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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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Country Pointe Plainview
$700ks - $1Ms
Country Pointe Plainview, Plainview, NY
New Construction | 55+ age-restricted | Built 2017 - present | 660 homes
Stratford Park
$600ks - $800ks
Stratford Park, Melville, NY
Resale Only | 55+ age-restricted | Built 2011 - 2013 | 36 homes
The Village at Buckingham
$300ks - $400ks
The Village at Buckingham, Avon, CT
Resale Only | 55+ age-restricted | Built 2002 - 2006 | 56 homes
Vineyards at Moriches
$500ks - $600ks
Vineyards at Moriches, Center Moriches, NY
Resale Only | 55+ age-restricted | Built 2008 - 2014 | 92 homes
Beckley Farms
$300ks - $400ks
Beckley Farms, Berlin, CT
New and Resale | 55+ age-restricted | Built 2010 - present | 170 homes
Want to learn more about 55+ communities in New Fairfield? 55places can help!
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Castle Heights of Cheshir...
$500ks - $600ks
Castle Heights of Cheshir..., Cheshire, CT
Resale Only | 55+ age-restricted | Built 2007 - 2022 | 88 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
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 Powder Forest Homes
$500ks - $700ks
The Powder Forest Homes, Simsbury, CT
Resale Only | 55+ age-restricted | Built 2006 - 2016 | 182 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.
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
Autumn Estates
$500ks - $600ks
Autumn Estates, Farmington, CT
Resale Only | 55+ age-restricted | Built 2011 - 2017 | 30 homes
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The Atrium of Portland
<$100k
The Atrium of Portland, Portland, CT
Resale Only | 55+ age-restricted | Built 2004 - 2004 | 56 homes
Billingsgate
$400ks - $600ks
Billingsgate, Simsbury, CT
Resale Only | 55+ age-restricted | Built 2003 - 2006 | 37 homes
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Boulder Brook
$200ks
Boulder Brook, Prospect, CT
Resale Only | 55+ age-restricted | Built 2004 - 2006 | 35 homes
Hopmeadow Place
$200ks - $300ks
Hopmeadow Place, Simsbury, CT
Resale Only | 55+ age-restricted | Built 2005 - 2005 | 66 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.
Summer Wind Estates
$300ks - $400ks
Summer Wind Estates, North Haven, CT
New Construction | 55+ age-restricted | Built 2015 - present | 18 homes
Forest Mews
$300ks - $400ks
Forest Mews, Avon, CT
Resale Only | 55+ age-restricted | Built 2001 - 2004 | 40 homes
The Village at Hunt Glen
$300ks
The Village at Hunt Glen, Granby, CT
Resale Only | 55+ age-restricted | Built 2003 - 2006 | 69 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.
O'Meara Farm
$400ks
O'Meara Farm, Farmington, CT
Resale Only | 55+ age-restricted | Built 1998 - 2005 | 104 homes
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Bramble Ridge
$300ks
Bramble Ridge, Suffield, CT
Resale Only | 55+ age-restricted | Built 2005 - 2015 | 47 homes
5 rating (2 reviews) Benson Woods
$400ks - $600ks
Benson Woods, Middlebury, CT
New and Resale | 55+ age-restricted | Built 2004 - present | 79 homes
Newbury Village
$400ks - $500ks
Newbury Village, Brookfield, CT
New and Resale | 55+ age-restricted | Built 2005 - present | 120 homes
Clockmaker's Hill
$100ks
Clockmaker's Hill, Winsted, CT
Resale Only | 55+ age-restricted | Built 2005 - 2014 | 38 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.
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
4.9 rating (14 reviews) Chatfield Farms
$400ks - $700ks
Chatfield Farms, Beacon Falls, CT
New Construction | 55+ age-restricted | Built 2014 - present | 231 homes
77 Sunset Lane
$400ks - $700ks
77 Sunset Lane, Ridgefield, CT
Resale Only | 55+ age-restricted | Built 2016 - 2018 | 54 homes
Gloria Commons
$200ks - $300ks
Gloria Commons, Milford, CT
Resale Only | 55+ age-restricted | Built 2007 - 2015 | 50 homes
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.
Long Hill Village
$300ks - $400ks
Long Hill Village, Trumbull, CT
Resale Only | 55+ age-restricted | Built 1997 - 1999 | 71 homes
Park Glen
$300ks - $500ks
Park Glen, New Milford, CT
Resale Only | 55+ age-restricted | Built 2006 - 2015 | 17 homes
RiverBend Estates
$400ks
RiverBend Estates, Oxford, CT
New and Resale | 55+ age-restricted | Built 2012 - present | 25 homes
The Woods at Dunham Pond
$200ks - $400ks
The Woods at Dunham Pond, New Fairfield, CT
Resale Only | 55+ age-restricted | Built 2004 - 2015 | 33 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.
Regency Meadows
$500ks
Regency Meadows, Trumbull, CT
Resale Only | 55+ age-restricted | Built 2003 - 2005 | 51 homes
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Questions? Call us: (959) 214-2391
The Coach Homes at Ridgef...
$300ks - $400ks
The Coach Homes at Ridgef..., Ridgefield, CT
New Construction | 55+ age-restricted | Built 2019 - present | 30 homes
Whitney Glen
$500ks - $600ks
Whitney Glen, Westport, CT
Resale Only | 55+ age-restricted | Built 1982 - 1982 | 62 homes
Applegate Estates
$500ks - $400ks
Applegate Estates, Southington, CT
New and Resale | 55+ age-restricted | Built 2010 - 2025 | 94 homes
New Bald Eagle Commons 4 RICHMOND RD 215, WEST MILFORD, NJ, 074..., West Milford, NJ 07480
$260,000

2 beds

|

2 baths

|

Condo

4 RICHMOND RD 215, WEST MILFORD, NJ, 074...
Community: Bald Eagle Commons
New Wanaque Reserve 1118 WARRENS WAY, WANAQUE BORO, NJ, 0746..., Wanaque Boro, NJ 07465
$569,000

2 beds

|

2 baths

1118 WARRENS WAY, WANAQUE BORO, NJ, 0746...
Community: Wanaque Reserve
New Sunrise Village 93 REVERE DR, ISLIP, NY, 11782, Islip, NY 11782
$525,000

2 beds

|

2 baths

|

1,230 sq ft

|

Condo

93 REVERE DR, ISLIP, NY, 11782
Community: Sunrise Village
New The Villages at Mount Sinai Park 46 LOUDEN LOOP, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766
$899,000

3 beds

|

3 baths

|

2,455 sq ft

|

House

46 LOUDEN LOOP, BROOKHAVEN, NY, 11766
New Bald Eagle Commons 5301 RICHMOND RD 301, WEST MILFORD TWP.,..., West Milford Twp., NJ 07480
$269,900

2 beds

|

2 baths

5301 RICHMOND RD 301, WEST MILFORD TWP.,...
Community: Bald Eagle Commons
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 Jefferson Village 10 REGENTS PL D, YORKTOWN, NY, 10598, Yorktown, NY 10598
$240,000
|

1 baths

|

550 sq ft

|

Condo

10 REGENTS PL D, YORKTOWN, NY, 10598
Community: Jefferson Village
New O'Meara Farm 1 MAGNOLIA CIR 1, FARMINGTON, CT, 06032, Farmington, CT 06032
$480,000

2 beds

|

2 baths

|

1,416 sq ft

|

Condo

1 MAGNOLIA CIR 1, FARMINGTON, CT, 06032
Community: O'Meara Farm
New Bald Eagle Commons 4 RICHMOND RD 215, WEST MILFORD TWP., NJ..., West Milford Twp., NJ 07480
$260,000

2 beds

|

2 baths

4 RICHMOND RD 215, WEST MILFORD TWP., NJ...
Community: Bald Eagle Commons
New The Greens at Half Hollow 625 MADEIRA BLVD, HUNTINGTON, NY, 11747, Huntington, NY 11747
$980,000

2 beds

|

3 baths

|

1,940 sq ft

|

Condo

625 MADEIRA BLVD, HUNTINGTON, NY, 11747
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 Meadowbrooke Pointe East Meadow 137 EMANUEL WAY, HEMPSTEAD, NY, 11554, Hempstead, NY 11554
$839,000

2 beds

|

3 baths

|

1,390 sq ft

|

Condo

137 EMANUEL WAY, HEMPSTEAD, NY, 11554
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 Foxwood Village 1407 MIDDLE RD 91, RIVERHEAD, NY, 11933, Riverhead, NY 11933
$364,000

2 beds

|

2 baths

|

1,532 sq ft

|

House

1407 MIDDLE RD 91, RIVERHEAD, NY, 11933
Community: Foxwood Village
New Heritage Village 640 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$360,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

640 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
New Regency at Fishkill 145 REGENCY DR, FISHKILL, NY, 12524, Fishkill, NY 12524
$555,000

2 beds

|

2 baths

|

1,803 sq ft

|

Condo

145 REGENCY DR, FISHKILL, NY, 12524
Community: Regency at Fishkill
Want to learn more about 55+ communities in New Fairfield? 55places can help!
Questions? Call us: (959) 214-2391
New Oronoque Village 47 HURON LN A, STRATFORD, CT, 06614, Stratford, CT 06614
$409,000

2 beds

|

2 baths

|

1,360 sq ft

|

Condo

47 HURON LN A, STRATFORD, CT, 06614
Community: Oronoque Village
New Leisure Village 279 BERWICK CT B, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$299,999

2 beds

|

1 baths

|

875 sq ft

|

Condo

279 BERWICK CT B, BROOKHAVEN, NY, 11961
Community: Leisure Village
Want to learn more about 55+ rental communities in New Fairfield? 55places can help!
Questions? Call us: (959) 214-2391
New Country Village Estates 45 THEODORE DR, BROOKHAVEN, NY, 11727, Brookhaven, NY 11727
$475,000

2 beds

|

2 baths

|

1,305 sq ft

|

Condo

45 THEODORE DR, BROOKHAVEN, NY, 11727
New The Villages at Mount Sinai Park 3 LOUDEN LOOP, BROOKHAVEN, NY, 11766, Brookhaven, NY 11766
$675,000

2 beds

|

3 baths

|

1,736 sq ft

|

House

3 LOUDEN LOOP, BROOKHAVEN, NY, 11766
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 Regency at Prospect 104 CHERRY CIR 104, PROSPECT, CT, 06712, Prospect, CT 06712
$328,417

3 beds

|

2 baths

|

1,500 sq ft

|

Condo

104 CHERRY CIR 104, PROSPECT, CT, 06712
Community: Regency at Prospect
New Rivington 131 WINDING RIDGE WAY 131, DANBURY, CT, ..., Danbury, CT 06810
$770,000

3 beds

|

3 baths

|

1,592 sq ft

|

Condo

131 WINDING RIDGE WAY 131, DANBURY, CT, ...
Community: Rivington
New Regency at Woodbridge 27 HERITAGE LN, WOODBRIDGE, CT, 06525, Woodbridge, CT 06525
$599,900

3 beds

|

3 baths

|

Condo

27 HERITAGE LN, WOODBRIDGE, CT, 06525
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 Castle Heights of Cheshire 151 VICTORIA DR, CHESHIRE, CT, 06410, Cheshire, CT 06410
$769,900

2 beds

|

4 baths

|

2,843 sq ft

|

Condo

151 VICTORIA DR, CHESHIRE, CT, 06410
Want to learn more about 55+ communities in New Fairfield? 55places can help!
Questions? Call us: (959) 214-2391
New Country Village Estates 163 THEODORE DR, BROOKHAVEN, NY, 11727, Brookhaven, NY 11727
$454,500

2 beds

|

2 baths

|

1,261 sq ft

|

Condo

163 THEODORE DR, BROOKHAVEN, NY, 11727
New Apple Ridge 37 NIAGARA DR 37, MAHWAH, NJ, 07430, Mahwah, NJ 07430
$760,000

2 beds

|

3 baths

|

Townhouse

37 NIAGARA DR 37, MAHWAH, NJ, 07430
Community: Apple Ridge
New The Waterways at Moriches 188 RIVER DR, BROOKHAVEN, NY, 11955, Brookhaven, NY 11955
$775,000

2 beds

|

2 baths

|

2,100 sq ft

|

Condo

188 RIVER DR, BROOKHAVEN, NY, 11955
New Glenwood Village 1661 OLD COUNTRY RD 251, RIVERHEAD, NY, ..., Riverhead, NY 11901
$130,000

2 beds

|

1 baths

|

720 sq ft

|

Manufactured Home

1661 OLD COUNTRY RD 251, RIVERHEAD, NY, ...
Community: Glenwood 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.
New Heritage Village 101 HERITAGE VLG D, SOUTHBURY, CT, 06488, Southbury, CT 06488
$229,000

2 beds

|

2 baths

|

1,076 sq ft

|

Condo

101 HERITAGE VLG D, SOUTHBURY, CT, 06488
Community: Heritage Village
New Heritage Village 29 HERITAGE VLG D, SOUTHBURY, CT, 06488, Southbury, CT 06488
$325,000

2 beds

|

2 baths

|

1,076 sq ft

|

Condo

29 HERITAGE VLG D, SOUTHBURY, CT, 06488
Community: Heritage Village
New Four Seasons at Cedar Grove 1209 HOLLY LN 141, CEDAR GROVE, NJ, 0700..., Cedar Grove, NJ 07009
$750,000

2 beds

|

2 baths

|

Condo

1209 HOLLY LN 141, CEDAR GROVE, NJ, 0700...
New Four Seasons at Cedar Grove 1209 HOLLY LN, CEDAR GROVE TWP., NJ, 070..., Cedar Grove Twp., NJ 07009
$750,000

2 beds

|

2 baths

1209 HOLLY LN, CEDAR GROVE TWP., NJ, 070...
The Summit at Bethel 20 GREAT HILL DR 20, BETHEL, CT, 06801, Bethel, CT 06801
$649,000

3 beds

|

3 baths

|

2,159 sq ft

|

Condo

20 GREAT HILL DR 20, BETHEL, CT, 06801
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.
Heritage Hills 39 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589
$440,000

2 beds

|

2 baths

|

1,427 sq ft

|

Condo

39 HERITAGE HLS B, SOMERS, NY, 10589
Community: Heritage Hills
Jefferson Village 59 KIRBY CLOSE D, YORKTOWN, NY, 10598, Yorktown, NY 10598
$399,000

2 beds

|

2 baths

|

910 sq ft

|

Condo

59 KIRBY CLOSE D, YORKTOWN, NY, 10598
Community: Jefferson Village
Jefferson Village 51 JEFFERSON OVAL D, YORKTOWN, NY, 10598, Yorktown, NY 10598
$364,999

2 beds

|

2 baths

|

919 sq ft

|

Condo

51 JEFFERSON OVAL D, YORKTOWN, NY, 10598
Community: Jefferson Village
Heritage Village 401 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$353,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

401 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage 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.
Heritage Hills 415 HERITAGE HILLS DR D, SOMERS, NY, 105..., Somers, NY 10589
$875,000

2 beds

|

2 baths

|

1,663 sq ft

|

Condo

415 HERITAGE HILLS DR D, SOMERS, NY, 105...
Community: Heritage Hills
Want to learn more about 55+ rental communities in New Fairfield? 55places can help!
Questions? Call us: (959) 214-2391
Strathmore Gate East 42 FREEMONT LN, BROOKHAVEN, NY, 11727, Brookhaven, NY 11727
$425,000

2 beds

|

2 baths

|

1,112 sq ft

|

Condo

42 FREEMONT LN, BROOKHAVEN, NY, 11727
Leisure Glen 16 HUNTINGTON CT, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961
$505,000

2 beds

|

2 baths

|

1,312 sq ft

|

Condo

16 HUNTINGTON CT, BROOKHAVEN, NY, 11961
Community: Leisure Glen
The Pointe 5205 POINTE GATE DR, LIVINGSTON TWP., NJ..., Livingston Twp., NJ 07039
$650,000

2 beds

|

3 baths

5205 POINTE GATE DR, LIVINGSTON TWP., NJ...
Community: The Pointe
Want to learn more about 55+ communities in New Fairfield? 55places can help!
Questions? Call us: (959) 214-2391
Heritage Village 25 HERITAGE CRST C, SOUTHBURY, CT, 06488, Southbury, CT 06488
$439,900

2 beds

|

2 baths

|

1,447 sq ft

|

Condo

25 HERITAGE CRST C, SOUTHBURY, CT, 06488
Community: Heritage Village
Sunken Pond Estates 3006 AMEN COR, RIVERHEAD, NY, 11901, Riverhead, NY 11901
$499,000

2 beds

|

2 baths

|

1,587 sq ft

|

Condo

3006 AMEN COR, RIVERHEAD, NY, 11901
Community: Sunken Pond Estates

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