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

156 communities near New Fairfield

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The Woods at Dunham Pond
$400Ks - $500Ks
The Woods at Dunham Pond, New Fairfield, CT
Resale Only | 55+ age-restricted | Built 2004 - 2015 | 33 homes
3 rating (2 reviews) Heritage Hills
$300Ks - $900Ks
Heritage Hills, Somers, NY
Resale Only | Age-targeted | Built 1974 - 2006 | 2,600 homes
3.6 rating (7 reviews) Heritage Village
$100Ks - $500Ks
Heritage Village, Southbury, CT
Resale Only | 55+ age-restricted | Built 1967 - 2005 | 2,580 homes
Leisure Village
$200Ks - $400Ks
Leisure Village, Ridge, NY
Resale Only | 55+ age-restricted | Built 1969 - 1986 | 1,500 homes
The Greens at Half Hollow
$500Ks - $1Ms
The Greens at Half Hollow, Melville, NY
Resale Only | 55+ age-restricted | Built 1994 - 2005 | 1,200 homes
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Rivington
$600Ks - $600Ks
Rivington, Danbury, CT
New and Resale | Age-targeted | Built 2006 - present | 1,050 homes
4 rating (1 reviews) Jefferson Village
$200Ks - $600Ks
Jefferson Village, Yorktown Heights, NY
Resale Only | 55+ age-restricted | Built 1967 - 1982 | 1,000 homes
Oronoque Village
$200Ks - $600Ks
Oronoque Village, Stratford, CT
Resale Only | 55+ age-restricted | Built 1971 - 1977 | 929 homes
The Village at Oxford Gre...
$500Ks - $700Ks
The Village at Oxford Gre..., Oxford, CT
New and Resale | 55+ age-restricted | Built 2004 - present | 835 homes
5 rating (1 reviews) Four Seasons at Great Not...
$600Ks - $800Ks
Four Seasons at Great Not..., Woodland Park, NJ
Resale Only | 55+ age-restricted | Built 2005 - 2018 | 814 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.
4.8 rating (4 reviews) Wanaque Reserve
$400Ks - $400Ks
Wanaque Reserve, Wanaque, NJ
Resale Only | 55+ age-restricted | Built 2004 - 2014 | 755 homes
Meadowbrook Pointe Athlet...
$800Ks - $1Ms
Meadowbrook Pointe Athlet..., Westbury, NY
Resale Only | 55+ age-restricted | Built 2015 - 2016 | 720 homes
Leisure Knoll
$300Ks - $400Ks
Leisure Knoll, Ridge, NY
Resale Only | 55+ age-restricted | Built 1972 - 1982 | 701 homes
Country Pointe Plainview
$1Ms - $1Ms
Country Pointe Plainview, Plainview, NY
New Construction | 55+ age-restricted | Built 2017 - present | 660 homes
5 rating (2 reviews) Fairfield at St. James
$400Ks - $400Ks
Fairfield at St. James, St. James, NY
Resale Only | 55+ age-restricted | Built 1972 - 1989 | 653 homes
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Questions? Call us: (959) 214-2391
Leisure Glen
$400Ks - $400Ks
Leisure Glen, Ridge, NY
Resale Only | 55+ age-restricted | Built 1985 - 2010 | 646 homes
Spring Lake Village
$200Ks - $200Ks
Spring Lake Village, Southington, CT
Resale Only | 55+ age-restricted | Built 1970 - 2004 | 640 homes
4 rating (8 reviews) Glenwood Village
$100Ks - $400Ks
Glenwood Village, Riverhead, NY
New and Resale | 55+ age-restricted | Built 1959 - present | 588 homes
3.7 rating (3 reviews) Greenwood Village
$100Ks - $200Ks
Greenwood Village, Manorville, NY
Resale Only | 55+ age-restricted | Built 1980 - 2000 | 512 homes
Bald Eagle Commons
$100Ks - $200Ks
Bald Eagle Commons, West Milford, NJ
Resale Only | 55+ age-restricted | Built 1995 - 2005 | 463 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 Seasons at East Meado...
$500Ks - $600Ks
The Seasons at East Meado..., East Meadow, NY
Resale Only | 55+ age-restricted | Built 2009 - 2012 | 404 homes
Regency at Prospect
$300Ks - $500Ks
Regency at Prospect, Prospect, CT
Resale Only | 55+ age-restricted | Built 2006 - 2020 | 379 homes
Dutchgate
$400Ks - $400Ks
Dutchgate, Valley Stream, NY
Resale Only | 55+ age-restricted | Built 2009 - 2015 | 348 homes
The Waterways at Moriches
$400Ks - $600Ks
The Waterways at Moriches, Moriches, NY
Resale Only | 55+ age-restricted | Built 1985 - 1999 | 343 homes
The Retreat at Carmel
$400Ks - $600Ks
The Retreat at Carmel, Carmel, NY
Resale Only | 55+ age-restricted | Built 2008 - 2018 | 312 homes
Want to learn more about 55+ communities in New Fairfield? 55places can help!
Questions? Call us: (959) 214-2391
Overlook
$600Ks - $900Ks
Overlook, Carmel, NY
New Construction | 55+ age-restricted | 300 homes
3.5 rating (2 reviews) Foxwood Village
$300Ks - $400Ks
Foxwood Village, Calverton, NY
Resale Only | 55+ age-restricted | Built 1986 - 2007 | 294 homes
1 rating (1 reviews) Plymouth Estates at Mount...
$500Ks - $500Ks
Plymouth Estates at Mount..., Mount Sinai, NY
Resale Only | 55+ age-restricted | Built 2006 - 2013 | 285 homes
Wildflowers at Wallkill
$400Ks - $500Ks
Wildflowers at Wallkill, Middletown, NY
Resale Only | 55+ age-restricted | Built 2006 - 2017 | 283 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
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 (1 reviews) Vineyards at Blue Point
$800Ks - $800Ks
Vineyards at Blue Point, Blue Point, NY
Resale Only | 55+ age-restricted | Built 2016 - 2018 | 280 homes
Apple Ridge
$700Ks - $700Ks
Apple Ridge, Mahwah, NJ
Resale Only | Age-targeted | Built 1977 - 1991 | 276 homes
HarborView
$900Ks - $1Ms
HarborView, Port Washington, NY
Resale Only | 55+ age-restricted | Built 2002 - 2004 | 270 homes
Winthrop Court
$400Ks - $400Ks
Winthrop Court, Clifton, NJ
Resale Only | 55+ age-restricted | Built 2000 - 2010 | 270 homes
The Club at Melville
$500Ks - $500Ks
The Club at Melville, Melville, NY
Resale Only | 55+ age-restricted | Built 2015 - 2017 | 261 homes
Want to learn more about 55+ communities in New Fairfield? 55places can help!
Questions? Call us: (959) 214-2391
The Seasons at Elwood
$800Ks - $900Ks
The Seasons at Elwood, East Northport, NY
Resale Only | 55+ age-restricted | Built 2018 - 2020 | 256 homes
Meadow Brook Estates
$500Ks - $500Ks
Meadow Brook Estates, Oxford, CT
Resale Only | 55+ age-restricted | Built 2003 - 2020 | 246 homes
5 rating (1 reviews) Encore Atlantic Shores
$600Ks - $800Ks
Encore Atlantic Shores, Eastport, NY
Resale Only | 55+ age-restricted | Built 2004 - 2011 | 240 homes
The Summit at Bethel
$600Ks - $600Ks
The Summit at Bethel, Bethel, CT
Resale Only | 55+ age-restricted | Built 2010 - 2021 | 235 homes
4.9 rating (14 reviews) Chatfield Farms
$500Ks - $600Ks
Chatfield Farms, Beacon Falls, CT
New Construction | 55+ age-restricted | Built 2014 - present | 231 homes
Heritage Village 98 HERITAGE VLG D, SOUTHBURY, CT, 06488, Southbury, CT 06488
$309,900

2 beds

|

2 baths

|

1,044 sq ft

|

Condo

98 HERITAGE VLG D, SOUTHBURY, CT, 06488
Community: Heritage Village
Fieldstone Village 206 DEERFIELD LN # 206, ORANGE, CT, 0647..., Orange, CT 06477
$760,000

2 beds

|

3 baths

|

1,650 sq ft

|

Condo

206 DEERFIELD LN # 206, ORANGE, CT, 0647...
Community: Fieldstone Village
New Evergreen 2 GATESVILLE LN # 6, CROMWELL, CT, 06416, Cromwell, CT 06416
$599,900

3 beds

|

4 baths

|

2,194 sq ft

|

Condo

2 GATESVILLE LN # 6, CROMWELL, CT, 06416
Community: Evergreen
Oronoque Village 736 QUINNIPIAC LN B, STRATFORD, CT, 0661..., Stratford, CT 06614
$475,000

1 beds

|

3 baths

|

1,426 sq ft

|

Condo

736 QUINNIPIAC LN B, STRATFORD, CT, 0661...
Community: Oronoque Village
New Oronoque Village 164 BISON LN A, STRATFORD, CT, 06614, Stratford, CT 06614
$479,999

1 beds

|

2 baths

|

1,175 sq ft

|

Condo

164 BISON LN A, STRATFORD, CT, 06614
Community: Oronoque Village
Want to learn more about 55+ communities in New Fairfield? 55places can help!
Questions? Call us: (959) 214-2391
Evergreen 34 WOODSBORO CIR # 34, CROMWELL, CT, 064..., Cromwell, CT 06416
$539,000

2 beds

|

2 baths

|

1,758 sq ft

|

Condo

34 WOODSBORO CIR # 34, CROMWELL, CT, 064...
Community: Evergreen
Chatfield Farms 18 FIELDSTONE LN # 18, BEACON FALLS, CT,..., Beacon Falls, CT 06403
$599,000

2 beds

|

3 baths

|

2,719 sq ft

18 FIELDSTONE LN # 18, BEACON FALLS, CT,...
Community: Chatfield Farms
Newbury Village 21 GREAT HERON LN # 21, BROOKFIELD, CT, ..., Brookfield, CT 06804
$695,000

3 beds

|

4 baths

|

2,644 sq ft

|

Condo

21 GREAT HERON LN # 21, BROOKFIELD, CT, ...
Community: Newbury Village
Oronoque Village 289 AGAWAM DR B, STRATFORD, CT, 06614, Stratford, CT 06614
$639,900

2 beds

|

3 baths

|

1,620 sq ft

|

Condo

289 AGAWAM DR B, STRATFORD, CT, 06614
Community: Oronoque Village
Heritage Village 889 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$374,500

2 beds

|

2 baths

|

1,398 sq ft

|

Condo

889 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.
Heritage Village 644 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$539,000

3 beds

|

2 baths

|

1,716 sq ft

|

Condo

644 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 98 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$335,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

98 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 419 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$269,000

2 beds

|

2 baths

|

1,032 sq ft

|

Condo

419 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 966 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$350,000

2 beds

|

2 baths

|

1,398 sq ft

|

Condo

966 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 929 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$499,900

3 beds

|

2 baths

|

1,716 sq ft

|

Condo

929 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Want to learn more about 55+ communities in New Fairfield? 55places can help!
Questions? Call us: (959) 214-2391
Heritage Village 643 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$349,900

2 beds

|

2 baths

|

1,398 sq ft

|

Condo

643 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 1034 HERITAGE VLG B, SOUTHBURY, CT, 0648..., Southbury, CT 06488
$259,999

1 beds

|

1 baths

|

928 sq ft

|

Condo

1034 HERITAGE VLG B, SOUTHBURY, CT, 0648...
Community: Heritage Village
New Newtown Woods 433 BROOKSIDE CT 433, NEWTOWN, CT, 06470, Newtown, CT 06470
$500,000

2 beds

|

2 baths

|

1,504 sq ft

|

Condo

433 BROOKSIDE CT 433, NEWTOWN, CT, 06470
Community: Newtown Woods
Oronoque Village 375 PIUTE LN B, STRATFORD, CT, 06614, Stratford, CT 06614
$450,000

2 beds

|

3 baths

|

1,550 sq ft

|

Condo

375 PIUTE LN B, STRATFORD, CT, 06614
Community: Oronoque Village
New Heritage Village 876 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$390,000

2 beds

|

2 baths

|

1,398 sq ft

|

Condo

876 HERITAGE VLG A, 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.
Chatfield Farms 3 TIMBERLAND WAY # 3, BEACON FALLS, CT, ..., Beacon Falls, CT 06403
$629,900

3 beds

|

4 baths

|

2,052 sq ft

3 TIMBERLAND WAY # 3, BEACON FALLS, CT, ...
Community: Chatfield Farms
Heritage Village 701 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$329,000

3 beds

|

2 baths

|

1,716 sq ft

|

Condo

701 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
The Village at Oxford Greens 930 TILLINGHAST DR # 930, OXFORD, CT, 06..., Oxford, CT 06478
$759,900

2 beds

|

3 baths

|

2,365 sq ft

|

Condo

930 TILLINGHAST DR # 930, OXFORD, CT, 06...
The Village at Oxford Greens 413 MULLIGAN DR # 413, OXFORD, CT, 06478, Oxford, CT 06478
$539,000

2 beds

|

2 baths

|

1,590 sq ft

|

Condo

413 MULLIGAN DR # 413, OXFORD, CT, 06478
Heritage Village 916 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$415,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

916 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Want to learn more about 55+ communities in New Fairfield? 55places can help!
Questions? Call us: (959) 214-2391
Rivington 13 MERCY ST # 13, DANBURY, CT, 06810, Danbury, CT 06810
$650,000

3 beds

|

3 baths

|

1,572 sq ft

|

Condo

13 MERCY ST # 13, DANBURY, CT, 06810
Community: Rivington
Heritage Village 862 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$499,900

3 beds

|

2 baths

|

1,716 sq ft

|

Condo

862 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 825 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$289,900

2 beds

|

2 baths

|

1,365 sq ft

|

Condo

825 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 865 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$369,900

2 beds

|

2 baths

|

1,398 sq ft

|

Condo

865 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 746 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$305,000

2 beds

|

2 baths

|

1,063 sq ft

|

Condo

746 HERITAGE VLG A, 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.
South Pond Village 76 SILO WAY # 76, BLOOMFIELD, CT, 06002, Bloomfield, CT 06002
$285,000

3 beds

|

3 baths

|

1,545 sq ft

|

Condo

76 SILO WAY # 76, BLOOMFIELD, CT, 06002
Community: South Pond Village
Gloria Commons 10 LUCIUS CT # 10, MILFORD, CT, 06461, Milford, CT 06461
$465,000

2 beds

|

3 baths

|

2,061 sq ft

|

Condo

10 LUCIUS CT # 10, MILFORD, CT, 06461
Community: Gloria Commons
Spring Lake Village 8 VILLAGE RD # 8, SOUTHINGTON, CT, 06489, Southington, CT 06489
$229,900

2 beds

|

2 baths

|

1,314 sq ft

|

Condo

8 VILLAGE RD # 8, SOUTHINGTON, CT, 06489
Community: Spring Lake Village
Heritage Village 740 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$415,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

740 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 7 HERITAGE CRST B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$449,900

2 beds

|

2 baths

|

1,447 sq ft

|

Condo

7 HERITAGE CRST B, SOUTHBURY, CT, 06488
Community: Heritage Village
Want to learn more about 55+ communities in New Fairfield? 55places can help!
Questions? Call us: (959) 214-2391
New Heritage Village 39 HERITAGE VLG C, SOUTHBURY, CT, 06488, Southbury, CT 06488
$238,000

2 beds

|

2 baths

|

1,044 sq ft

|

Condo

39 HERITAGE VLG C, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 73 HERITAGE VLG D, SOUTHBURY, CT, 06488, Southbury, CT 06488
$259,900

2 beds

|

2 baths

|

1,044 sq ft

|

Condo

73 HERITAGE VLG D, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 563 HERITAGE VLG F, SOUTHBURY, CT, 06488, Southbury, CT 06488
$263,000

2 beds

|

2 baths

|

1,308 sq ft

|

Condo

563 HERITAGE VLG F, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 132 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$379,000

3 beds

|

2 baths

|

1,716 sq ft

|

Condo

132 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Oronoque Village 488 COMMANCHE LN A, STRATFORD, CT, 06614, Stratford, CT 06614
$619,000

2 beds

|

3 baths

|

1,438 sq ft

|

Condo

488 COMMANCHE LN A, STRATFORD, CT, 06614
Community: Oronoque Village

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156 communities near New Fairfield
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