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New Fairfield, CT 55+ active adult communities & homes for sale - Page 4

163 communities near New Fairfield

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RiverWalk
$500ks - $600ks
RiverWalk, Branford, CT
New and Resale | 55+ age-restricted | Built 2007 - present | 60 homes
Chimney Hill
$500ks - $700ks
Chimney Hill, Farmington, CT
Resale Only | 55+ age-restricted | Built 2006 - 2013 | 44 homes
The Coves at Melville
$500ks
The Coves at Melville, Melville, NY
Resale Only | 62+ age-restricted | Built 2004 - 2005 | 175 homes
5 rating (2 reviews) Benson Woods
$400ks - $600ks
Benson Woods, Middlebury, CT
New and Resale | 55+ age-restricted | Built 2004 - present | 79 homes
4.9 rating (14 reviews) Chatfield Farms
$400ks - $700ks
Chatfield Farms, Beacon Falls, CT
New Construction | 55+ age-restricted | Built 2014 - present | 231 homes
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Questions? Call us: (959) 214-2391
Castle Heights of Cheshir...
$500ks - $600ks
Castle Heights of Cheshir..., Cheshire, CT
Resale Only | 55+ age-restricted | Built 2007 - 2022 | 88 homes
Applegate Estates
$500ks - $400ks
Applegate Estates, Southington, CT
New and Resale | 55+ age-restricted | Built 2010 - 2025 | 94 homes
The Club at Melville
$500ks
The Club at Melville, Melville, NY
Resale Only | 55+ age-restricted | Built 2015 - 2017 | 261 homes
The Seasons at Seaford
$600ks
The Seasons at Seaford, Seaford, NY
Resale Only | 55+ age-restricted | Built 2015 - 2017 | 112 homes
Northgate at Florham Park
$900ks - $1Ms
Northgate at Florham Park, Florham Park, NJ
Resale Only | 55+ age-restricted | Built 2008 - 2009 | 33 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 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
Newbury Village
$400ks - $500ks
Newbury Village, Brookfield, CT
New and Resale | 55+ age-restricted | Built 2005 - present | 120 homes
Knickerbocker Bay Club
$700ks - $3Ms
Knickerbocker Bay Club, Port Washington, NY
New and Resale | 55+ age-restricted | Built 2014 - present | 32 homes
1 rating (1 reviews) Beckley Farms
$300ks - $400ks
Beckley Farms, Berlin, CT
New and Resale | 55+ age-restricted | Built 2010 - present | 170 homes
Pond Spring Village
$300ks
Pond Spring Village, Beacon Falls, CT
New and Resale | 55+ age-restricted | Built 2005 - present | 92 homes
Rivington Landing
$500ks
Rivington Landing, Danbury, CT
New Construction | Age-targeted | Built 2025 - 2026 | 25 homes
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Questions? Call us: (959) 214-2391
5 rating (2 reviews) Blackburne Farm Townhomes
$400ks
Blackburne Farm Townhomes, Campbell Hall, NY
New Construction | 55+ age-restricted | Built 2019 - present | 29 homes
The Residences at Butterf...
$500ks - $600ks
The Residences at Butterf..., Cold Spring, NY
Resale Only | 55+ age-restricted | Built 2018 - 2023 | 49 homes
Regency at Pearl River
$800ks - $1Ms
Regency at Pearl River, Pearl River, NY
New Construction | 55+ age-restricted | Built 2026 - present | 36 homes
Four Seasons at Wayne
$300ks - $400ks
Four Seasons at Wayne, Wayne, NJ
Resale Only | 55+ age-restricted | Built 1999 - 2001 | 230 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.
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
Enclave at Shackamaxon
$1Ms
Enclave at Shackamaxon, Scotch Plains, NJ
Resale Only | 55+ age-restricted | Built 2016 - 2018 | 56 homes
Four Seasons at Troy Hill...
$500ks
Four Seasons at Troy Hill..., Parsippany, NJ
Resale Only | 55+ age-restricted | Built 2007 - 2007 | 46 homes
The Pointe
$300ks - $600ks
The Pointe, Livingston, NJ
Resale Only | 55+ age-restricted | Built 2004 - 2007 | 180 homes
Sterling Mist
$500ks - $600ks
Sterling Mist, Parsippany, NJ
Resale Only | 55+ age-restricted | Built 2002 - 2006 | 28 homes
Briar Hill
$600ks - $700ks
Briar Hill, Montville Township, NJ
Resale Only | 55+ age-restricted | Built 2012 - 2015 | 28 homes
Jessup's Landing
$1Ms
Jessup's Landing, Quogue, NY
New and Resale | 55+ age-restricted | Built 2009 - 2016 | 31 homes
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Questions? Call us: (959) 214-2391
Whitfield
$600ks - $700ks
Whitfield, Metuchen, NJ
Resale Only | 55+ age-restricted | 17 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
Villas at Seminary Hill
$200ks - $300ks
Villas at Seminary Hill, Carmel, NY
New Construction | 55+ age-restricted | Built 2018 - present | 50 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 Pointe at Garwood
$600ks - $700ks
The Pointe at Garwood, Garwood, NJ
Resale Only | 55+ age-restricted | Built 2006 - 2007 | 44 homes
Brooklake Park
$400ks
Brooklake Park, Florham Park, NJ
Resale Only | 55+ age-restricted | Built 2008 - 2008 | 25 homes
Eagle Ridge at East Hanov...
$200ks - $300ks
Eagle Ridge at East Hanov..., East Hanover, NJ
Resale Only | 55+ age-restricted | Built 1992 - 1993 | 50 homes
Meadowbrooke Pointe East ...
$500ks - $600ks
Meadowbrooke Pointe East ..., East Meadow, NY
New Construction | 62+ age-restricted | Built 2019 - present | 104 homes
Hidden Harbor Estates
$500ks - $600ks
Hidden Harbor Estates, Copiague, NY
Resale Only | 55+ age-restricted | Built 2010 - 2015 | 38 homes
1 rating (2 reviews) Knoll Edge
$600ks - $700ks
Knoll Edge, Boonton, NJ
New Construction | 55+ age-restricted | Built 2024 - present | 16 homes
Scotchtown Oaks
$500ks
Scotchtown Oaks, Goshen, NY
New Construction | 55+ age-restricted | Built 2025 - present | 12 homes
Winthrop Court
$400ks - $600ks
Winthrop Court, Clifton, NJ
Resale Only | 55+ age-restricted | Built 2000 - 2010 | 270 homes
Want to learn more about 55+ communities in New Fairfield? 55places can help!
Questions? Call us: (959) 214-2391
Bramble Ridge
$300ks
Bramble Ridge, Suffield, CT
Resale Only | 55+ age-restricted | Built 2005 - 2015 | 47 homes
Whitney Glen
$500ks - $600ks
Whitney Glen, Westport, CT
Resale Only | 55+ age-restricted | Built 1982 - 1982 | 62 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 201 VILLAGE CIR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949
$250,000

2 beds

|

2 baths

|

1,078 sq ft

|

Condo

201 VILLAGE CIR, BROOKHAVEN, NY, 11949
Community: Greenwood Village
Greenwood Village 105 W VILLAGE CIR 105, BROOKHAVEN, NY, 1..., Brookhaven, NY 11949
$245,000

2 beds

|

2 baths

|

1,130 sq ft

|

Condo

105 W VILLAGE CIR 105, BROOKHAVEN, NY, 1...
Community: Greenwood Village
Glenwood Village 1661 OLD COUNTRY RD 516, RIVERHEAD, NY, ..., Riverhead, NY 11901
$410,000

2 beds

|

2 baths

|

1,624 sq ft

|

Manufactured Home

1661 OLD COUNTRY RD 516, RIVERHEAD, NY, ...
Community: Glenwood Village
New Fairfield at St. James 1102 GOTHAM PATH, SMITHTOWN, NY, 11780, Smithtown, NY 11780
$639,900

3 beds

|

3 baths

|

1,601 sq ft

|

Condo

1102 GOTHAM PATH, SMITHTOWN, NY, 11780
New Leisure Knoll 257 EDINBURGH DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$539,900

2 beds

|

2 baths

|

1,000 sq ft

|

Condo

257 EDINBURGH DR, 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 Beckley Farms 91 SCENIC DR 91, BERLIN, CT, 06037, Berlin, CT 06037
$679,900

3 beds

|

3 baths

|

2,068 sq ft

|

Condo

91 SCENIC DR 91, BERLIN, CT, 06037
Community: Beckley Farms
New Foxwood Village 1407 MIDDLE RD 45, RIVERHEAD, NY, 11933, Riverhead, NY 11933
$315,000

2 beds

|

2 baths

|

1,100 sq ft

|

House

1407 MIDDLE RD 45, RIVERHEAD, NY, 11933
Community: Foxwood Village
New Heritage Village 162 HERITAGE VLG D, SOUTHBURY, CT, 06488, Southbury, CT 06488
$249,000

2 beds

|

2 baths

|

1,076 sq ft

|

Condo

162 HERITAGE VLG D, SOUTHBURY, CT, 06488
Community: Heritage Village
New Woodridge Strathmore Terrace 55 STANDISH DR, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766
$499,000

2 beds

|

2 baths

|

1,501 sq ft

|

House

55 STANDISH DR, BROOKHAVEN, NY, 11766
New Greenwood Village 33A LIMETREE DR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949
$99,999

1 beds

|

1 baths

|

460 sq ft

|

Condo

33A LIMETREE DR, BROOKHAVEN, NY, 11949
Community: Greenwood 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.
New Country Pointe Plainview 52102 BEECH TREE LN, OYSTER BAY, NY, 118..., Oyster Bay, NY 11803
$1,664,990

3 beds

|

3 baths

|

1,730 sq ft

|

Condo

52102 BEECH TREE LN, OYSTER BAY, NY, 118...
New Heritage Hills 823 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589
$750,000

2 beds

|

3 baths

|

1,531 sq ft

|

Condo

823 HERITAGE HLS A, SOMERS, NY, 10589
Community: Heritage Hills
New Heritage Village 397 KRUEGER CIR A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$439,700

3 beds

|

2 baths

|

1,716 sq ft

|

Condo

397 KRUEGER CIR A, SOUTHBURY, CT, 06488
Community: Heritage Village
New The Village at Oxford Greens 1073 AUGUSTA DR 1073, OXFORD, CT, 06478, Oxford, CT 06478
$629,900

2 beds

|

3 baths

|

2,232 sq ft

|

Condo

1073 AUGUSTA DR 1073, OXFORD, CT, 06478
New Fairview at Oxford Greens 1073 AUGUSTA DR 1073, OXFORD, CT, 06478, Oxford, CT 06478
$629,900

2 beds

|

3 baths

|

2,232 sq ft

|

Condo

1073 AUGUSTA DR 1073, OXFORD, CT, 06478
New Oronoque Village 55 BLACK HAWK LN B, STRATFORD, CT, 06614, Stratford, CT 06614
$639,000

2 beds

|

3 baths

|

1,360 sq ft

|

Condo

55 BLACK HAWK 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
New Meadowbrook Pointe Links & Spa 38 AUGUSTA DR, BROOKHAVEN, NY, 11763, Brookhaven, NY 11763
$400,697

2 beds

|

3 baths

|

1,440 sq ft

|

Condo

38 AUGUSTA DR, BROOKHAVEN, NY, 11763
New Oronoque Village 209 ACORN LN B, STRATFORD, CT, 06614, Stratford, CT 06614
$554,000

2 beds

|

3 baths

|

1,438 sq ft

|

Condo

209 ACORN LN B, STRATFORD, CT, 06614
Community: Oronoque Village
New Spring Lake Village 764 KETTLE PATH 764, SOUTHINGTON, CT, 06..., Southington, CT 06489
$355,000

2 beds

|

2 baths

|

1,445 sq ft

|

Condo

764 KETTLE PATH 764, SOUTHINGTON, CT, 06...
Community: Spring Lake Village
New Heritage Village 633 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$400,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

633 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.
New Heritage Village 626 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$300,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

626 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
New Windmill Gate 27 KATHLEEN DR, ISLIP, NY, 11769, Islip, NY 11769
$699,900

2 beds

|

2 baths

|

1,321 sq ft

|

House

27 KATHLEEN DR, ISLIP, NY, 11769
Community: Windmill Gate
New Heritage Hills 593 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589
$995,000

3 beds

|

2 baths

|

1,905 sq ft

|

Condo

593 HERITAGE HLS B, SOMERS, NY, 10589
Community: Heritage Hills
New The Seasons at Plainview 53 AUTUMN DR, OYSTER BAY, NY, 11803, Oyster Bay, NY 11803
$829,000

2 beds

|

2 baths

|

1,379 sq ft

|

Condo

53 AUTUMN DR, OYSTER BAY, NY, 11803
New Parkview Crossings at Woodbridge 323 REGENCY PL, WOODBRIDGE PROPER, NJ, 0..., Woodbridge Proper, NJ 07095
$449,900

2 beds

|

2 baths

|

1,605 sq ft

|

Condo

323 REGENCY PL, WOODBRIDGE PROPER, NJ, 0...
New Heritage Hills 154 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589
$525,000

2 beds

|

2 baths

|

1,396 sq ft

|

Condo

154 HERITAGE HLS B, SOMERS, NY, 10589
Community: Heritage Hills
New The Village at Buckingham 3 CAVENDISH PL 3, AVON, CT, 06001, Avon, CT 06001
$689,000

3 beds

|

3 baths

|

2,730 sq ft

3 CAVENDISH PL 3, AVON, CT, 06001
Want to learn more about 55+ communities in New Fairfield? 55places can help!
Questions? Call us: (959) 214-2391
New Fairfield at St. James 705 ALDEN CT, SMITHTOWN, NY, 11780, Smithtown, NY 11780
$559,803

2 beds

|

2 baths

|

954 sq ft

|

Condo

705 ALDEN CT, SMITHTOWN, NY, 11780
New The Savannah 111 PROSPECT ST 4C, WESTFIELD TOWN, NJ, ..., Westfield Town, NJ 07090
$1,199,000

2 beds

|

3 baths

|

2,615 sq ft

111 PROSPECT ST 4C, WESTFIELD TOWN, NJ, ...
Community: The Savannah
New Jefferson Village 45 JEFFERSON OVAL G, YORKTOWN, NY, 10598, Yorktown, NY 10598
$429,900

2 beds

|

2 baths

|

1,100 sq ft

|

Condo

45 JEFFERSON OVAL G, YORKTOWN, NY, 10598
Community: Jefferson 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.
New Heritage Hills 446 HERITAGE HLS D, SOMERS, NY, 10589, Somers, NY 10589
$679,000

2 beds

|

2 baths

|

1,559 sq ft

|

Condo

446 HERITAGE HLS D, SOMERS, NY, 10589
Community: Heritage Hills
New Rivington 11 MERCY ST 11, DANBURY, CT, 06810, Danbury, CT 06810
$600,000

2 beds

|

4 baths

|

1,572 sq ft

|

Condo

11 MERCY ST 11, DANBURY, CT, 06810
Community: Rivington
New Jefferson Village 18L HASTINGS CT, YORKTOWN, NY, 10598, Yorktown, NY 10598
$340,000

2 beds

|

1 baths

|

1,000 sq ft

|

Condo

18L HASTINGS CT, YORKTOWN, NY, 10598
Community: Jefferson Village
New Heritage Village 149 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$198,000

1 beds

|

1 baths

|

928 sq ft

|

Condo

149 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
New The Greens at Half Hollow 119 MADEIRA BLVD, HUNTINGTON, NY, 11747, Huntington, NY 11747
$1,525,000

3 beds

|

3 baths

|

2,700 sq ft

|

Condo

119 MADEIRA BLVD, HUNTINGTON, NY, 11747
New Sunken Pond Estates 3704 AMEN COR, RIVERHEAD, NY, 11901, Riverhead, NY 11901
$529,000

2 beds

|

3 baths

|

1,350 sq ft

|

Condo

3704 AMEN COR, RIVERHEAD, NY, 11901
Community: Sunken Pond Estates
New Leisure Village 395 WOODBRIDGE DR E, BROOKHAVEN, NY, 119..., Brookhaven, NY 11961
$322,900

2 beds

|

1 baths

|

875 sq ft

|

Condo

395 WOODBRIDGE DR E, BROOKHAVEN, NY, 119...
Community: Leisure Village
New Plymouth Estates at Mount Sinai 240 IRA RD, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766
$599,999

2 beds

|

2 baths

|

1,396 sq ft

|

Condo

240 IRA RD, BROOKHAVEN, NY, 11766
Want to learn more about 55+ communities in New Fairfield? 55places can help!
Questions? Call us: (959) 214-2391
New Overlook 2011 SUMMIT LOOP 86, CARMEL, NY, 10512, Carmel, NY 10512
$936,000

2 beds

|

3 baths

|

2,873 sq ft

|

Condo

2011 SUMMIT LOOP 86, CARMEL, NY, 10512
Community: Overlook
New Overlook 2037 SUMMIT LOOP 92, CARMEL, NY, 10512, Carmel, NY 10512
$899,000

2 beds

|

2 baths

|

2,102 sq ft

|

Condo

2037 SUMMIT LOOP 92, CARMEL, NY, 10512
Community: Overlook
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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