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New Fairfield, CT 55+ active adult communities & homes for sale - Page 3

159 communities near New Fairfield

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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
Eastport Meadows
$400ks
Eastport Meadows, Eastport, NY
Resale Only | 55+ age-restricted | Built 2009 - 2016 | 50 homes
Stoneleigh Woods at Carme...
$400ks
Stoneleigh Woods at Carme..., Carmel, NY
Resale Only | 55+ age-restricted | Built 2012 - 2017 | 68 homes
The Seasons at Plainview
$500ks - $600ks
The Seasons at Plainview, Plainview, NY
Resale Only | 55+ age-restricted | Built 2006 - 2007 | 134 homes
Village Vistas
$800ks - $1Ms
Village Vistas, Port Jefferson, NY
Resale Only | 55+ age-restricted | Built 2013 - 2017 | 43 homes
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Questions? Call us: (959) 214-2391
Woodcrest at Jacobs Hill
$200ks - $300ks
Woodcrest at Jacobs Hill, Cortlandt, NY
Resale Only | 55+ age-restricted | Built 2005 - 2006 | 58 homes
Glassbury Court at Hunter...
$500ks - $700ks
Glassbury Court at Hunter..., Cortlandt, NY
Resale Only | 55+ age-restricted | Built 2007 - 2014 | 64 homes
Wolfe Landing
$500ks - $600ks
Wolfe Landing, Clarkstown, NY
Resale Only | 55+ age-restricted | Built 2015 - 2016 | 43 homes
Eden Park
$500ks - $600ks
Eden Park, Clarkstown, NY
Resale Only | 55+ age-restricted | Built 2011 - 2011 | 34 homes
5 rating (1 reviews) Sunrise Village
$400ks
Sunrise Village, Sayville, NY
Resale Only | 55+ age-restricted | Built 1985 - 1990 | 213 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 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
Knickerbocker Bay Club
$700ks - $3Ms
Knickerbocker Bay Club, Port Washington, NY
New and Resale | 55+ age-restricted | Built 2014 - present | 32 homes
Kensington Estates
$1Ms
Kensington Estates, Woodbury, NY
New Construction | 55+ age-restricted | Built 2019 - 2021 | 80 homes
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
Want to learn more about 55+ communities in New Fairfield? 55places can help!
Questions? Call us: (959) 214-2391
Jessup's Landing
$1Ms
Jessup's Landing, Quogue, NY
New and Resale | 55+ age-restricted | Built 2009 - 2016 | 31 homes
Villas at Seminary Hill
$200ks - $300ks
Villas at Seminary Hill, Carmel, NY
New Construction | 55+ age-restricted | Built 2018 - present | 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
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 Pines at Bohemia
$400ks - $500ks
The Pines at Bohemia, Bohemia, NY
New Construction | 55+ age-restricted | Built 2019 - present | 20 homes
The Polo Club at Islandia
$600ks - $700ks
The Polo Club at Islandia, Islandia, NY
New Construction | 55+ age-restricted | Built 2019 - present | 72 homes
Breton Hills
$500ks
Breton Hills, Glen Cove, NY
New Construction | 55+ age-restricted | Built 2019 - present | 72 homes
Stratford Park
$600ks - $800ks
Stratford Park, Melville, NY
Resale Only | 55+ age-restricted | Built 2011 - 2013 | 36 homes
The Bridges at Oxford Gre...
$600ks
The Bridges at Oxford Gre..., Oxford, CT
New Construction | 55+ age-restricted | Built 2025 - present | 99 homes
The Seasons at East North...
$700ks
The Seasons at East North..., East Northport, NY
New Construction | 55+ age-restricted | Built 2023 - present | 190 homes
Applegate Estates
$500ks - $400ks
Applegate Estates, Southington, CT
New and Resale | 55+ age-restricted | Built 2010 - 2025 | 94 homes
Want to learn more about 55+ communities in New Fairfield? 55places can help!
Questions? Call us: (959) 214-2391
Northgate at Florham Park
$900ks - $1Ms
Northgate at Florham Park, Florham Park, NJ
Resale Only | 55+ age-restricted | Built 2008 - 2009 | 33 homes
Rivington Landing
$500ks
Rivington Landing, Danbury, CT
New Construction | Age-targeted | Built 2025 - 2026 | 25 homes
Regency at Prospect
$300ks - $400ks
Regency at Prospect, Prospect, CT
Resale Only | 55+ age-restricted | Built 2006 - 2020 | 379 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 (2 reviews) Benson Woods
$400ks - $600ks
Benson Woods, Middlebury, CT
New and Resale | 55+ age-restricted | Built 2004 - present | 79 homes
Newbury Village
$400ks - $500ks
Newbury Village, Brookfield, CT
New and Resale | 55+ age-restricted | Built 2005 - present | 120 homes
Clockmaker's Hill
$100ks
Clockmaker's Hill, Winsted, CT
Resale Only | 55+ age-restricted | Built 2005 - 2014 | 38 homes
The Village at Buckingham
$300ks - $400ks
The Village at Buckingham, Avon, CT
Resale Only | 55+ age-restricted | Built 2002 - 2006 | 56 homes
Bartlett Hill
$300ks - $400ks
Bartlett Hill, Portland, CT
Resale Only | 55+ age-restricted | Built 2005 - 2011 | 82 homes
1 rating (1 reviews) Beckley Farms
$300ks - $400ks
Beckley Farms, Berlin, CT
New and Resale | 55+ age-restricted | Built 2010 - present | 170 homes
Castle Heights of Cheshir...
$500ks - $600ks
Castle Heights of Cheshir..., Cheshire, CT
Resale Only | 55+ age-restricted | Built 2007 - 2022 | 88 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
Want to learn more about 55+ communities in New Fairfield? 55places can help!
Questions? Call us: (959) 214-2391
Chimney Hill
$500ks - $700ks
Chimney Hill, Farmington, CT
Resale Only | 55+ age-restricted | Built 2006 - 2013 | 44 homes
RiverWalk
$500ks - $600ks
RiverWalk, Branford, CT
New and Resale | 55+ age-restricted | Built 2007 - present | 60 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.
Jefferson Village 39 SUSSEX DR B, YORKTOWN, NY, 10598, Yorktown, NY 10598
$379,000

2 beds

|

2 baths

|

1,000 sq ft

|

Condo

39 SUSSEX DR B, YORKTOWN, NY, 10598
Community: Jefferson Village
Heritage Village 345 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$386,000

3 beds

|

2 baths

|

1,716 sq ft

|

Condo

345 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage 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
$419,000

2 beds

|

2 baths

|

1,624 sq ft

|

Manufactured Home

1661 OLD COUNTRY RD 516, RIVERHEAD, NY, ...
Community: Glenwood Village
New Heritage Village 65 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$219,900

1 beds

|

1 baths

|

928 sq ft

|

Condo

65 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
New Heritage Village 261B HERITAGE VLG, SOUTHBURY, CT, 06488, Southbury, CT 06488
$240,000

2 beds

|

2 baths

|

1,032 sq ft

|

Condo

261B HERITAGE VLG, SOUTHBURY, CT, 06488
Community: Heritage Village
New Westhampton Pines 179 CARLY LN, SOUTHAMPTON, NY, 11977, Southampton, NY 11977
$899,000

2 beds

|

2 baths

|

2,000 sq ft

|

Condo

179 CARLY LN, SOUTHAMPTON, NY, 11977
Community: Westhampton Pines
New Heritage Village 1016 HERITAGE VLG A, SOUTHBURY, CT, 0648..., Southbury, CT 06488
$245,000

1 beds

|

1 baths

|

928 sq ft

|

Condo

1016 HERITAGE VLG A, SOUTHBURY, CT, 0648...
Community: Heritage Village
New Bald Eagle Commons 162 RICHMOND RD, WEST MILFORD, NJ, 07480, West Milford, NJ 07480
$529,000

3 beds

|

4 baths

|

Townhouse

162 RICHMOND RD, WEST MILFORD, NJ, 07480
Community: Bald Eagle Commons
New Spring Lake Village 504 CARRIAGE DR 504, SOUTHINGTON, CT, 06..., Southington, CT 06489
$330,000

2 beds

|

2 baths

|

1,313 sq ft

|

Condo

504 CARRIAGE DR 504, SOUTHINGTON, CT, 06...
Community: Spring Lake 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 Oronoque Village 522 IROQUOIS LN B, STRATFORD, CT, 06614, Stratford, CT 06614
$649,900
|

3 baths

|

2,375 sq ft

|

Condo

522 IROQUOIS LN B, STRATFORD, CT, 06614
Community: Oronoque Village
New Bald Eagle Commons 162 RICHMOND RD, WEST MILFORD TWP., NJ, ..., West Milford Twp., NJ 07480
$529,000

3 beds

|

4 baths

162 RICHMOND RD, WEST MILFORD TWP., NJ, ...
Community: Bald Eagle Commons
New The Savannah 111 PROSPECT ST 4A, WESTFIELD TOWN, NJ, ..., Westfield Town, NJ 07090
$1,599,000

2 beds

|

3 baths

111 PROSPECT ST 4A, WESTFIELD TOWN, NJ, ...
Community: The Savannah
New Stoneleigh Woods at Riverhead 158 STONELEIGH DR, RIVERHEAD, NY, 11901, Riverhead, NY 11901
$699,000

2 beds

|

3 baths

|

2,071 sq ft

|

Condo

158 STONELEIGH DR, RIVERHEAD, NY, 11901
New Heritage Hills 220 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589
$699,000

3 beds

|

2 baths

|

1,689 sq ft

|

Condo

220 HERITAGE HLS B, SOMERS, NY, 10589
Community: Heritage Hills
New The Seasons at East Meadow 421 AUTUMN DR, HEMPSTEAD, NY, 11554, Hempstead, NY 11554
$635,000

2 beds

|

2 baths

|

1,272 sq ft

|

Condo

421 AUTUMN DR, HEMPSTEAD, NY, 11554
Want to learn more about 55+ communities in New Fairfield? 55places can help!
Questions? Call us: (959) 214-2391
New Country Pointe Preserve 128 JUNIPER LN 26, BROOKHAVEN, NY, 11980, Brookhaven, NY 11980
$875,000

2 beds

|

3 baths

|

1,998 sq ft

|

Condo

128 JUNIPER LN 26, BROOKHAVEN, NY, 11980
New Apple Ridge 239 WESTERVELT LN, MAHWAH TWP., NJ, 0743..., Mahwah Twp., NJ 07430
$950,000

3 beds

|

4 baths

|

2,966 sq ft

239 WESTERVELT LN, MAHWAH TWP., NJ, 0743...
Community: Apple Ridge
New Rivington 424 CENTER MEADOW LN 424, DANBURY, CT, 0..., Danbury, CT 06810
$479,900

2 beds

|

2 baths

|

1,258 sq ft

|

Condo

424 CENTER MEADOW LN 424, DANBURY, CT, 0...
Community: Rivington
New Windmill Gate 18 KATHLEEN DR, ISLIP, NY, 11769, Islip, NY 11769
$600,000

2 beds

|

2 baths

|

1,413 sq ft

|

Condo

18 KATHLEEN DR, ISLIP, NY, 11769
Community: Windmill Gate
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
$1,669,990

2 beds

|

3 baths

|

1,750 sq ft

|

Condo

52102 BEECH TREE LN, OYSTER BAY, NY, 118...
New Glenwood Village 1661 OLD COUNTRY RD 454, RIVERHEAD, NY, ..., Riverhead, NY 11901
$329,000

2 beds

|

2 baths

|

1,152 sq ft

|

Manufactured Home

1661 OLD COUNTRY RD 454, RIVERHEAD, NY, ...
Community: Glenwood Village
New The Seasons at Elwood 63 WINTER PL, HUNTINGTON, NY, 11731, Huntington, NY 11731
$427,767

2 beds

|

2 baths

|

1,108 sq ft

|

Condo

63 WINTER PL, HUNTINGTON, NY, 11731
New Stone Ridge Estates 110 JOSEPH LN, HUNTINGTON, NY, 11746, Huntington, NY 11746
$779,000

2 beds

|

2 baths

|

1,695 sq ft

|

Condo

110 JOSEPH LN, HUNTINGTON, NY, 11746
Community: Stone Ridge Estates
New Encore Atlantic Shores 140 CHOPIN PL, BROOKHAVEN, NY, 11941, Brookhaven, NY 11941
$865,000

2 beds

|

3 baths

|

2,236 sq ft

|

Condo

140 CHOPIN PL, BROOKHAVEN, NY, 11941
New Leisure Village 89 ENFIELD CT B, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$469,000

2 beds

|

2 baths

|

1,308 sq ft

|

Condo

89 ENFIELD CT B, BROOKHAVEN, NY, 11961
Community: Leisure Village
New Apple Ridge 239 WESTERVELT LN, MAHWAH, NJ, 07430, Mahwah, NJ 07430
$950,000

3 beds

|

4 baths

|

Townhouse

239 WESTERVELT LN, MAHWAH, NJ, 07430
Community: Apple Ridge
Want to learn more about 55+ communities in New Fairfield? 55places can help!
Questions? Call us: (959) 214-2391
New Village Vistas 35 THERESA LN, BROOKHAVEN, NY, 11777, Brookhaven, NY 11777
$1,300,000

3 beds

|

4 baths

|

3,000 sq ft

|

Condo

35 THERESA LN, BROOKHAVEN, NY, 11777
Community: Village Vistas
New Wildflowers at Wallkill 25 SUNFLOWER ST, MIDDLETOWN, NY, 10940, Middletown, NY 10940
$535,500

2 beds

|

2 baths

|

1,868 sq ft

|

Condo

25 SUNFLOWER ST, MIDDLETOWN, NY, 10940
New The Village at Oxford Greens 171 COUNTRY CLUB DR 171, OXFORD, CT, 064..., Oxford, CT 06478
$775,000

3 beds

|

3 baths

|

2,750 sq ft

|

Condo

171 COUNTRY CLUB DR 171, OXFORD, CT, 064...
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 Oronoque Village 621 ONONDAGA LN B, STRATFORD, CT, 06614, Stratford, CT 06614
$499,000

1 beds

|

3 baths

|

2,325 sq ft

|

Condo

621 ONONDAGA LN B, STRATFORD, CT, 06614
Community: Oronoque Village
New Westhampton Pines 79 SAMANTHA CIR, SOUTHAMPTON, NY, 11977, Southampton, NY 11977
$1,295,000

2 beds

|

3 baths

|

2,440 sq ft

|

Condo

79 SAMANTHA CIR, SOUTHAMPTON, NY, 11977
Community: Westhampton Pines
New Heritage Hills 88 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589
$699,000

2 beds

|

3 baths

|

1,585 sq ft

|

Condo

88 HERITAGE HLS B, SOMERS, NY, 10589
Community: Heritage Hills
New Leisure Glen 19 SAYVILLE CT, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$615,000

2 beds

|

2 baths

|

1,666 sq ft

|

Condo

19 SAYVILLE CT, BROOKHAVEN, NY, 11961
Community: Leisure Glen
New Jefferson Village 196 LONG HILL DR B, YORKTOWN, NY, 10598, Yorktown, NY 10598
$675,000

2 beds

|

2 baths

|

1,550 sq ft

|

Condo

196 LONG HILL DR B, YORKTOWN, NY, 10598
Community: Jefferson Village
Hopmeadow Place 1 W ST 215, SIMSBURY, CT, 06070, Simsbury, CT 06070
$385,000

2 beds

|

2 baths

|

1,477 sq ft

|

Condo

1 W ST 215, SIMSBURY, CT, 06070
Community: Hopmeadow Place
Glenwood Village 1661 OLD COUNTRY RD 258, RIVERHEAD, NY, ..., Riverhead, NY 11901
$389,999

2 beds

|

2 baths

|

1,310 sq ft

|

House

1661 OLD COUNTRY RD 258, RIVERHEAD, NY, ...
Community: Glenwood Village
Leisure Village 344 WOODBRIDGE DR B, BROOKHAVEN, NY, 119..., Brookhaven, NY 11961
$365,000

2 beds

|

2 baths

|

1,168 sq ft

|

Condo

344 WOODBRIDGE DR B, BROOKHAVEN, NY, 119...
Community: Leisure Village
Want to learn more about 55+ communities in New Fairfield? 55places can help!
Questions? Call us: (959) 214-2391
Leisure Village 275 BERWICK CT A, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$355,000

2 beds

|

1 baths

|

875 sq ft

|

Condo

275 BERWICK CT A, BROOKHAVEN, NY, 11961
Community: Leisure Village
The Summit at Bethel 78 GREAT HILL DR 78, BETHEL, CT, 06801, Bethel, CT 06801
$700,000

3 beds

|

4 baths

|

Condo

78 GREAT HILL DR 78, BETHEL, CT, 06801
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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