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New Fairfield, CT 55+ active adult communities & homes for sale - Page 2

156 communities near New Fairfield

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No reviews yet Four Seasons at Wayne
$500Ks - $500Ks
Four Seasons at Wayne, Wayne, NJ
Resale Only | 55+ age-restricted | Built 1999 - 2001 | 230 homes
5 rating (1 reviews) Encore at Lake Grove
$600Ks - $800Ks
Encore at Lake Grove, Lake Grove, NY
Resale Only | 55+ age-restricted | Built 2006 - 2007 | 228 homes
No reviews yet Woodridge Strathmore Terr...
$400Ks - $400Ks
Woodridge Strathmore Terr..., Mount Sinai, NY
Resale Only | 55+ age-restricted | Built 1974 - 1985 | 226 homes
No reviews yet Regency at Wappinger
$600Ks - $700Ks
Regency at Wappinger, Wappingers Falls, NY
Resale Only | 55+ age-restricted | Built 2014 - 2020 | 225 homes
5 rating (1 reviews) Warwick Grove
$600Ks - $900Ks
Warwick Grove, Warwick, NY
New and Resale | 55+ age-restricted | Built 2004 - present | 215 homes
Want to learn more about 55+ communities in New Fairfield? 55places can help!
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5 rating (1 reviews) Sunrise Village
$400Ks - $500Ks
Sunrise Village, Sayville, NY
Resale Only | 55+ age-restricted | Built 1985 - 1990 | 213 homes
No reviews yet Saddle Lakes
$400Ks - $400Ks
Saddle Lakes, Riverhead, NY
Resale Only | 55+ age-restricted | Built 2000 - 2002 | 196 homes
No reviews yet Country Village Estates
$400Ks - $400Ks
Country Village Estates, Coram, NY
Resale Only | 55+ age-restricted | Built 1993 - 2001 | 195 homes
5 rating (1 reviews) Sunken Pond Estates
$400Ks - $500Ks
Sunken Pond Estates, Riverhead, NY
Resale Only | 55+ age-restricted | Built 2003 - 2005 | 194 homes
No reviews yet The Seasons at East North...
$700Ks - $700Ks
The Seasons at East North..., East Northport, NY
New Construction | 55+ age-restricted | Built 2023 - present | 190 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.
5 rating (1 reviews) Westhampton Pines
$900Ks - $1Ms
Westhampton Pines, Westhampton, NY
Resale Only | 55+ age-restricted | Built 2005 - 2013 | 189 homes
5 rating (1 reviews) The Villages at Mount Sin...
$600Ks - $700Ks
The Villages at Mount Sin..., Mount Sinai, NY
Resale Only | 55+ age-restricted | Built 2005 - 2007 | 185 homes
No reviews yet The Powder Forest Homes
$600Ks - $700Ks
The Powder Forest Homes, Simsbury, CT
Resale Only | 55+ age-restricted | Built 2006 - 2016 | 182 homes
No reviews yet The Pointe
$500Ks - $500Ks
The Pointe, Livingston, NJ
Resale Only | 55+ age-restricted | Built 2004 - 2007 | 180 homes
5 rating (1 reviews) Newtown Woods
$400Ks - $400Ks
Newtown Woods, Newtown, CT
New and Resale | 55+ age-restricted | Built 2011 - present | 178 homes
Want to learn more about 55+ communities in New Fairfield? 55places can help!
Questions? Call us: (959) 214-2391
No reviews yet Stoneleigh Woods at River...
$600Ks - $600Ks
Stoneleigh Woods at River..., Riverhead, NY
Resale Only | 55+ age-restricted | Built 2007 - 2016 | 176 homes
No reviews yet Snug Harbor
$600Ks - $700Ks
Snug Harbor, Amityville, NY
Resale Only | 55+ age-restricted | Built 1970 - 1974 | 176 homes
No reviews yet The Coves at Melville
$500Ks - $500Ks
The Coves at Melville, Melville, NY
Resale Only | 62+ age-restricted | Built 2004 - 2005 | 175 homes
No reviews yet Strathmore Gate East
$300Ks - $400Ks
Strathmore Gate East, Coram, NY
Resale Only | 55+ age-restricted | Built 1970 - 1975 | 174 homes
No reviews yet Beckley Farms
$300Ks - $400Ks
Beckley Farms, Berlin, CT
New and Resale | 55+ age-restricted | Built 2010 - present | 170 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.
No reviews yet Regency at Fishkill
$400Ks - $500Ks
Regency at Fishkill, Fishkill, NY
Resale Only | 55+ age-restricted | Built 2008 - 2020 | 164 homes
No reviews yet Four Seasons at Cedar Gro...
$600Ks - $600Ks
Four Seasons at Cedar Gro..., Cedar Grove, NJ
Resale Only | 55+ age-restricted | Built 2000 - 2005 | 156 homes
No reviews yet South Pond Village
$100Ks - $200Ks
South Pond Village, Bloomfield, CT
Resale Only | 55+ age-restricted | Built 1999 - 2005 | 151 homes
No reviews yet The Manors at The Colony ...
$400Ks - $500Ks
The Manors at The Colony ..., Shirley, NY
New Construction | 55+ age-restricted | Built 2013 - present | 150 homes
No reviews yet Setauket Meadows
$600Ks - $700Ks
Setauket Meadows, Setauket, NY
Resale Only | 55+ age-restricted | Built 2005 - 2007 | 150 homes
Want to learn more about 55+ communities in New Fairfield? 55places can help!
Questions? Call us: (959) 214-2391
No reviews yet Vineyards at Brookfield
$700Ks - $700Ks
Vineyards at Brookfield, Center Moriches, NY
New Construction | 55+ age-restricted | Built 2019 - present | 146 homes
No reviews yet Fieldstone Village
$500Ks - $800Ks
Fieldstone Village, Orange, CT
Resale Only | 55+ age-restricted | Built 2010 - 2018 | 142 homes
No reviews yet Village Estates
$500Ks - $500Ks
Village Estates, Amityville, NY
Resale Only | 55+ age-restricted | Built 2006 - 2008 | 138 homes
No reviews yet The Villas at Narraganset...
$600Ks - $600Ks
The Villas at Narraganset..., Lindenhurst, NY
Resale Only | 55+ age-restricted | Built 2004 - 2005 | 138 homes
No reviews yet Campagna
$300Ks - $300Ks
Campagna, Montville Township, NJ
Resale Only | 55+ age-restricted | Built 1980 - 1986 | 136 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.
No reviews yet The Seasons at Plainview
$600Ks - $700Ks
The Seasons at Plainview, Plainview, NY
Resale Only | 55+ age-restricted | Built 2006 - 2007 | 134 homes
No reviews yet The Hollows at Blue Hill
$1Ms - $1Ms
The Hollows at Blue Hill, Pearl River, NY
Resale Only | 55+ age-restricted | Built 2008 - 2014 | 126 homes
No reviews yet Windcrest East
$600Ks - $600Ks
Windcrest East, Calverton, NY
Resale Only | 55+ age-restricted | Built 2004 - 2005 | 126 homes
No reviews yet Fairview at Oxford Greens
$600Ks - $600Ks
Fairview at Oxford Greens, Oxford, CT
New and Resale | 55+ age-restricted | Built 2019 - present | 125 homes
No reviews yet Newbury Village
$600Ks - $700Ks
Newbury Village, Brookfield, CT
New and Resale | 55+ age-restricted | Built 2005 - present | 120 homes
Want to learn more about 55+ communities in New Fairfield? 55places can help!
Questions? Call us: (959) 214-2391
No reviews yet The Seasons at Seaford
$700Ks - $700Ks
The Seasons at Seaford, Seaford, NY
Resale Only | 55+ age-restricted | Built 2015 - 2017 | 112 homes
No reviews yet Windmill Gate
$300Ks - $400Ks
Windmill Gate, Oakdale, NY
Resale Only | 55+ age-restricted | Built 1989 - 1991 | 110 homes
5 rating (1 reviews) Four Seasons at North Cal...
$700Ks - $800Ks
Four Seasons at North Cal..., North Caldwell, NJ
Resale Only | 55+ age-restricted | Built 2011 - 2015 | 108 homes
No reviews yet Four Seasons at Ridgemont
$800Ks - $1Ms
Four Seasons at Ridgemont, Montvale, NJ
Resale Only | 55+ age-restricted | Built 2011 - 2014 | 108 homes
No reviews yet Meadowbrooke Pointe East ...
$700Ks - $800Ks
Meadowbrooke Pointe East ..., East Meadow, NY
New Construction | 62+ age-restricted | Built 2019 - present | 104 homes
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 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 568A HERITAGE VLG, SOUTHBURY, CT, 06488, Southbury, CT 06488
$429,900

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

568A HERITAGE VLG, 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
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
Want to learn more about 55+ communities in New Fairfield? 55places can help!
Questions? Call us: (959) 214-2391
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
Heritage Village 966 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$375,000

2 beds

|

2 baths

|

1,398 sq ft

|

Condo

966 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
New 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 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
Rivington 416 CENTER MEADOW LN # 416, DANBURY, CT,..., Danbury, CT 06810
$489,000

2 beds

|

2 baths

|

1,312 sq ft

|

Condo

416 CENTER MEADOW LN # 416, DANBURY, CT,...
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.
Oronoque Village 193 BAYFIELD LN B, STRATFORD, CT, 06614, Stratford, CT 06614
$559,000

2 beds

|

3 baths

|

1,620 sq ft

|

Condo

193 BAYFIELD LN B, STRATFORD, CT, 06614
Community: Oronoque Village
The Woods at Dunham Pond 12 HERON VIEW RD # 12, NEW FAIRFIELD, CT..., New Fairfield, CT 06812
$419,900

1 beds

|

2 baths

|

1,550 sq ft

12 HERON VIEW RD # 12, NEW FAIRFIELD, CT...
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
Oronoque Village 445 NORTH TRL A, STRATFORD, CT, 06614, Stratford, CT 06614
$400,000

1 beds

|

3 baths

|

1,620 sq ft

|

Condo

445 NORTH TRL A, STRATFORD, CT, 06614
Community: Oronoque Village
Newbury Village 21 GREAT HERON LN # 21, BROOKFIELD, CT, ..., Brookfield, CT 06804
$720,000

3 beds

|

4 baths

|

2,644 sq ft

|

Condo

21 GREAT HERON LN # 21, BROOKFIELD, CT, ...
Community: Newbury Village
Want to learn more about 55+ communities in New Fairfield? 55places can help!
Questions? Call us: (959) 214-2391
Heritage Village 929 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$299,000

3 beds

|

2 baths

|

1,716 sq ft

|

Condo

929 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Regency at Prospect 11 POPLAR DR # 11, PROSPECT, CT, 06712, Prospect, CT 06712
$549,000

3 beds

|

3 baths

|

2,058 sq ft

|

Condo

11 POPLAR DR # 11, PROSPECT, CT, 06712
Community: Regency at Prospect
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
Heritage Village 665 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$329,900

3 beds

|

2 baths

|

1,716 sq ft

|

Condo

665 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
The Village at Oxford Greens 185 COUNTRY CLUB DR # 185, OXFORD, CT, 0..., Oxford, CT 06478
$660,000

3 beds

|

3 baths

|

2,595 sq ft

|

Condo

185 COUNTRY CLUB DR # 185, OXFORD, CT, 0...
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 Powder Forest Homes 1 ASHTON CIR # 1, SIMSBURY, CT, 06070, Simsbury, CT 06070
$625,000

2 beds

|

2 baths

|

1,546 sq ft

1 ASHTON CIR # 1, SIMSBURY, CT, 06070
The Summit at Bethel 17 BRIAR RIDGE DR # 17, BETHEL, CT, 0680..., Bethel, CT 06801
$695,000

3 beds

|

4 baths

|

3,012 sq ft

|

Condo

17 BRIAR RIDGE DR # 17, BETHEL, CT, 0680...
Heritage Village 176 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$249,900

2 beds

|

2 baths

|

1,032 sq ft

|

Condo

176 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Spring Lake Village 1 COACH DR # 1, SOUTHINGTON, CT, 06489, Southington, CT 06489
$295,000

2 beds

|

2 baths

|

1,323 sq ft

|

Condo

1 COACH DR # 1, SOUTHINGTON, CT, 06489
Community: Spring Lake 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
Want to learn more about 55+ communities in New Fairfield? 55places can help!
Questions? Call us: (959) 214-2391
Heritage Village 1008 HERITAGE VLG B, SOUTHBURY, CT, 0648..., Southbury, CT 06488
$399,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

1008 HERITAGE VLG B, SOUTHBURY, CT, 0648...
Community: Heritage Village
Regency at Woodbridge 21 HERITAGE LN # 60, WOODBRIDGE, CT, 065..., Woodbridge, CT 06525
$729,000

3 beds

|

3 baths

|

Condo

21 HERITAGE LN # 60, WOODBRIDGE, CT, 065...
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 709 CHAMPIONSHIP DR # 709, OXFORD, CT, 0..., Oxford, CT 06478
$615,000

2 beds

|

2 baths

|

1,532 sq ft

|

Condo

709 CHAMPIONSHIP DR # 709, OXFORD, CT, 0...
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
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 87 CREEK LN A, STRATFORD, CT, 06614, Stratford, CT 06614
$447,000

1 beds

|

2 baths

|

1,454 sq ft

|

Condo

87 CREEK LN A, STRATFORD, CT, 06614
Community: Oronoque Village
Heritage Village 859 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$380,000

3 beds

|

2 baths

|

1,716 sq ft

|

Condo

859 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 890 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$325,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

890 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Fairview at Oxford Greens 709 CHAMPIONSHIP DR # 709, OXFORD, CT, 0..., Oxford, CT 06478
$615,000

2 beds

|

2 baths

|

1,532 sq ft

|

Condo

709 CHAMPIONSHIP DR # 709, OXFORD, CT, 0...
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
Want to learn more about 55+ communities in New Fairfield? 55places can help!
Questions? Call us: (959) 214-2391
Heritage Village 123 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$399,900

2 beds

|

2 baths

|

1,398 sq ft

|

Condo

123 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 69 HERITAGE VLG E, SOUTHBURY, CT, 06488, Southbury, CT 06488
$339,900

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

69 HERITAGE VLG E, SOUTHBURY, CT, 06488
Community: Heritage Village
Rivington 47 WARRINGTON ROUND # 47, DANBURY, CT, 0..., Danbury, CT 06810
$650,000

3 beds

|

3 baths

|

1,704 sq ft

|

Condo

47 WARRINGTON ROUND # 47, DANBURY, CT, 0...
Community: Rivington
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 919 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$299,900

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

919 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village

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156 communities near New Fairfield
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