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

157 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
$200Ks - $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
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
$300Ks - $600Ks
Oronoque Village, Stratford, CT
Resale Only | 55+ age-restricted | Built 1971 - 1977 | 929 homes
The Village at Oxford Gre...
$500Ks - $600Ks
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
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
Country Pointe Plainview, Plainview, NY
New Construction | 55+ age-restricted | Built 2017 - present | 660 homes
5 rating (2 reviews) Fairfield at St. James
$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
Leisure Glen, Ridge, NY
Resale Only | 55+ age-restricted | Built 1985 - 2010 | 646 homes
Spring Lake Village
$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
Dutchgate, Valley Stream, NY
Resale Only | 55+ age-restricted | Built 2009 - 2015 | 348 homes
The Waterways at Moriches
$400Ks - $700Ks
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
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Questions? Call us: (959) 214-2391
Overlook
$600Ks - $800Ks
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
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 rating (1 reviews) Vineyards at Blue Point
$800Ks
Vineyards at Blue Point, Blue Point, NY
Resale Only | 55+ age-restricted | Built 2016 - 2018 | 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.
4.6 rating (9 reviews) Meadowbrook Pointe Links ...
$300Ks - $700Ks
Meadowbrook Pointe Links ..., Medford, NY
New and Resale | 55+ age-restricted | Built 2010 - present | 280 homes
Apple Ridge
$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
Winthrop Court, Clifton, NJ
Resale Only | 55+ age-restricted | Built 2000 - 2010 | 270 homes
The Club at Melville
$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
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
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
Regency at Woodbridge 6 WHISPER RIDGE WAY # 42, WOODBRIDGE, CT..., Woodbridge, CT 06525
$619,000

3 beds

|

3 baths

|

Condo

6 WHISPER RIDGE WAY # 42, WOODBRIDGE, CT...
Heritage Village 133 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$300,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

133 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Rivington 94 WARRINGTON ROUND # 94, DANBURY, CT, 0..., Danbury, CT 06810
$585,000

2 beds

|

3 baths

|

1,600 sq ft

|

Condo

94 WARRINGTON ROUND # 94, DANBURY, CT, 0...
Community: Rivington
Newtown Woods 603 BROOKSIDE CT # 603, NEWTOWN, CT, 064..., Newtown, CT 06470
$489,000

2 beds

|

2 baths

|

1,504 sq ft

|

Condo

603 BROOKSIDE CT # 603, NEWTOWN, CT, 064...
Community: Newtown Woods
Heritage Village 1 HERITAGE VLG C, SOUTHBURY, CT, 06488, Southbury, CT 06488
$265,000

2 beds

|

2 baths

|

1,044 sq ft

|

Condo

1 HERITAGE VLG C, 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
Park Glen 1 BLOSSOM CT # 1, NEW MILFORD, CT, 06776, New Milford, CT 06776
$545,000

2 beds

|

2 baths

|

1,880 sq ft

|

Condo

1 BLOSSOM CT # 1, NEW MILFORD, CT, 06776
Community: Park Glen
Heritage Village 93 HERITAGE VLG E, SOUTHBURY, CT, 06488, Southbury, CT 06488
$265,000

2 beds

|

2 baths

|

1,365 sq ft

|

Condo

93 HERITAGE VLG E, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 902 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$389,900

2 beds

|

2 baths

|

1,398 sq ft

|

Condo

902 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 793 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$234,900

2 beds

|

2 baths

|

1,365 sq ft

|

Condo

793 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Oronoque Village 664 OSAGE LN A, STRATFORD, CT, 06614, Stratford, CT 06614
$549,900

1 beds

|

3 baths

|

1,438 sq ft

|

Condo

664 OSAGE LN A, 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.
Heritage Village 313 HERITAGE VLG D, SOUTHBURY, CT, 06488, Southbury, CT 06488
$219,900

2 beds

|

2 baths

|

1,044 sq ft

|

Condo

313 HERITAGE VLG D, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 26 HERITAGE CRST C, SOUTHBURY, CT, 06488, Southbury, CT 06488
$399,900

2 beds

|

2 baths

|

1,217 sq ft

|

Condo

26 HERITAGE CRST C, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 626 HERITAGE VLG, SOUTHBURY, CT, 06488, Southbury, CT 06488
$350,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

626 HERITAGE VLG, SOUTHBURY, CT, 06488
Community: Heritage Village
Oak Meadow Estates 65 OAK MEADOW LN # 65, HARWINTON, CT, 06..., Harwinton, CT 06791
$495,000

2 beds

|

4 baths

|

2,164 sq ft

|

Condo

65 OAK MEADOW LN # 65, HARWINTON, CT, 06...
Community: Oak Meadow Estates
Heritage Village 8 HERITAGE VLG D, SOUTHBURY, CT, 06488, Southbury, CT 06488
$264,900

2 beds

|

2 baths

|

1,076 sq ft

|

Condo

8 HERITAGE VLG D, 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 786 HERITAGE VLG D, SOUTHBURY, CT, 06488, Southbury, CT 06488
$295,000

2 beds

|

2 baths

|

1,063 sq ft

|

Condo

786 HERITAGE VLG D, SOUTHBURY, CT, 06488
Community: Heritage Village
Spring Lake Village 543 S FARMS TER # 543, SOUTHINGTON, CT, ..., Southington, CT 06489
$225,000

2 beds

|

3 baths

|

1,782 sq ft

|

Condo

543 S FARMS TER # 543, SOUTHINGTON, CT, ...
Community: Spring Lake Village
Regency at Prospect 8 HICKORY DR # 8, PROSPECT, CT, 06712, Prospect, CT 06712
$347,184

3 beds

|

2 baths

|

1,500 sq ft

|

Condo

8 HICKORY DR # 8, PROSPECT, CT, 06712
Community: Regency at Prospect
Heritage Village 192 HERITAGE VLG C, SOUTHBURY, CT, 06488, Southbury, CT 06488
$260,000

2 beds

|

2 baths

|

1,308 sq ft

|

Condo

192 HERITAGE VLG C, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 132 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$299,900

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

132 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.
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
Oronoque Village 638 ONONDAGA LN A, STRATFORD, CT, 06614, Stratford, CT 06614
$384,000

1 beds

|

3 baths

|

2,071 sq ft

|

Condo

638 ONONDAGA LN A, STRATFORD, CT, 06614
Community: Oronoque Village
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 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 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
Want to learn more about 55+ communities in New Fairfield? 55places can help!
Questions? Call us: (959) 214-2391
New Oronoque Village 516 OPA LN A, STRATFORD, CT, 06614, Stratford, CT 06614
$459,900

2 beds

|

2 baths

|

1,426 sq ft

|

Condo

516 OPA LN A, STRATFORD, CT, 06614
Community: Oronoque Village
Gloria Commons 10 LUCIUS CT # 10, MILFORD, CT, 06461, Milford, CT 06461
$450,000

2 beds

|

3 baths

|

2,061 sq ft

|

Condo

10 LUCIUS CT # 10, MILFORD, CT, 06461
Community: Gloria Commons
Oronoque Village 195 BAYFIELD LN A, STRATFORD, CT, 06614, Stratford, CT 06614
$549,900

1 beds

|

3 baths

|

1,575 sq ft

|

Condo

195 BAYFIELD LN A, STRATFORD, CT, 06614
Community: Oronoque Village
New Heritage Village 723 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$259,900

2 beds

|

2 baths

|

1,365 sq ft

|

Condo

723 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 44 HERITAGE VLG F, SOUTHBURY, CT, 06488, Southbury, CT 06488
$239,000

2 beds

|

2 baths

|

1,308 sq ft

|

Condo

44 HERITAGE VLG F, 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 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
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

930 TILLINGHAST DR # 930, OXFORD, CT, 06...
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
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
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
Want to learn more about 55+ communities in New Fairfield? 55places can help!
Questions? Call us: (959) 214-2391
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
Spring Lake Village 1 COACH DR # 1, SOUTHINGTON, CT, 06489, Southington, CT 06489
$280,000

2 beds

|

2 baths

|

1,323 sq ft

|

Condo

1 COACH DR # 1, SOUTHINGTON, CT, 06489
Community: Spring Lake Village
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
Heritage Village 623 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$535,000

3 beds

|

2 baths

|

1,716 sq ft

|

Condo

623 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 568A HERITAGE VLG, SOUTHBURY, CT, 06488, Southbury, CT 06488
$409,900

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

568A HERITAGE VLG, SOUTHBURY, CT, 06488
Community: Heritage Village

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157 communities near New Fairfield
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