Call us at (959) 214-2391 to learn more about active adult communities in New Fairfield

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

159 communities near New Fairfield

Sort by:

Relevance

Relevance

3.6 rating (7 reviews) Heritage Village
$200ks - $500ks
Heritage Village, Southbury, CT
Resale Only | 55+ age-restricted | Built 1967 - 2005 | 2,580 homes
Bald Eagle Commons
$100ks - $300ks
Bald Eagle Commons, West Milford, NJ
Resale Only | 55+ age-restricted | Built 1995 - 2005 | 463 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
3 rating (2 reviews) Heritage Hills
$400ks - $800ks
Heritage Hills, Somers, NY
Resale Only | Age-targeted | Built 1974 - 2006 | 2,600 homes
Want to learn more about 55+ communities in New Fairfield? 55places can help!
Questions? Call us: (959) 214-2391
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
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
4 rating (1 reviews) Jefferson Village
$100ks - $500ks
Jefferson Village, Yorktown Heights, NY
Resale Only | 55+ age-restricted | Built 1967 - 1982 | 1,000 homes
3.7 rating (3 reviews) Greenwood Village
$100ks
Greenwood Village, Manorville, NY
Resale Only | 55+ age-restricted | Built 1980 - 2000 | 512 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.
Country Pointe Plainview
$700ks - $1Ms
Country Pointe Plainview, Plainview, NY
New Construction | 55+ age-restricted | Built 2017 - present | 660 homes
Leisure Village
$100ks - $300ks
Leisure Village, Ridge, NY
Resale Only | 55+ age-restricted | Built 1969 - 1986 | 1,500 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
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
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
Dutchgate
$300ks - $500ks
Dutchgate, Valley Stream, NY
Resale Only | 55+ age-restricted | Built 2009 - 2015 | 348 homes
Regency at Fishkill
$300ks - $400ks
Regency at Fishkill, Fishkill, NY
Resale Only | 55+ age-restricted | Built 2008 - 2020 | 164 homes
Leisure Knoll
$200ks - $400ks
Leisure Knoll, Ridge, NY
Resale Only | 55+ age-restricted | Built 1972 - 1982 | 701 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 Atlantic Shores
$500ks - $800ks
Encore Atlantic Shores, Eastport, NY
Resale Only | 55+ age-restricted | Built 2004 - 2011 | 240 homes
3.5 rating (2 reviews) Foxwood Village
$200ks - $400ks
Foxwood Village, Calverton, NY
Resale Only | 55+ age-restricted | Built 1986 - 2007 | 294 homes
Rivington
$300ks - $900ks
Rivington, Danbury, CT
New and Resale | Age-targeted | Built 2006 - present | 1,050 homes
Leisure Glen
$300ks - $400ks
Leisure Glen, Ridge, NY
Resale Only | 55+ age-restricted | Built 1985 - 2010 | 646 homes
5 rating (1 reviews) Newtown Woods
$300ks - $500ks
Newtown Woods, Newtown, CT
New and Resale | 55+ age-restricted | Built 2011 - present | 178 homes
Liberty at Newtown
$300ks - $400ks
Liberty at Newtown, Newtown, CT
Resale Only | 55+ age-restricted | Built 2003 - 2007 | 96 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
Winthrop Court
$400ks - $600ks
Winthrop Court, Clifton, NJ
Resale Only | 55+ age-restricted | Built 2000 - 2010 | 270 homes
Spring Lake Village
$100ks - $200ks
Spring Lake Village, Southington, CT
Resale Only | 55+ age-restricted | Built 1970 - 2004 | 640 homes
HarborView
$800ks - $1Ms
HarborView, Port Washington, NY
Resale Only | 55+ age-restricted | Built 2002 - 2004 | 270 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.
Vineyards at Moriches
$500ks - $600ks
Vineyards at Moriches, Center Moriches, NY
Resale Only | 55+ age-restricted | Built 2008 - 2014 | 92 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
Country Pointe Preserve
$600ks - $900ks
Country Pointe PreserveYaphank, NY
New Construction | 55+ age-restricted | Built 2024 - present | 152 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
4.6 rating (9 reviews) Meadowbrook Pointe Links ...
$300ks - $700ks
Meadowbrook Pointe Links ..., Medford, NY
New and Resale | 55+ age-restricted | Built 2010 - present | 280 homes
5 rating (1 reviews) Westhampton Pines
$900ks - $1Ms
Westhampton Pines, Westhampton, NY
Resale Only | 55+ age-restricted | Built 2005 - 2013 | 189 homes
5 rating (1 reviews) Sunken Pond Estates
$400ks
Sunken Pond Estates, Riverhead, NY
Resale Only | 55+ age-restricted | Built 2003 - 2005 | 194 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
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
Saddle Lakes
$400ks - $500ks
Saddle Lakes, Riverhead, NY
Resale Only | 55+ age-restricted | Built 2000 - 2002 | 196 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 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 Dutchgate 301 WILLOW LN VALLEY STRM, HEMPSTEAD, NY..., Hempstead, NY 11580
$510,000

2 beds

|

2 baths

|

941 sq ft

|

Condo

301 WILLOW LN VALLEY STRM, HEMPSTEAD, NY...
Community: Dutchgate
New Overlook 4095 FAIRWAYS DR 148, CARMEL, NY, 10512, Carmel, NY 10512
$699,000

3 beds

|

3 baths

|

1,914 sq ft

|

Condo

4095 FAIRWAYS DR 148, CARMEL, NY, 10512
Community: Overlook
New Heritage Hills 241 HERITAGE HLS D, SOMERS, NY, 10589, Somers, NY 10589
$499,900

2 beds

|

2 baths

|

1,138 sq ft

|

Condo

241 HERITAGE HLS D, SOMERS, NY, 10589
Community: Heritage Hills
Want to learn more about 55+ communities in New Fairfield? 55places can help!
Questions? Call us: (959) 214-2391
New Four Seasons at Great Notch Spa and Club 8 PEBBLE RD C2, WOODLAND PARK, NJ, 07424, Woodland Park, NJ 07424
$699,900

2 beds

|

2 baths

|

Townhouse

8 PEBBLE RD C2, WOODLAND PARK, NJ, 07424
New The Pointe 5103 POINTE GATE DR, LIVINGSTON TWP., NJ..., Livingston Twp., NJ 07039
$649,900

2 beds

|

3 baths

5103 POINTE GATE DR, LIVINGSTON TWP., NJ...
Community: The Pointe
New Country Pointe Plainview 52102 BEECH TREE LN, OYSTER BAY, NY, 118..., Oyster Bay, NY 11803
$1,649,990

2 beds

|

3 baths

|

1,750 sq ft

|

Condo

52102 BEECH TREE LN, OYSTER BAY, NY, 118...
New Encore Atlantic Shores 216 SONATA CT, BROOKHAVEN, NY, 11941, Brookhaven, NY 11941
$899,000

2 beds

|

3 baths

|

2,439 sq ft

|

Condo

216 SONATA CT, BROOKHAVEN, NY, 11941
New The Waterways at Moriches 132 CAPTAINS CT, BROOKHAVEN, NY, 11955, Brookhaven, NY 11955
$550,000

2 beds

|

2 baths

|

1,544 sq ft

|

Condo

132 CAPTAINS CT, BROOKHAVEN, NY, 11955
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 Wanaque Reserve 8107 WARRENS WAY, WANAQUE BORO, NJ, 0746..., Wanaque Boro, NJ 07465
$419,900

2 beds

|

2 baths

|

1,768 sq ft

8107 WARRENS WAY, WANAQUE BORO, NJ, 0746...
Community: Wanaque Reserve
New Vineyards at Blue Point 37 HALLEY DR 17, BROOKHAVEN, NY, 11772, Brookhaven, NY 11772
$660,000

2 beds

|

2 baths

|

1,220 sq ft

|

Condo

37 HALLEY DR 17, BROOKHAVEN, NY, 11772
New Wanaque Reserve 7111 WARRENS WAY, WANAQUE BORO, NJ, 0746..., Wanaque Boro, NJ 07465
$382,000

2 beds

|

2 baths

7111 WARRENS WAY, WANAQUE BORO, NJ, 0746...
Community: Wanaque Reserve
New Woodridge Strathmore Terrace 32 CHIPPENDALE DR, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766
$579,999

2 beds

|

2 baths

|

1,501 sq ft

|

Condo

32 CHIPPENDALE DR, BROOKHAVEN, NY, 11766
New Heritage Village 786 HERITAGE VLG C, SOUTHBURY, CT, 06488, Southbury, CT 06488
$200,000

2 beds

|

2 baths

|

1,000 sq ft

|

Condo

786 HERITAGE VLG C, SOUTHBURY, CT, 06488
Community: Heritage Village
New Newtown Woods 1227 BROOKSIDE CT 1227, NEWTOWN, CT, 064..., Newtown, CT 06470
$500,000

2 beds

|

2 baths

|

1,483 sq ft

|

Condo

1227 BROOKSIDE CT 1227, NEWTOWN, CT, 064...
Community: Newtown Woods
Want to learn more about 55+ communities in New Fairfield? 55places can help!
Questions? Call us: (959) 214-2391
New Newtown Woods 23 WOODS LN 23, NEWTOWN, CT, 06470, Newtown, CT 06470
$600,000

2 beds

|

3 baths

|

2,073 sq ft

|

Condo

23 WOODS LN 23, NEWTOWN, CT, 06470
Community: Newtown Woods
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 HarborView 100 HARBOR VIEW DR 335, NORTH HEMPSTEAD,..., North Hempstead, NY 11050
$1,199,000

3 beds

|

3 baths

|

2,216 sq ft

|

Condo

100 HARBOR VIEW DR 335, NORTH HEMPSTEAD,...
Community: HarborView
New HarborView 123 LINKS CT, NORTH HEMPSTEAD, NY, 11050, North Hempstead, NY 11050
$1,299,000

3 beds

|

3 baths

|

2,160 sq ft

|

Condo

123 LINKS CT, NORTH HEMPSTEAD, NY, 11050
Community: HarborView
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 581 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$350,000

2 beds

|

2 baths

|

1,398 sq ft

|

Condo

581 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
New Jefferson Village 56 KIRBY CLOSE B, YORKTOWN, NY, 10598, Yorktown, NY 10598
$489,500

2 beds

|

2 baths

|

970 sq ft

|

Condo

56 KIRBY CLOSE B, YORKTOWN, NY, 10598
Community: Jefferson Village
New Heritage Hills 828 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589
$650,000

2 beds

|

2 baths

|

1,296 sq ft

|

Condo

828 HERITAGE HLS B, SOMERS, NY, 10589
Community: Heritage Hills
New Windcrest East 5 GREEN ASH ST, RIVERHEAD, NY, 11933, Riverhead, NY 11933
$775,000

3 beds

|

3 baths

|

2,449 sq ft

|

House

5 GREEN ASH ST, RIVERHEAD, NY, 11933
Community: Windcrest East
New Oronoque Village 212 AGAWAM DR B, STRATFORD, CT, 06614, Stratford, CT 06614
$319,000

1 beds

|

2 baths

|

1,426 sq ft

|

Condo

212 AGAWAM DR B, STRATFORD, CT, 06614
Community: Oronoque Village
New The Views at Pomona 2202 VIEWS WAY, RAMAPO, NY, 10970, Ramapo, NY 10970
$469,000

2 beds

|

2 baths

|

1,360 sq ft

|

Condo

2202 VIEWS WAY, RAMAPO, NY, 10970
Community: The Views at Pomona
New Oronoque Village 383 SEQUOIA LN B, STRATFORD, CT, 06614, Stratford, CT 06614
$485,000

1 beds

|

3 baths

|

1,360 sq ft

|

Condo

383 SEQUOIA 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 Glassbury Court at Cold Spring 1 MAGGIE MAY WAY, PHILIPSTOWN, NY, 10516, Philipstown, NY 10516
$715,000

2 beds

|

2 baths

|

1,974 sq ft

|

House

1 MAGGIE MAY WAY, PHILIPSTOWN, NY, 10516
New Heritage Village 895 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$349,900

2 beds

|

2 baths

|

1,398 sq ft

|

Condo

895 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
New Stoneleigh Woods at Riverhead 159 STONELEIGH DR, RIVERHEAD, NY, 11901, Riverhead, NY 11901
$674,999

2 beds

|

3 baths

|

2,172 sq ft

|

Condo

159 STONELEIGH DR, RIVERHEAD, NY, 11901
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 181 HERITAGE HLS F, SOMERS, NY, 10589, Somers, NY 10589
$499,999

2 beds

|

2 baths

|

1,205 sq ft

|

Condo

181 HERITAGE HLS F, SOMERS, NY, 10589
Community: Heritage Hills
Heritage Village 16 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$389,900

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

16 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Leisure Village 274 BERWICK CT C, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$359,000

2 beds

|

1 baths

|

836 sq ft

|

Condo

274 BERWICK CT C, BROOKHAVEN, NY, 11961
Community: Leisure Village
Spring Lake Village 626 OVERLOOK PATH 626, SOUTHINGTON, CT, ..., Southington, CT 06489
$350,000

2 beds

|

2 baths

|

1,230 sq ft

|

Condo

626 OVERLOOK PATH 626, SOUTHINGTON, CT, ...
Community: Spring Lake Village
Bartlett Hill 19 PLUMROSE CT 19, PORTLAND, CT, 06480, Portland, CT 06480
$500,000

2 beds

|

3 baths

|

1,503 sq ft

19 PLUMROSE CT 19, PORTLAND, CT, 06480
Community: Bartlett Hill
Bald Eagle Commons 5409 RICHMOND RD 409, WEST MILFORD TWP.,..., West Milford Twp., NJ 07480
$239,900

2 beds

|

1 baths

5409 RICHMOND RD 409, WEST MILFORD TWP.,...
Community: Bald Eagle Commons
Heritage Village 38 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$299,900

2 beds

|

2 baths

|

1,032 sq ft

|

Condo

38 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Oronoque Village 407 MONTAUK LN B, STRATFORD, CT, 06614, Stratford, CT 06614
$450,000

1 beds

|

2 baths

|

1,360 sq ft

|

Condo

407 MONTAUK 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
Bald Eagle Commons 9106 RICHMOND RD, WEST MILFORD TWP., NJ,..., West Milford Twp., NJ 07480
$179,000

1 beds

|

1 baths

9106 RICHMOND RD, WEST MILFORD TWP., NJ,...
Community: Bald Eagle Commons
Wanaque Reserve 2107 WARRENS WAY 107, WANAQUE, NJ, 07465, Wanaque, NJ 07465
$379,000

2 beds

|

2 baths

|

Condo

2107 WARRENS WAY 107, WANAQUE, NJ, 07465
Community: Wanaque Reserve
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.

Frequently Asked Questions


Want more information about active adult communities around New Fairfield?

Global - Lead Form - Buyer or Renter
*55places does not provide or maintain community HOA information.
By requesting more information, you agree that 55places may call, text, or email you about your inquiry, which may be made with automated means (including recorded voice messages, SMS, or text messages). You understand that your consent is not a prerequisite for buying, selling or renting a property. You may revoke your consent at any time by contacting optout@55places.com. Message/data rates may apply. You also agree to 55places.com’s Privacy Policy and Terms of Use.

Want to learn more about 55+ communities in New Fairfield?

Call us: (959) 214-2391
159 communities
Remove Boundaries ×
Map Satellite

Reinmlsx

The listings data displayed on this medium comes in part from the Real Estate Information Network Inc. (REIN) and has been authorized by participating listing Broker Members of REIN for display. REIN's listings are based upon Data submitted by its Broker Members, and REIN therefore makes no representation or warranty regarding the accuracy of the Data. All users of REIN's listings database should confirm the accuracy of the listing information directly with the listing agent.
© 2026 REIN. REIN's listings Data and information is protected under federal copyright laws. Federal law prohibits, among other acts, the unauthorized copying or alteration of, or preparation of derivative works from, all or any part of copyrighted materials, including certain compilations of Data and information. COPYRIGHT VIOLATORS MAY BE SUBJECT TO SEVERE FINES AND PENALTIES UNDER FEDERAL LAW.
REIN updates its listings on a daily basis. Data last updated: Jul 23, 2026.
This application does not include information on all of the properties available for sale at this time.

Call Us Call Us
Scroll to Top