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New Fairfield, CT 55+ active adult communities & homes for sale - Page 4

158 communities near New Fairfield

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Stratford Park
$600ks - $800ks
Stratford Park, Melville, NY
Resale Only | 55+ age-restricted | Built 2011 - 2013 | 36 homes
Four Seasons at Ridgemont
$800ks - $1Ms
Four Seasons at Ridgemont, Montvale, NJ
Resale Only | 55+ age-restricted | Built 2011 - 2014 | 108 homes
Winthrop Court
$400ks - $600ks
Winthrop Court, Clifton, NJ
Resale Only | 55+ age-restricted | Built 2000 - 2010 | 270 homes
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
Four Seasons at Cedar Gro...
$400ks - $600ks
Four Seasons at Cedar Gro..., Cedar Grove, NJ
Resale Only | 55+ age-restricted | Built 2000 - 2005 | 156 homes
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Questions? Call us: (959) 214-2391
Four Seasons at Wayne
$300ks - $400ks
Four Seasons at Wayne, Wayne, NJ
Resale Only | 55+ age-restricted | Built 1999 - 2001 | 230 homes
Enclave at Shackamaxon
$1Ms
Enclave at Shackamaxon, Scotch Plains, NJ
Resale Only | 55+ age-restricted | Built 2016 - 2018 | 56 homes
Four Seasons at Troy Hill...
$500ks
Four Seasons at Troy Hill..., Parsippany, NJ
Resale Only | 55+ age-restricted | Built 2007 - 2007 | 46 homes
The Pointe
$300ks - $600ks
The Pointe, Livingston, NJ
Resale Only | 55+ age-restricted | Built 2004 - 2007 | 180 homes
Sterling Mist
$500ks - $600ks
Sterling Mist, Parsippany, NJ
Resale Only | 55+ age-restricted | Built 2002 - 2006 | 28 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.
Briar Hill
$600ks - $700ks
Briar Hill, Montville Township, NJ
Resale Only | 55+ age-restricted | Built 2012 - 2015 | 28 homes
Campagna
$300ks - $400ks
Campagna, Montville Township, NJ
Resale Only | 55+ age-restricted | Built 1980 - 1986 | 136 homes
Whitfield
$600ks - $700ks
Whitfield, Metuchen, NJ
Resale Only | 55+ age-restricted | 17 homes
The Savannah
$600ks - $700ks
The Savannah, Westfield, NJ
Resale Only | 55+ age-restricted | Built 2009 - 2009 | 35 homes
The Pointe at Garwood
$600ks - $700ks
The Pointe at Garwood, Garwood, NJ
Resale Only | 55+ age-restricted | Built 2006 - 2007 | 44 homes
Brooklake Park
$400ks
Brooklake Park, Florham Park, NJ
Resale Only | 55+ age-restricted | Built 2008 - 2008 | 25 homes
Want to learn more about 55+ communities in New Fairfield? 55places can help!
Questions? Call us: (959) 214-2391
Eagle Ridge at East Hanov...
$200ks - $300ks
Eagle Ridge at East Hanov..., East Hanover, NJ
Resale Only | 55+ age-restricted | Built 1992 - 1993 | 50 homes
Granite Woods
$600ks - $700ks
Granite Woods, Middlebury, CT
New Construction | 55+ age-restricted | Built 2020 - present | 24 homes
1 rating (2 reviews) Knoll Edge
$600ks - $700ks
Knoll Edge, Boonton, NJ
New Construction | 55+ age-restricted | Built 2024 - present | 16 homes
The Bridges at Oxford Gre...
$600ks
The Bridges at Oxford Gre..., Oxford, CT
New Construction | 55+ age-restricted | Built 2025 - present | 99 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 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
Northgate at Florham Park
$900ks - $1Ms
Northgate at Florham Park, Florham Park, NJ
Resale Only | 55+ age-restricted | Built 2008 - 2009 | 33 homes
5 rating (2 reviews) Benson Woods
$400ks - $600ks
Benson Woods, Middlebury, CT
New and Resale | 55+ age-restricted | Built 2004 - present | 79 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
Sonoma Woods
$300ks
Sonoma Woods, Middletown, CT
Resale Only | 55+ age-restricted | Built 2005 - 2015 | 68 homes
Want to learn more about 55+ communities in New Fairfield? 55places can help!
Questions? Call us: (959) 214-2391
Fieldstone Village
$500ks - $800ks
Fieldstone Village, Orange, CT
Resale Only | 55+ age-restricted | Built 2010 - 2018 | 142 homes
Pond Spring Village
$300ks
Pond Spring Village, Beacon Falls, CT
New and Resale | 55+ age-restricted | Built 2005 - present | 92 homes
Meadow Brook Estates
$300ks - $400ks
Meadow Brook Estates, Oxford, CT
Resale Only | 55+ age-restricted | Built 2003 - 2020 | 246 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.
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
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
Newington Ridge Preserve
$300ks - $400ks
Newington Ridge Preserve, Newington, CT
New Construction | 55+ age-restricted | Built 2014 - present | 16 homes
The Powder Forest Homes
$500ks - $700ks
The Powder Forest Homes, Simsbury, CT
Resale Only | 55+ age-restricted | Built 2006 - 2016 | 182 homes
5 rating (3 reviews) Founders Ridge
$300ks - $400ks
Founders Ridge, Middletown, CT
New Construction | 55+ age-restricted | Built 2017 - present | 75 homes
77 Sunset Lane
$400ks - $700ks
77 Sunset Lane, Ridgefield, CT
Resale Only | 55+ age-restricted | Built 2016 - 2018 | 54 homes
Want to learn more about 55+ communities in New Fairfield? 55places can help!
Questions? Call us: (959) 214-2391
New Winthrop Court 7101 RAVENSCROFT RD, CLIFTON CITY, NJ, 0..., Clifton City, NJ 07013
$595,000

2 beds

|

2 baths

|

1,875 sq ft

7101 RAVENSCROFT RD, CLIFTON CITY, NJ, 0...
Community: Winthrop Court
New The Villages at Mount Sinai Park 10 LOUDEN LOOP, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766
$749,000

3 beds

|

3 baths

|

2,500 sq ft

|

House

10 LOUDEN LOOP, BROOKHAVEN, NY, 11766
New Four Seasons at Great Notch Spa and Club 3 PEBBLE RD D1, WOODLAND PARK, NJ, 07424, Woodland Park, NJ 07424
$649,000

2 beds

|

2 baths

|

Condo

3 PEBBLE RD D1, WOODLAND PARK, NJ, 07424
New Leisure Knoll 225 KINGSTON DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$540,000

2 beds

|

2 baths

|

1,094 sq ft

|

House

225 KINGSTON DR, BROOKHAVEN, NY, 11961
Community: Leisure Knoll
New The Villages at Mount Sinai Park 54 LOUDEN LOOP, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766
$929,000

3 beds

|

3 baths

|

2,816 sq ft

|

House

54 LOUDEN LOOP, BROOKHAVEN, NY, 11766
Want to learn more about 55+ communities in New Fairfield? 55places can help!
Questions? Call us: (959) 214-2391
New Glassbury Court at Hunterbrook 1803 SUMMERHILL CT, YORKTOWN, NY, 10567, Yorktown, NY 10567
$728,000

2 beds

|

3 baths

|

1,797 sq ft

|

Condo

1803 SUMMERHILL CT, YORKTOWN, NY, 10567
New Country Pointe Plainview 12103 ASPENWOOD DR, OYSTER BAY, NY, 1180..., Oyster Bay, NY 11803
$1,075,000

2 beds

|

2 baths

|

1,335 sq ft

|

Condo

12103 ASPENWOOD DR, OYSTER BAY, NY, 1180...
New The Greens at Half Hollow 385 ALTESSA BLVD, HUNTINGTON, NY, 11747, Huntington, NY 11747
$1,299,999

3 beds

|

3 baths

|

3,060 sq ft

|

Condo

385 ALTESSA BLVD, HUNTINGTON, NY, 11747
New The Villages at Mount Sinai Park 68 LOUDEN LOOP, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766
$839,999

2 beds

|

2 baths

|

1,736 sq ft

|

House

68 LOUDEN LOOP, BROOKHAVEN, NY, 11766
New Village Estates 12 SARAH CT, BABYLON, NY, 11701, Babylon, NY 11701
$579,000

2 beds

|

2 baths

|

1,243 sq ft

|

Condo

12 SARAH CT, BABYLON, NY, 11701
Community: Village Estates
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 Snug Harbor 66 HARBOR N, BABYLON, NY, 11701, Babylon, NY 11701
$589,500

1 beds

|

1 baths

|

727 sq ft

|

Condo

66 HARBOR N, BABYLON, NY, 11701
Community: Snug Harbor
New Saddle Lakes 156 SCENIC LAKE DR, RIVERHEAD, NY, 11901, Riverhead, NY 11901
$629,000

3 beds

|

3 baths

|

1,837 sq ft

|

Condo

156 SCENIC LAKE DR, RIVERHEAD, NY, 11901
Community: Saddle Lakes
New Encore at Lake Grove 8 SYMPHONY DR, BROOKHAVEN, NY, 11755, Brookhaven, NY 11755
$634,000

2 beds

|

3 baths

|

1,378 sq ft

|

Condo

8 SYMPHONY DR, BROOKHAVEN, NY, 11755
New Leisure Knoll 257 EDINBURGH DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$399,000

2 beds

|

2 baths

|

1,000 sq ft

|

Condo

257 EDINBURGH DR, BROOKHAVEN, NY, 11961
Community: Leisure Knoll
New The Village at Oxford Greens 505 TRADITIONS CT 505, OXFORD, CT, 06478, Oxford, CT 06478
$775,000

3 beds

|

3 baths

|

2,652 sq ft

|

Condo

505 TRADITIONS CT 505, OXFORD, CT, 06478
New Stoneleigh Woods at Riverhead 47 STONELEIGH DR, RIVERHEAD, NY, 11901, Riverhead, NY 11901
$699,000

2 beds

|

3 baths

|

1,942 sq ft

|

Condo

47 STONELEIGH DR, RIVERHEAD, NY, 11901
Want to learn more about 55+ communities in New Fairfield? 55places can help!
Questions? Call us: (959) 214-2391
New Heritage Hills 415 HERITAGE HLS C, SOMERS, NY, 10589, Somers, NY 10589
$875,000

3 beds

|

2 baths

|

1,909 sq ft

|

Condo

415 HERITAGE HLS C, SOMERS, NY, 10589
Community: Heritage Hills
New Meadowbrook Pointe Athletic Club & Spa 401 PACING WAY 4101, HEMPSTEAD, NY, 1159..., Hempstead, NY 11590
$875,000

2 beds

|

2 baths

|

1,353 sq ft

|

Condo

401 PACING WAY 4101, HEMPSTEAD, NY, 1159...
New Baldwin Station 69 JASMINE CIR 69, MILFORD, CT, 06461, Milford, CT 06461
$820,000

2 beds

|

3 baths

|

2,820 sq ft

|

Condo

69 JASMINE CIR 69, MILFORD, CT, 06461
Community: Baldwin Station
New Westhampton Pines 49 SAMANTHA CIR 49, SOUTHAMPTON, NY, 119..., Southampton, NY 11977
$999,000

2 beds

|

2 baths

|

1,944 sq ft

|

Condo

49 SAMANTHA CIR 49, SOUTHAMPTON, NY, 119...
Community: Westhampton Pines
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 Overlook 2084 SUMMIT LOOP 77, CARMEL, NY, 10512, Carmel, NY 10512
$779,000

2 beds

|

3 baths

|

2,214 sq ft

|

Condo

2084 SUMMIT LOOP 77, CARMEL, NY, 10512
Community: Overlook
New Stoneleigh Woods at Riverhead 1302 BALTUSROL BLVD, RIVERHEAD, NY, 1190..., Riverhead, NY 11901
$515,000

2 beds

|

3 baths

|

1,350 sq ft

|

Condo

1302 BALTUSROL BLVD, RIVERHEAD, NY, 1190...
New Oronoque Village 664 OSAGE LN A, STRATFORD, CT, 06614, Stratford, CT 06614
$499,000

1 beds

|

3 baths

|

1,438 sq ft

664 OSAGE LN A, STRATFORD, CT, 06614
Community: Oronoque Village
New The Greens at Half Hollow 398 ALTESSA BLVD, HUNTINGTON, NY, 11747, Huntington, NY 11747
$1,599,999

2 beds

|

2 baths

|

2,525 sq ft

|

Condo

398 ALTESSA BLVD, HUNTINGTON, NY, 11747
New Oronoque Village 543 N TRL A, STRATFORD, CT, 06614, Stratford, CT 06614
$585,000

1 beds

|

3 baths

|

1,426 sq ft

|

Condo

543 N TRL A, STRATFORD, CT, 06614
Community: Oronoque Village
New Encore at Lake Grove 176 SYMPHONY DR, BROOKHAVEN, NY, 11755, Brookhaven, NY 11755
$609,000

2 beds

|

2 baths

|

1,429 sq ft

|

Condo

176 SYMPHONY DR, BROOKHAVEN, NY, 11755
New Regency at Prospect 196 SYCAMORE DR 196, PROSPECT, CT, 06712, Prospect, CT 06712
$307,127

3 beds

|

2 baths

|

1,500 sq ft

|

Condo

196 SYCAMORE DR 196, PROSPECT, CT, 06712
Community: Regency at Prospect
Want to learn more about 55+ communities in New Fairfield? 55places can help!
Questions? Call us: (959) 214-2391
New The Seasons at Elwood 244 FALL CT, HUNTINGTON, NY, 11731, Huntington, NY 11731
$1,375,000

2 beds

|

3 baths

|

2,256 sq ft

|

Condo

244 FALL CT, HUNTINGTON, NY, 11731
Heritage Village 916 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$390,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

916 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Oronoque Village 96 SEMINOLE LN A, STRATFORD, CT, 06614, Stratford, CT 06614
$469,000

2 beds

|

3 baths

|

1,438 sq ft

|

Condo

96 SEMINOLE LN A, STRATFORD, CT, 06614
Community: Oronoque 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.
Bear's Cove 33 WINDSOR LN, RAMSEY, NJ, 07446, Ramsey, NJ 07446
$1,250,000

3 beds

|

4 baths

|

Townhouse

33 WINDSOR LN, RAMSEY, NJ, 07446
Community: Bear's Cove
Leisure Knoll 1 AVON CT, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$489,999

2 beds

|

2 baths

|

1,070 sq ft

|

Condo

1 AVON CT, BROOKHAVEN, NY, 11961
Community: Leisure Knoll
Snug Harbor 47 HARBOR N, BABYLON, NY, 11701, Babylon, NY 11701
$549,999

1 beds

|

1 baths

|

806 sq ft

|

Condo

47 HARBOR N, BABYLON, NY, 11701
Community: Snug Harbor
Leisure Village 54 AYLESBURY CT B, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$349,000

2 beds

|

1 baths

|

1,085 sq ft

|

Condo

54 AYLESBURY CT B, BROOKHAVEN, NY, 11961
Community: Leisure Village
Setauket Meadows 100 COVE LN 100, BROOKHAVEN, NY, 11733, Brookhaven, NY 11733
$769,000

2 beds

|

3 baths

|

1,820 sq ft

|

Condo

100 COVE LN 100, BROOKHAVEN, NY, 11733
Community: Setauket Meadows
Oronoque Village 315 NAVAJO LN A, STRATFORD, CT, 06614, Stratford, CT 06614
$549,000

2 beds

|

3 baths

|

1,434 sq ft

|

Condo

315 NAVAJO LN A, STRATFORD, CT, 06614
Community: Oronoque Village
Leisure Village 395 WOODBRIDGE DR 395E, BROOKHAVEN, NY, ..., Brookhaven, NY 11961
$299,000

2 beds

|

1 baths

|

875 sq ft

|

Condo

395 WOODBRIDGE DR 395E, BROOKHAVEN, NY, ...
Community: Leisure Village
Heritage Village 14 HERITAGE CIR B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$269,000

2 beds

|

2 baths

|

1,000 sq ft

|

Condo

14 HERITAGE CIR 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
Bald Eagle Commons 1302 RICHMOND RD 302, WEST MILFORD TWP.,..., West Milford Twp., NJ 07480
$179,900

1 beds

|

1 baths

|

655 sq ft

1302 RICHMOND RD 302, WEST MILFORD TWP.,...
Community: Bald Eagle Commons
The Manors at The Colony Preserve 17 GREENTREE CT, BROOKHAVEN, NY, 11967, Brookhaven, NY 11967
$559,000

2 beds

|

2 baths

|

1,557 sq ft

|

Condo

17 GREENTREE CT, BROOKHAVEN, NY, 11967
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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