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

159 communities near New Fairfield

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Country Village Estates
$300ks
Country Village Estates, Coram, NY
Resale Only | 55+ age-restricted | Built 1993 - 2001 | 195 homes
Vineyards at Brookfield
$400ks - $500ks
Vineyards at Brookfield, Center Moriches, NY
New Construction | 55+ age-restricted | Built 2019 - present | 146 homes
3.5 rating (2 reviews) Foxwood Village
$200ks - $400ks
Foxwood Village, Calverton, NY
Resale Only | 55+ age-restricted | Built 1986 - 2007 | 294 homes
The Coves at Melville
$500ks
The Coves at Melville, Melville, NY
Resale Only | 62+ age-restricted | Built 2004 - 2005 | 175 homes
Windcrest East
$400ks - $500ks
Windcrest East, Calverton, NY
Resale Only | 55+ age-restricted | Built 2004 - 2005 | 126 homes
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Questions? Call us: (959) 214-2391
5 rating (1 reviews) Paris Square
$500ks - $700ks
Paris Square, Northvale, NJ
New and Resale | 55+ age-restricted | Built 2000 - present | 88 homes
Village Estates
$300ks - $400ks
Village Estates, Amityville, NY
Resale Only | 55+ age-restricted | Built 2006 - 2008 | 138 homes
Winthrop Court
$400ks - $600ks
Winthrop Court, Clifton, NJ
Resale Only | 55+ age-restricted | Built 2000 - 2010 | 270 homes
Breton Hills
$500ks
Breton Hills, Glen Cove, NY
New Construction | 55+ age-restricted | Built 2019 - present | 72 homes
Dutchgate
$300ks - $500ks
Dutchgate, Valley Stream, NY
Resale Only | 55+ age-restricted | Built 2009 - 2015 | 348 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.
Bear's Cove
$800ks - $900ks
Bear's Cove, Ramsey, NJ
Resale Only | 55+ age-restricted | Built 2006 - 2014 | 104 homes
Four Seasons at Troy Hill...
$500ks
Four Seasons at Troy Hill..., Parsippany, NJ
Resale Only | 55+ age-restricted | Built 2007 - 2007 | 46 homes
Newbury Village
$400ks - $500ks
Newbury Village, Brookfield, CT
New and Resale | 55+ age-restricted | Built 2005 - present | 120 homes
Sterling Mist
$500ks - $600ks
Sterling Mist, Parsippany, NJ
Resale Only | 55+ age-restricted | Built 2002 - 2006 | 28 homes
1 rating (1 reviews) Plymouth Estates at Mount...
$400ks - $500ks
Plymouth Estates at Mount..., Mount Sinai, NY
Resale Only | 55+ age-restricted | Built 2006 - 2013 | 285 homes
The Vineyards at Miller P...
$500ks
The Vineyards at Miller P..., Miller Place, NY
Resale Only | 55+ age-restricted | Built 2004 - 2005 | 85 homes
Want to learn more about 55+ communities in New Fairfield? 55places can help!
Questions? Call us: (959) 214-2391
Applegate Estates
$500ks - $400ks
Applegate Estates, Southington, CT
New and Resale | 55+ age-restricted | Built 2010 - 2025 | 94 homes
Baldwin Station
$400ks
Baldwin Station, Milford, CT
Resale Only | 55+ age-restricted | Built 2001 - 2003 | 82 homes
The Bel Aire at East Mead...
$300ks - $400ks
The Bel Aire at East Mead..., East Meadow, NY
Resale Only | 55+ age-restricted | Built 2004 - 2005 | 95 homes
The Seasons at East Meado...
$400ks - $600ks
The Seasons at East Meado..., East Meadow, NY
Resale Only | 55+ age-restricted | Built 2009 - 2012 | 404 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.
Billingsgate
$400ks - $600ks
Billingsgate, Simsbury, CT
Resale Only | 55+ age-restricted | Built 2003 - 2006 | 37 homes
Stone Ridge Estates
$500ks - $600ks
Stone Ridge Estates, Dix Hills, NY
Resale Only | 55+ age-restricted | Built 2004 - 2013 | 76 homes
The Seasons at Plainview
$500ks - $600ks
The Seasons at Plainview, Plainview, NY
Resale Only | 55+ age-restricted | Built 2006 - 2007 | 134 homes
Hopmeadow Place
$200ks - $300ks
Hopmeadow Place, Simsbury, CT
Resale Only | 55+ age-restricted | Built 2005 - 2005 | 66 homes
Meadowbrook Pointe Athlet...
$700ks - $1Ms
Meadowbrook Pointe Athlet..., Westbury, NY
Resale Only | 55+ age-restricted | Built 2015 - 2016 | 720 homes
Harbor View Estates
$400ks - $600ks
Harbor View Estates, Copiague, NY
New Construction | 55+ age-restricted | Built 2017 - 2018 | 40 homes
Kensington Estates
$1Ms
Kensington Estates, Woodbury, NY
New Construction | 55+ age-restricted | Built 2019 - 2021 | 80 homes
Want to learn more about 55+ communities in New Fairfield? 55places can help!
Questions? Call us: (959) 214-2391
Village Vistas
$800ks - $1Ms
Village Vistas, Port Jefferson, NY
Resale Only | 55+ age-restricted | Built 2013 - 2017 | 43 homes
Regency Meadows
$500ks
Regency Meadows, Trumbull, CT
Resale Only | 55+ age-restricted | Built 2003 - 2005 | 51 homes
South Pond Village
$300ks - $400ks
South Pond Village, Bloomfield, CT
Resale Only | 55+ age-restricted | Built 1999 - 2005 | 151 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.
Meadow Brook Estates
$300ks - $400ks
Meadow Brook Estates, Oxford, CT
Resale Only | 55+ age-restricted | Built 2003 - 2020 | 246 homes
Regency at Wappinger
$500ks
Regency at Wappinger, Wappingers Falls, NY
Resale Only | 55+ age-restricted | Built 2014 - 2020 | 225 homes
Regency at Prospect
$300ks - $400ks
Regency at Prospect, Prospect, CT
Resale Only | 55+ age-restricted | Built 2006 - 2020 | 379 homes
The Vineyards at Mount Si...
$800ks - $1Ms
The Vineyards at Mount Si..., Mount Sinai, NY
New Construction | 55+ age-restricted | Built 2020 - present | 91 homes
Four Seasons at Cedar Gro...
$400ks - $600ks
Four Seasons at Cedar Gro..., Cedar Grove, NJ
Resale Only | 55+ age-restricted | Built 2000 - 2005 | 156 homes
Four Seasons at Wayne
$300ks - $400ks
Four Seasons at Wayne, Wayne, NJ
Resale Only | 55+ age-restricted | Built 1999 - 2001 | 230 homes
Enclave at Shackamaxon
$1Ms
Enclave at Shackamaxon, Scotch Plains, NJ
Resale Only | 55+ age-restricted | Built 2016 - 2018 | 56 homes
The Pointe
$300ks - $600ks
The Pointe, Livingston, NJ
Resale Only | 55+ age-restricted | Built 2004 - 2007 | 180 homes
Want to learn more about 55+ communities in New Fairfield? 55places can help!
Questions? Call us: (959) 214-2391
Briar Hill
$600ks - $700ks
Briar Hill, Montville Township, NJ
Resale Only | 55+ age-restricted | Built 2012 - 2015 | 28 homes
Whitfield
$600ks - $700ks
Whitfield, Metuchen, NJ
Resale Only | 55+ age-restricted | 17 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.
Greenwood Village 5190 VILLAGE CIR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949
$239,000

2 beds

|

2 baths

|

1,258 sq ft

|

Condo

5190 VILLAGE CIR, BROOKHAVEN, NY, 11949
Community: Greenwood Village
Glenwood Village 1661 OLD COUNTRY RD 516, RIVERHEAD, NY, ..., Riverhead, NY 11901
$419,000

2 beds

|

2 baths

|

1,624 sq ft

|

Manufactured Home

1661 OLD COUNTRY RD 516, RIVERHEAD, NY, ...
Community: Glenwood Village
New Country Pointe Plainview 17101 ASPENWOOD DR, OYSTER BAY, NY, 1180..., Oyster Bay, NY 11803
$1,100,000

2 beds

|

2 baths

|

1,400 sq ft

|

Condo

17101 ASPENWOOD DR, OYSTER BAY, NY, 1180...
New Liberty at Newtown 76 SUZIE DR 76, NEWTOWN, CT, 06470, Newtown, CT 06470
$648,000

2 beds

|

3 baths

|

2,341 sq ft

|

Condo

76 SUZIE DR 76, NEWTOWN, CT, 06470
Community: Liberty at Newtown
New Wanaque Reserve 4301 WARRENS WAY, WANAQUE BORO, NJ, 0746..., Wanaque Boro, NJ 07465
$410,000

2 beds

|

2 baths

4301 WARRENS WAY, WANAQUE BORO, NJ, 0746...
Community: Wanaque Reserve
Want to learn more about 55+ communities in New Fairfield? 55places can help!
Questions? Call us: (959) 214-2391
New Heritage Village 804 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$259,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

804 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
New Strathmore Gate East 4 FLAIR WAY, BROOKHAVEN, NY, 11727, Brookhaven, NY 11727
$495,000

2 beds

|

2 baths

|

1,112 sq ft

|

House

4 FLAIR WAY, BROOKHAVEN, NY, 11727
New The Greens at Half Hollow 1130 SAVOY DR, HUNTINGTON, NY, 11747, Huntington, NY 11747
$710,000

2 beds

|

2 baths

|

1,140 sq ft

|

Condo

1130 SAVOY DR, HUNTINGTON, NY, 11747
New Oronoque Village 89 S TRL A, STRATFORD, CT, 06614, Stratford, CT 06614
$649,000

1 beds

|

3 baths

|

1,438 sq ft

|

Condo

89 S TRL A, STRATFORD, CT, 06614
Community: Oronoque Village
New Oak Meadow Estates 197 OAK MEADOW LN 197, TORRINGTON, CT, 0..., Torrington, CT 06790
$399,000

2 beds

|

2 baths

|

1,419 sq ft

|

Condo

197 OAK MEADOW LN 197, TORRINGTON, CT, 0...
Community: Oak Meadow Estates
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 Strathmore Gate East 9 FREEDOM LN, BROOKHAVEN, NY, 11727, Brookhaven, NY 11727
$289,000

1 beds

|

1 baths

|

728 sq ft

|

Condo

9 FREEDOM LN, BROOKHAVEN, NY, 11727
New Jefferson Village 27 WALDEN CT J, YORKTOWN, NY, 10598, Yorktown, NY 10598
$375,000

1 beds

|

1 baths

|

800 sq ft

|

Condo

27 WALDEN CT J, YORKTOWN, NY, 10598
Community: Jefferson Village
New Leisure Knoll 338 EDINBURGH DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$419,990

2 beds

|

1 baths

|

960 sq ft

|

Condo

338 EDINBURGH DR, BROOKHAVEN, NY, 11961
Community: Leisure Knoll
New Greenwood Village 5127 VILLAGE CIR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949
$227,000

2 beds

|

2 baths

|

1,291 sq ft

|

Condo

5127 VILLAGE CIR, BROOKHAVEN, NY, 11949
Community: Greenwood Village
New Billingsgate 14 BILLINGSGATE DR 14, SIMSBURY, CT, 060..., Simsbury, CT 06070
$750,000

2 beds

|

3 baths

|

2,729 sq ft

|

Condo

14 BILLINGSGATE DR 14, SIMSBURY, CT, 060...
Community: Billingsgate
New Encore Atlantic Shores 11 OVATION PL, BROOKHAVEN, NY, 11941, Brookhaven, NY 11941
$925,000

2 beds

|

3 baths

|

2,900 sq ft

|

Condo

11 OVATION PL, BROOKHAVEN, NY, 11941
Want to learn more about 55+ communities in New Fairfield? 55places can help!
Questions? Call us: (959) 214-2391
New Leisure Village 312 WOODBRIDGE DR B, BROOKHAVEN, NY, 119..., Brookhaven, NY 11961
$239,000

1 beds

|

1 baths

|

684 sq ft

|

Condo

312 WOODBRIDGE DR B, BROOKHAVEN, NY, 119...
Community: Leisure Village
New Heritage Village 184 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$209,000

1 beds

|

1 baths

|

928 sq ft

|

Condo

184 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
New The Powder Forest Homes 6 PROSPECT RDG 6, SIMSBURY, CT, 06070, Simsbury, CT 06070
$715,000

3 beds

|

3 baths

|

2,183 sq ft

6 PROSPECT RDG 6, SIMSBURY, CT, 06070
New Bear's Cove 75 WINDSOR LN, RAMSEY, NJ, 07446, Ramsey, NJ 07446
$1,333,000

3 beds

|

4 baths

|

Condo

75 WINDSOR LN, RAMSEY, NJ, 07446
Community: Bear's Cove
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 The Manors at The Colony Preserve 22 CRICKET CT, BROOKHAVEN, NY, 11967, Brookhaven, NY 11967
$425,000

2 beds

|

2 baths

|

1,500 sq ft

|

Condo

22 CRICKET CT, BROOKHAVEN, NY, 11967
New Country Pointe Preserve 3 JUNIPER LN 94, BROOKHAVEN, NY, 11980, Brookhaven, NY 11980
$975,000

2 beds

|

3 baths

|

2,389 sq ft

|

Condo

3 JUNIPER LN 94, BROOKHAVEN, NY, 11980
New Fairfield at St. James 210 ELTON CT, SMITHTOWN, NY, 11780, Smithtown, NY 11780
$655,000

2 beds

|

2 baths

|

1,357 sq ft

|

Condo

210 ELTON CT, SMITHTOWN, NY, 11780
New Heritage Village 333 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$335,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

333 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
New The Greens at Half Hollow 891 ALTESSA BLVD, HUNTINGTON, NY, 11747, Huntington, NY 11747
$739,000

2 beds

|

2 baths

|

1,000 sq ft

|

Condo

891 ALTESSA BLVD, HUNTINGTON, NY, 11747
New Heritage Hills 334 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589
$659,000

2 beds

|

2 baths

|

1,428 sq ft

|

Condo

334 HERITAGE HLS B, SOMERS, NY, 10589
Community: Heritage Hills
New Sunken Pond Estates 102 WINGED FOOT WAY, RIVERHEAD, NY, 1190..., Riverhead, NY 11901
$515,000

2 beds

|

3 baths

|

1,350 sq ft

|

Condo

102 WINGED FOOT WAY, RIVERHEAD, NY, 1190...
Community: Sunken Pond Estates
Want to learn more about 55+ communities in New Fairfield? 55places can help!
Questions? Call us: (959) 214-2391
New Heritage Hills 103 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589
$780,000

3 beds

|

2 baths

|

1,780 sq ft

|

Condo

103 HERITAGE HLS B, SOMERS, NY, 10589
Community: Heritage Hills
New Country Pointe Plainview 33204 SPRUCE POND CIR, OYSTER BAY, NY, 1..., Oyster Bay, NY 11803
$1,735,000

2 beds

|

2 baths

|

1,976 sq ft

|

Condo

33204 SPRUCE POND CIR, OYSTER BAY, NY, 1...
Woodcrest at Jacobs Hill 2306 JACOBS HILL RD 306, CORTLANDT, NY, ..., Cortlandt, NY 10567
$425,000

2 beds

|

2 baths

|

1,145 sq ft

|

Condo

2306 JACOBS HILL RD 306, CORTLANDT, NY, ...
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.
Warwick Grove 50 CROPSEY ST, WARWICK (TOWN), NY, 10990, Warwick (town), NY 10990
$750,000

3 beds

|

3 baths

|

2,482 sq ft

|

Condo

50 CROPSEY ST, WARWICK (TOWN), NY, 10990
Community: Warwick Grove
Leisure Village 158 FALMOUTH CT A, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$228,888

2 beds

|

1 baths

|

836 sq ft

|

Condo

158 FALMOUTH CT A, BROOKHAVEN, NY, 11961
Community: Leisure Village
The Village at Oxford Greens 443 TEE SHOT DR 443, OXFORD, CT, 06478, Oxford, CT 06478
$689,900

3 beds

|

3 baths

|

2,759 sq ft

|

Condo

443 TEE SHOT DR 443, OXFORD, CT, 06478
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
Heritage Hills 606 HERITAGE HILLS DR C, SOMERS, NY, 105..., Somers, NY 10589
$825,000

3 beds

|

2 baths

|

1,905 sq ft

|

Condo

606 HERITAGE HILLS DR C, SOMERS, NY, 105...
Community: Heritage Hills
Hopmeadow Place 1 W ST 310, SIMSBURY, CT, 06070, Simsbury, CT 06070
$385,000

2 beds

|

2 baths

|

1,430 sq ft

|

Condo

1 W ST 310, SIMSBURY, CT, 06070
Community: Hopmeadow Place
Leisure Knoll 152B LAURANCE LN, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$374,000

1 beds

|

1 baths

|

530 sq ft

|

Condo

152B LAURANCE LN, BROOKHAVEN, NY, 11961
Community: Leisure Knoll
The Bel Aire at East Meadow 50 MERRICK AVE 415, HEMPSTEAD, NY, 11554, Hempstead, NY 11554
$500,000

2 beds

|

2 baths

|

1,000 sq ft

|

Condo

50 MERRICK AVE 415, HEMPSTEAD, NY, 11554
Want to learn more about 55+ communities in New Fairfield? 55places can help!
Questions? Call us: (959) 214-2391
HarborView 100 HARBOR VIEW DR 251, NORTH HEMPSTEAD,..., North Hempstead, NY 11050
$829,000

2 beds

|

3 baths

|

Condo

100 HARBOR VIEW DR 251, NORTH HEMPSTEAD,...
Community: HarborView
Oronoque Village 448 HAMMERSTONE LN B, STRATFORD, CT, 066..., Stratford, CT 06614
$525,000

1 beds

|

3 baths

|

1,438 sq ft

|

Condo

448 HAMMERSTONE LN B, STRATFORD, CT, 066...
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.

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