2016 | 720 homes
5 rating (1 reviews) Westhampton Pines
$900ks - $1Ms
Westhampton Pines, Westhampton, NY
Resale Only | 55+ age-restricted | Built 2005 - 2013 | 189 homes
4.6 rating (9 reviews) Meadowbrook Pointe Links ...
$300ks - $700ks
Meadowbrook Pointe Links ..., Medford, NY
New and Resale | 55+ age-restricted | Built 2010 - present | 280 homes
Chelsea Square
$300ks - $400ks
Chelsea Square, Morganville, NJ
New and Resale | 55+ age-restricted | Built 2007 - present | 225 homes
The Seasons at East Meado...
$400ks - $600ks
The Seasons at East Meado..., East Meadow, NY
Resale Only | 55+ age-restricted | Built 2009 - 2012 | 404 homes
Vineyards at Moriches
$500ks - $600ks
Vineyards at Moriches, Center Moriches, NY
Resale Only | 55+ age-restricted | Built 2008 - 2014 | 92 homes
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
Stone Ridge Estates
$500ks - $600ks
Stone Ridge Estates, Dix Hills, NY
Resale Only | 55+ age-restricted | Built 2004 - 2013 | 76 homes
Country Pointe Preserve
$600ks - $900ks
Country Pointe PreserveYaphank, NY
New Construction | 55+ age-restricted | Built 2024 - present | 152 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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Park Glen 4 RAINBOW CT 4, NEW MILFORD, CT, 06776, New Milford, CT 06776
$649,000

2 beds

|

4 baths

|

2,600 sq ft

|

Condo

4 RAINBOW CT 4, NEW MILFORD, CT, 06776
Community: Park Glen
Heritage Village 783 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$395,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

783 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 738 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$329,900

2 beds

|

2 baths

|

1,398 sq ft

|

Condo

738 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Granite Woods 35 NUTMEG RD B2, MIDDLEBURY, CT, 06762, Middlebury, CT 06762
$224,900

1 beds

|

1 baths

|

889 sq ft

|

Condo

35 NUTMEG RD B2, MIDDLEBURY, CT, 06762
Community: Granite Woods
Woodridge Strathmore Terrace 6 COBBLESTONE WAY, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766
$430,000

2 beds

|

2 baths

|

1,151 sq ft

|

Condo

6 COBBLESTONE WAY, BROOKHAVEN, NY, 11766
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
Cheesequake Village 10 HAVEN DR B, MATAWAN, NJ, 07747, Matawan, NJ 07747
$255,000

1 beds

|

1 baths

|

664 sq ft

|

Adult Community

10 HAVEN DR B, MATAWAN, NJ, 07747
Community: Cheesequake Village
Oronoque Village 393 OTTAWA LN B, STRATFORD, CT, 06614, Stratford, CT 06614
$350,000

1 beds

|

3 baths

|

1,118 sq ft

|

Condo

393 OTTAWA LN B, STRATFORD, CT, 06614
Community: Oronoque Village
Foxwood Village 1407 MIDDLE RD 265, RIVERHEAD, NY, 11933, Riverhead, NY 11933
$469,999

3 beds

|

2 baths

|

1,792 sq ft

|

Manufactured Home

1407 MIDDLE RD 265, RIVERHEAD, NY, 11933
Community: Foxwood Village
The Greens at Half Hollow 602 BARDINI DR, HUNTINGTON, NY, 11747, Huntington, NY 11747
$1,199,000

2 beds

|

4 baths

|

1,941 sq ft

|

Condo

602 BARDINI DR, HUNTINGTON, NY, 11747
Leisure Village 463 B OLDHAM CT, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$389,990

2 beds

|

1 baths

|

1,074 sq ft

|

Condo

463 B OLDHAM 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.
Leisure Village 472A DARWEN DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$408,000

2 beds

|

2 baths

|

1,200 sq ft

|

Condo

472A DARWEN DR, BROOKHAVEN, NY, 11961
Community: Leisure Village
Cheesequake Village 6 MINNESOTA DR A, MATAWAN, NJ, 07747, Matawan, NJ 07747
$325,000

2 beds

|

1 baths

|

914 sq ft

|

Adult Community

6 MINNESOTA DR A, MATAWAN, NJ, 07747
Community: Cheesequake Village
South Pond Village 78 SILO WAY 78, BLOOMFIELD, CT, 06002, Bloomfield, CT 06002
$289,500

3 beds

|

3 baths

|

1,639 sq ft

|

Condo

78 SILO WAY 78, BLOOMFIELD, CT, 06002
Community: South Pond Village
Plymouth Estates at Mount Sinai 7 POND CIR, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766
$665,000

2 beds

|

2 baths

|

1,274 sq ft

|

Condo

7 POND CIR, BROOKHAVEN, NY, 11766
Heritage Hills 332 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589
$599,000

2 beds

|

3 baths

|

1,550 sq ft

|

Condo

332 HERITAGE HLS B, SOMERS, NY, 10589
Community: Heritage Hills
Leisure Knoll 152A LAURANCE LN A, BROOKHAVEN, NY, 1196..., Brookhaven, NY 11961
$399,999

2 beds

|

1 baths

|

724 sq ft

|

Condo

152A LAURANCE LN A, BROOKHAVEN, NY, 1196...
Community: Leisure Knoll
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
Stratford Park 104 VICTORIA PL, HUNTINGTON, NY, 11747, Huntington, NY 11747
$949,999

3 beds

|

3 baths

|

2,423 sq ft

|

House

104 VICTORIA PL, HUNTINGTON, NY, 11747
Community: Stratford Park
Newbury Village 23 STILL WATER CIR 23, BROOKFIELD, CT, 0..., Brookfield, CT 06804
$735,000

3 beds

|

4 baths

|

2,684 sq ft

|

Condo

23 STILL WATER CIR 23, BROOKFIELD, CT, 0...
Community: Newbury Village
Chelsea Square 207 KNIGHTSBRIDGE LN 1207, MORGANVILLE, ..., Morganville, NJ 07751
$489,000

2 beds

|

2 baths

|

1,494 sq ft

|

Adult Community

207 KNIGHTSBRIDGE LN 1207, MORGANVILLE, ...
Community: Chelsea Square
Leisure Glen 6 OAKDALE CT, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$559,000

2 beds

|

2 baths

|

1,666 sq ft

|

Condo

6 OAKDALE CT, BROOKHAVEN, NY, 11961
Community: Leisure Glen
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.
Leisure Glen 428 LEISURE DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$649,000

2 beds

|

2 baths

|

1,652 sq ft

|

Condo

428 LEISURE DR, BROOKHAVEN, NY, 11961
Community: Leisure Glen
Leisure Village 134 EASTBOURNE CT A, BROOKHAVEN, NY, 119..., Brookhaven, NY 11961
$349,999

2 beds

|

1 baths

|

836 sq ft

|

Condo

134 EASTBOURNE CT A, BROOKHAVEN, NY, 119...
Community: Leisure Village
Sunrise Village 17 REVERE DR, ISLIP, NY, 11782, Islip, NY 11782
$439,999

2 beds

|

1 baths

|

871 sq ft

|

Condo

17 REVERE DR, ISLIP, NY, 11782
Community: Sunrise Village
Leisure Glen 454 LEISURE DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$649,000

2 beds

|

2 baths

|

1,652 sq ft

|

Condo

454 LEISURE DR, BROOKHAVEN, NY, 11961
Community: Leisure Glen
Heritage Village 857 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$235,000

2 beds

|

2 baths

|

1,071 sq ft

|

Condo

857 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 9 HERITAGE CIR A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$275,000

2 beds

|

2 baths

|

1,071 sq ft

|

Condo

9 HERITAGE CIR A, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 353 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$329,900

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

353 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
Woodridge Strathmore Terrace 89 HEARTHSIDE DR, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766
$409,999

1 beds

|

1 baths

|

720 sq ft

|

Condo

89 HEARTHSIDE DR, BROOKHAVEN, NY, 11766
Heritage Village 559 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$315,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

559 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Shady Oaks 100 VIBURNUM TER 300, RED BANK, NJ, 0770..., Red Bank, NJ 07701
$485,000

2 beds

|

2 baths

|

1,147 sq ft

|

Ranch

100 VIBURNUM TER 300, RED BANK, NJ, 0770...
Community: Shady Oaks
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.
Paris Square 1206 RIO VISTA LN, NORTHVALE, NJ, 07647, Northvale, NJ 07647
$649,900

2 beds

|

2 baths

|

Condo

1206 RIO VISTA LN, NORTHVALE, NJ, 07647
Community: Paris Square
The Seasons at Seaford 41 SPRING DR, HEMPSTEAD, NY, 11783, Hempstead, NY 11783
$875,000

2 beds

|

2 baths

|

1,408 sq ft

|

Condo

41 SPRING DR, HEMPSTEAD, NY, 11783
Heritage Hills 590 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589
$849,000

3 beds

|

2 baths

|

1,793 sq ft

|

Condo

590 HERITAGE HLS B, SOMERS, NY, 10589
Community: Heritage Hills
Rivington 714 CENTER MEADOW LN 714, DANBURY, CT, 0..., Danbury, CT 06810
$497,000

2 beds

|

2 baths

|

1,258 sq ft

|

Condo

714 CENTER MEADOW LN 714, DANBURY, CT, 0...
Community: Rivington
Vineyards at Blue Point 132 HALLEY DR, BROOKHAVEN, NY, 11772, Brookhaven, NY 11772
$879,999

2 beds

|

4 baths

|

2,290 sq ft

|

Condo

132 HALLEY DR, BROOKHAVEN, NY, 11772
Eagles Walk at East Quogue 1401 AERIE WAY, SOUTHAMPTON, NY, 11942, Southampton, NY 11942
$565,000

2 beds

|

2 baths

|

1,271 sq ft

|

Condo

1401 AERIE WAY, SOUTHAMPTON, NY, 11942
Heritage Village 397 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$419,900

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

397 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
HarborView 100 HARBOR VIEW DR 117, NORTH HEMPSTEAD,..., North Hempstead, NY 11050
$699,000

1 beds

|

2 baths

|

1,262 sq ft

|

Condo

100 HARBOR VIEW DR 117, NORTH HEMPSTEAD,...
Community: HarborView
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
Jefferson Village 3 HAMPTON CT B, YORKTOWN, NY, 10598, Yorktown, NY 10598
$199,000
|

1 baths

|

550 sq ft

|

Condo

3 HAMPTON CT B, YORKTOWN, NY, 10598
Community: Jefferson Village
Surrey Downs 3 IVY RDG, FREEHOLD, NJ, 07728, Freehold, NJ 07728
$375,000

2 beds

|

2 baths

|

1,261 sq ft

|

Ranch

3 IVY RDG, 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.

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