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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
Oronoque Village
$200ks - $400ks
Oronoque Village, Stratford, CT
Resale Only | 55+ age-restricted | Built 1971 - 1977 | 929 homes
4.8 rating (4 reviews) Wanaque Reserve
$300ks - $500ks
Wanaque Reserve, Wanaque, NJ
Resale Only | 55+ age-restricted | Built 2004 - 2014 | 755 homes
3 rating (2 reviews) Heritage Hills
$400ks - $800ks
Heritage Hills, Somers, NY
Resale Only | Age-targeted | Built 1974 - 2006 | 2,600 homes
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4 rating (1 reviews) Jefferson Village
$100ks - $500ks
Jefferson Village, Yorktown Heights, NY
Resale Only | 55+ age-restricted | Built 1967 - 1982 | 1,000 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
3.7 rating (3 reviews) Greenwood Village
$100ks
Greenwood Village, Manorville, NY
Resale Only | 55+ age-restricted | Built 1980 - 2000 | 512 homes
The Waterways at Moriches
$300ks - $600ks
The Waterways at Moriches, Moriches, NY
Resale Only | 55+ age-restricted | Built 1985 - 1999 | 343 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
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
Leisure Village
$100ks - $300ks
Leisure Village, Ridge, NY
Resale Only | 55+ age-restricted | Built 1969 - 1986 | 1,500 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
4 rating (8 reviews) Glenwood Village
$100ks - $200ks
Glenwood Village, Riverhead, NY
New and Resale | 55+ age-restricted | Built 1959 - present | 588 homes
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Questions? Call us: (959) 214-2391
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) Warwick Grove
$400ks - $600ks
Warwick Grove, Warwick, NY
New and Resale | 55+ age-restricted | Built 2004 - present | 215 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
Liberty at Newtown
$300ks - $400ks
Liberty at Newtown, Newtown, CT
Resale Only | 55+ age-restricted | Built 2003 - 2007 | 96 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
Leisure Glen
$300ks - $400ks
Leisure Glen, Ridge, NY
Resale Only | 55+ age-restricted | Built 1985 - 2010 | 646 homes
Rivington
$300ks - $900ks
Rivington, Danbury, CT
New and Resale | Age-targeted | Built 2006 - present | 1,050 homes
Stoneleigh Woods at River...
$500ks
Stoneleigh Woods at River..., Riverhead, NY
Resale Only | 55+ age-restricted | Built 2007 - 2016 | 176 homes
HarborView
$800ks - $1Ms
HarborView, Port Washington, NY
Resale Only | 55+ age-restricted | Built 2002 - 2004 | 270 homes
Regency at Fishkill
$300ks - $400ks
Regency at Fishkill, Fishkill, NY
Resale Only | 55+ age-restricted | Built 2008 - 2020 | 164 homes
5 rating (1 reviews) Newtown Woods
$300ks - $500ks
Newtown Woods, Newtown, CT
New and Resale | 55+ age-restricted | Built 2011 - present | 178 homes
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Questions? Call us: (959) 214-2391
5 rating (1 reviews) Westhampton Pines
$900ks - $1Ms
Westhampton Pines, Westhampton, NY
Resale Only | 55+ age-restricted | Built 2005 - 2013 | 189 homes
Winthrop Court
$400ks - $600ks
Winthrop Court, Clifton, NJ
Resale Only | 55+ age-restricted | Built 2000 - 2010 | 270 homes
3.5 rating (2 reviews) Foxwood Village
$200ks - $400ks
Foxwood Village, Calverton, NY
Resale Only | 55+ age-restricted | Built 1986 - 2007 | 294 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.
Country Pointe Preserve
$600ks - $900ks
Country Pointe PreserveYaphank, NY
New Construction | 55+ age-restricted | Built 2024 - present | 152 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
Baldwin Station
$400ks
Baldwin Station, Milford, CT
Resale Only | 55+ age-restricted | Built 2001 - 2003 | 82 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
Leisure Knoll
$200ks - $400ks
Leisure Knoll, Ridge, NY
Resale Only | 55+ age-restricted | Built 1972 - 1982 | 701 homes
Vineyards at Moriches
$500ks - $600ks
Vineyards at Moriches, Center Moriches, NY
Resale Only | 55+ age-restricted | Built 2008 - 2014 | 92 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
Want to learn more about 55+ communities in New Fairfield? 55places can help!
Questions? Call us: (959) 214-2391
Snug Harbor
$600ks - $700ks
Snug Harbor, Amityville, NY
Resale Only | 55+ age-restricted | Built 1970 - 1974 | 176 homes
Village Estates
$300ks - $400ks
Village Estates, Amityville, NY
Resale Only | 55+ age-restricted | Built 2006 - 2008 | 138 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
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 Greenwood Village 69 DOGWOOD LN, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949
$139,000

2 beds

|

2 baths

|

1,134 sq ft

|

Condo

69 DOGWOOD LN, BROOKHAVEN, NY, 11949
Community: Greenwood Village
New Oronoque Village 585 PEQUOT LN B, STRATFORD, CT, 06614, Stratford, CT 06614
$640,000

1 beds

|

3 baths

|

1,583 sq ft

|

Condo

585 PEQUOT LN B, STRATFORD, CT, 06614
Community: Oronoque Village
New Encore Atlantic Shores 228 SONATA CT, BROOKHAVEN, NY, 11941, Brookhaven, NY 11941
$749,000

2 beds

|

2 baths

|

1,605 sq ft

|

Condo

228 SONATA CT, BROOKHAVEN, NY, 11941
Want to learn more about 55+ communities in New Fairfield? 55places can help!
Questions? Call us: (959) 214-2391
New Liberty at Newtown 16 FRANKLIN CT 16, NEWTOWN, CT, 06470, Newtown, CT 06470
$599,000

2 beds

|

3 baths

|

1,940 sq ft

|

Condo

16 FRANKLIN CT 16, NEWTOWN, CT, 06470
Community: Liberty at Newtown
New Oronoque Village 632A OLD KNIFE LN 632A, STRATFORD, CT, 0..., Stratford, CT 06614
$570,000

2 beds

|

3 baths

|

1,876 sq ft

|

Condo

632A OLD KNIFE LN 632A, STRATFORD, CT, 0...
Community: Oronoque Village
New The Villas at Narragansett 406 NARRAGANSETT VILLAS DR, BABYLON, NY,..., Babylon, NY 11757
$599,000

2 beds

|

2 baths

|

1,215 sq ft

|

Condo

406 NARRAGANSETT VILLAS DR, BABYLON, NY,...
New Fairfield at St. James 1203 CABOT CT, SMITHTOWN, NY, 11780, Smithtown, NY 11780
$399,000

1 beds

|

1 baths

|

793 sq ft

|

Condo

1203 CABOT CT, SMITHTOWN, NY, 11780
New Fairview at Oxford Greens 1129 ST ANDREWS DR 49, OXFORD, CT, 06478, Oxford, CT 06478
$663,775

2 beds

|

3 baths

|

2,454 sq ft

|

Condo

1129 ST ANDREWS DR 49, OXFORD, CT, 06478
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 Village at Oxford Greens 1129 ST ANDREWS DR 49, OXFORD, CT, 06478, Oxford, CT 06478
$663,775

2 beds

|

3 baths

|

2,454 sq ft

|

Condo

1129 ST ANDREWS DR 49, OXFORD, CT, 06478
New Fairview at Oxford Greens 1111 ST ANDREWS DR 16, OXFORD, CT, 06478, Oxford, CT 06478
$778,160

2 beds

|

3 baths

|

2,454 sq ft

|

Condo

1111 ST ANDREWS DR 16, OXFORD, CT, 06478
New The Village at Oxford Greens 1111 ST ANDREWS DR 16, OXFORD, CT, 06478, Oxford, CT 06478
$778,160

2 beds

|

3 baths

|

2,454 sq ft

|

Condo

1111 ST ANDREWS DR 16, OXFORD, CT, 06478
New Fairview at Oxford Greens 1138 ST ANDREWS DR 90, OXFORD, CT, 06478, Oxford, CT 06478
$754,150

2 beds

|

3 baths

|

1,955 sq ft

|

Condo

1138 ST ANDREWS DR 90, OXFORD, CT, 06478
New The Village at Oxford Greens 1138 ST ANDREWS DR 90, OXFORD, CT, 06478, Oxford, CT 06478
$754,150

2 beds

|

3 baths

|

1,955 sq ft

|

Condo

1138 ST ANDREWS DR 90, OXFORD, CT, 06478
New Fairfield at St. James 302 BENTLEY CT, SMITHTOWN, NY, 11780, Smithtown, NY 11780
$499,000

2 beds

|

2 baths

|

1,067 sq ft

|

Condo

302 BENTLEY CT, SMITHTOWN, NY, 11780
Want to learn more about 55+ communities in New Fairfield? 55places can help!
Questions? Call us: (959) 214-2391
New Encore Atlantic Shores 78 BALLAD CT, BROOKHAVEN, NY, 11941, Brookhaven, NY 11941
$925,000

2 beds

|

3 baths

|

2,625 sq ft

|

Condo

78 BALLAD CT, BROOKHAVEN, NY, 11941
New Heritage Hills 12 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589
$474,000

2 beds

|

2 baths

|

1,710 sq ft

|

Condo

12 HERITAGE HLS A, SOMERS, NY, 10589
Community: Heritage Hills
New Baldwin Station 99 JASMINE CIR 99, MILFORD, CT, 06461, Milford, CT 06461
$859,000

2 beds

|

3 baths

|

2,820 sq ft

|

Condo

99 JASMINE CIR 99, MILFORD, CT, 06461
Community: Baldwin Station
New Oronoque Village 372 PIUTE LN B, STRATFORD, CT, 06614, Stratford, CT 06614
$389,900

1 beds

|

2 baths

|

1,375 sq ft

|

Condo

372 PIUTE LN B, STRATFORD, CT, 06614
Community: Oronoque 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 Encore Atlantic Shores 63 ENCORE BLVD, BROOKHAVEN, NY, 11941, Brookhaven, NY 11941
$918,000

2 beds

|

3 baths

|

2,769 sq ft

|

Condo

63 ENCORE BLVD, BROOKHAVEN, NY, 11941
New Heritage Hills 371 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589
$699,000

2 beds

|

2 baths

|

1,470 sq ft

|

Condo

371 HERITAGE HLS A, SOMERS, NY, 10589
Community: Heritage Hills
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
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
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
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
Want to learn more about 55+ communities in New Fairfield? 55places can help!
Questions? Call us: (959) 214-2391
Dutchgate 301 WILLOW LN, HEMPSTEAD, NY, 11580, Hempstead, NY 11580
$535,000

2 beds

|

2 baths

|

941 sq ft

|

Condo

301 WILLOW LN, HEMPSTEAD, NY, 11580
Community: Dutchgate
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
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
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.
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
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...
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
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
Wanaque Reserve 8107 WARRENS WAY, WANAQUE BORO, NJ, 0746..., Wanaque Boro, NJ 07465
$419,900

2 beds

|

2 baths

|

1,768 sq ft

8107 WARRENS WAY, WANAQUE BORO, NJ, 0746...
Community: Wanaque Reserve
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
Wanaque Reserve 7111 WARRENS WAY, WANAQUE BORO, NJ, 0746..., Wanaque Boro, NJ 07465
$382,000

2 beds

|

2 baths

7111 WARRENS WAY, WANAQUE BORO, NJ, 0746...
Community: Wanaque Reserve
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
Want to learn more about 55+ communities in New Fairfield? 55places can help!
Questions? Call us: (959) 214-2391
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
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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