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Westport, CT 55+ active adult communities & homes for sale - Page 5

348 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
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
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
Leisure Village
$100ks - $300ks
Leisure Village, Ridge, NY
Resale Only | 55+ age-restricted | Built 1969 - 1986 | 1,500 homes
3 rating (2 reviews) Heritage Hills
$400ks - $800ks
Heritage Hills, Somers, NY
Resale Only | Age-targeted | Built 1974 - 2006 | 2,600 homes
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
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
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 Knoll
$200ks - $400ks
Leisure Knoll, Ridge, NY
Resale Only | 55+ age-restricted | Built 1972 - 1982 | 701 homes
Regency at Fishkill
$300ks - $400ks
Regency at Fishkill, Fishkill, NY
Resale Only | 55+ age-restricted | Built 2008 - 2020 | 164 homes
3.7 rating (3 reviews) Greenwood Village
$100ks
Greenwood Village, Manorville, NY
Resale Only | 55+ age-restricted | Built 1980 - 2000 | 512 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
Overlook
$600ks - $900ks
Overlook, Carmel, NY
New Construction | 55+ age-restricted | 300 homes
Apple Ridge
$500ks - $1Ms
Apple Ridge, Mahwah, NJ
Resale Only | Age-targeted | Built 1977 - 1991 | 276 homes
Want to learn more about 55+ communities in Westport? 55places can help!
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
4 rating (8 reviews) Glenwood Village
$100ks - $200ks
Glenwood Village, Riverhead, NY
New and Resale | 55+ age-restricted | Built 1959 - present | 588 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
5 rating (1 reviews) The Villages at Mount Sin...
$600ks
The Villages at Mount Sin..., Mount Sinai, NY
Resale Only | 55+ age-restricted | Built 2005 - 2007 | 185 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.
Fairview at Oxford Greens
$400ks - $600ks
Fairview at Oxford Greens, Oxford, CT
New and Resale | 55+ age-restricted | Built 2019 - present | 125 homes
5 rating (1 reviews) Four Seasons at Great Not...
$400ks - $700ks
Four Seasons at Great Not..., Woodland Park, NJ
Resale Only | 55+ age-restricted | Built 2005 - 2018 | 814 homes
The Summit at Bethel
$500ks - $700ks
The Summit at Bethel, Bethel, CT
Resale Only | 55+ age-restricted | Built 2010 - 2021 | 235 homes
The Seasons at Elwood
$800ks - $900ks
The Seasons at Elwood, East Northport, NY
Resale Only | 55+ age-restricted | Built 2018 - 2020 | 256 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
3.7 rating (3 reviews) Rosemont Estates
$500ks - $700ks
Rosemont Estates, Marlboro, NJ
Resale Only | 55+ age-restricted | Built 2004 - 2014 | 242 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
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Questions? Call us: (475) 471-1908
Meadowbrook Pointe Athlet...
$700ks - $1Ms
Meadowbrook Pointe Athlet..., Westbury, NY
Resale Only | 55+ age-restricted | Built 2015 - 2016 | 720 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
Leisure Glen
$300ks - $400ks
Leisure Glen, Ridge, NY
Resale Only | 55+ age-restricted | Built 1985 - 2010 | 646 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.
South Pond Village
$300ks - $400ks
South Pond Village, Bloomfield, CT
Resale Only | 55+ age-restricted | Built 1999 - 2005 | 151 homes
Regency at Holmdel
$900ks - $1Ms
Regency at Holmdel, Holmdel, NJ
Resale Only | 55+ age-restricted | Built 2016 - 2019 | 181 homes
The Hollows at Blue Hill
$500ks - $700ks
The Hollows at Blue Hill, Pearl River, NY
Resale Only | 55+ age-restricted | Built 2008 - 2014 | 126 homes
5 rating (1 reviews) Shady Oaks
$200ks - $400ks
Shady Oaks, Red Bank, NJ
Resale Only | 55+ age-restricted | Built 1982 - 1983 | 366 homes
5 rating (1 reviews) Westhampton Pines
$900ks - $1Ms
Westhampton Pines, Westhampton, NY
Resale Only | 55+ age-restricted | Built 2005 - 2013 | 189 homes
Rivington
$300ks - $900ks
Rivington, Danbury, CT
New and Resale | Age-targeted | Built 2006 - present | 1,050 homes
3.5 rating (2 reviews) Foxwood Village
$200ks - $400ks
Foxwood Village, Calverton, NY
Resale Only | 55+ age-restricted | Built 1986 - 2007 | 294 homes
5 rating (1 reviews) Sunken Pond Estates
$400ks
Sunken Pond Estates, Riverhead, NY
Resale Only | 55+ age-restricted | Built 2003 - 2005 | 194 homes
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
Four Seasons at Colts Far...
$600ks - $800ks
Four Seasons at Colts Far..., Farmingdale, NJ
New Construction | 55+ age-restricted | Built 2021 - present | 111 homes
5 rating (1 reviews) Newtown Woods
$300ks - $500ks
Newtown Woods, Newtown, CT
New and Resale | 55+ age-restricted | Built 2011 - present | 178 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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The Greens at Half Hollow 398 ALTESSA BLVD, HUNTINGTON, NY, 11747, Huntington, NY 11747
$1,599,999

2 beds

|

2 baths

|

2,525 sq ft

|

Condo

398 ALTESSA BLVD, HUNTINGTON, NY, 11747
The Villages NJ 137 HALDEN STRASSE C, FREEHOLD, NJ, 0772..., Freehold, NJ 07728
$355,000

2 beds

|

1 baths

|

1,008 sq ft

|

Ranch

137 HALDEN STRASSE C, FREEHOLD, NJ, 0772...
Community: The Villages NJ
Regency at Prospect 196 SYCAMORE DR 196, PROSPECT, CT, 06712, Prospect, CT 06712
$307,127

3 beds

|

2 baths

|

1,500 sq ft

|

Condo

196 SYCAMORE DR 196, PROSPECT, CT, 06712
Community: Regency at Prospect
The Seasons at Elwood 244 FALL CT, HUNTINGTON, NY, 11731, Huntington, NY 11731
$1,375,000

2 beds

|

3 baths

|

2,256 sq ft

|

Condo

244 FALL CT, HUNTINGTON, NY, 11731
Surrey Downs 7 EDGEWARE CLOSE, FREEHOLD, NJ, 07728, Freehold, NJ 07728
$465,000

2 beds

|

2 baths

|

1,383 sq ft

|

House

7 EDGEWARE CLOSE, FREEHOLD, NJ, 07728
Community: Surrey Downs
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
Heritage Village 916 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$390,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

916 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Oronoque Village 96 SEMINOLE LN A, STRATFORD, CT, 06614, Stratford, CT 06614
$449,900

2 beds

|

3 baths

|

1,438 sq ft

|

Condo

96 SEMINOLE LN A, STRATFORD, CT, 06614
Community: Oronoque Village
Bear's Cove 33 WINDSOR LN, RAMSEY, NJ, 07446, Ramsey, NJ 07446
$1,250,000

3 beds

|

4 baths

|

Townhouse

33 WINDSOR LN, RAMSEY, NJ, 07446
Community: Bear's Cove
Equestra at Colts Neck Crossing 70 E BOSWORTH BLVD, FARMINGDALE, NJ, 077..., Farmingdale, NJ 07727
$935,000

4 beds

|

3 baths

|

2,700 sq ft

|

House

70 E BOSWORTH BLVD, FARMINGDALE, NJ, 077...
Setauket Meadows 100 COVE LN 100, BROOKHAVEN, NY, 11733, Brookhaven, NY 11733
$769,000

2 beds

|

3 baths

|

1,820 sq ft

|

Condo

100 COVE LN 100, 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.
Oronoque Village 315 NAVAJO LN A, STRATFORD, CT, 06614, Stratford, CT 06614
$549,000

2 beds

|

3 baths

|

1,434 sq ft

|

Condo

315 NAVAJO LN A, STRATFORD, CT, 06614
Community: Oronoque Village
Leisure Village 395 WOODBRIDGE DR 395E, BROOKHAVEN, NY, ..., Brookhaven, NY 11961
$299,000

2 beds

|

1 baths

|

875 sq ft

|

Condo

395 WOODBRIDGE DR 395E, BROOKHAVEN, NY, ...
Community: Leisure Village
Heritage Village 14 HERITAGE CIR B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$269,000

2 beds

|

2 baths

|

1,000 sq ft

|

Condo

14 HERITAGE CIR B, SOUTHBURY, CT, 06488
Community: Heritage Village
The Manors at The Colony Preserve 17 GREENTREE CT, BROOKHAVEN, NY, 11967, Brookhaven, NY 11967
$559,000

2 beds

|

2 baths

|

1,557 sq ft

|

Condo

17 GREENTREE CT, BROOKHAVEN, NY, 11967
Leisure Knoll 541 STRATFORD LN, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$519,000

3 beds

|

2 baths

|

1,412 sq ft

|

Condo

541 STRATFORD LN, BROOKHAVEN, NY, 11961
Community: Leisure Knoll
Heritage Village 847 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$309,000

3 beds

|

2 baths

|

1,716 sq ft

|

Condo

847 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
Cheesequake Village 12 LOUISIANA DR D, OLD BRIDGE TWP., NJ, ..., Old Bridge Twp., NJ 07747
$265,000

2 beds

|

1 baths

|

949 sq ft

12 LOUISIANA DR D, OLD BRIDGE TWP., NJ, ...
Community: Cheesequake Village
Heritage Village 648 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$405,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

648 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Fairfield at St. James 309 FLAIR DR, SMITHTOWN, NY, 11780, Smithtown, NY 11780
$439,000

1 beds

|

2 baths

|

983 sq ft

|

Condo

309 FLAIR DR, SMITHTOWN, NY, 11780
Cheesequake Village 12 UTAH DR A, OLD BRIDGE, NJ, 07747, Old Bridge, NJ 07747
$300,000

2 beds

|

1 baths

|

Condo

12 UTAH DR A, OLD BRIDGE, 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.
The Seasons at Seaford 107 SPRING DR, HEMPSTEAD, NY, 11783, Hempstead, NY 11783
$799,000

2 beds

|

2 baths

|

1,408 sq ft

|

Condo

107 SPRING DR, HEMPSTEAD, NY, 11783
Leisure Village 265 NEWCASTLE CT B, BROOKHAVEN, NY, 1196..., Brookhaven, NY 11961
$335,000

2 beds

|

1 baths

|

875 sq ft

|

Condo

265 NEWCASTLE CT B, BROOKHAVEN, NY, 1196...
Community: Leisure Village
Apple Ridge 134 FISHER RD, MAHWAH, NJ, 07430, Mahwah, NJ 07430
$950,000

4 beds

|

4 baths

|

Townhouse

134 FISHER RD, MAHWAH, NJ, 07430
Community: Apple Ridge
Cheesequake Village 54 GALEWOOD DR, OLD BRIDGE, NJ, 07747, Old Bridge, NJ 07747
$325,000

2 beds

|

1 baths

|

875 sq ft

|

Condo

54 GALEWOOD DR, OLD BRIDGE, NJ, 07747
Community: Cheesequake Village
The Villages NJ 66B CORSO ITALIA, FREEHOLD, NJ, 07728, Freehold, NJ 07728
$414,000

2 beds

|

2 baths

|

1,388 sq ft

|

Ranch

66B CORSO ITALIA, FREEHOLD, NJ, 07728
Community: The Villages NJ
The Hollows at Blue Hill 4201 FRED ILL JR CT, ORANGETOWN, NY, 109..., Orangetown, NY 10965
$699,000

2 beds

|

2 baths

|

1,245 sq ft

|

Condo

4201 FRED ILL JR CT, ORANGETOWN, NY, 109...
Encore at Lake Grove 58 SYMPHONY DR, BROOKHAVEN, NY, 11755, Brookhaven, NY 11755
$599,990

2 beds

|

3 baths

|

Condo

58 SYMPHONY DR, BROOKHAVEN, NY, 11755
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
South Pond Village 20 REED CT 20, BLOOMFIELD, CT, 06002, Bloomfield, CT 06002
$245,000

2 beds

|

2 baths

|

1,202 sq ft

|

Condo

20 REED CT 20, BLOOMFIELD, CT, 06002
Community: South Pond Village
Leisure Knoll 520 CRANSTON LN, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$499,999

2 beds

|

2 baths

|

1,574 sq ft

|

Condo

520 CRANSTON LN, BROOKHAVEN, NY, 11961
Community: Leisure Knoll
Heritage Village 551 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$239,000

1 beds

|

1 baths

|

928 sq ft

|

Condo

551 HERITAGE VLG B, 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.
Oronoque Village 298 BATON LN 298 A, STRATFORD, CT, 06614, Stratford, CT 06614
$435,000

1 beds

|

2 baths

|

1,175 sq ft

|

Condo

298 BATON LN 298 A, STRATFORD, CT, 06614
Community: Oronoque Village
Rosemont Estates 407 EDINBURGH PL, MARLBORO, NJ, 07746, Marlboro, NJ 07746
$899,000

2 beds

|

3 baths

|

2,547 sq ft

|

Adult Community

407 EDINBURGH PL, MARLBORO, NJ, 07746
Community: Rosemont Estates
Heritage Hills 798 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589
$875,000

2 beds

|

2 baths

|

1,663 sq ft

|

Condo

798 HERITAGE HLS A, SOMERS, NY, 10589
Community: Heritage Hills
Jefferson Village 142 FLINTLOCK WAY F, YORKTOWN, NY, 10598, Yorktown, NY 10598
$609,000

2 beds

|

2 baths

|

1,302 sq ft

|

Condo

142 FLINTLOCK WAY F, YORKTOWN, NY, 10598
Community: Jefferson Village
Apple Ridge 41 LITCHULT LN, MAHWAH, NJ, 07430, Mahwah, NJ 07430
$810,000

3 beds

|

3 baths

|

Townhouse

41 LITCHULT LN, MAHWAH, NJ, 07430
Community: Apple Ridge
Jefferson Village 15F ESSEX PL F, YORKTOWN, NY, 10598, Yorktown, NY 10598
$425,000

2 beds

|

1 baths

|

925 sq ft

|

Condo

15F ESSEX PL F, YORKTOWN, NY, 10598
Community: Jefferson Village
Regency at Prospect 156 SYCAMORE DR 156, PROSPECT, CT, 06712, Prospect, CT 06712
$559,000

2 beds

|

3 baths

|

2,067 sq ft

|

Condo

156 SYCAMORE DR 156, PROSPECT, CT, 06712
Community: Regency at Prospect
Jefferson Village 37 SUSSEX DR B, YORKTOWN, NY, 10598, Yorktown, NY 10598
$359,000

2 beds

|

1 baths

|

935 sq ft

|

Condo

37 SUSSEX DR B, YORKTOWN, NY, 10598
Community: Jefferson Village
Want to learn more about 55+ communities in Westport? 55places can help!
Questions? Call us: (475) 471-1908
Heritage Village 149 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$219,000

1 beds

|

1 baths

|

928 sq ft

|

Condo

149 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Meadowbrook Pointe Links & Spa 48 AUGUSTA DR, BROOKHAVEN, NY, 11763, Brookhaven, NY 11763
$749,990

2 beds

|

4 baths

|

1,553 sq ft

|

Condo

48 AUGUSTA DR, BROOKHAVEN, NY, 11763
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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