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New Fairfield, CT 55+ active adult communities & homes for sale - Page 3
163 communities near New Fairfield
371 homes near New Fairfield
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$1Ms
The Cottages at Wire Mill, Stamford, CT
New Construction
|
55+ age-restricted
|
Built 2026 - present
|
9 homes
$300ks
The Village at Hunt Glen, Granby, CT
Resale Only
|
55+ age-restricted
|
Built 2003 - 2006
|
69 homes
$300ks
- $800ks
The Retreat at Carmel, Carmel, NY
Resale Only
|
55+ age-restricted
|
Built 2008 - 2018
|
312 homes
$300ks
- $400ks
Forest Mews, Avon, CT
Resale Only
|
55+ age-restricted
|
Built 2001 - 2004
|
40 homes
$200ks
- $400ks
The Woods at Dunham Pond, New Fairfield, CT
Resale Only
|
55+ age-restricted
|
Built 2004 - 2015
|
33 homes
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$300ks
- $400ks
Summer Wind Estates, North Haven, CT
New Construction
|
55+ age-restricted
|
Built 2015 - present
|
18 homes
$400ks
Eastport Meadows, Eastport, NY
Resale Only
|
55+ age-restricted
|
Built 2009 - 2016
|
50 homes
$400ks
Stoneleigh Woods at Carme..., Carmel, NY
Resale Only
|
55+ age-restricted
|
Built 2012 - 2017
|
68 homes
$800ks
- $1Ms
The Vineyards at Mount Si..., Mount Sinai, NY
New Construction
|
55+ age-restricted
|
Built 2020 - present
|
91 homes
$400ks
RiverBend Estates, Oxford, CT
New and Resale
|
55+ age-restricted
|
Built 2012 - present
|
25 homes
Download the Ultimate 55+ Homebuying Guide
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$200ks
- $300ks
Oak Meadow Estates, Torrington, CT
New and Resale
|
55+ age-restricted
|
Built 2013 - present
|
31 homes
$500ks
- $600ks
The Seasons at Plainview, Plainview, NY
Resale Only
|
55+ age-restricted
|
Built 2006 - 2007
|
134 homes
$400ks
- $600ks
The Seasons at East Meado..., East Meadow, NY
Resale Only
|
55+ age-restricted
|
Built 2009 - 2012
|
404 homes
$400ks
- $500ks
The Pines at Bohemia, Bohemia, NY
New Construction
|
55+ age-restricted
|
Built 2019 - present
|
20 homes
$300ks
- $400ks
Long Hill Village, Trumbull, CT
Resale Only
|
55+ age-restricted
|
Built 1997 - 1999
|
71 homes
$200ks
- $300ks
Gloria Commons, Milford, CT
Resale Only
|
55+ age-restricted
|
Built 2007 - 2015
|
50 homes
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$600ks
- $700ks
The Polo Club at Islandia, Islandia, NY
New Construction
|
55+ age-restricted
|
Built 2019 - present
|
72 homes
$200ks
Boulder Brook, Prospect, CT
Resale Only
|
55+ age-restricted
|
Built 2004 - 2006
|
35 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
$800ks
- $1Ms
Village Vistas, Port Jefferson, NY
Resale Only
|
55+ age-restricted
|
Built 2013 - 2017
|
43 homes
Download the Ultimate 55+ Homebuying Guide
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$500ks
- $600ks
Setauket Meadows, Setauket, NY
Resale Only
|
55+ age-restricted
|
Built 2005 - 2007
|
150 homes
<$100k
The Atrium of Portland, Portland, CT
Resale Only
|
55+ age-restricted
|
Built 2004 - 2004
|
56 homes
$500ks
Regency at Wappinger, Wappingers Falls, NY
Resale Only
|
55+ age-restricted
|
Built 2014 - 2020
|
225 homes
$500ks
- $800ks
Fieldstone Village, Orange, CT
Resale Only
|
55+ age-restricted
|
Built 2010 - 2018
|
142 homes
$500ks
Breton Hills, Glen Cove, NY
New Construction
|
55+ age-restricted
|
Built 2019 - present
|
72 homes
$500ks
- $600ks
Autumn Estates, Farmington, CT
Resale Only
|
55+ age-restricted
|
Built 2011 - 2017
|
30 homes
$200ks
- $400ks
Bartlett Hollow, Middletown, CT
New Construction
|
55+ age-restricted
|
Built 2015 - present
|
25 homes
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$400ks
- $700ks
77 Sunset Lane, Ridgefield, CT
Resale Only
|
55+ age-restricted
|
Built 2016 - 2018
|
54 homes
$500ks
- $700ks
The Powder Forest Homes, Simsbury, CT
Resale Only
|
55+ age-restricted
|
Built 2006 - 2016
|
182 homes
$500ks
- $700ks
Glassbury Court at Hunter..., Cortlandt, NY
Resale Only
|
55+ age-restricted
|
Built 2007 - 2014
|
64 homes
Download the Ultimate 55+ Homebuying Guide
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$500ks
- $600ks
Wolfe Landing, Clarkstown, NY
Resale Only
|
55+ age-restricted
|
Built 2015 - 2016
|
43 homes
$500ks
- $600ks
Eden Park, Clarkstown, NY
Resale Only
|
55+ age-restricted
|
Built 2011 - 2011
|
34 homes
$200ks
- $400ks
The Views at Pomona, Pomona, NY
Resale Only
|
55+ age-restricted
|
Built 2011 - 2011
|
56 homes
$600ks
- $800ks
Stratford Park, Melville, NY
Resale Only
|
55+ age-restricted
|
Built 2011 - 2013
|
36 homes
$300ks
- $400ks
Bartlett Hill, Portland, CT
Resale Only
|
55+ age-restricted
|
Built 2005 - 2011
|
82 homes
$400ks
Baldwin Station, Milford, CT
Resale Only
|
55+ age-restricted
|
Built 2001 - 2003
|
82 homes
$300ks
- $400ks
Newington Ridge Preserve, Newington, CT
New Construction
|
55+ age-restricted
|
Built 2014 - present
|
16 homes
5 rating (1 reviews)
![Paris Square]()
$500ks
- $700ks
Paris Square, Northvale, NJ
New and Resale
|
55+ age-restricted
|
Built 2000 - present
|
88 homes
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$600ks
The Bridges at Oxford Gre..., Oxford, CT
New Construction
|
55+ age-restricted
|
Built 2025 - present
|
99 homes
$100ks
Clockmaker's Hill, Winsted, CT
Resale Only
|
55+ age-restricted
|
Built 2005 - 2014
|
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.
Greenwood Village
![201 VILLAGE CIR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949]()
2 beds
|2 baths
|1,078 sq ft
|Condo
201 VILLAGE CIR, BROOKHAVEN, NY, 11949
Community: Greenwood Village
MLS 1050162 • Gateway to The Hamptons R E, Vivian... • Gateway to The Hamptons R E
Greenwood Village
![105 W VILLAGE CIR 105, BROOKHAVEN, NY, 1..., Brookhaven, NY 11949]()
2 beds
|2 baths
|1,130 sq ft
|Condo
105 W VILLAGE CIR 105, BROOKHAVEN, NY, 1...
Community: Greenwood Village
MLS 1029061 • Gateway to The Hamptons R E, Janet ... • Gateway to The Hamptons R E
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
Fairfield at St. James
![1102 GOTHAM PATH, SMITHTOWN, NY, 11780, Smithtown, NY 11780]()
3 beds
|3 baths
|1,601 sq ft
|Condo
1102 GOTHAM PATH, SMITHTOWN, NY, 11780
Community: Fairfield at St. James
MLS 1047276 • BH&G R E Realty Connect, Lanette Hi... • BH&G R E Realty Connect
New
Leisure Knoll
![257 EDINBURGH DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961]()
2 beds
|2 baths
|1,000 sq ft
|Condo
257 EDINBURGH DR, BROOKHAVEN, NY, 11961
Community: Leisure Knoll
MLS 1055365 • Coldwell Banker American Homes, Joy... • Coldwell Banker American Homes
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New
Beckley Farms
![91 SCENIC DR 91, BERLIN, CT, 06037, Berlin, CT 06037]()
MLS 24210010 • Century 21 AllPoints Realty, Mark ... • Century 21 AllPoints Realty
New
Foxwood Village
![1407 MIDDLE RD 45, RIVERHEAD, NY, 11933, Riverhead, NY 11933]()
2 beds
|2 baths
|1,100 sq ft
|House
1407 MIDDLE RD 45, RIVERHEAD, NY, 11933
Community: Foxwood Village
MLS 1053923 • Frontline Realty Group LLC, Lindsey... • Frontline Realty Group LLC
New
Heritage Village
![162 HERITAGE VLG D, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,076 sq ft
|Condo
162 HERITAGE VLG D, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24208530 • Keller Williams Realty, Gabby Addi... • Keller Williams Realty
New
Woodridge Strathmore Terrace
![55 STANDISH DR, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766]()
2 beds
|2 baths
|1,501 sq ft
|House
55 STANDISH DR, BROOKHAVEN, NY, 11766
Community: Woodridge Strathmore Terrace
MLS 1054180 • Long Island Homes & Horse Prop, Car... • Long Island Homes & Horse Prop
New
Greenwood Village
![33A LIMETREE DR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949]()
1 beds
|1 baths
|460 sq ft
|Condo
33A LIMETREE DR, BROOKHAVEN, NY, 11949
Community: Greenwood Village
MLS 1055442 • Dream Select Realty Corp, Altiman H... • Dream Select Realty Corp
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]()
3 beds
|3 baths
|1,730 sq ft
|Condo
52102 BEECH TREE LN, OYSTER BAY, NY, 118...
Community: Country Pointe Plainview
MLS 1055418 • Douglas Elliman Real Estate, Ronni ... • Douglas Elliman Real Estate
New
Heritage Hills
![823 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589]()
2 beds
|3 baths
|1,531 sq ft
|Condo
823 HERITAGE HLS A, SOMERS, NY, 10589
Community: Heritage Hills
MLS 1055161 • Houlihan Lawrence Inc., Teresa Chan... • Houlihan Lawrence Inc.
New
Heritage Village
![397 KRUEGER CIR A, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
3 beds
|2 baths
|1,716 sq ft
|Condo
397 KRUEGER CIR A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24209719 • Berkshire Hathaway NE Prop., Ginny... • Berkshire Hathaway NE Prop.
New
The Village at Oxford Greens
![1073 AUGUSTA DR 1073, OXFORD, CT, 06478, Oxford, CT 06478]()
2 beds
|3 baths
|2,232 sq ft
|Condo
1073 AUGUSTA DR 1073, OXFORD, CT, 06478
Community: The Village at Oxford Greens
MLS 24209721 • Real Estate Two, Karen Berwick • Real Estate Two
New
Fairview at Oxford Greens
![1073 AUGUSTA DR 1073, OXFORD, CT, 06478, Oxford, CT 06478]()
2 beds
|3 baths
|2,232 sq ft
|Condo
1073 AUGUSTA DR 1073, OXFORD, CT, 06478
Community: Fairview at Oxford Greens
MLS 24209721 • Real Estate Two, Karen Berwick • Real Estate Two
New
Oronoque Village
![55 BLACK HAWK LN B, STRATFORD, CT, 06614, Stratford, CT 06614]()
2 beds
|3 baths
|1,360 sq ft
|Condo
55 BLACK HAWK LN B, STRATFORD, CT, 06614
Community: Oronoque Village
MLS 24209592 • Coldwell Banker Realty, Mary Kelle... • Coldwell Banker Realty
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New
Meadowbrook Pointe Links & Spa
![38 AUGUSTA DR, BROOKHAVEN, NY, 11763, Brookhaven, NY 11763]()
2 beds
|3 baths
|1,440 sq ft
|Condo
38 AUGUSTA DR, BROOKHAVEN, NY, 11763
Community: Meadowbrook Pointe Links & Spa
MLS 1055265 • Signature Premier Properties, Matth... • Signature Premier Properties
New
Oronoque Village
![209 ACORN LN B, STRATFORD, CT, 06614, Stratford, CT 06614]()
2 beds
|3 baths
|1,438 sq ft
|Condo
209 ACORN LN B, STRATFORD, CT, 06614
Community: Oronoque Village
MLS 24208698 • Coldwell Banker Realty, Mary Kelle... • Coldwell Banker Realty
New
Spring Lake Village
![764 KETTLE PATH 764, SOUTHINGTON, CT, 06..., Southington, CT 06489]()
2 beds
|2 baths
|1,445 sq ft
|Condo
764 KETTLE PATH 764, SOUTHINGTON, CT, 06...
Community: Spring Lake Village
MLS 24209115 • Century 21 AllPoints Realty, Betty... • Century 21 AllPoints Realty
New
Heritage Village
![633 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
2 beds
|2 baths
|1,432 sq ft
|Condo
633 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24208641 • Berkshire Hathaway NE Prop., Bonni... • Berkshire Hathaway NE Prop.
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]()
2 beds
|2 baths
|1,432 sq ft
|Condo
626 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24209764 • Coldwell Banker Realty, Kary Apano... • Coldwell Banker Realty
New
Windmill Gate
![27 KATHLEEN DR, ISLIP, NY, 11769, Islip, NY 11769]()
MLS 1054955 • HomeSmart Dynamic Realty, Sean Conr... • HomeSmart Dynamic Realty
New
Heritage Hills
![593 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589]()
3 beds
|2 baths
|1,905 sq ft
|Condo
593 HERITAGE HLS B, SOMERS, NY, 10589
Community: Heritage Hills
MLS 1053566 • Houlihan Lawrence Inc., Franklin J.... • Houlihan Lawrence Inc.
New
The Seasons at Plainview
![53 AUTUMN DR, OYSTER BAY, NY, 11803, Oyster Bay, NY 11803]()
2 beds
|2 baths
|1,379 sq ft
|Condo
53 AUTUMN DR, OYSTER BAY, NY, 11803
Community: The Seasons at Plainview
MLS 1054684 • ZI Realty LLC, Michelle Zhao CBR • ZI Realty LLC
New
Parkview Crossings at Woodbridge
![323 REGENCY PL, WOODBRIDGE PROPER, NJ, 0..., Woodbridge Proper, NJ 07095]()
2 beds
|2 baths
|1,605 sq ft
|Condo
323 REGENCY PL, WOODBRIDGE PROPER, NJ, 0...
Community: Parkview Crossings at Woodbridge
MLS 2705100R • MJ HOMES REALTY, LLC., BHUPINDERPA... • MJ HOMES REALTY, LLC.
New
Heritage Hills
![154 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589]()
2 beds
|2 baths
|1,396 sq ft
|Condo
154 HERITAGE HLS B, SOMERS, NY, 10589
Community: Heritage Hills
MLS 1048278 • William Raveis-New York LLC, Jared ... • William Raveis-New York LLC
New
The Village at Buckingham
![3 CAVENDISH PL 3, AVON, CT, 06001, Avon, CT 06001]()
3 beds
|3 baths
|2,730 sq ft
3 CAVENDISH PL 3, AVON, CT, 06001
Community: The Village at Buckingham
MLS 24209565 • Berkshire Hathaway NE Prop., Fern ... • Berkshire Hathaway NE Prop.
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New
Fairfield at St. James
![705 ALDEN CT, SMITHTOWN, NY, 11780, Smithtown, NY 11780]()
2 beds
|2 baths
|954 sq ft
|Condo
705 ALDEN CT, SMITHTOWN, NY, 11780
Community: Fairfield at St. James
MLS 1054169 • Signature Premier Properties, Steph... • Signature Premier Properties
New
The Savannah
![111 PROSPECT ST 4C, WESTFIELD TOWN, NJ, ..., Westfield Town, NJ 07090]()
MLS 4054877 • COLDWELL BANKER REALTY, COLDWELL BA... • COLDWELL BANKER REALTY
New
Jefferson Village
![45 JEFFERSON OVAL G, YORKTOWN, NY, 10598, Yorktown, NY 10598]()
2 beds
|2 baths
|1,100 sq ft
|Condo
45 JEFFERSON OVAL G, YORKTOWN, NY, 10598
Community: Jefferson Village
MLS 1054519 • Coldwell Banker Realty, Denise A. G... • Coldwell Banker Realty
Download the Ultimate 55+ Homebuying Guide
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New
Heritage Hills
![446 HERITAGE HLS D, SOMERS, NY, 10589, Somers, NY 10589]()
2 beds
|2 baths
|1,559 sq ft
|Condo
446 HERITAGE HLS D, SOMERS, NY, 10589
Community: Heritage Hills
MLS 1041193 • Houlihan Lawrence Inc., Donna T. Gr... • Houlihan Lawrence Inc.
New
Rivington
![11 MERCY ST 11, DANBURY, CT, 06810, Danbury, CT 06810]()
MLS 24208646 • Keller Williams Realty Partner, Ce... • Keller Williams Realty Partner
New
Jefferson Village
![18L HASTINGS CT, YORKTOWN, NY, 10598, Yorktown, NY 10598]()
2 beds
|1 baths
|1,000 sq ft
|Condo
18L HASTINGS CT, YORKTOWN, NY, 10598
Community: Jefferson Village
MLS 1054688 • Ortiz Home Selling Team LLC, Santo ... • Ortiz Home Selling Team LLC
New
Heritage Village
![149 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488]()
1 beds
|1 baths
|928 sq ft
|Condo
149 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
MLS 24209196 • Coldwell Banker Realty, Maryanne B... • Coldwell Banker Realty
New
The Greens at Half Hollow
![119 MADEIRA BLVD, HUNTINGTON, NY, 11747, Huntington, NY 11747]()
3 beds
|3 baths
|2,700 sq ft
|Condo
119 MADEIRA BLVD, HUNTINGTON, NY, 11747
Community: The Greens at Half Hollow
MLS 1039592 • Howard Hanna Coach, Betty Anne Smit... • Howard Hanna Coach
New
Sunken Pond Estates
![3704 AMEN COR, RIVERHEAD, NY, 11901, Riverhead, NY 11901]()
2 beds
|3 baths
|1,350 sq ft
|Condo
3704 AMEN COR, RIVERHEAD, NY, 11901
Community: Sunken Pond Estates
MLS 1052244 • Century 21 Albertson Realty, Thomas... • Century 21 Albertson Realty
New
Leisure Village
![395 WOODBRIDGE DR E, BROOKHAVEN, NY, 119..., Brookhaven, NY 11961]()
2 beds
|1 baths
|875 sq ft
|Condo
395 WOODBRIDGE DR E, BROOKHAVEN, NY, 119...
Community: Leisure Village
MLS 1051844 • Howard Hanna Coach, Stephen L. Demo... • Howard Hanna Coach
New
Plymouth Estates at Mount Sinai
![240 IRA RD, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766]()
2 beds
|2 baths
|1,396 sq ft
|Condo
240 IRA RD, BROOKHAVEN, NY, 11766
Community: Plymouth Estates at Mount Sinai
MLS 1053961 • Serhant East End LLC, Matthew J. Mi... • Serhant East End LLC
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New
Overlook
![2011 SUMMIT LOOP 86, CARMEL, NY, 10512, Carmel, NY 10512]()
MLS 1054199 • Toll Brothers Real Estate Inc., Tho... • Toll Brothers Real Estate Inc.
New
Overlook
![2037 SUMMIT LOOP 92, CARMEL, NY, 10512, Carmel, NY 10512]()
MLS 1054193 • Toll Brothers Real Estate Inc., Tho... • Toll Brothers Real Estate Inc.
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
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?
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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: Sep 28, 2026.
This application does not include information on all of the properties available for sale at this time.
