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

373 homes near New Fairfield

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Bald Eagle Commons
$100ks - $300ks
Bald Eagle Commons, West Milford, NJ
Resale Only | 55+ age-restricted | Built 1995 - 2005 | 463 homes
3.6 rating (7 reviews) Heritage Village
$200ks - $500ks
Heritage Village, Southbury, CT
Resale Only | 55+ age-restricted | Built 1967 - 2005 | 2,580 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
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
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5 rating (2 reviews) Oronoque Village
$200ks - $400ks
Oronoque Village, Stratford, CT
Resale Only | 55+ age-restricted | Built 1971 - 1977 | 929 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 Village at Oxford Gre...
$400ks - $500ks
The Village at Oxford Gre..., Oxford, CT
New and Resale | 55+ age-restricted | Built 2004 - present | 835 homes
The Waterways at Moriches
$300ks - $600ks
The Waterways at Moriches, Moriches, NY
Resale Only | 55+ age-restricted | Built 1985 - 1999 | 343 homes
3.7 rating (3 reviews) Greenwood Village
$100ks
Greenwood Village, Manorville, NY
Resale Only | 55+ age-restricted | Built 1980 - 2000 | 512 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 Greens at Half Hollow
$600ks - $1Ms
The Greens at Half Hollow, Melville, NY
Resale Only | 55+ age-restricted | Built 1994 - 2005 | 1,200 homes
Overlook
$600ks - $900ks
Overlook, Carmel, NY
New Construction | 55+ age-restricted | 300 homes
Rivington
$300ks - $900ks
Rivington, Danbury, CT
New and Resale | Age-targeted | Built 2006 - present | 1,050 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
The Manors at The Colony ...
$300ks - $400ks
The Manors at The Colony ..., Shirley, NY
New Construction | 55+ age-restricted | Built 2013 - present | 150 homes
Leisure Village
$100ks - $300ks
Leisure Village, Ridge, NY
Resale Only | 55+ age-restricted | Built 1969 - 1986 | 1,500 homes
Want to learn more about 55+ communities in New Fairfield? 55places can help!
Questions? Call us: (959) 214-2391
Country Pointe Plainview
$700ks - $1Ms
Country Pointe Plainview, Plainview, NY
New Construction | 55+ age-restricted | Built 2017 - present | 660 homes
Fairview at Oxford Greens
$400ks - $600ks
Fairview at Oxford Greens, Oxford, CT
New and Resale | 55+ age-restricted | Built 2019 - present | 125 homes
Regency at Fishkill
$300ks - $400ks
Regency at Fishkill, Fishkill, NY
Resale Only | 55+ age-restricted | Built 2008 - 2020 | 164 homes
Stoneleigh Woods at River...
$500ks
Stoneleigh Woods at River..., Riverhead, NY
Resale Only | 55+ age-restricted | Built 2007 - 2016 | 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.
HarborView
$600ks - $1Ms
HarborView, Port Washington, NY
Resale Only | 55+ age-restricted | Built 2002 - 2004 | 270 homes
Leisure Glen
$300ks - $400ks
Leisure Glen, Ridge, NY
Resale Only | 55+ age-restricted | Built 1985 - 2010 | 646 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 Knoll
$200ks - $400ks
Leisure Knoll, Ridge, NY
Resale Only | 55+ age-restricted | Built 1972 - 1982 | 701 homes
Apple Ridge
$500ks - $1Ms
Apple Ridge, Mahwah, NJ
Resale Only | Age-targeted | Built 1977 - 1991 | 276 homes
5 rating (1 reviews) Warwick Grove
$400ks - $600ks
Warwick Grove, Warwick, NY
New and Resale | 55+ age-restricted | Built 2004 - present | 215 homes
Snug Harbor
$600ks - $700ks
Snug Harbor, Amityville, NY
Resale Only | 55+ age-restricted | Built 1970 - 1974 | 176 homes
Want to learn more about 55+ communities in New Fairfield? 55places can help!
Questions? Call us: (959) 214-2391
Dutchgate
$300ks - $500ks
Dutchgate, Valley Stream, NY
Resale Only | 55+ age-restricted | Built 2009 - 2015 | 348 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) 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.
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
Spring Lake Village
$100ks - $200ks
Spring Lake Village, Southington, CT
Resale Only | 55+ age-restricted | Built 1970 - 2004 | 640 homes
5 rating (1 reviews) Westhampton Pines
$900ks - $1Ms
Westhampton Pines, Westhampton, NY
Resale Only | 55+ age-restricted | Built 2005 - 2013 | 189 homes
Liberty at Newtown
$300ks - $400ks
Liberty at Newtown, Newtown, CT
Resale Only | 55+ age-restricted | Built 2003 - 2007 | 96 homes
The Views at Pomona
$200ks - $400ks
The Views at Pomona, Pomona, NY
Resale Only | 55+ age-restricted | Built 2011 - 2011 | 56 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
Vineyards at Moriches
$500ks - $600ks
Vineyards at Moriches, Center Moriches, NY
Resale Only | 55+ age-restricted | Built 2008 - 2014 | 92 homes
Country Pointe Preserve
$600ks - $900ks
Country Pointe PreserveYaphank, NY
New Construction | 55+ age-restricted | Built 2024 - present | 152 homes
Want to learn more about 55+ communities in New Fairfield? 55places can help!
Questions? Call us: (959) 214-2391
Setauket Meadows
$500ks - $600ks
Setauket Meadows, Setauket, NY
Resale Only | 55+ age-restricted | Built 2005 - 2007 | 150 homes
Wildflowers at Wallkill
$400ks - $500ks
Wildflowers at Wallkill, Middletown, NY
Resale Only | 55+ age-restricted | Built 2006 - 2017 | 283 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 Summit at Bethel 78 GREAT HILL DR 78, BETHEL, CT, 06801, Bethel, CT 06801
$700,000

3 beds

|

4 baths

|

Condo

78 GREAT HILL DR 78, BETHEL, CT, 06801
Meadow Brook Estates 169 MEADOW BROOK RD 169, OXFORD, CT, 064..., Oxford, CT 06478
$625,000

2 beds

|

3 baths

|

1,821 sq ft

|

Condo

169 MEADOW BROOK RD 169, OXFORD, CT, 064...
Spring Lake Village 116 TIMBER RDG, SOUTHINGTON, CT, 06489, Southington, CT 06489
$304,900

2 beds

|

2 baths

|

1,128 sq ft

|

Condo

116 TIMBER RDG, SOUTHINGTON, CT, 06489
Community: Spring Lake Village
Jefferson Village 34 WARWICK PL B, YORKTOWN, NY, 10598, Yorktown, NY 10598
$375,000

2 beds

|

2 baths

|

1,000 sq ft

|

Condo

34 WARWICK PL B, YORKTOWN, NY, 10598
Community: Jefferson Village
Heritage Hills 537 HERITAGE HILLS DR F, SOMERS, NY, 105..., Somers, NY 10589
$629,000

2 beds

|

2 baths

|

1,265 sq ft

|

Condo

537 HERITAGE HILLS DR F, SOMERS, NY, 105...
Community: Heritage Hills
Want to learn more about 55+ communities in New Fairfield? 55places can help!
Questions? Call us: (959) 214-2391
Heritage Village 170 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$349,900

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

170 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Hills 159 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589
$569,000

2 beds

|

2 baths

|

1,500 sq ft

|

Condo

159 HERITAGE HLS B, SOMERS, NY, 10589
Community: Heritage Hills
Oronoque Village 511 OPA LN B, STRATFORD, CT, 06614, Stratford, CT 06614
$589,900

2 beds

|

2 baths

|

1,620 sq ft

|

Condo

511 OPA LN B, STRATFORD, CT, 06614
Community: Oronoque Village
Jefferson Village 184 LONG HILL DR A, YORKTOWN, NY, 10598, Yorktown, NY 10598
$489,000

2 beds

|

2 baths

|

1,200 sq ft

|

Condo

184 LONG HILL DR A, YORKTOWN, NY, 10598
Community: Jefferson Village
The Vineyards at Mount Sinai 72 FARM ACRE CIR, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766
$999,999

2 beds

|

4 baths

|

3,736 sq ft

|

Condo

72 FARM ACRE CIR, BROOKHAVEN, NY, 11766
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.
Wildflowers at Wallkill 111 JASMINE DR, MIDDLETOWN, NY, 10940, Middletown, NY 10940
$505,000

2 beds

|

2 baths

|

1,473 sq ft

|

House

111 JASMINE DR, MIDDLETOWN, NY, 10940
Apple Ridge 89 FISHER RD, MAHWAH, NJ, 07430, Mahwah, NJ 07430
$990,000

3 beds

|

3 baths

|

Townhouse

89 FISHER RD, MAHWAH, NJ, 07430
Community: Apple Ridge
Apple Ridge 89 FISHER RD, MAHWAH TWP., NJ, 07430, Mahwah Twp., NJ 07430
$990,000

3 beds

|

3 baths

|

2,112 sq ft

89 FISHER RD, MAHWAH TWP., NJ, 07430
Community: Apple Ridge
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
Jefferson Village 20 HASTINGS CT A, YORKTOWN, NY, 10598, Yorktown, NY 10598
$345,000

1 beds

|

1 baths

|

800 sq ft

|

Condo

20 HASTINGS CT A, YORKTOWN, NY, 10598
Community: Jefferson Village
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
Want to learn more about 55+ communities in New Fairfield? 55places can help!
Questions? Call us: (959) 214-2391
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
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
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
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.
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
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
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
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
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
Glenwood Village 1661 OLD COUNTRY RD 476, RIVERHEAD, NY, ..., Riverhead, NY 11901
$349,000

2 beds

|

2 baths

|

960 sq ft

|

Manufactured Home

1661 OLD COUNTRY RD 476, RIVERHEAD, NY, ...
Community: Glenwood Village
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
Want to learn more about 55+ communities in New Fairfield? 55places can help!
Questions? Call us: (959) 214-2391
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
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
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
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 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
The Village at Oxford Greens 1159 ST ANDREWS DR 80, OXFORD, CT, 06478, Oxford, CT 06478
$799,900

2 beds

|

3 baths

|

1,955 sq ft

|

Condo

1159 ST ANDREWS DR 80, OXFORD, CT, 06478
Fairview at Oxford Greens 1159 ST ANDREWS DR 80, OXFORD, CT, 06478, Oxford, CT 06478
$799,900

2 beds

|

3 baths

|

1,955 sq ft

|

Condo

1159 ST ANDREWS DR 80, OXFORD, CT, 06478
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
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
The Greens at Half Hollow 1116 SAVOY DR, HUNTINGTON, NY, 11747, Huntington, NY 11747
$719,999

2 beds

|

2 baths

|

1,100 sq ft

|

Condo

1116 SAVOY DR, HUNTINGTON, NY, 11747
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
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
Want to learn more about 55+ communities in New Fairfield? 55places can help!
Questions? Call us: (959) 214-2391
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
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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