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

329 homes 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
Oronoque Village
$200ks - $400ks
Oronoque Village, Stratford, CT
Resale Only | 55+ age-restricted | Built 1971 - 1977 | 929 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
$400ks - $900ks
Heritage Hills, Somers, NY
Resale Only | Age-targeted | Built 1974 - 2006 | 2,600 homes
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3.7 rating (3 reviews) Greenwood Village
$100ks
Greenwood Village, Manorville, NY
Resale Only | 55+ age-restricted | Built 1980 - 2000 | 512 homes
Bald Eagle Commons
$100ks - $300ks
Bald Eagle Commons, West Milford, NJ
Resale Only | 55+ age-restricted | Built 1995 - 2005 | 463 homes
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
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.
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
Fairview at Oxford Greens
$400ks - $600ks
Fairview at Oxford Greens, Oxford, CT
New and Resale | 55+ age-restricted | Built 2019 - present | 125 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
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Rivington
$300ks - $900ks
Rivington, Danbury, CT
New and Resale | Age-targeted | Built 2006 - present | 1,050 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
Spring Lake Village
$100ks - $200ks
Spring Lake Village, Southington, CT
Resale Only | 55+ age-restricted | Built 1970 - 2004 | 640 homes
5 rating (1 reviews) Warwick Grove
$400ks - $600ks
Warwick Grove, Warwick, NY
New and Resale | 55+ age-restricted | Built 2004 - present | 215 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) Four Seasons at Great Not...
$400ks - $700ks
Four Seasons at Great Not..., Woodland Park, NJ
Resale Only | 55+ age-restricted | Built 2005 - 2018 | 814 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) The Villages at Mount Sin...
$600ks
The Villages at Mount Sin..., Mount Sinai, NY
Resale Only | 55+ age-restricted | Built 2005 - 2007 | 185 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
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Questions? Call us: (959) 214-2391
4 rating (8 reviews) Glenwood Village
$100ks - $200ks
Glenwood Village, Riverhead, NY
New and Resale | 55+ age-restricted | Built 1959 - present | 588 homes
5 rating (1 reviews) Newtown Woods
$300ks - $500ks
Newtown Woods, Newtown, CT
New and Resale | 55+ age-restricted | Built 2011 - present | 178 homes
Leisure Knoll
$200ks - $400ks
Leisure Knoll, Ridge, NY
Resale Only | 55+ age-restricted | Built 1972 - 1982 | 701 homes
Leisure Glen
$300ks - $400ks
Leisure Glen, Ridge, NY
Resale Only | 55+ age-restricted | Built 1985 - 2010 | 646 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.
Kensington Estates
$1Ms
Kensington Estates, Woodbury, NY
New Construction | 55+ age-restricted | Built 2019 - 2021 | 80 homes
Country Pointe Plainview
$700ks - $1Ms
Country Pointe Plainview, Plainview, NY
New Construction | 55+ age-restricted | Built 2017 - present | 660 homes
The Villas at Narraganset...
$400ks
The Villas at Narraganset..., Lindenhurst, NY
Resale Only | 55+ age-restricted | Built 2004 - 2005 | 138 homes
Strathmore Gate East
$300ks
Strathmore Gate East, Coram, NY
Resale Only | 55+ age-restricted | Built 1970 - 1975 | 174 homes
The Seasons at Seaford
$600ks
The Seasons at Seaford, Seaford, NY
Resale Only | 55+ age-restricted | Built 2015 - 2017 | 112 homes
Want to learn more about 55+ communities in New Fairfield? 55places can help!
Questions? Call us: (959) 214-2391
Village Estates
$300ks - $400ks
Village Estates, Amityville, NY
Resale Only | 55+ age-restricted | Built 2006 - 2008 | 138 homes
The Coves at Melville
$500ks
The Coves at Melville, Melville, NY
Resale Only | 62+ age-restricted | Built 2004 - 2005 | 175 homes
HarborView
$600ks - $1Ms
HarborView, Port Washington, NY
Resale Only | 55+ age-restricted | Built 2002 - 2004 | 270 homes
Breton Hills
$500ks
Breton Hills, Glen Cove, NY
New Construction | 55+ age-restricted | Built 2019 - present | 72 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.
3.5 rating (2 reviews) Foxwood Village
$200ks - $400ks
Foxwood Village, Calverton, NY
Resale Only | 55+ age-restricted | Built 1986 - 2007 | 294 homes
5 rating (1 reviews) Westhampton Pines
$900ks - $1Ms
Westhampton Pines, Westhampton, NY
Resale Only | 55+ age-restricted | Built 2005 - 2013 | 189 homes
The Retreat at Carmel
$300ks - $800ks
The Retreat at Carmel, Carmel, NY
Resale Only | 55+ age-restricted | Built 2008 - 2018 | 312 homes
5 rating (1 reviews) Sunrise Village
$400ks
Sunrise Village, Sayville, NY
Resale Only | 55+ age-restricted | Built 1985 - 1990 | 213 homes
Want to learn more about 55+ communities in New Fairfield? 55places can help!
Questions? Call us: (959) 214-2391
The Summit at Bethel
$500ks - $700ks
The Summit at Bethel, Bethel, CT
Resale Only | 55+ age-restricted | Built 2010 - 2021 | 235 homes
Dutchgate
$300ks - $500ks
Dutchgate, Valley Stream, NY
Resale Only | 55+ age-restricted | Built 2009 - 2015 | 348 homes
123...4
Four Seasons at Great Notch Spa and Club 5 SLATE CT, WOODLAND PARK, NJ, 07424, Woodland Park, NJ 07424
$615,000

2 beds

|

2 baths

|

1,466 sq ft

5 SLATE CT, WOODLAND PARK, NJ, 07424
Village Estates 105 FRANCESCA WAY 105, BABYLON, NY, 1170..., Babylon, NY 11701
$559,000

2 beds

|

1 baths

|

1,229 sq ft

|

Condo

105 FRANCESCA WAY 105, BABYLON, NY, 1170...
Community: Village Estates
Overlook 2079 SUMMIT LOOP 103, CARMEL, NY, 10512, Carmel, NY 10512
$899,000

2 beds

|

2 baths

|

1,948 sq ft

|

Condo

2079 SUMMIT LOOP 103, CARMEL, NY, 10512
Community: Overlook
Glenwood Village 1661 OLD COUNTRY RD 62, RIVERHEAD, NY, 1..., Riverhead, NY 11901
$449,999

3 beds

|

2 baths

|

1,680 sq ft

|

Manufactured Home

1661 OLD COUNTRY RD 62, RIVERHEAD, NY, 1...
Community: Glenwood Village
Leisure Village 72 ENFIELD CT A, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$359,900

2 beds

|

1 baths

|

1,085 sq ft

|

Condo

72 ENFIELD CT A, BROOKHAVEN, NY, 11961
Community: Leisure Village
Want to learn more about 55+ communities in New Fairfield? 55places can help!
Questions? Call us: (959) 214-2391
Four Seasons at Great Notch Spa and Club 5 SLATE CT A3, WOODLAND PARK, NJ, 07424, Woodland Park, NJ 07424
$615,000

2 beds

|

2 baths

|

Condo

5 SLATE CT A3, WOODLAND PARK, NJ, 07424
Winthrop Court 1107 WICKHAM TER 374, CLIFTON, NJ, 07013, Clifton, NJ 07013
$559,000

2 beds

|

2 baths

|

Condo

1107 WICKHAM TER 374, CLIFTON, NJ, 07013
Community: Winthrop Court
Pond Spring Village 17 PONDVIEW CIR 17, BEACON FALLS, CT, 06..., Beacon Falls, CT 06403
$474,900

2 beds

|

2 baths

|

1,474 sq ft

|

Condo

17 PONDVIEW CIR 17, BEACON FALLS, CT, 06...
Community: Pond Spring Village
Heritage Village 331 HERITAGE VLG D, SOUTHBURY, CT, 06488, Southbury, CT 06488
$189,000

2 beds

|

2 baths

|

1,044 sq ft

|

Condo

331 HERITAGE VLG D, 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.
Winthrop Court 9210 RAVENSCROFT RD 627, CLIFTON, NJ, 07..., Clifton, NJ 07013
$585,000

2 beds

|

2 baths

|

Condo

9210 RAVENSCROFT RD 627, CLIFTON, NJ, 07...
Community: Winthrop Court
Winthrop Court 9210 RAVENSCROFT RD, CLIFTON CITY, NJ, 0..., Clifton City, NJ 07013
$585,000

2 beds

|

2 baths

|

1,871 sq ft

9210 RAVENSCROFT RD, CLIFTON CITY, NJ, 0...
Community: Winthrop Court
Wildflowers at Wallkill 10 CYPRUS DR, MIDDLETOWN, NY, 10940, Middletown, NY 10940
$489,999

2 beds

|

2 baths

|

1,612 sq ft

|

House

10 CYPRUS DR, MIDDLETOWN, NY, 10940
Country Pointe Preserve 118 JUNIPER LN 31, BROOKHAVEN, NY, 11980, Brookhaven, NY 11980
$865,000

2 beds

|

3 baths

|

1,998 sq ft

|

Condo

118 JUNIPER LN 31, BROOKHAVEN, NY, 11980
Want to learn more about 55+ communities in New Fairfield? 55places can help!
Questions? Call us: (959) 214-2391
Heritage Hills 29 HERITAGE HLS 29D, SOMERS, NY, 10589, Somers, NY 10589
$495,000

2 beds

|

3 baths

|

1,340 sq ft

|

Condo

29 HERITAGE HLS 29D, SOMERS, NY, 10589
Community: Heritage Hills
Oronoque Village 99 SEMINOLE LN A, STRATFORD, CT, 06614, Stratford, CT 06614
$485,000

1 beds

|

3 baths

|

1,426 sq ft

|

Condo

99 SEMINOLE LN A, STRATFORD, CT, 06614
Community: Oronoque Village
The Waterways at Moriches 290 W MIDLAND POND CT 290, BROOKHAVEN, N..., Brookhaven, NY 11955
$629,000

2 beds

|

2 baths

|

1,440 sq ft

|

Condo

290 W MIDLAND POND CT 290, BROOKHAVEN, N...
The Seasons at Seaford 56 SPRING DR, HEMPSTEAD, NY, 11783, Hempstead, NY 11783
$820,000

2 beds

|

3 baths

|

1,034 sq ft

|

Condo

56 SPRING DR, HEMPSTEAD, NY, 11783
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 Plainview 31201 SPRUCE POND CIR, OYSTER BAY, NY, 1..., Oyster Bay, NY 11803
$1,150,000

2 beds

|

2 baths

|

1,379 sq ft

|

Condo

31201 SPRUCE POND CIR, OYSTER BAY, NY, 1...
Bald Eagle Commons 5301 RICHMOND RD, WEST MILFORD, NJ, 0748..., West Milford, NJ 07480
$269,900

2 beds

|

2 baths

5301 RICHMOND RD, WEST MILFORD, NJ, 0748...
Community: Bald Eagle Commons
Bald Eagle Commons 5320 RICHMOND RD, WEST MILFORD, NJ, 0748..., West Milford, NJ 07480
$225,000

1 beds

|

1 baths

|

Condo

5320 RICHMOND RD, WEST MILFORD, NJ, 0748...
Community: Bald Eagle Commons
Bald Eagle Commons 5320 RICHMOND RD 320, WEST MILFORD TWP.,..., West Milford Twp., NJ 07480
$225,000

1 beds

|

1 baths

|

655 sq ft

5320 RICHMOND RD 320, WEST MILFORD TWP.,...
Community: Bald Eagle Commons
Want to learn more about 55+ communities in New Fairfield? 55places can help!
Questions? Call us: (959) 214-2391
Heritage Village 53 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$279,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

53 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Oronoque Village 196 APACHE LN A, STRATFORD, CT, 06614, Stratford, CT 06614
$365,000

1 beds

|

2 baths

|

1,175 sq ft

|

Condo

196 APACHE LN A, STRATFORD, CT, 06614
Community: Oronoque Village
Breton Hills 401 BRETON WAY, GLEN COVE, NY, 11542, Glen Cove, NY 11542
$699,999

2 beds

|

2 baths

|

1,300 sq ft

|

Condo

401 BRETON WAY, GLEN COVE, NY, 11542
Community: Breton Hills
Bald Eagle Commons 4 RICHMOND RD 215, WEST MILFORD, NJ, 074..., West Milford, NJ 07480
$260,000

2 beds

|

2 baths

|

Condo

4 RICHMOND RD 215, WEST MILFORD, NJ, 074...
Community: Bald Eagle Commons
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.
Wanaque Reserve 1118 WARRENS WAY, WANAQUE BORO, NJ, 0746..., Wanaque Boro, NJ 07465
$569,000

2 beds

|

2 baths

1118 WARRENS WAY, WANAQUE BORO, NJ, 0746...
Community: Wanaque Reserve
Sunrise Village 93 REVERE DR, ISLIP, NY, 11782, Islip, NY 11782
$525,000

2 beds

|

2 baths

|

1,230 sq ft

|

Condo

93 REVERE DR, ISLIP, NY, 11782
Community: Sunrise Village
The Villages at Mount Sinai Park 46 LOUDEN LOOP, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766
$899,000

3 beds

|

3 baths

|

2,455 sq ft

|

House

46 LOUDEN LOOP, BROOKHAVEN, NY, 11766
Bald Eagle Commons 5301 RICHMOND RD 301, WEST MILFORD TWP.,..., West Milford Twp., NJ 07480
$269,900

2 beds

|

2 baths

5301 RICHMOND RD 301, WEST MILFORD TWP.,...
Community: Bald Eagle Commons
Jefferson Village 10 REGENTS PL D, YORKTOWN, NY, 10598, Yorktown, NY 10598
$240,000
|

1 baths

|

550 sq ft

|

Condo

10 REGENTS PL D, YORKTOWN, NY, 10598
Community: Jefferson Village
Want to learn more about 55+ communities in New Fairfield? 55places can help!
Questions? Call us: (959) 214-2391
O'Meara Farm 1 MAGNOLIA CIR 1, FARMINGTON, CT, 06032, Farmington, CT 06032
$480,000

2 beds

|

2 baths

|

1,416 sq ft

|

Condo

1 MAGNOLIA CIR 1, FARMINGTON, CT, 06032
Community: O'Meara Farm
Bald Eagle Commons 4 RICHMOND RD 215, WEST MILFORD TWP., NJ..., West Milford Twp., NJ 07480
$260,000

2 beds

|

2 baths

4 RICHMOND RD 215, WEST MILFORD TWP., NJ...
Community: Bald Eagle Commons
The Greens at Half Hollow 625 MADEIRA BLVD, HUNTINGTON, NY, 11747, Huntington, NY 11747
$980,000

2 beds

|

3 baths

|

1,940 sq ft

|

Condo

625 MADEIRA BLVD, HUNTINGTON, NY, 11747
Meadowbrooke Pointe East Meadow 137 EMANUEL WAY, HEMPSTEAD, NY, 11554, Hempstead, NY 11554
$839,000

2 beds

|

3 baths

|

1,390 sq ft

|

Condo

137 EMANUEL WAY, HEMPSTEAD, NY, 11554
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.
Foxwood Village 1407 MIDDLE RD 91, RIVERHEAD, NY, 11933, Riverhead, NY 11933
$364,000

2 beds

|

2 baths

|

1,532 sq ft

|

House

1407 MIDDLE RD 91, RIVERHEAD, NY, 11933
Community: Foxwood Village
Heritage Village 640 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$360,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

640 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Regency at Fishkill 145 REGENCY DR, FISHKILL, NY, 12524, Fishkill, NY 12524
$549,999

2 beds

|

2 baths

|

1,803 sq ft

|

Condo

145 REGENCY DR, FISHKILL, NY, 12524
Community: Regency at Fishkill
Oronoque Village 47 HURON LN A, STRATFORD, CT, 06614, Stratford, CT 06614
$409,000

2 beds

|

2 baths

|

1,360 sq ft

|

Condo

47 HURON 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
Leisure Village 279 BERWICK CT B, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$299,999

2 beds

|

1 baths

|

875 sq ft

|

Condo

279 BERWICK CT B, BROOKHAVEN, NY, 11961
Community: Leisure Village
Country Village Estates 45 THEODORE DR, BROOKHAVEN, NY, 11727, Brookhaven, NY 11727
$452,000

2 beds

|

2 baths

|

1,305 sq ft

|

Condo

45 THEODORE DR, BROOKHAVEN, NY, 11727

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