Call us at (959) 214-2391 to learn more about active adult communities near New Fairfield
New Fairfield, CT 55+ active adult communities & homes for sale
156 communities near New Fairfield
336 homes near New Fairfield
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![The Woods at Dunham Pond]()
$400Ks
- $500Ks
The Woods at Dunham Pond, New Fairfield, CT
Resale Only
|
55+ age-restricted
|
Built 2004 - 2015
|
33 homes
3 rating (2 reviews)
![Heritage Hills]()
$300Ks
- $900Ks
Heritage Hills, Somers, NY
Resale Only
|
Age-targeted
|
Built 1974 - 2006
|
2,600 homes
3.6 rating (7 reviews)
![Heritage Village]()
$100Ks
- $500Ks
Heritage Village, Southbury, CT
Resale Only
|
55+ age-restricted
|
Built 1967 - 2005
|
2,580 homes
No reviews yet
![Leisure Village]()
$200Ks
- $400Ks
Leisure Village, Ridge, NY
Resale Only
|
55+ age-restricted
|
Built 1969 - 1986
|
1,500 homes
No reviews yet
![The Greens at Half Hollow]()
$500Ks
- $1Ms
The Greens at Half Hollow, Melville, NY
Resale Only
|
55+ age-restricted
|
Built 1994 - 2005
|
1,200 homes
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(959) 214-2391
No reviews yet
![Rivington]()
$400Ks
- $600Ks
Rivington, Danbury, CT
New and Resale
|
Age-targeted
|
Built 2006 - present
|
1,050 homes
4 rating (1 reviews)
![Jefferson Village]()
$200Ks
- $600Ks
Jefferson Village, Yorktown Heights, NY
Resale Only
|
55+ age-restricted
|
Built 1967 - 1982
|
1,000 homes
No reviews yet
![Oronoque Village]()
$200Ks
- $600Ks
Oronoque Village, Stratford, CT
Resale Only
|
55+ age-restricted
|
Built 1971 - 1977
|
929 homes
No reviews yet
![The Village at Oxford Gre...]()
$500Ks
- $700Ks
The Village at Oxford Gre..., Oxford, CT
New and Resale
|
55+ age-restricted
|
Built 2004 - present
|
835 homes
5 rating (1 reviews)
![Four Seasons at Great Not...]()
$600Ks
- $800Ks
Four Seasons at Great Not..., Woodland Park, NJ
Resale Only
|
55+ age-restricted
|
Built 2005 - 2018
|
814 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.
4.8 rating (4 reviews)
![Wanaque Reserve]()
$400Ks
- $400Ks
Wanaque Reserve, Wanaque, NJ
Resale Only
|
55+ age-restricted
|
Built 2004 - 2014
|
755 homes
No reviews yet
![Meadowbrook Pointe Athlet...]()
$800Ks
- $1Ms
Meadowbrook Pointe Athlet..., Westbury, NY
Resale Only
|
55+ age-restricted
|
Built 2015 - 2016
|
720 homes
No reviews yet
![Leisure Knoll]()
$300Ks
- $400Ks
Leisure Knoll, Ridge, NY
Resale Only
|
55+ age-restricted
|
Built 1972 - 1982
|
701 homes
No reviews yet
![Country Pointe Plainview]()
$1Ms
- $1Ms
Country Pointe Plainview, Plainview, NY
New Construction
|
55+ age-restricted
|
Built 2017 - present
|
660 homes
5 rating (2 reviews)
![Fairfield at St. James]()
$400Ks
- $500Ks
Fairfield at St. James, St. James, NY
Resale Only
|
55+ age-restricted
|
Built 1972 - 1989
|
653 homes
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No reviews yet
![Leisure Glen]()
$400Ks
- $400Ks
Leisure Glen, Ridge, NY
Resale Only
|
55+ age-restricted
|
Built 1985 - 2010
|
646 homes
No reviews yet
![Spring Lake Village]()
$200Ks
- $200Ks
Spring Lake Village, Southington, CT
Resale Only
|
55+ age-restricted
|
Built 1970 - 2004
|
640 homes
4 rating (8 reviews)
![Glenwood Village]()
$100Ks
- $400Ks
Glenwood Village, Riverhead, NY
New and Resale
|
55+ age-restricted
|
Built 1959 - present
|
588 homes
3.7 rating (3 reviews)
![Greenwood Village]()
$100Ks
- $200Ks
Greenwood Village, Manorville, NY
Resale Only
|
55+ age-restricted
|
Built 1980 - 2000
|
512 homes
No reviews yet
![Bald Eagle Commons]()
$100Ks
- $300Ks
Bald Eagle Commons, West Milford, NJ
Resale Only
|
55+ age-restricted
|
Built 1995 - 2005
|
463 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.
No reviews yet
![The Seasons at East Meado...]()
$500Ks
- $600Ks
The Seasons at East Meado..., East Meadow, NY
Resale Only
|
55+ age-restricted
|
Built 2009 - 2012
|
404 homes
No reviews yet
![Regency at Prospect]()
$300Ks
- $500Ks
Regency at Prospect, Prospect, CT
Resale Only
|
55+ age-restricted
|
Built 2006 - 2020
|
379 homes
No reviews yet
![Dutchgate]()
$400Ks
- $400Ks
Dutchgate, Valley Stream, NY
Resale Only
|
55+ age-restricted
|
Built 2009 - 2015
|
348 homes
No reviews yet
![The Waterways at Moriches]()
$400Ks
- $700Ks
The Waterways at Moriches, Moriches, NY
Resale Only
|
55+ age-restricted
|
Built 1985 - 1999
|
343 homes
No reviews yet
![The Retreat at Carmel]()
$400Ks
- $600Ks
The Retreat at Carmel, Carmel, NY
Resale Only
|
55+ age-restricted
|
Built 2008 - 2018
|
312 homes
Want to learn more about 55+ communities in New Fairfield?
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Questions? Call us:
(959) 214-2391
3.5 rating (2 reviews)
![Foxwood Village]()
$300Ks
- $400Ks
Foxwood Village, Calverton, NY
Resale Only
|
55+ age-restricted
|
Built 1986 - 2007
|
294 homes
1 rating (1 reviews)
![Plymouth Estates at Mount...]()
$500Ks
- $500Ks
Plymouth Estates at Mount..., Mount Sinai, NY
Resale Only
|
55+ age-restricted
|
Built 2006 - 2013
|
285 homes
No reviews yet
![Wildflowers at Wallkill]()
$400Ks
- $500Ks
Wildflowers at Wallkill, Middletown, NY
Resale Only
|
55+ age-restricted
|
Built 2006 - 2017
|
283 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
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.
4 rating (1 reviews)
![Vineyards at Blue Point]()
$800Ks
- $800Ks
Vineyards at Blue Point, Blue Point, NY
Resale Only
|
55+ age-restricted
|
Built 2016 - 2018
|
280 homes
No reviews yet
![Apple Ridge]()
$700Ks
- $700Ks
Apple Ridge, Mahwah, NJ
Resale Only
|
Age-targeted
|
Built 1977 - 1991
|
276 homes
No reviews yet
![HarborView]()
$900Ks
- $1Ms
HarborView, Port Washington, NY
Resale Only
|
55+ age-restricted
|
Built 2002 - 2004
|
270 homes
No reviews yet
![Winthrop Court]()
$400Ks
- $500Ks
Winthrop Court, Clifton, NJ
Resale Only
|
55+ age-restricted
|
Built 2000 - 2010
|
270 homes
No reviews yet
![The Club at Melville]()
$500Ks
- $500Ks
The Club at Melville, Melville, NY
Resale Only
|
55+ age-restricted
|
Built 2015 - 2017
|
261 homes
Want to learn more about 55+ communities in New Fairfield?
55places can help!
Questions? Call us:
(959) 214-2391
No reviews yet
![The Seasons at Elwood]()
$800Ks
- $900Ks
The Seasons at Elwood, East Northport, NY
Resale Only
|
55+ age-restricted
|
Built 2018 - 2020
|
256 homes
No reviews yet
![Meadow Brook Estates]()
$500Ks
- $500Ks
Meadow Brook Estates, Oxford, CT
Resale Only
|
55+ age-restricted
|
Built 2003 - 2020
|
246 homes
5 rating (1 reviews)
![Encore Atlantic Shores]()
$600Ks
- $800Ks
Encore Atlantic Shores, Eastport, NY
Resale Only
|
55+ age-restricted
|
Built 2004 - 2011
|
240 homes
No reviews yet
![The Summit at Bethel]()
$600Ks
- $600Ks
The Summit at Bethel, Bethel, CT
Resale Only
|
55+ age-restricted
|
Built 2010 - 2021
|
235 homes
4.9 rating (14 reviews)
![Chatfield Farms]()
$500Ks
- $600Ks
Chatfield Farms, Beacon Falls, CT
New Construction
|
55+ age-restricted
|
Built 2014 - present
|
231 homes
Greenwood Village
![93 VILLAGE CIR, MANORVILLE, NY, 11949, Manorville, NY 11949]()
2 beds
|2 baths
|1,100 sq ft
|Condo
93 VILLAGE CIR, MANORVILLE, NY, 11949
Community: Greenwood Village
MLS 897304 • Aliano Real Estate, Dorothy Farrell
Leisure Village
![329 WOODBRIDGE DR A, RIDGE, NY, 11961, Ridge, NY 11961]()
2 beds
|2 baths
|1,130 sq ft
|Condo
329 WOODBRIDGE DR A, RIDGE, NY, 11961
Community: Leisure Village
MLS 905779 • Realty Connect USA L I Inc, Sandi M....
Greenwood Village
![45 DOGWOOD LN, MANORVILLE, NY, 11949, Manorville, NY 11949]()
2 beds
|2 baths
|1,134 sq ft
|Condo
45 DOGWOOD LN, MANORVILLE, NY, 11949
Community: Greenwood Village
MLS 928399 • BERKSHIRE HATHAWAY, Geri M. Monzillo
Leisure Village
![69 ENFIELD CT UNIT B B, RIDGE, NY, 11961, Ridge, NY 11961]()
2 beds
|1 baths
|1,278 sq ft
|Condo
69 ENFIELD CT UNIT B B, RIDGE, NY, 11961
Community: Leisure Village
MLS 905718 • Leisure Living Realty Inc, Catherine...
Fairfield at St. James
![204 BENTLEY CT 204, SMITHTOWN, NY, 11780, Smithtown, NY 11780]()
1 beds
|1 baths
|750 sq ft
|Condo
204 BENTLEY CT 204, SMITHTOWN, NY, 11780
Community: Fairfield at St. James
MLS 915693 • Aliano Real Estate, Diana Snyder
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Leisure Village
![171B VENTRY CT 171B, BROOKHAVEN, NY, 119..., Brookhaven, NY 11961]()
1 beds
|1 baths
|679 sq ft
|Condo
171B VENTRY CT 171B, BROOKHAVEN, NY, 119...
Community: Leisure Village
MLS 904701 • Leisure Living Realty Inc, Laura Ruh...
Breton Hills
![704 BRETON WAY # 704, GLEN COVE, NY, 115..., Glen Cove, NY 11542]()
2 beds
|2 baths
|1,440 sq ft
|Condo
704 BRETON WAY # 704, GLEN COVE, NY, 115...
Community: Breton Hills
MLS 920295 • Keller Williams Realty Elite, Patric...
Warwick Grove
![21 LONG HOUSE RD, WARWICK, NY, 10990, Warwick, NY 10990]()
3 beds
|3 baths
|2,782 sq ft
|House
21 LONG HOUSE RD, WARWICK, NY, 10990
Community: Warwick Grove
MLS 899630 • Howard Hanna Rand Realty, Carole E. ...
Leisure Glen
![12 BALDWIN CT, RIDGE, NY, 11961, Ridge, NY 11961]()
MLS 897659 • Homeside Realty, Frank Profeta
Stone Ridge Estates
![156 CHRISTINE DR, DIX HILLS, NY, 11746, Dix Hills, NY 11746]()
2 beds
|2 baths
|1,700 sq ft
|Condo
156 CHRISTINE DR, DIX HILLS, NY, 11746
Community: Stone Ridge Estates
MLS 859377 • Howard Hanna Coach, Susan Catik
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 Manors at The Colony Preserve
![41 GREENTREE CT, SHIRLEY, NY, 11967, Shirley, NY 11967]()
2 beds
|2 baths
|1,800 sq ft
|Condo
41 GREENTREE CT, SHIRLEY, NY, 11967
Community: The Manors at The Colony Preserve
MLS 920956 • Leesa Byrnes Realty Inc, Leesa Byrne...
Jefferson Village
![84 MOLLY PITCHER LN H, YORKTOWN HEIGHTS,..., Yorktown Heights, NY 10598]()
2 beds
|2 baths
|1,100 sq ft
|Condo
84 MOLLY PITCHER LN H, YORKTOWN HEIGHTS,...
Community: Jefferson Village
MLS 877595 • Coldwell Banker Realty, Maureen Conn...
Leisure Village
![4 GUILFORD CT UNIT C, RIDGE, NY, 11961, Ridge, NY 11961]()
2 beds
|2 baths
|1,486 sq ft
|Condo
4 GUILFORD CT UNIT C, RIDGE, NY, 11961
Community: Leisure Village
MLS 924288 • Coldwell Banker American Homes, Joy ...
The Waterways at Moriches
![204 RIVER DR, MORICHES, NY, 11955, Moriches, NY 11955]()
2 beds
|2 baths
|1,790 sq ft
|Condo
204 RIVER DR, MORICHES, NY, 11955
Community: The Waterways at Moriches
MLS 915032 • Douglas Elliman Real Estate, Jo Ann ...
Fairfield at St. James
![607 CABOT CT 607, SMITHTOWN, NY, 11780, Smithtown, NY 11780]()
1 beds
|2 baths
|929 sq ft
|Condo
607 CABOT CT 607, SMITHTOWN, NY, 11780
Community: Fairfield at St. James
MLS 920102 • Howard Hanna Coach, Kathleen E. Beck...
Want to learn more about 55+ communities in New Fairfield?
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(959) 214-2391
The Vineyards at Miller Place
![48 AVERY LN, MILLER PLACE, NY, 11764, Miller Place, NY 11764]()
2 beds
|3 baths
|1,486 sq ft
|Condo
48 AVERY LN, MILLER PLACE, NY, 11764
Community: The Vineyards at Miller Place
MLS 925827 • Aliano Real Estate, Nicholas R. Alia...
The Seasons at East Meadow
![383 SUMMER CT, EAST MEADOW, NY, 11554, East Meadow, NY 11554]()
2 beds
|2 baths
|1,272 sq ft
|Condo
383 SUMMER CT, EAST MEADOW, NY, 11554
Community: The Seasons at East Meadow
MLS 917407 • Coldwell Banker American Homes, Mich...
Leisure Village
![48 TRENT CT B, RIDGE, NY, 11961, Ridge, NY 11961]()
MLS 906943 • Coldwell Banker American Homes, Rona...
The Greens at Half Hollow
![1126 SAVOY DR, MELVILLE, NY, 11747, Melville, NY 11747]()
2 beds
|2 baths
|1,150 sq ft
|Condo
1126 SAVOY DR, MELVILLE, NY, 11747
Community: The Greens at Half Hollow
MLS 884448 • Signature Premier Properties, Margue...
Glenwood Village
![1661 OLD COUNTRY RD UNIT 563, RIVERHEAD,..., Riverhead, NY 11901]()
2 beds
|2 baths
|1,500 sq ft
|Manufactured Home
1661 OLD COUNTRY RD UNIT 563, RIVERHEAD,...
Community: Glenwood Village
MLS 909205 • Keystone Realty USA Corp, Janet I. P...
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.
Leisure Village
![311 WOODBRIDGE DR 311-C, RIDGE, NY, 1196..., Ridge, NY 11961]()
1 beds
|1 baths
|684 sq ft
|Condo
311 WOODBRIDGE DR 311-C, RIDGE, NY, 1196...
Community: Leisure Village
MLS 879843 • Coldwell Banker American Homes, Ther...
Glenwood Village
![1661 OLD COUNTRY OLD COUNTRY RD, RIVERHE..., Riverhead, NY 11901]()
2 beds
|2 baths
|1,232 sq ft
|Manufactured Home
1661 OLD COUNTRY OLD COUNTRY RD, RIVERHE...
Community: Glenwood Village
MLS 925912 • Joanne Kane Gigantiello, Joanne Giga...
Leisure Village
![22B GUILFORD CT # 22B, RIDGE, NY, 11961, Ridge, NY 11961]()
2 beds
|1 baths
|1,085 sq ft
|Condo
22B GUILFORD CT # 22B, RIDGE, NY, 11961
Community: Leisure Village
MLS 923135 • Leisure Living Realty Inc, Heather B...
The Seasons at East Meadow
![272 SPRING DR, EAST MEADOW, NY, 11554, East Meadow, NY 11554]()
2 beds
|3 baths
|1,030 sq ft
|Condo
272 SPRING DR, EAST MEADOW, NY, 11554
Community: The Seasons at East Meadow
MLS 924891 • Birch Hill Realty Consultants, Josep...
Leisure Village
![412 WEYMOUTH CT UNIT B, RIDGE, NY, 11961, Ridge, NY 11961]()
2 beds
|1 baths
|1,100 sq ft
|Condo
412 WEYMOUTH CT UNIT B, RIDGE, NY, 11961
Community: Leisure Village
MLS 924555 • Keller Williams Rlty Landmark, Anton...
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Questions? Call us:
(959) 214-2391
Leisure Village
![474 DARWEN DR B, RIDGE, NY, 11961, Ridge, NY 11961]()
MLS 911211 • Douglas Elliman Real Estate, Nicole ...
Leisure Village
![259 NEWCASTLE CT E, RIDGE, NY, 11961, Ridge, NY 11961]()
1 beds
|1 baths
|875 sq ft
|Condo
259 NEWCASTLE CT E, RIDGE, NY, 11961
Community: Leisure Village
MLS 878336 • Barons Real Estate Associates, David...
The Coves at Melville
![95 MORLEY CIR, MELVILLE, NY, 11747, Melville, NY 11747]()
2 beds
|2 baths
|1,100 sq ft
|Condo
95 MORLEY CIR, MELVILLE, NY, 11747
Community: The Coves at Melville
MLS 923311 • Douglas Elliman Real Estate, Elyse B...
Dutchgate
![1002 WILLOW LN, VALLEY STREAM, NY, 11580, Valley Stream, NY 11580]()
MLS 894656 • Signature Premier Properties, Michel...
Meadowbrook Pointe Links & Spa
![60 PACIFIC DUNES CT, MEDFORD, NY, 11763, Medford, NY 11763]()
2 beds
|3 baths
|2,191 sq ft
|Condo
60 PACIFIC DUNES CT, MEDFORD, NY, 11763
Community: Meadowbrook Pointe Links & Spa
MLS 915123 • Signature Premier Properties, Matthe...
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.
Leisure Knoll
![323 BROWNFIELD DR, RIDGE, NY, 11961, Ridge, NY 11961]()
MLS 919433 • Daniel Gale Sothebys Intl Rlty, Bonn...
Jefferson Village
![15 ESSEX PL 15K, YORKTOWN, NY, 10598, Yorktown, NY 10598]()
2 beds
|1 baths
|1,000 sq ft
|Condo
15 ESSEX PL 15K, YORKTOWN, NY, 10598
Community: Jefferson Village
MLS 903883 • Keller Williams Realty Group, Erin E...
Heritage Hills
![972 C HERITAGE HLS Y., SOMERS, NY, 10589, Somers, NY 10589]()
2 beds
|2 baths
|1,468 sq ft
|Condo
972 C HERITAGE HLS Y., SOMERS, NY, 10589
Community: Heritage Hills
MLS 886325 • Houlihan Lawrence Inc., Rita Carrozz...
Meadowbrook Pointe Links & Spa
![279 AUGUSTA DR, MEDFORD, NY, 11763, Medford, NY 11763]()
2 beds
|2 baths
|1,133 sq ft
|Condo
279 AUGUSTA DR, MEDFORD, NY, 11763
Community: Meadowbrook Pointe Links & Spa
MLS 901359 • Signature Premier Properties, Matthe...
Leisure Village
![310 WOODBRIDGE DR UNIT C, RIDGE, NY, 119..., Ridge, NY 11961]()
2 beds
|1 baths
|1,278 sq ft
|Condo
310 WOODBRIDGE DR UNIT C, RIDGE, NY, 119...
Community: Leisure Village
MLS 889288 • Coldwell Banker American Homes, Kath...
Want to learn more about 55+ communities in New Fairfield?
55places can help!
Questions? Call us:
(959) 214-2391
Sunken Pond Estates
![4006 SAINT ANDREWS AVE, RIVERHEAD, NY, 1..., Riverhead, NY 11901]()
2 beds
|2 baths
|1,587 sq ft
|Condo
4006 SAINT ANDREWS AVE, RIVERHEAD, NY, 1...
Community: Sunken Pond Estates
MLS 917567 • Douglas Elliman Real Estate, Janet R...
Regency at Fishkill
![334 REGENCY DR, FISHKILL, NY, 12524, Fishkill, NY 12524]()
2 beds
|2 baths
|1,499 sq ft
|Condo
334 REGENCY DR, FISHKILL, NY, 12524
Community: Regency at Fishkill
MLS 910750 • Serhant LLC, Steven Wrobel Jr
Westhampton Pines
![112 ASHLEY DR, WESTHAMPTON, NY, 11977, Westhampton, NY 11977]()
3 beds
|3 baths
|2,306 sq ft
|Condo
112 ASHLEY DR, WESTHAMPTON, NY, 11977
Community: Westhampton Pines
MLS 907102 • William Raveis New York LLC, Margare...
Glenwood Village
![1661 OLD COUNTRY RD 308, RIVERHEAD, NY, ..., Riverhead, NY 11901]()
2 beds
|1 baths
|840 sq ft
|Mobile Home
1661 OLD COUNTRY RD 308, RIVERHEAD, NY, ...
Community: Glenwood Village
MLS 922155 • Realty Connect USA L I Inc, Fengxia ...
Dutchgate
![802 WILLOW LN UPPR LEVEL, VALLEY STREAM,..., Valley Stream, NY 11580]()
2 beds
|2 baths
|941 sq ft
|Condo
802 WILLOW LN UPPR LEVEL, VALLEY STREAM,...
Community: Dutchgate
MLS 912526 • Douglas Elliman Real Estate, Susan K...
Frequently Asked Questions
In New Fairfield, there is 1 small community with less than 500 homes.
The smallest 55+ community in New Fairfield has 33 homes, the largest has 33 homes, and the average community consists of 33 homes.
No, there are no gated 55+ communities in New Fairfield.
On average, listings in 55+ community in New Fairfield stay on the market for around 84 days. The average price of homes for sale in this community is approximately $457,774, though prices can range widely based on the size, location, and amenities of the community. For example, homes in The Woods at Dunham Pond average around $457,774.
Want more information about active adult communities around New Fairfield?
Want to learn more about 55+ communities in New Fairfield?
336
homes
near New Fairfield
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© 2025 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: Nov 05, 2025.
This application does not include information on all of the properties available for sale at this time.
