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

158 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
4.8 rating (4 reviews) Wanaque Reserve
$300ks - $500ks
Wanaque Reserve, Wanaque, NJ
Resale Only | 55+ age-restricted | Built 2004 - 2014 | 755 homes
Bald Eagle Commons
$100ks - $300ks
Bald Eagle Commons, West Milford, NJ
Resale Only | 55+ age-restricted | Built 1995 - 2005 | 463 homes
Leisure Village
$100ks - $300ks
Leisure Village, Ridge, NY
Resale Only | 55+ age-restricted | Built 1969 - 1986 | 1,500 homes
3 rating (2 reviews) Heritage Hills
- $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
Oronoque Village
$200ks - $400ks
Oronoque Village, Stratford, CT
Resale Only | 55+ age-restricted | Built 1971 - 1977 | 929 homes
Leisure Knoll
$200ks - $400ks
Leisure Knoll, Ridge, NY
Resale Only | 55+ age-restricted | Built 1972 - 1982 | 701 homes
Overlook
$600ks - $900ks
Overlook, Carmel, NY
New Construction | 55+ age-restricted | 300 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.
3.7 rating (3 reviews) Greenwood Village
$100ks
Greenwood Village, Manorville, NY
Resale Only | 55+ age-restricted | Built 1980 - 2000 | 512 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
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 Glen
$300ks - $400ks
Leisure Glen, Ridge, NY
Resale Only | 55+ age-restricted | Built 1985 - 2010 | 646 homes
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
4 rating (8 reviews) Glenwood Village
$100ks - $200ks
Glenwood Village, Riverhead, NY
New and Resale | 55+ age-restricted | Built 1959 - present | 588 homes
Want to learn more about 55+ communities in New Fairfield? 55places can help!
Questions? Call us: (959) 214-2391
5 rating (1 reviews) Warwick Grove
$400ks - $600ks
Warwick Grove, Warwick, NY
New and Resale | 55+ age-restricted | Built 2004 - present | 215 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
Fairview at Oxford Greens
$400ks - $600ks
Fairview at Oxford Greens, Oxford, CT
New and Resale | 55+ age-restricted | Built 2019 - present | 125 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.
5 rating (1 reviews) Encore at Lake Grove
$500ks - $700ks
Encore at Lake Grove, Lake Grove, NY
Resale Only | 55+ age-restricted | Built 2006 - 2007 | 228 homes
HarborView
$600ks - $1Ms
HarborView, Port Washington, NY
Resale Only | 55+ age-restricted | Built 2002 - 2004 | 270 homes
5 rating (1 reviews) Westhampton Pines
$900ks - $1Ms
Westhampton Pines, Westhampton, NY
Resale Only | 55+ age-restricted | Built 2005 - 2013 | 189 homes
3.5 rating (2 reviews) Foxwood Village
$200ks - $400ks
Foxwood Village, Calverton, NY
Resale Only | 55+ age-restricted | Built 1986 - 2007 | 294 homes
Village Estates
$300ks - $400ks
Village Estates, Amityville, NY
Resale Only | 55+ age-restricted | Built 2006 - 2008 | 138 homes
Apple Ridge
$500ks - $1Ms
Apple Ridge, Mahwah, NJ
Resale Only | Age-targeted | Built 1977 - 1991 | 276 homes
Stoneleigh Woods at River...
$500ks
Stoneleigh Woods at River..., Riverhead, NY
Resale Only | 55+ age-restricted | Built 2007 - 2016 | 176 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
Meadowbrook Pointe Athlet...
$700ks - $1Ms
Meadowbrook Pointe Athlet..., Westbury, NY
Resale Only | 55+ age-restricted | Built 2015 - 2016 | 720 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
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 Coves at Melville
$500ks
The Coves at Melville, Melville, NY
Resale Only | 62+ age-restricted | Built 2004 - 2005 | 175 homes
The Seasons at Seaford
$600ks
The Seasons at Seaford, Seaford, NY
Resale Only | 55+ age-restricted | Built 2015 - 2017 | 112 homes
South Pond Village
$300ks - $400ks
South Pond Village, Bloomfield, CT
Resale Only | 55+ age-restricted | Built 1999 - 2005 | 151 homes
Breton Hills
$500ks
Breton Hills, Glen Cove, NY
New Construction | 55+ age-restricted | Built 2019 - present | 72 homes
Regency at Fishkill
$300ks - $400ks
Regency at Fishkill, Fishkill, NY
Resale Only | 55+ age-restricted | Built 2008 - 2020 | 164 homes
Country Pointe Preserve
$600ks - $900ks
Country Pointe PreserveYaphank, NY
New Construction | 55+ age-restricted | Built 2024 - present | 152 homes
Snug Harbor
$600ks - $700ks
Snug Harbor, Amityville, NY
Resale Only | 55+ age-restricted | Built 1970 - 1974 | 176 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
Want to learn more about 55+ communities in New Fairfield? 55places can help!
Questions? Call us: (959) 214-2391
The Hollows at Blue Hill
$500ks - $700ks
The Hollows at Blue Hill, Pearl River, NY
Resale Only | 55+ age-restricted | Built 2008 - 2014 | 126 homes
Country Pointe Plainview
$700ks - $1Ms
Country Pointe Plainview, Plainview, NY
New Construction | 55+ age-restricted | Built 2017 - present | 660 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
New The Greens at Half Hollow 385 ALTESSA BLVD, HUNTINGTON, NY, 11747, Huntington, NY 11747
$1,299,999

3 beds

|

3 baths

|

3,060 sq ft

|

Condo

385 ALTESSA BLVD, HUNTINGTON, NY, 11747
New The Villages at Mount Sinai Park 68 LOUDEN LOOP, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766
$839,999

2 beds

|

2 baths

|

1,736 sq ft

|

House

68 LOUDEN LOOP, BROOKHAVEN, NY, 11766
New Village Estates 12 SARAH CT, BABYLON, NY, 11701, Babylon, NY 11701
$579,000

2 beds

|

2 baths

|

1,243 sq ft

|

Condo

12 SARAH CT, BABYLON, NY, 11701
Community: Village Estates
New Snug Harbor 66 HARBOR N, BABYLON, NY, 11701, Babylon, NY 11701
$589,500

1 beds

|

1 baths

|

727 sq ft

|

Condo

66 HARBOR N, BABYLON, NY, 11701
Community: Snug Harbor
New Saddle Lakes 156 SCENIC LAKE DR, RIVERHEAD, NY, 11901, Riverhead, NY 11901
$629,000

3 beds

|

3 baths

|

1,837 sq ft

|

Condo

156 SCENIC LAKE DR, RIVERHEAD, NY, 11901
Community: Saddle Lakes
Want to learn more about 55+ communities in New Fairfield? 55places can help!
Questions? Call us: (959) 214-2391
New Encore at Lake Grove 8 SYMPHONY DR, BROOKHAVEN, NY, 11755, Brookhaven, NY 11755
$634,000

2 beds

|

3 baths

|

1,378 sq ft

|

Condo

8 SYMPHONY DR, BROOKHAVEN, NY, 11755
New Leisure Knoll 257 EDINBURGH DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$399,000

2 beds

|

2 baths

|

1,000 sq ft

|

Condo

257 EDINBURGH DR, BROOKHAVEN, NY, 11961
Community: Leisure Knoll
New The Village at Oxford Greens 505 TRADITIONS CT 505, OXFORD, CT, 06478, Oxford, CT 06478
$775,000

3 beds

|

3 baths

|

2,652 sq ft

|

Condo

505 TRADITIONS CT 505, OXFORD, CT, 06478
New Stoneleigh Woods at Riverhead 47 STONELEIGH DR, RIVERHEAD, NY, 11901, Riverhead, NY 11901
$699,000

2 beds

|

3 baths

|

1,942 sq ft

|

Condo

47 STONELEIGH DR, RIVERHEAD, NY, 11901
New Heritage Hills 415 HERITAGE HLS C, SOMERS, NY, 10589, Somers, NY 10589
$875,000

3 beds

|

2 baths

|

1,909 sq ft

|

Condo

415 HERITAGE HLS C, 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.
New Meadowbrook Pointe Athletic Club & Spa 401 PACING WAY 4101, HEMPSTEAD, NY, 1159..., Hempstead, NY 11590
$875,000

2 beds

|

2 baths

|

1,353 sq ft

|

Condo

401 PACING WAY 4101, HEMPSTEAD, NY, 1159...
New Baldwin Station 69 JASMINE CIR 69, MILFORD, CT, 06461, Milford, CT 06461
$820,000

2 beds

|

3 baths

|

2,820 sq ft

|

Condo

69 JASMINE CIR 69, MILFORD, CT, 06461
Community: Baldwin Station
New Westhampton Pines 49 SAMANTHA CIR 49, SOUTHAMPTON, NY, 119..., Southampton, NY 11977
$999,000

2 beds

|

2 baths

|

1,944 sq ft

|

Condo

49 SAMANTHA CIR 49, SOUTHAMPTON, NY, 119...
Community: Westhampton Pines
New Overlook 2084 SUMMIT LOOP 77, CARMEL, NY, 10512, Carmel, NY 10512
$779,000

2 beds

|

3 baths

|

2,214 sq ft

|

Condo

2084 SUMMIT LOOP 77, CARMEL, NY, 10512
Community: Overlook
New Stoneleigh Woods at Riverhead 1302 BALTUSROL BLVD, RIVERHEAD, NY, 1190..., Riverhead, NY 11901
$515,000

2 beds

|

3 baths

|

1,350 sq ft

|

Condo

1302 BALTUSROL BLVD, RIVERHEAD, NY, 1190...
New Oronoque Village 664 OSAGE LN A, STRATFORD, CT, 06614, Stratford, CT 06614
$499,000

1 beds

|

3 baths

|

1,438 sq ft

664 OSAGE 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
New The Greens at Half Hollow 398 ALTESSA BLVD, HUNTINGTON, NY, 11747, Huntington, NY 11747
$1,599,999

2 beds

|

2 baths

|

2,525 sq ft

|

Condo

398 ALTESSA BLVD, HUNTINGTON, NY, 11747
New Oronoque Village 543 N TRL A, STRATFORD, CT, 06614, Stratford, CT 06614
$585,000

1 beds

|

3 baths

|

1,426 sq ft

|

Condo

543 N TRL A, STRATFORD, CT, 06614
Community: Oronoque Village
New Encore at Lake Grove 176 SYMPHONY DR, BROOKHAVEN, NY, 11755, Brookhaven, NY 11755
$609,000

2 beds

|

2 baths

|

1,429 sq ft

|

Condo

176 SYMPHONY DR, BROOKHAVEN, NY, 11755
New Campagna 136 CHANGEBRIDGE RD 3, MONTVILLE TWP., N..., Montville Twp., NJ 07045
$409,900

1 beds

|

1 baths

136 CHANGEBRIDGE RD 3, MONTVILLE TWP., N...
Community: Campagna
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 Regency at Prospect 196 SYCAMORE DR 196, PROSPECT, CT, 06712, Prospect, CT 06712
$307,127

3 beds

|

2 baths

|

1,500 sq ft

|

Condo

196 SYCAMORE DR 196, PROSPECT, CT, 06712
Community: Regency at Prospect
New The Seasons at Elwood 244 FALL CT, HUNTINGTON, NY, 11731, Huntington, NY 11731
$1,375,000

2 beds

|

3 baths

|

2,256 sq ft

|

Condo

244 FALL CT, HUNTINGTON, NY, 11731
New Founders Ridge 11 WEBSTER LN 6, MIDDLETOWN, CT, 06457, Middletown, CT 06457
$599,900

3 beds

|

3 baths

|

1,579 sq ft

11 WEBSTER LN 6, MIDDLETOWN, CT, 06457
Community: Founders Ridge
New Heritage Village 916 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$390,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

916 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
New Oronoque Village 96 SEMINOLE LN A, STRATFORD, CT, 06614, Stratford, CT 06614
$469,000

2 beds

|

3 baths

|

1,438 sq ft

|

Condo

96 SEMINOLE LN A, STRATFORD, CT, 06614
Community: Oronoque Village
New Bear's Cove 33 WINDSOR LN, RAMSEY, NJ, 07446, Ramsey, NJ 07446
$1,250,000

3 beds

|

4 baths

|

Townhouse

33 WINDSOR LN, RAMSEY, NJ, 07446
Community: Bear's Cove
New Leisure Knoll 1 AVON CT, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$489,999

2 beds

|

2 baths

|

1,070 sq ft

|

Condo

1 AVON CT, BROOKHAVEN, NY, 11961
Community: Leisure Knoll
Want to learn more about 55+ communities in New Fairfield? 55places can help!
Questions? Call us: (959) 214-2391
New Snug Harbor 47 HARBOR N, BABYLON, NY, 11701, Babylon, NY 11701
$549,999

1 beds

|

1 baths

|

806 sq ft

|

Condo

47 HARBOR N, BABYLON, NY, 11701
Community: Snug Harbor
Leisure Village 54 AYLESBURY CT B, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$349,000

2 beds

|

1 baths

|

1,085 sq ft

|

Condo

54 AYLESBURY CT B, BROOKHAVEN, NY, 11961
Community: Leisure Village
Setauket Meadows 100 COVE LN 100, BROOKHAVEN, NY, 11733, Brookhaven, NY 11733
$769,000

2 beds

|

3 baths

|

1,820 sq ft

|

Condo

100 COVE LN 100, BROOKHAVEN, NY, 11733
Community: Setauket Meadows
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 315 NAVAJO LN A, STRATFORD, CT, 06614, Stratford, CT 06614
$549,000

2 beds

|

3 baths

|

1,434 sq ft

|

Condo

315 NAVAJO LN A, STRATFORD, CT, 06614
Community: Oronoque Village
Leisure Village 395 WOODBRIDGE DR 395E, BROOKHAVEN, NY, ..., Brookhaven, NY 11961
$299,000

2 beds

|

1 baths

|

875 sq ft

|

Condo

395 WOODBRIDGE DR 395E, BROOKHAVEN, NY, ...
Community: Leisure Village
Heritage Village 14 HERITAGE CIR B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$269,000

2 beds

|

2 baths

|

1,000 sq ft

|

Condo

14 HERITAGE CIR B, SOUTHBURY, CT, 06488
Community: Heritage Village
Bald Eagle Commons 1302 RICHMOND RD 302, WEST MILFORD TWP.,..., West Milford Twp., NJ 07480
$179,900

1 beds

|

1 baths

|

655 sq ft

1302 RICHMOND RD 302, WEST MILFORD TWP.,...
Community: Bald Eagle Commons
The Manors at The Colony Preserve 17 GREENTREE CT, BROOKHAVEN, NY, 11967, Brookhaven, NY 11967
$559,000

2 beds

|

2 baths

|

1,557 sq ft

|

Condo

17 GREENTREE CT, BROOKHAVEN, NY, 11967
Leisure Knoll 541 STRATFORD LN, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$529,000

3 beds

|

2 baths

|

1,412 sq ft

|

Condo

541 STRATFORD LN, BROOKHAVEN, NY, 11961
Community: Leisure Knoll
Heritage Village 847 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$309,000

3 beds

|

2 baths

|

1,716 sq ft

|

Condo

847 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Oronoque Village 132 BISON LN B, STRATFORD, CT, 06614, Stratford, CT 06614
$470,000

1 beds

|

3 baths

|

1,426 sq ft

|

Condo

132 BISON LN B, 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
Wanaque Reserve 10402 WARRENS WAY 4TH  NEW, WANAQUE, NJ,..., Wanaque, NJ 07465
$409,988

2 beds

|

2 baths

|

Condo

10402 WARRENS WAY 4TH NEW, WANAQUE, NJ,...
Community: Wanaque Reserve
Heritage Hills 969 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589
$490,000

1 beds

|

2 baths

|

967 sq ft

|

Condo

969 HERITAGE HLS B, 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.

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