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New Fairfield, CT 55+ active adult communities & homes for sale

159 communities near New Fairfield

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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
Bald Eagle Commons
$100ks - $300ks
Bald Eagle Commons, West Milford, NJ
Resale Only | 55+ age-restricted | Built 1995 - 2005 | 463 homes
3 rating (2 reviews) Heritage Hills
$400ks - $800ks
Heritage Hills, Somers, NY
Resale Only | Age-targeted | Built 1974 - 2006 | 2,600 homes
4.8 rating (4 reviews) Wanaque Reserve
$300ks - $500ks
Wanaque Reserve, Wanaque, NJ
Resale Only | 55+ age-restricted | Built 2004 - 2014 | 755 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
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Questions? Call us: (959) 214-2391
Oronoque Village
$200ks - $400ks
Oronoque Village, Stratford, CT
Resale Only | 55+ age-restricted | Built 1971 - 1977 | 929 homes
The Waterways at Moriches
$300ks - $600ks
The Waterways at Moriches, Moriches, NY
Resale Only | 55+ age-restricted | Built 1985 - 1999 | 343 homes
Overlook
$600ks - $900ks
Overlook, Carmel, NY
New Construction | 55+ age-restricted | 300 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
Leisure Village
$100ks - $300ks
Leisure Village, Ridge, NY
Resale Only | 55+ age-restricted | Built 1969 - 1986 | 1,500 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.
4 rating (8 reviews) Glenwood Village
$100ks - $200ks
Glenwood Village, Riverhead, NY
New and Resale | 55+ age-restricted | Built 1959 - present | 588 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
3.7 rating (3 reviews) Greenwood Village
$100ks
Greenwood Village, Manorville, NY
Resale Only | 55+ age-restricted | Built 1980 - 2000 | 512 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 (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
Fairview at Oxford Greens
$400ks - $600ks
Fairview at Oxford Greens, Oxford, CT
New and Resale | 55+ age-restricted | Built 2019 - present | 125 homes
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Questions? Call us: (959) 214-2391
5 rating (1 reviews) Encore Atlantic Shores
$500ks - $800ks
Encore Atlantic Shores, Eastport, NY
Resale Only | 55+ age-restricted | Built 2004 - 2011 | 240 homes
Country Pointe Plainview
$700ks - $1Ms
Country Pointe Plainview, Plainview, NY
New Construction | 55+ age-restricted | Built 2017 - present | 660 homes
5 rating (1 reviews) Warwick Grove
$400ks - $600ks
Warwick Grove, Warwick, NY
New and Resale | 55+ age-restricted | Built 2004 - present | 215 homes
Regency at Fishkill
$300ks - $400ks
Regency at Fishkill, Fishkill, NY
Resale Only | 55+ age-restricted | Built 2008 - 2020 | 164 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
HarborView
$800ks - $1Ms
HarborView, Port Washington, NY
Resale Only | 55+ age-restricted | Built 2002 - 2004 | 270 homes
5 rating (1 reviews) Newtown Woods
$300ks - $500ks
Newtown Woods, Newtown, CT
New and Resale | 55+ age-restricted | Built 2011 - present | 178 homes
Rivington
$300ks - $900ks
Rivington, Danbury, CT
New and Resale | Age-targeted | Built 2006 - present | 1,050 homes
Spring Lake Village
$100ks - $200ks
Spring Lake Village, Southington, CT
Resale Only | 55+ age-restricted | Built 1970 - 2004 | 640 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
Leisure Glen
$300ks - $400ks
Leisure Glen, Ridge, NY
Resale Only | 55+ age-restricted | Built 1985 - 2010 | 646 homes
Want to learn more about 55+ communities in New Fairfield? 55places can help!
Questions? Call us: (959) 214-2391
Leisure Knoll
$200ks - $400ks
Leisure Knoll, Ridge, NY
Resale Only | 55+ age-restricted | Built 1972 - 1982 | 701 homes
Stoneleigh Woods at River...
$500ks
Stoneleigh Woods at River..., Riverhead, NY
Resale Only | 55+ age-restricted | Built 2007 - 2016 | 176 homes
Vineyards at Moriches
$500ks - $600ks
Vineyards at Moriches, Center Moriches, NY
Resale Only | 55+ age-restricted | Built 2008 - 2014 | 92 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.
3.5 rating (2 reviews) Foxwood Village
$200ks - $400ks
Foxwood Village, Calverton, NY
Resale Only | 55+ age-restricted | Built 1986 - 2007 | 294 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
The Views at Pomona
$200ks - $400ks
The Views at Pomona, Pomona, NY
Resale Only | 55+ age-restricted | Built 2011 - 2011 | 56 homes
Snug Harbor
$600ks - $700ks
Snug Harbor, Amityville, NY
Resale Only | 55+ age-restricted | Built 1970 - 1974 | 176 homes
Vineyards at Brookfield
$400ks - $500ks
Vineyards at Brookfield, Center Moriches, NY
New Construction | 55+ age-restricted | Built 2019 - present | 146 homes
Country Pointe Preserve
$600ks - $900ks
Country Pointe PreserveYaphank, NY
New Construction | 55+ age-restricted | Built 2024 - present | 152 homes
Liberty at Newtown
$300ks - $400ks
Liberty at Newtown, Newtown, CT
Resale Only | 55+ age-restricted | Built 2003 - 2007 | 96 homes
Winthrop Court
$400ks - $600ks
Winthrop Court, Clifton, NJ
Resale Only | 55+ age-restricted | Built 2000 - 2010 | 270 homes
Want to learn more about 55+ communities in New Fairfield? 55places can help!
Questions? Call us: (959) 214-2391
The Retreat at Carmel
$300ks - $800ks
The Retreat at Carmel, Carmel, NY
Resale Only | 55+ age-restricted | Built 2008 - 2018 | 312 homes
1 rating (1 reviews) Plymouth Estates at Mount...
$400ks - $500ks
Plymouth Estates at Mount..., Mount Sinai, NY
Resale Only | 55+ age-restricted | Built 2006 - 2013 | 285 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.
123...4
New Heritage Village 345 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$386,000

3 beds

|

2 baths

|

1,716 sq ft

|

Condo

345 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
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
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 Heritage Village 643 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$374,500

2 beds

|

2 baths

|

1,398 sq ft

|

Condo

643 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
New Jefferson Village 20A HASTINGS CT 20A, YORKTOWN, NY, 10598, Yorktown, NY 10598
$345,000

1 beds

|

1 baths

|

800 sq ft

|

Condo

20A HASTINGS CT 20A, YORKTOWN, NY, 10598
Community: Jefferson Village
Want to learn more about 55+ communities in New Fairfield? 55places can help!
Questions? Call us: (959) 214-2391
New Leisure Glen 276 GLEN DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$585,000

2 beds

|

2 baths

|

1,666 sq ft

|

Condo

276 GLEN DR, BROOKHAVEN, NY, 11961
Community: Leisure Glen
New Glenwood Village 1661 OLD COUNTRY RD 254, RIVERHEAD, NY, ..., Riverhead, NY 11901
$185,000

2 beds

|

2 baths

|

1,036 sq ft

|

Manufactured Home

1661 OLD COUNTRY RD 254, RIVERHEAD, NY, ...
Community: Glenwood Village
New The Waterways at Moriches 533 HIGHLAND CT, BROOKHAVEN, NY, 11955, Brookhaven, NY 11955
$499,000

2 beds

|

2 baths

|

1,771 sq ft

|

Condo

533 HIGHLAND CT, BROOKHAVEN, NY, 11955
New Greenwood Village 28 GREENWOOD BLVD, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949
$149,999

2 beds

|

2 baths

|

938 sq ft

|

Condo

28 GREENWOOD BLVD, BROOKHAVEN, NY, 11949
Community: Greenwood Village
New Rivington 215 CENTER MEADOW LN 215, DANBURY, CT, 0..., Danbury, CT 06810
$499,000

2 beds

|

2 baths

|

1,258 sq ft

|

Condo

215 CENTER MEADOW LN 215, DANBURY, CT, 0...
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.
New The Waterways at Moriches 416 LINDSAY LN, BROOKHAVEN, NY, 11955, Brookhaven, NY 11955
$599,999

2 beds

|

2 baths

|

1,440 sq ft

|

Condo

416 LINDSAY LN, BROOKHAVEN, NY, 11955
New Heritage Village 4 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$245,000

1 beds

|

1 baths

|

928 sq ft

|

Condo

4 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
New Leisure Village 404 WOODBRIDGE DR D, BROOKHAVEN, NY, 119..., Brookhaven, NY 11961
$369,000

2 beds

|

1 baths

|

874 sq ft

|

Condo

404 WOODBRIDGE DR D, BROOKHAVEN, NY, 119...
Community: Leisure Village
New Leisure Knoll 7 AVON CT, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$479,999

2 beds

|

2 baths

|

1,070 sq ft

|

Condo

7 AVON CT, BROOKHAVEN, NY, 11961
Community: Leisure Knoll
New Leisure Knoll 545 STRATFORD LN, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$429,000

2 beds

|

2 baths

|

1,172 sq ft

|

Condo

545 STRATFORD LN, BROOKHAVEN, NY, 11961
Community: Leisure Knoll
New Overlook 2040 SUMMIT LOOP 57, CARMEL, NY, 10512, Carmel, NY 10512
$899,000

2 beds

|

2 baths

|

1,948 sq ft

|

Condo

2040 SUMMIT LOOP 57, CARMEL, NY, 10512
Community: Overlook
Want to learn more about 55+ communities in New Fairfield? 55places can help!
Questions? Call us: (959) 214-2391
New Wildflowers at Wallkill 65 JASMINE DR, MIDDLETOWN, NY, 10940, Middletown, NY 10940
$579,000

2 beds

|

2 baths

|

1,875 sq ft

|

House

65 JASMINE DR, MIDDLETOWN, NY, 10940
New Strathmore Gate East 15 FORGE LN, BROOKHAVEN, NY, 11727, Brookhaven, NY 11727
$299,990

1 beds

|

1 baths

|

750 sq ft

|

Condo

15 FORGE LN, BROOKHAVEN, NY, 11727
New Leisure Knoll 254 EDINBURGH DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$450,000

2 beds

|

1 baths

|

1,020 sq ft

|

Condo

254 EDINBURGH DR, BROOKHAVEN, NY, 11961
Community: Leisure Knoll
New Regency at Woodbridge 27 HERITAGE LN, WOODBRIDGE, CT, 06525, Woodbridge, CT 06525
$599,900

3 beds

|

3 baths

|

Condo

27 HERITAGE LN, WOODBRIDGE, CT, 06525
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 Fairfield at St. James 708 W CABOT CT 708, SMITHTOWN, NY, 11780, Smithtown, NY 11780
$515,000

1 beds

|

1 baths

|

886 sq ft

|

Condo

708 W CABOT CT 708, SMITHTOWN, NY, 11780
New Heritage Hills 813 HERITAGE HLS, SOMERS, NY, 10589, Somers, NY 10589
$899,000

2 beds

|

2 baths

|

1,663 sq ft

|

Condo

813 HERITAGE HLS, SOMERS, NY, 10589
Community: Heritage Hills
New Fairview at Oxford Greens 1159 ST ANDREWS DR 90, OXFORD, CT, 06478, Oxford, CT 06478
$799,900

2 beds

|

3 baths

|

1,955 sq ft

|

Condo

1159 ST ANDREWS DR 90, OXFORD, CT, 06478
New The Village at Oxford Greens 1159 ST ANDREWS DR 90, OXFORD, CT, 06478, Oxford, CT 06478
$799,900

2 beds

|

3 baths

|

1,955 sq ft

|

Condo

1159 ST ANDREWS DR 90, OXFORD, CT, 06478
New Fairfield at St. James 1006 CABOT PATH, SMITHTOWN, NY, 11780, Smithtown, NY 11780
$399,000

1 beds

|

2 baths

|

1,003 sq ft

|

Condo

1006 CABOT PATH, SMITHTOWN, NY, 11780
New Regency at Fishkill 732 REGENCY DR, FISHKILL, NY, 12524, Fishkill, NY 12524
$505,000

1 beds

|

2 baths

|

1,499 sq ft

|

Condo

732 REGENCY DR, FISHKILL, NY, 12524
Community: Regency at Fishkill
New Regency at Fishkill 622 REGENCY DR, WAPPINGER, NY, 12524, Wappinger, NY 12524
$510,000

1 beds

|

2 baths

|

1,450 sq ft

|

Condo

622 REGENCY DR, WAPPINGER, NY, 12524
Community: Regency at Fishkill
Want to learn more about 55+ communities in New Fairfield? 55places can help!
Questions? Call us: (959) 214-2391
New Encore at Lake Grove 14 CONCERTO DR, BROOKHAVEN, NY, 11755, Brookhaven, NY 11755
$970,000

2 beds

|

3 baths

|

1,986 sq ft

|

Condo

14 CONCERTO DR, BROOKHAVEN, NY, 11755
New The Greens at Half Hollow 1116 SAVOY DR, HUNTINGTON, NY, 11747, Huntington, NY 11747
$719,999

2 beds

|

2 baths

|

1,200 sq ft

|

Condo

1116 SAVOY DR, HUNTINGTON, NY, 11747
New Fieldstone Village 101 SUNRISE HILL CIR 101, ORANGE, CT, 06..., Orange, CT 06477
$875,000

2 beds

|

3 baths

|

2,350 sq ft

|

Condo

101 SUNRISE HILL CIR 101, ORANGE, CT, 06...
Community: Fieldstone 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 Sonoma Woods 52 SONOMA LN 52, MIDDLETOWN, CT, 06457, Middletown, CT 06457
$559,900

3 beds

|

3 baths

|

1,996 sq ft

|

Condo

52 SONOMA LN 52, MIDDLETOWN, CT, 06457
Community: Sonoma Woods
New Glenwood Village 1661 OLD COUNTRY RD 377, RIVERHEAD, NY, ..., Riverhead, NY 11901
$375,000

3 beds

|

2 baths

|

1,317 sq ft

|

Manufactured Home

1661 OLD COUNTRY RD 377, RIVERHEAD, NY, ...
Community: Glenwood Village
Leisure Village 232 BLACKPOOL CT F, BROOKHAVEN, NY, 1196..., Brookhaven, NY 11961
$349,000

2 beds

|

1 baths

|

875 sq ft

|

Condo

232 BLACKPOOL CT F, BROOKHAVEN, NY, 1196...
Community: Leisure Village
Vineyards at Brookfield 61 AVERY DR, BROOKHAVEN, NY, 11934, Brookhaven, NY 11934
$695,000

2 beds

|

2 baths

|

1,557 sq ft

|

Condo

61 AVERY DR, BROOKHAVEN, NY, 11934
Woodridge Strathmore Terrace 18 CHIPPENDALE DR, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766
$525,000

2 beds

|

2 baths

|

1,240 sq ft

|

Condo

18 CHIPPENDALE DR, BROOKHAVEN, NY, 11766
The Views at Pomona 1309 VIEWS WAY, RAMAPO, NY, 10970, Ramapo, NY 10970
$429,000

2 beds

|

2 baths

|

1,245 sq ft

|

Condo

1309 VIEWS WAY, RAMAPO, NY, 10970
Community: The Views at Pomona
The Retreat at Carmel 8 ATKINS CT, CARMEL, NY, 10512, Carmel, NY 10512
$690,000

2 beds

|

3 baths

|

2,148 sq ft

|

Condo

8 ATKINS CT, CARMEL, NY, 10512
Leisure Glen 29 GLEN DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$549,900

2 beds

|

2 baths

|

1,314 sq ft

|

Condo

29 GLEN DR, BROOKHAVEN, NY, 11961
Community: Leisure Glen
Want to learn more about 55+ communities in New Fairfield? 55places can help!
Questions? Call us: (959) 214-2391
Wanaque Reserve 2202 WARRENS WAY, WANAQUE BORO, NJ, 0746..., Wanaque Boro, NJ 07465
$344,900

2 beds

|

2 baths

2202 WARRENS WAY, WANAQUE BORO, NJ, 0746...
Community: Wanaque Reserve
Spring Lake Village 142 TIMBER RDG 142, SOUTHINGTON, CT, 064..., Southington, CT 06489
$359,900

2 beds

|

3 baths

|

1,601 sq ft

|

Condo

142 TIMBER RDG 142, SOUTHINGTON, CT, 064...
Community: Spring Lake 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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