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
351 homes near New Fairfield
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3.6 rating (7 reviews)
![Heritage Village]()
$200ks
- $500ks
Heritage Village, Southbury, CT
Resale Only
|
55+ age-restricted
|
Built 1967 - 2005
|
2,580 homes
$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
$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
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(959) 214-2391
$600ks
- $1Ms
The Greens at Half Hollow, Melville, NY
Resale Only
|
55+ age-restricted
|
Built 1994 - 2005
|
1,200 homes
$400ks
- $500ks
The Village at Oxford Gre..., Oxford, CT
New and Resale
|
55+ age-restricted
|
Built 2004 - present
|
835 homes
$300ks
- $600ks
The Waterways at Moriches, Moriches, NY
Resale Only
|
55+ age-restricted
|
Built 1985 - 1999
|
343 homes
$100ks
- $300ks
Leisure Village, Ridge, NY
Resale Only
|
55+ age-restricted
|
Built 1969 - 1986
|
1,500 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
Download the Ultimate 55+ Homebuying Guide
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3.7 rating (3 reviews)
![Greenwood Village]()
$100ks
Greenwood Village, Manorville, NY
Resale Only
|
55+ age-restricted
|
Built 1980 - 2000
|
512 homes
$700ks
- $1Ms
Country Pointe Plainview, Plainview, NY
New Construction
|
55+ age-restricted
|
Built 2017 - present
|
660 homes
4 rating (8 reviews)
![Glenwood Village]()
$100ks
- $200ks
Glenwood Village, Riverhead, NY
New and Resale
|
55+ age-restricted
|
Built 1959 - present
|
588 homes
$300ks
- $400ks
The Manors at The Colony ..., Shirley, NY
New Construction
|
55+ age-restricted
|
Built 2013 - present
|
150 homes
5 rating (1 reviews)
![Warwick Grove]()
$400ks
- $600ks
Warwick Grove, Warwick, NY
New and Resale
|
55+ age-restricted
|
Built 2004 - present
|
215 homes
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(959) 214-2391
$400ks
- $600ks
Fairview at Oxford Greens, Oxford, CT
New and Resale
|
55+ age-restricted
|
Built 2019 - present
|
125 homes
$300ks
- $400ks
Leisure Glen, Ridge, NY
Resale Only
|
55+ age-restricted
|
Built 1985 - 2010
|
646 homes
$200ks
- $400ks
Leisure Knoll, Ridge, NY
Resale Only
|
55+ age-restricted
|
Built 1972 - 1982
|
701 homes
$800ks
- $1Ms
HarborView, Port Washington, NY
Resale Only
|
55+ age-restricted
|
Built 2002 - 2004
|
270 homes
Download the Ultimate 55+ Homebuying Guide
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$300ks
- $900ks
Rivington, Danbury, CT
New and Resale
|
Age-targeted
|
Built 2006 - present
|
1,050 homes
$300ks
- $400ks
Liberty at Newtown, Newtown, CT
Resale Only
|
55+ age-restricted
|
Built 2003 - 2007
|
96 homes
$300ks
- $500ks
Dutchgate, Valley Stream, NY
Resale Only
|
55+ age-restricted
|
Built 2009 - 2015
|
348 homes
$300ks
- $400ks
Regency at Fishkill, Fishkill, NY
Resale Only
|
55+ age-restricted
|
Built 2008 - 2020
|
164 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
5 rating (1 reviews)
![Westhampton Pines]()
$900ks
- $1Ms
Westhampton Pines, Westhampton, NY
Resale Only
|
55+ age-restricted
|
Built 2005 - 2013
|
189 homes
$100ks
- $200ks
Spring Lake Village, Southington, CT
Resale Only
|
55+ age-restricted
|
Built 1970 - 2004
|
640 homes
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Questions? Call us:
(959) 214-2391
3.5 rating (2 reviews)
![Foxwood Village]()
$200ks
- $400ks
Foxwood Village, Calverton, NY
Resale Only
|
55+ age-restricted
|
Built 1986 - 2007
|
294 homes
5 rating (1 reviews)
![Encore Atlantic Shores]()
$500ks
- $800ks
Encore Atlantic Shores, Eastport, NY
Resale Only
|
55+ age-restricted
|
Built 2004 - 2011
|
240 homes
$500ks
Stoneleigh Woods at River..., Riverhead, NY
Resale Only
|
55+ age-restricted
|
Built 2007 - 2016
|
176 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.
$400ks
- $500ks
Vineyards at Brookfield, Center Moriches, NY
New Construction
|
55+ age-restricted
|
Built 2019 - present
|
146 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
$500ks
- $600ks
Vineyards at Moriches, Center Moriches, NY
Resale Only
|
55+ age-restricted
|
Built 2008 - 2014
|
92 homes
$600ks
- $900ks
Country Pointe PreserveYaphank, NY
New Construction
|
55+ age-restricted
|
Built 2024 - present
|
152 homes
$700ks
- $1Ms
Meadowbrook Pointe Athlet..., Westbury, NY
Resale Only
|
55+ age-restricted
|
Built 2015 - 2016
|
720 homes
5 rating (1 reviews)
![Newtown Woods]()
$300ks
- $500ks
Newtown Woods, Newtown, CT
New and Resale
|
55+ age-restricted
|
Built 2011 - present
|
178 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
$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?
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Questions? Call us:
(959) 214-2391
5 rating (1 reviews)
![Sunken Pond Estates]()
$400ks
Sunken Pond Estates, Riverhead, NY
Resale Only
|
55+ age-restricted
|
Built 2003 - 2005
|
194 homes
$300ks
Pond Spring Village, Beacon Falls, CT
New and Resale
|
55+ age-restricted
|
Built 2005 - present
|
92 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.
Glenwood Village
![1661 OLD COUNTRY RD 516, RIVERHEAD, NY, ..., Riverhead, NY 11901]()
2 beds
|2 baths
|1,624 sq ft
|Manufactured Home
1661 OLD COUNTRY RD 516, RIVERHEAD, NY, ...
Community: Glenwood Village
MLS 1011541 • Gateway to The Hamptons R E, Vivian... • Gateway to The Hamptons R E
New
Oronoque Village
![407 MONTAUK LN B, STRATFORD, CT, 06614, Stratford, CT 06614]()
1 beds
|2 baths
|1,360 sq ft
|Condo
407 MONTAUK LN B, STRATFORD, CT, 06614
Community: Oronoque Village
MLS 24186313 • Coldwell Banker Realty, Mary Kelle... • Coldwell Banker Realty
New
Bald Eagle Commons
![9106 RICHMOND RD, WEST MILFORD TWP., NJ,..., West Milford Twp., NJ 07480]()
MLS 4041260 • RE/MAX COUNTRY REALTY, RE/MAX COUNT... • RE/MAX COUNTRY REALTY
New
Wanaque Reserve
![2107 WARRENS WAY 107, WANAQUE, NJ, 07465, Wanaque, NJ 07465]()
MLS 26026741 • Coldwell Banker, Wayne, Christine ... • Coldwell Banker, Wayne
New
Leisure Village
![368 WOODBRIDGE DR A, BROOKHAVEN, NY, 119..., Brookhaven, NY 11961]()
MLS 1027091 • Figs Real Estate Group, Edward S. F... • Figs Real Estate Group
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New
Baldwin Station
![15 JASMINE CIR 15, MILFORD, CT, 06461, Milford, CT 06461]()
2 beds
|3 baths
|2,331 sq ft
|Condo
15 JASMINE CIR 15, MILFORD, CT, 06461
Community: Baldwin Station
MLS 24192124 • Berkshire Hathaway NE Prop., Aurel... • Berkshire Hathaway NE Prop.
New
Wanaque Reserve
![2107 WARRENS WAY 107, WANAQUE BORO, NJ, ..., Wanaque Boro, NJ 07465]()
2 beds
|2 baths
|1,768 sq ft
2107 WARRENS WAY 107, WANAQUE BORO, NJ, ...
Community: Wanaque Reserve
MLS 4041207 • COLDWELL BANKER REALTY, COLDWELL BA... • COLDWELL BANKER REALTY
New
Country Pointe Plainview
![67101 RED CEDAR RD, OYSTER BAY, NY, 1180..., Oyster Bay, NY 11803]()
3 beds
|4 baths
|2,484 sq ft
|House
67101 RED CEDAR RD, OYSTER BAY, NY, 1180...
Community: Country Pointe Plainview
MLS 1025424 • Daniel Gale Sothebys Intl Rlty, Mar... • Daniel Gale Sothebys Intl Rlty
New
The Village at Oxford Greens
![941 MACKENZIE LN 941, OXFORD, CT, 06478, Oxford, CT 06478]()
2 beds
|2 baths
|1,682 sq ft
941 MACKENZIE LN 941, OXFORD, CT, 06478
Community: The Village at Oxford Greens
MLS 24192068 • Real Estate Two, Karen Berwick • Real Estate Two
New
Fairview at Oxford Greens
![941 MACKENZIE LN 941, OXFORD, CT, 06478, Oxford, CT 06478]()
2 beds
|2 baths
|1,682 sq ft
941 MACKENZIE LN 941, OXFORD, CT, 06478
Community: Fairview at Oxford Greens
MLS 24192068 • Real Estate Two, Karen Berwick • Real Estate Two
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
Leisure Glen
![581 LEISURE DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961]()
2 beds
|2 baths
|1,685 sq ft
|Condo
581 LEISURE DR, BROOKHAVEN, NY, 11961
Community: Leisure Glen
MLS 1026532 • Signature Premier Properties, Maure... • Signature Premier Properties
New
Meadowbrook Pointe Links & Spa
![252 SAND HILLS LN, BROOKHAVEN, NY, 11763, Brookhaven, NY 11763]()
2 beds
|2 baths
|1,133 sq ft
|Condo
252 SAND HILLS LN, BROOKHAVEN, NY, 11763
Community: Meadowbrook Pointe Links & Spa
MLS 1026906 • Signature Premier Properties, Matth... • Signature Premier Properties
New
Snug Harbor
![58 HARBOR RD, BABYLON, NY, 11701, Babylon, NY 11701]()
MLS 992241 • Daniel Gale Sothebys Intl Rlty, Kim ... • Daniel Gale Sothebys Intl Rlty
New
Rivington
![64 WARRINGTON ROUND 64, DANBURY, CT, 068..., Danbury, CT 06810]()
3 beds
|3 baths
|1,600 sq ft
|Condo
64 WARRINGTON ROUND 64, DANBURY, CT, 068...
Community: Rivington
MLS 24191321 • Coldwell Banker Realty, Antonio Za... • Coldwell Banker Realty
New
Leisure Knoll
![190 CANTERBURY DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961]()
2 beds
|1 baths
|1,020 sq ft
|Condo
190 CANTERBURY DR, BROOKHAVEN, NY, 11961
Community: Leisure Knoll
MLS 1026762 • Howard Hanna Coach, Kalliopi C. Sua... • Howard Hanna Coach
New
Glenwood Village
![1661 OLD COUNTRY RD 156D, RIVERHEAD, NY,..., Riverhead, NY 11901]()
2 beds
|2 baths
|1,500 sq ft
|Manufactured Home
1661 OLD COUNTRY RD 156D, RIVERHEAD, NY,...
Community: Glenwood Village
MLS 1025609 • R & R Duo Realty Inc, Irina V. Renn... • R & R Duo Realty Inc
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(959) 214-2391
New
Foxwood Village
![1407 MIDDLE RD 277, RIVERHEAD, NY, 11933, Riverhead, NY 11933]()
2 beds
|2 baths
|1,568 sq ft
|Manufactured Home
1407 MIDDLE RD 277, RIVERHEAD, NY, 11933
Community: Foxwood Village
MLS 1026622 • Bagshaw Real Estate L.L.C, Joan M. ... • Bagshaw Real Estate L.L.C
New
Meadowbrook Pointe Athletic Club & Spa
![348 TROTTING LN, HEMPSTEAD, NY, 11590, Hempstead, NY 11590]()
2 beds
|2 baths
|1,319 sq ft
|Condo
348 TROTTING LN, HEMPSTEAD, NY, 11590
Community: Meadowbrook Pointe Athletic Club & Spa
MLS 1024788 • Douglas Elliman Real Estate, Matthe... • Douglas Elliman Real Estate
New
Regency at Wappinger
![36 FARMINGTON RD, WAPPINGER, NY, 12590, Wappinger, NY 12590]()
2 beds
|3 baths
|2,600 sq ft
|House
36 FARMINGTON RD, WAPPINGER, NY, 12590
Community: Regency at Wappinger
MLS 1025987 • Houlihan Lawrence Inc., Nicole Bois... • Houlihan Lawrence Inc.
New
Encore at Lake Grove
![189 SYMPHONY DR, BROOKHAVEN, NY, 11755, Brookhaven, NY 11755]()
2 beds
|3 baths
|1,378 sq ft
|Condo
189 SYMPHONY DR, BROOKHAVEN, NY, 11755
Community: Encore at Lake Grove
MLS 1022885 • Signature Premier Properties, JoAnn... • Signature Premier Properties
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
Bear's Cove
![125 WINDSOR LN, RAMSEY, NJ, 07446, Ramsey, NJ 07446]()
MLS 26026554 • Keller Williams Valley Realty, Jai... • Keller Williams Valley Realty
New
Heritage Village
![1008 HERITAGE VLG A, SOUTHBURY, CT, 0648..., Southbury, CT 06488]()
3 beds
|2 baths
|1,716 sq ft
|Condo
1008 HERITAGE VLG A, SOUTHBURY, CT, 0648...
Community: Heritage Village
MLS 24191347 • Real Broker CT, LLC, Tricia Farin • Real Broker CT, LLC
New
Jefferson Village
![18 HASTINGS CT B, YORKTOWN, NY, 10598, Yorktown, NY 10598]()
1 beds
|1 baths
|850 sq ft
|Condo
18 HASTINGS CT B, YORKTOWN, NY, 10598
Community: Jefferson Village
MLS 1025022 • Houlihan Lawrence Inc., Barbara J. ... • Houlihan Lawrence Inc.
New
Winthrop Court
![8205 HARCOURT 8205, CLIFTON, NJ, 07013, Clifton, NJ 07013]()
MLS 26026448 • Keller Williams Prosperity Realty,... • Keller Williams Prosperity Realty
New
Leisure Village
![66 ENFIELD CT B, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961]()
2 beds
|1 baths
|1,085 sq ft
|Condo
66 ENFIELD CT B, BROOKHAVEN, NY, 11961
Community: Leisure Village
MLS 1025693 • Leisure Living Realty Inc, Paulina ... • Leisure Living Realty Inc
New
Bald Eagle Commons
![1316 RICHMOND RD, WEST MILFORD, NJ, 0748..., West Milford, NJ 07480]()
MLS 26026359 • Realty Executives Exceptional Real... • Realty Executives Exceptional Realtors-Kinnelon
New
Heritage Village
![76 HERITAGE VLG C, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,308 sq ft
|Condo
76 HERITAGE VLG C, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24188643 • William Pitt Sotheby's Int'l, Beck... • William Pitt Sotheby's Int'l
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New
Bald Eagle Commons
![1316 RICHMOND RD 316, WEST MILFORD TWP.,..., West Milford Twp., NJ 07480]()
MLS 4040437 • REALTY EXECUTIVES EXCEPTIONAL, REAL... • REALTY EXECUTIVES EXCEPTIONAL
New
Greenwood Village
![89 VILLAGE CIR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949]()
1 beds
|1 baths
|812 sq ft
|Condo
89 VILLAGE CIR, BROOKHAVEN, NY, 11949
Community: Greenwood Village
MLS 1025221 • Coldwell Banker American Homes, Kel... • Coldwell Banker American Homes
New
Setauket Meadows
![66 BRIANNA DR, BROOKHAVEN, NY, 11733, Brookhaven, NY 11733]()
2 beds
|3 baths
|1,878 sq ft
|Condo
66 BRIANNA DR, BROOKHAVEN, NY, 11733
Community: Setauket Meadows
MLS 1024202 • The Agency Northshore NY, Jenna Sto... • The Agency Northshore 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.
New
Winthrop Court
![8205 HARCOURT RD, CLIFTON CITY, NJ, 0701..., Clifton City, NJ 07013]()
2 beds
|2 baths
|1,534 sq ft
8205 HARCOURT RD, CLIFTON CITY, NJ, 0701...
Community: Winthrop Court
MLS 4040313 • KELLER WILLIAMS PROSPERITY REALTY, ... • KELLER WILLIAMS PROSPERITY REALTY
New
Dutchgate
![1132 WILLOW LN 1131, HEMPSTEAD, NY, 1158..., Hempstead, NY 11580]()
2 beds
|2 baths
|941 sq ft
|Condo
1132 WILLOW LN 1131, HEMPSTEAD, NY, 1158...
Community: Dutchgate
MLS 1014384 • Coldwell Banker American Homes, Ran... • Coldwell Banker American Homes
Heritage Village
![773 HERITAGE VLG D, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,071 sq ft
|Condo
773 HERITAGE VLG D, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24190666 • William Raveis Real Estate, Ruth Z... • William Raveis Real Estate
Heritage Hills
![358 HERITAGE HLS C, SOMERS, NY, 10589, Somers, NY 10589]()
2 beds
|3 baths
|1,550 sq ft
|Condo
358 HERITAGE HLS C, SOMERS, NY, 10589
Community: Heritage Hills
MLS 1024317 • Houlihan Lawrence Inc., Annpauline ... • Houlihan Lawrence Inc.
Newtown Woods
![232 BROOKSIDE CT 232, NEWTOWN, CT, 06470, Newtown, CT 06470]()
2 beds
|2 baths
|1,747 sq ft
|Condo
232 BROOKSIDE CT 232, NEWTOWN, CT, 06470
Community: Newtown Woods
MLS 24190305 • McGrath Realty Inc., Claudia Jiskr... • McGrath Realty Inc.
Glassbury Court at Cold Spring
![10 MAGGIE MAY WAY, PHILIPSTOWN, NY, 1051..., Philipstown, NY 10516]()
2 beds
|2 baths
|1,974 sq ft
|Condo
10 MAGGIE MAY WAY, PHILIPSTOWN, NY, 1051...
Community: Glassbury Court at Cold Spring
MLS 1024506 • Keller Williams Realty Partner, Chr... • Keller Williams Realty Partner
Four Seasons at Cedar Grove
![505 HOLLY LN, CEDAR GROVE TWP., NJ, 0700..., Cedar Grove Twp., NJ 07009]()
MLS 4039918 • COLDWELL BANKER REALTY, COLDWELL BA... • COLDWELL BANKER REALTY
Heritage Village
![818 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,432 sq ft
|Condo
818 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24190528 • William Pitt Sotheby's Int'l, Liz ... • William Pitt Sotheby's Int'l
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Leisure Village
![176 VENTRY CT A, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961]()
2 beds
|1 baths
|1,085 sq ft
|Condo
176 VENTRY CT A, BROOKHAVEN, NY, 11961
Community: Leisure Village
MLS 1021851 • Coldwell Banker American Homes, Kat... • Coldwell Banker American Homes
Country Pointe Plainview
![46102 SILVER BIRCH LN, OYSTER BAY, NY, 1..., Oyster Bay, NY 11803]()
3 beds
|3 baths
|2,499 sq ft
|Condo
46102 SILVER BIRCH LN, OYSTER BAY, NY, 1...
Community: Country Pointe Plainview
MLS 1024287 • Douglas Elliman Real Estate, Reena ... • Douglas Elliman Real Estate
Download the Ultimate 55+ Homebuying Guide
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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 421 days. The average price of homes for sale in this community is approximately $482,355, 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 $482,355.
Want more information about active adult communities around New Fairfield?
Want to learn more about 55+ communities in New Fairfield?
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© 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 17, 2026.
This application does not include information on all of the properties available for sale at this time.
