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New Fairfield, CT 55+ active adult communities & homes for sale - Page 2

157 communities near New Fairfield

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Evergreen
$400ks - $500ks
Evergreen, Cromwell, CT
New and Resale | 55+ age-restricted | Built 2005 - present | 52 homes
Regency at Wappinger
$500ks
Regency at Wappinger, Wappingers Falls, NY
Resale Only | 55+ age-restricted | Built 2014 - 2020 | 225 homes
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) Paris Square
$600ks - $900ks
Paris Square, Northvale, NJ
New and Resale | 55+ age-restricted | Built 2000 - present | 88 homes
Country Village Estates
$300ks
Country Village Estates, Coram, NY
Resale Only | 55+ age-restricted | Built 1993 - 2001 | 195 homes
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Glassbury Court at Hunter...
$500ks - $700ks
Glassbury Court at Hunter..., Cortlandt, NY
Resale Only | 55+ age-restricted | Built 2007 - 2014 | 64 homes
Stoneleigh Woods at River...
$500ks
Stoneleigh Woods at River..., Riverhead, NY
Resale Only | 55+ age-restricted | Built 2007 - 2016 | 176 homes
Oak Meadow Estates
$200ks - $300ks
Oak Meadow Estates, Torrington, CT
New and Resale | 55+ age-restricted | Built 2013 - present | 31 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
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.
4.6 rating (9 reviews) Meadowbrook Pointe Links ...
$300ks - $700ks
Meadowbrook Pointe Links ..., Medford, NY
New and Resale | 55+ age-restricted | Built 2010 - present | 280 homes
Read the Ultimate 55+ Rental Guide Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
Liberty at Newtown
$300ks - $400ks
Liberty at Newtown, Newtown, CT
Resale Only | 55+ age-restricted | Built 2003 - 2007 | 96 homes
Apple Ridge
$500ks - $1Ms
Apple Ridge, Mahwah, NJ
Resale Only | Age-targeted | Built 1977 - 1991 | 276 homes
Meadow Brook Estates
$300ks - $400ks
Meadow Brook Estates, Oxford, CT
Resale Only | 55+ age-restricted | Built 2003 - 2020 | 246 homes
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4.9 rating (14 reviews) Chatfield Farms
$400ks - $700ks
Chatfield Farms, Beacon Falls, CT
New Construction | 55+ age-restricted | Built 2014 - present | 231 homes
The Seasons at East North...
$700ks
The Seasons at East North..., East Northport, NY
New Construction | 55+ age-restricted | Built 2023 - present | 190 homes
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The Bel Aire at East Mead...
$300ks - $400ks
The Bel Aire at East Mead..., East Meadow, NY
Resale Only | 55+ age-restricted | Built 2004 - 2005 | 95 homes
Baldwin Station
$400ks
Baldwin Station, Milford, CT
Resale Only | 55+ age-restricted | Built 2001 - 2003 | 82 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.
Knickerbocker Bay Club
$700ks - $3Ms
Knickerbocker Bay Club, Port Washington, NY
New and Resale | 55+ age-restricted | Built 2014 - present | 32 homes
HarborView
$600ks - $800ks
HarborView, Port Washington, NY
Resale Only | 55+ age-restricted | Built 2002 - 2004 | 270 homes
The Residences at Butterf...
$500ks - $600ks
The Residences at Butterf..., Cold Spring, NY
Resale Only | 55+ age-restricted | Built 2018 - 2023 | 49 homes
Read the Ultimate 55+ Rental Guide Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
Wildflowers at Wallkill
$400ks - $500ks
Wildflowers at Wallkill, Middletown, NY
Resale Only | 55+ age-restricted | Built 2006 - 2017 | 283 homes
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Glassbury Court at Cold S...
$500ks - $700ks
Glassbury Court at Cold S..., Cold Spring, NY
Resale Only | 55+ age-restricted | Built 2009 - 2014 | 90 homes
Granite Woods
$600ks - $700ks
Granite Woods, Middlebury, CT
New Construction | 55+ age-restricted | Built 2020 - present | 24 homes
Villas at Seminary Hill
$200ks - $300ks
Villas at Seminary Hill, Carmel, NY
New Construction | 55+ age-restricted | Built 2018 - present | 50 homes
Snug Harbor
$600ks - $700ks
Snug Harbor, Amityville, NY
Resale Only | 55+ age-restricted | Built 1970 - 1974 | 176 homes
Want to learn more about 55+ rental communities in New Fairfield? 55places can help!
Questions? Call us: (959) 214-2391
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.
Strathmore Gate East
$300ks
Strathmore Gate East, Coram, NY
Resale Only | 55+ age-restricted | Built 1970 - 1975 | 174 homes
Bartlett Hill
$300ks - $400ks
Bartlett Hill, Portland, CT
Resale Only | 55+ age-restricted | Built 2005 - 2011 | 82 homes
The Pointe at Garwood
$600ks - $700ks
The Pointe at Garwood, Garwood, NJ
Resale Only | 55+ age-restricted | Built 2006 - 2007 | 44 homes
Breton Hills
$500ks
Breton Hills, Glen Cove, NY
New Construction | 55+ age-restricted | Built 2019 - present | 72 homes
The Village at Buckingham
$300ks - $400ks
The Village at Buckingham, Avon, CT
Resale Only | 55+ age-restricted | Built 2002 - 2006 | 56 homes
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Questions? Call us: (959) 214-2391
Read the Ultimate 55+ Rental Guide Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
Sonoma Woods
$300ks
Sonoma Woods, Middletown, CT
Resale Only | 55+ age-restricted | Built 2005 - 2015 | 68 homes
Beckley Farms
$300ks - $400ks
Beckley Farms, Berlin, CT
New and Resale | 55+ age-restricted | Built 2010 - present | 170 homes
Vineyards at Moriches
$500ks - $600ks
Vineyards at Moriches, Center Moriches, NY
Resale Only | 55+ age-restricted | Built 2008 - 2014 | 92 homes
Chimney Hill
$500ks - $700ks
Chimney Hill, Farmington, CT
Resale Only | 55+ age-restricted | Built 2006 - 2013 | 44 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.
Newington Ridge Preserve
$300ks - $400ks
Newington Ridge Preserve, Newington, CT
New Construction | 55+ age-restricted | Built 2014 - present | 16 homes
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Questions? Call us: (959) 214-2391
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
Bartlett Hollow
$200ks - $400ks
Bartlett Hollow, Middletown, CT
New Construction | 55+ age-restricted | Built 2015 - present | 25 homes
Want to learn more about 55+ communities in New Fairfield? 55places can help!
Questions? Call us: (959) 214-2391
Autumn Estates
$500ks - $600ks
Autumn Estates, Farmington, CT
Resale Only | 55+ age-restricted | Built 2011 - 2017 | 30 homes
The Atrium of Portland
<$100k
The Atrium of Portland, Portland, CT
Resale Only | 55+ age-restricted | Built 2004 - 2004 | 56 homes
New Dutchgate 203 WILLOW LN, VALLEY STREAM, NY, 11580, Valley Stream, NY 11580
$520,000

2 beds

|

2 baths

|

941 sq ft

|

Condo

203 WILLOW LN, VALLEY STREAM, NY, 11580
Community: Dutchgate
New Heritage Hills 40 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589
$633,000

2 beds

|

2 baths

|

1,139 sq ft

|

Condo

40 HERITAGE HLS A, SOMERS, NY, 10589
Community: Heritage Hills
New The Greens at Half Hollow 833 MADEIRA BLVD, HUNTINGTON, NY, 11747, Huntington, NY 11747
$699,888

2 beds

|

2 baths

|

1,150 sq ft

|

Condo

833 MADEIRA BLVD, HUNTINGTON, NY, 11747
New Meadowbrook Pointe Athletic Club & Spa 366 ROOSEVELT WAY, NORTH HEMPSTEAD, NY, ..., North Hempstead, NY 11590
$799,000

2 beds

|

2 baths

|

1,342 sq ft

|

Condo

366 ROOSEVELT WAY, NORTH HEMPSTEAD, NY, ...
New Fairfield at St. James 203 CABOT CT, SMITHTOWN, NY, 11780, Smithtown, NY 11780
$475,000

1 beds

|

1 baths

|

841 sq ft

|

Condo

203 CABOT CT, SMITHTOWN, NY, 11780
Want to learn more about 55+ communities in New Fairfield? 55places can help!
Questions? Call us: (959) 214-2391
Want to learn more about 55+ rental communities in New Fairfield? 55places can help!
Questions? Call us: (959) 214-2391
New Heritage Village 575 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$399,000

3 beds

|

2 baths

|

1,716 sq ft

|

Condo

575 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
New Breton Hills 709 BRETON WAY, GLEN COVE, NY, 11542, Glen Cove, NY 11542
$675,000

2 beds

|

2 baths

|

1,362 sq ft

|

Condo

709 BRETON WAY, GLEN COVE, NY, 11542
Community: Breton Hills
New Stratford Park 106 VICTORIA PL, HUNTINGTON, NY, 11747, Huntington, NY 11747
$888,888

3 beds

|

3 baths

|

2,100 sq ft

|

Condo

106 VICTORIA PL, HUNTINGTON, NY, 11747
Community: Stratford Park
New Bald Eagle Commons 1202 RICHMOND RD 202, WEST MILFORD TWP.,..., West Milford Twp., NJ 07480
$179,000

1 beds

|

1 baths

|

655 sq ft

1202 RICHMOND RD 202, WEST MILFORD TWP.,...
Community: Bald Eagle Commons
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 701 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$260,000

2 beds

|

2 baths

|

1,398 sq ft

|

Condo

701 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Read the Ultimate 55+ Rental Guide Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
New Leisure Village 430 FALMOUTH CT A, RIDGE, NY, 11961, Ridge, NY 11961
$369,000

2 beds

|

2 baths

|

1,200 sq ft

|

House

430 FALMOUTH CT A, RIDGE, NY, 11961
Community: Leisure Village
New Leisure Village 258 NEWCASTLE CT F, RIDGE, NY, 11961, Ridge, NY 11961
$279,000

2 beds

|

1 baths

|

875 sq ft

|

Condo

258 NEWCASTLE CT F, RIDGE, NY, 11961
Community: Leisure Village
New Oak Meadow Estates 65 OAK MEADOW LN # 65, HARWINTON, CT, 06..., Harwinton, CT 06791
$495,000

2 beds

|

4 baths

|

2,164 sq ft

|

Condo

65 OAK MEADOW LN # 65, HARWINTON, CT, 06...
Community: Oak Meadow Estates
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Questions? Call us: (959) 214-2391
New The Greens at Half Hollow 843 MADEIRA BLVD, HUNTINGTON, NY, 11747, Huntington, NY 11747
$699,000

2 beds

|

2 baths

|

1,150 sq ft

|

Condo

843 MADEIRA BLVD, HUNTINGTON, NY, 11747
New South Pond Village 81 SILO WAY 81, BLOOMFIELD, CT, 06002, Bloomfield, CT 06002
$259,999

2 beds

|

2 baths

|

1,204 sq ft

|

Condo

81 SILO WAY 81, BLOOMFIELD, CT, 06002
Community: South Pond Village
Want to learn more about 55+ rental communities in New Fairfield? 55places can help!
Questions? Call us: (959) 214-2391
New The Coves at Melville 54 MORLEY CIR, HUNTINGTON, NY, 11747, Huntington, NY 11747
$579,000

2 beds

|

2 baths

|

1,162 sq ft

|

Condo

54 MORLEY CIR, HUNTINGTON, NY, 11747
New Heritage Hills 680 HERITAGE HILL DR C, SOMERS, NY, 1058..., Somers, NY 10589
$599,000

1 beds

|

2 baths

|

1,296 sq ft

|

Condo

680 HERITAGE HILL DR C, SOMERS, NY, 1058...
Community: Heritage Hills
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 Villas at Seminary Hill 7102 PANKIN DR, CARMEL, NY, 10512, Carmel, NY 10512
$439,999

2 beds

|

2 baths

|

1,144 sq ft

|

Condo

7102 PANKIN DR, CARMEL, NY, 10512
New Leisure Knoll 304 KINGSTON CT, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$530,000

2 beds

|

2 baths

|

1,000 sq ft

|

Condo

304 KINGSTON CT, BROOKHAVEN, NY, 11961
Community: Leisure Knoll
New Heritage Hills 243 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589
$749,000

3 beds

|

2 baths

|

1,689 sq ft

|

Condo

243 HERITAGE HLS B, SOMERS, NY, 10589
Community: Heritage Hills
Read the Ultimate 55+ Rental Guide Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
Oronoque Village 133 BANNOCK LN, STRATFORD, CT, 06614, Stratford, CT 06614
$635,000

2 beds

|

3 baths

|

2,038 sq ft

|

Condo

133 BANNOCK LN, 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
Heritage Village 914 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$299,900

2 beds

|

2 baths

|

1,144 sq ft

|

Condo

914 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Chatfield Farms 8 WOODLAND PATH 8, BEACON FALLS, CT, 064..., Beacon Falls, CT 06403
$724,900

3 beds

|

4 baths

|

2,610 sq ft

|

Condo

8 WOODLAND PATH 8, BEACON FALLS, CT, 064...
Community: Chatfield Farms
Warwick Grove 15 COWDREY ST, WARWICK, NY, 10990, Warwick, NY 10990
$839,000

3 beds

|

3 baths

|

2,482 sq ft

|

House

15 COWDREY ST, WARWICK, NY, 10990
Community: Warwick Grove
Heritage Village 419 HERITAGE VLG E, SOUTHBURY, CT, 06488, Southbury, CT 06488
$500,000

3 beds

|

2 baths

|

1,716 sq ft

|

Condo

419 HERITAGE VLG E, SOUTHBURY, CT, 06488
Community: Heritage Village
Want to learn more about 55+ rental communities in New Fairfield? 55places can help!
Questions? Call us: (959) 214-2391
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 16 VILLAGE CIR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949
$167,000

2 beds

|

2 baths

|

1,164 sq ft

|

Condo

16 VILLAGE CIR, BROOKHAVEN, NY, 11949
Community: Greenwood Village
Wanaque Reserve 5408 WARRENS WAY, WANAQUE, NJ, 07465, Wanaque, NJ 07465
$449,000

2 beds

|

2 baths

|

Condo

5408 WARRENS WAY, WANAQUE, NJ, 07465
Community: Wanaque Reserve
Leisure Village 230 BLACKPOOL CT A, RIDGE, NY, 11961, Ridge, NY 11961
$289,900

2 beds

|

1 baths

|

836 sq ft

|

Condo

230 BLACKPOOL CT A, RIDGE, NY, 11961
Community: Leisure Village
The Seasons at East Meadow 479 SPRING DR, EAST MEADOW, NY, 11554, East Meadow, NY 11554
$619,000

2 beds

|

2 baths

|

1,358 sq ft

|

House

479 SPRING DR, EAST MEADOW, NY, 11554
Encore at Lake Grove 17 SONATA CT, LAKE GROVE, NY, 11755, Lake Grove, NY 11755
$635,000

2 beds

|

3 baths

|

1,486 sq ft

|

Condo

17 SONATA CT, LAKE GROVE, NY, 11755
Want to learn more about 55+ communities in New Fairfield? 55places can help!
Questions? Call us: (959) 214-2391
Read the Ultimate 55+ Rental Guide Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
Four Seasons at Wayne 109 FOUR SEASONS DR # 109, WAYNE, NJ, 07..., Wayne, NJ 07470
$525,000

2 beds

|

2 baths

|

Condo

109 FOUR SEASONS DR # 109, WAYNE, NJ, 07...
Meadow Brook Estates 215 MEADOW BROOK RD # 215, OXFORD, CT, 0..., Oxford, CT 06478
$589,000

3 beds

|

3 baths

|

2,207 sq ft

|

Condo

215 MEADOW BROOK RD # 215, OXFORD, CT, 0...
The Residences at Butterfield 19 BUTTERFIELD RD UNIT 102B 102B, COLD S..., Cold Spring, NY 10516
$649,000

2 beds

|

2 baths

|

1,322 sq ft

|

Condo

19 BUTTERFIELD RD UNIT 102B 102B, COLD S...
Leisure Village 406 WOODBRIDGE DR B, RIDGE, NY, 11961, Ridge, NY 11961
$245,000

1 beds

|

1 baths

|

704 sq ft

|

Condo

406 WOODBRIDGE DR B, RIDGE, NY, 11961
Community: Leisure 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.
Long Hill Village 71 CIDER MILL LN, TRUMBULL, CT, 06611, Trumbull, CT 06611
$539,900

1 beds

|

3 baths

|

1,370 sq ft

|

Condo

71 CIDER MILL LN, TRUMBULL, CT, 06611
Community: Long Hill Village
Want to learn more about 55+ rental communities in New Fairfield? 55places can help!
Questions? Call us: (959) 214-2391
Four Seasons at Wayne 109 FOUR SEASONS DR, WAYNE TWP., NJ, 074..., Wayne Twp., NJ 07470
$525,000

2 beds

|

2 baths

109 FOUR SEASONS DR, WAYNE TWP., NJ, 074...
Leisure Knoll 190 EDINBURGH DR, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$479,999

2 beds

|

1 baths

|

913 sq ft

|

House

190 EDINBURGH DR, BROOKHAVEN, NY, 11961
Community: Leisure Knoll
Village Estates 34 SARAH CT, AMITYVILLE, NY, 11701, Amityville, NY 11701
$569,999

2 beds

|

2 baths

|

1,251 sq ft

|

Condo

34 SARAH CT, AMITYVILLE, NY, 11701
Community: Village Estates
Want to learn more about 55+ communities in New Fairfield? 55places can help!
Questions? Call us: (959) 214-2391
Heritage Village 915 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$295,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

915 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Greenwood Village 126 VILLAGE CIR, BROOKHAVEN, NY, 11949, Brookhaven, NY 11949
$225,000

2 beds

|

2 baths

|

1,032 sq ft

|

Condo

126 VILLAGE CIR, BROOKHAVEN, NY, 11949
Community: Greenwood Village

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