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New Fairfield, CT 55+ active adult communities & homes for sale - Page 3

239 homes near New Fairfield

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The Woods at Dunham Pond
$400Ks - $500Ks
The Woods at Dunham Pond, New Fairfield, CT
Resale Only | 55+ age-restricted | Built 2004 - 2015 | 33 homes
3 rating (2 reviews) Heritage Hills
$300Ks - $900Ks
Heritage Hills, Somers, NY
Resale Only | Age-targeted | Built 1974 - 2006 | 2,600 homes
3.6 rating (7 reviews) Heritage Village
$200Ks - $500Ks
Heritage Village, Southbury, CT
Resale Only | 55+ age-restricted | Built 1967 - 2005 | 2,580 homes
Leisure Village
$200Ks - $400Ks
Leisure Village, Ridge, NY
Resale Only | 55+ age-restricted | Built 1969 - 1986 | 1,500 homes
The Greens at Half Hollow
$600Ks - $1Ms
The Greens at Half Hollow, Melville, NY
Resale Only | 55+ age-restricted | Built 1994 - 2005 | 1,200 homes
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Rivington
$400Ks - $600Ks
Rivington, Danbury, CT
New and Resale | Age-targeted | Built 2006 - present | 1,050 homes
4 rating (1 reviews) Jefferson Village
$200Ks - $600Ks
Jefferson Village, Yorktown Heights, NY
Resale Only | 55+ age-restricted | Built 1967 - 1982 | 1,000 homes
Oronoque Village
$200Ks - $600Ks
Oronoque Village, Stratford, CT
Resale Only | 55+ age-restricted | Built 1971 - 1977 | 929 homes
The Village at Oxford Gre...
$500Ks - $700Ks
The Village at Oxford Gre..., Oxford, CT
New and Resale | 55+ age-restricted | Built 2004 - present | 835 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.
5 rating (1 reviews) Four Seasons at Great Not...
$600Ks - $800Ks
Four Seasons at Great Not..., Woodland Park, NJ
Resale Only | 55+ age-restricted | Built 2005 - 2018 | 814 homes
4.8 rating (4 reviews) Wanaque Reserve
$400Ks
Wanaque Reserve, Wanaque, NJ
Resale Only | 55+ age-restricted | Built 2004 - 2014 | 755 homes
Meadowbrook Pointe Athlet...
$800Ks - $1Ms
Meadowbrook Pointe Athlet..., Westbury, NY
Resale Only | 55+ age-restricted | Built 2015 - 2016 | 720 homes
Leisure Knoll
$400Ks
Leisure Knoll, Ridge, NY
Resale Only | 55+ age-restricted | Built 1972 - 1982 | 701 homes
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Country Pointe Plainview
$1Ms
Country Pointe Plainview, Plainview, NY
New Construction | 55+ age-restricted | Built 2017 - present | 660 homes
5 rating (2 reviews) Fairfield at St. James
$400Ks - $500Ks
Fairfield at St. James, St. James, NY
Resale Only | 55+ age-restricted | Built 1972 - 1989 | 653 homes
Leisure Glen
$500Ks
Leisure Glen, Ridge, NY
Resale Only | 55+ age-restricted | Built 1985 - 2010 | 646 homes
Spring Lake Village
$200Ks - $300Ks
Spring Lake Village, Southington, CT
Resale Only | 55+ age-restricted | Built 1970 - 2004 | 640 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 rating (8 reviews) Glenwood Village
$100Ks - $200Ks
Glenwood Village, Riverhead, NY
New and Resale | 55+ age-restricted | Built 1959 - present | 588 homes
3.7 rating (3 reviews) Greenwood Village
$100Ks - $200Ks
Greenwood Village, Manorville, NY
Resale Only | 55+ age-restricted | Built 1980 - 2000 | 512 homes
Bald Eagle Commons
$100Ks - $200Ks
Bald Eagle Commons, West Milford, NJ
Resale Only | 55+ age-restricted | Built 1995 - 2005 | 463 homes
The Seasons at East Meado...
$500Ks - $600Ks
The Seasons at East Meado..., East Meadow, NY
Resale Only | 55+ age-restricted | Built 2009 - 2012 | 404 homes
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Regency at Prospect
$400Ks - $500Ks
Regency at Prospect, Prospect, CT
Resale Only | 55+ age-restricted | Built 2006 - 2020 | 379 homes
Dutchgate
$400Ks - $500Ks
Dutchgate, Valley Stream, NY
Resale Only | 55+ age-restricted | Built 2009 - 2015 | 348 homes
The Waterways at Moriches
$400Ks - $500Ks
The Waterways at Moriches, Moriches, NY
Resale Only | 55+ age-restricted | Built 1985 - 1999 | 343 homes
The Retreat at Carmel
$400Ks - $600Ks
The Retreat at Carmel, Carmel, NY
Resale Only | 55+ age-restricted | Built 2008 - 2018 | 312 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.
Overlook
$600Ks
Overlook, Carmel, NY
New Construction | 55+ age-restricted | 300 homes
3.5 rating (2 reviews) Foxwood Village
$400Ks - $500Ks
Foxwood Village, Calverton, NY
Resale Only | 55+ age-restricted | Built 1986 - 2007 | 294 homes
1 rating (1 reviews) Plymouth Estates at Mount...
$500Ks
Plymouth Estates at Mount..., Mount Sinai, NY
Resale Only | 55+ age-restricted | Built 2006 - 2013 | 285 homes
Wildflowers at Wallkill
$500Ks - $600Ks
Wildflowers at Wallkill, Middletown, NY
Resale Only | 55+ age-restricted | Built 2006 - 2017 | 283 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
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4 rating (1 reviews) Vineyards at Blue Point
$800Ks
Vineyards at Blue Point, Blue Point, NY
Resale Only | 55+ age-restricted | Built 2016 - 2018 | 280 homes
Apple Ridge
$700Ks
Apple Ridge, Mahwah, NJ
Resale Only | Age-targeted | Built 1977 - 1991 | 276 homes
Winthrop Court
$400Ks
Winthrop Court, Clifton, NJ
Resale Only | 55+ age-restricted | Built 2000 - 2010 | 270 homes
HarborView
$900Ks - $1Ms
HarborView, Port Washington, NY
Resale Only | 55+ age-restricted | Built 2002 - 2004 | 270 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 Club at Melville
$500Ks
The Club at Melville, Melville, NY
Resale Only | 55+ age-restricted | Built 2015 - 2017 | 261 homes
The Seasons at Elwood
$800Ks - $900Ks
The Seasons at Elwood, East Northport, NY
Resale Only | 55+ age-restricted | Built 2018 - 2020 | 256 homes
Meadow Brook Estates
$500Ks
Meadow Brook Estates, Oxford, CT
Resale Only | 55+ age-restricted | Built 2003 - 2020 | 246 homes
5 rating (1 reviews) Encore Atlantic Shores
$700Ks - $800Ks
Encore Atlantic Shores, Eastport, NY
Resale Only | 55+ age-restricted | Built 2004 - 2011 | 240 homes
Want to learn more about 55+ communities in New Fairfield? 55places can help!
Questions? Call us: (959) 214-2391
The Summit at Bethel
$600Ks
The Summit at Bethel, Bethel, CT
Resale Only | 55+ age-restricted | Built 2010 - 2021 | 235 homes
4.9 rating (14 reviews) Chatfield Farms
$500Ks - $600Ks
Chatfield Farms, Beacon Falls, CT
New Construction | 55+ age-restricted | Built 2014 - present | 231 homes
The Vineyards at Miller Place 45 HALLEY LN, MILLER PLACE, NY, 11764, Miller Place, NY 11764
$650,000

2 beds

|

3 baths

|

1,853 sq ft

|

Condo

45 HALLEY LN, MILLER PLACE, NY, 11764
Heritage Hills 798 HERITAGE HLS D, SOMERS, NY, 10589, Somers, NY 10589
$609,000

2 beds

|

2 baths

|

1,296 sq ft

|

Condo

798 HERITAGE HLS D, SOMERS, NY, 10589
Community: Heritage Hills
Overlook 4073 FAIRWAYS DR # 137, CARMEL, NY, 1051..., Carmel, NY 10512
$665,000

3 beds

|

3 baths

|

1,914 sq ft

|

Condo

4073 FAIRWAYS DR # 137, CARMEL, NY, 1051...
Community: Overlook
Heritage Hills 55 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589
$675,000

2 beds

|

2 baths

|

1,500 sq ft

|

Condo

55 HERITAGE HLS A, SOMERS, NY, 10589
Community: Heritage Hills
The Retreat at Carmel 14 LANGDON GROVE, CARMEL, NY, 10512, Carmel, NY 10512
$699,900

2 beds

|

3 baths

|

1,957 sq ft

|

Condo

14 LANGDON GROVE, CARMEL, NY, 10512
Want to learn more about 55+ communities in New Fairfield? 55places can help!
Questions? Call us: (959) 214-2391
Leisure Village 310 WOODBRIDGE DR UNIT C, RIDGE, NY, 119..., Ridge, NY 11961
$342,000

2 beds

|

1 baths

|

1,278 sq ft

|

Condo

310 WOODBRIDGE DR UNIT C, RIDGE, NY, 119...
Community: Leisure Village
Sunken Pond Estates 4006 SAINT ANDREWS AVE, RIVERHEAD, NY, 1..., Riverhead, NY 11901
$519,888

2 beds

|

2 baths

|

1,587 sq ft

|

Condo

4006 SAINT ANDREWS AVE, RIVERHEAD, NY, 1...
Community: Sunken Pond Estates
HarborView 100 HARBOR VIEW DR 423, PORT WASHINGTON,..., Port Washington, NY 11050
$658,000

1 beds

|

2 baths

|

1,161 sq ft

|

Condo

100 HARBOR VIEW DR 423, PORT WASHINGTON,...
Community: HarborView
Leisure Village 380 WOODBRIDGE DR D, RIDGE, NY, 11961, Ridge, NY 11961
$439,000

2 beds

|

2 baths

|

1,147 sq ft

|

Condo

380 WOODBRIDGE DR D, 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.
Heritage Hills 348 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589
$596,000

2 beds

|

2 baths

|

1,428 sq ft

|

Condo

348 HERITAGE HLS A, SOMERS, NY, 10589
Community: Heritage Hills
Saddle Lakes 98 SCENIC LAKE DR, RIVERHEAD, NY, 11901, Riverhead, NY 11901
$749,990

3 beds

|

3 baths

|

1,837 sq ft

|

Condo

98 SCENIC LAKE DR, RIVERHEAD, NY, 11901
Community: Saddle Lakes
Stoneleigh Woods at Riverhead 67 STONELEIGH DR, RIVERHEAD, NY, 11901, Riverhead, NY 11901
$619,000

2 beds

|

3 baths

|

1,972 sq ft

|

Condo

67 STONELEIGH DR, RIVERHEAD, NY, 11901
Leisure Village 289 CARDIFF CT B, RIDGE, NY, 11961, Ridge, NY 11961
$420,000

2 beds

|

2 baths

|

1,308 sq ft

|

Condo

289 CARDIFF CT B, RIDGE, NY, 11961
Community: Leisure Village
Want to learn more about 55+ communities in New Fairfield? 55places can help!
Questions? Call us: (959) 214-2391
Blackburne Farm Townhomes 32 OTTAWAY LN, CAMPBELL HALL, NY, 10916, Campbell Hall, NY 10916
$700,000

2 beds

|

4 baths

|

3,600 sq ft

|

House

32 OTTAWAY LN, CAMPBELL HALL, NY, 10916
The Seasons at East Northport 142 AUGUST CIR, EAST NORTHPORT, NY, 1173..., East Northport, NY 11731
$780,302

2 beds

|

2 baths

|

1,536 sq ft

|

Condo

142 AUGUST CIR, EAST NORTHPORT, NY, 1173...
The Seasons at East Meadow 434 AUTUMN DR, EAST MEADOW, NY, 11554, East Meadow, NY 11554
$680,000

2 beds

|

3 baths

|

1,030 sq ft

|

Condo

434 AUTUMN DR, EAST MEADOW, NY, 11554
Jefferson Village 45 JEFFERSON OVAL D, YORKTOWN HEIGHTS, N..., Yorktown Heights, NY 10598
$375,000

2 beds

|

2 baths

|

1,100 sq ft

|

Condo

45 JEFFERSON OVAL D, YORKTOWN HEIGHTS, N...
Community: Jefferson 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.
Glenwood Village 1661 OLD COUNTRY RD 163, RIVERHEAD, NY, ..., Riverhead, NY 11901
$139,999

2 beds

|

1 baths

|

816 sq ft

|

Mobile Home

1661 OLD COUNTRY RD 163, RIVERHEAD, NY, ...
Community: Glenwood Village
Leisure Village 474 DARWEN DR B, RIDGE, NY, 11961, Ridge, NY 11961
$400,000

2 beds

|

2 baths

|

1,200 sq ft

|

Condo

474 DARWEN DR B, RIDGE, NY, 11961
Community: Leisure Village
Leisure Village 167 VENTRY CT UNIT C, RIDGE, NY, 11961, Ridge, NY 11961
$210,000

1 beds

|

1 baths

|

684 sq ft

|

Condo

167 VENTRY CT UNIT C, RIDGE, NY, 11961
Community: Leisure Village
The Waterways at Moriches 477 WOODSCREEK CT, MORICHES, NY, 11955, Moriches, NY 11955
$565,000

3 beds

|

2 baths

|

1,839 sq ft

|

Condo

477 WOODSCREEK CT, MORICHES, NY, 11955
Want to learn more about 55+ communities in New Fairfield? 55places can help!
Questions? Call us: (959) 214-2391
Greenwood Village 91 VILLAGE CIR, MANORVILLE, NY, 11949, Manorville, NY 11949
$155,000

2 beds

|

2 baths

|

938 sq ft

|

Condo

91 VILLAGE CIR, MANORVILLE, NY, 11949
Community: Greenwood Village
Breton Hills 209 BRETON WAY, GLEN COVE, NY, 11542, Glen Cove, NY 11542
$699,888

2 beds

|

2 baths

|

1,300 sq ft

|

Condo

209 BRETON WAY, GLEN COVE, NY, 11542
Community: Breton Hills
Leisure Knoll 145 EDINBURGH DR, RIDGE, NY, 11961, Ridge, NY 11961
$489,999

2 beds

|

2 baths

|

913 sq ft

|

House

145 EDINBURGH DR, RIDGE, NY, 11961
Community: Leisure Knoll
The Seasons at East Meadow 419 AUTUMN DR, EAST MEADOW, NY, 11554, East Meadow, NY 11554
$608,000

2 beds

|

2 baths

|

1,272 sq ft

|

Condo

419 AUTUMN DR, EAST MEADOW, NY, 11554
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.
Foxwood Village 1407 MIDDLE RD 275, CALVERTON, NY, 11933, Calverton, NY 11933
$425,000

3 beds

|

2 baths

|

1,530 sq ft

|

House

1407 MIDDLE RD 275, CALVERTON, NY, 11933
Community: Foxwood Village
The Seasons at East Meadow 357 SPRING DR, EAST MEADOW, NY, 11554, East Meadow, NY 11554
$585,000

2 beds

|

2 baths

|

1,272 sq ft

|

Condo

357 SPRING DR, EAST MEADOW, NY, 11554
Greenwood Village 409 VILLAGE CIR, MANORVILLE, NY, 11949, Manorville, NY 11949
$175,000

2 beds

|

2 baths

|

1,655 sq ft

|

Condo

409 VILLAGE CIR, MANORVILLE, NY, 11949
Community: Greenwood Village
The Manors at The Colony Preserve 41 GREENTREE CT, SHIRLEY, NY, 11967, Shirley, NY 11967
$535,000

2 beds

|

2 baths

|

1,800 sq ft

|

Condo

41 GREENTREE CT, SHIRLEY, NY, 11967
The Seasons at Plainview 119 AUTUMN DR, PLAINVIEW, NY, 11803, Plainview, NY 11803
$799,000

2 beds

|

2 baths

|

1,379 sq ft

|

Condo

119 AUTUMN DR, PLAINVIEW, NY, 11803
Want to learn more about 55+ communities in New Fairfield? 55places can help!
Questions? Call us: (959) 214-2391
Jefferson Village 175 LONG HILL DR B, YORKTOWN HEIGHTS, NY..., Yorktown Heights, NY 10598
$399,999

2 beds

|

2 baths

|

1,159 sq ft

|

Condo

175 LONG HILL DR B, YORKTOWN HEIGHTS, NY...
Community: Jefferson Village
Leisure Village 412 WEYMOUTH CT UNIT B, RIDGE, NY, 11961, Ridge, NY 11961
$415,500

2 beds

|

1 baths

|

1,100 sq ft

|

Condo

412 WEYMOUTH CT UNIT B, RIDGE, NY, 11961
Community: Leisure Village
The Villages at Mount Sinai Park 68 LOUDEN LOOP, MOUNT SINAI, NY, 11766, Mount Sinai, NY 11766
$584,000

2 beds

|

2 baths

|

1,736 sq ft

|

Condo

68 LOUDEN LOOP, MOUNT SINAI, NY, 11766
Greenwood Village 99 VILLAGE CIR, MANORVILLE, NY, 11949, Manorville, NY 11949
$269,988

2 beds

|

2 baths

|

1,487 sq ft

|

Condo

99 VILLAGE CIR, MANORVILLE, NY, 11949
Community: Greenwood 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.
The Villas at Narragansett 512 NARRAGANSETT VILLAS DR, LINDENHURST,..., Lindenhurst, NY 11757
$609,000

2 beds

|

2 baths

|

1,227 sq ft

|

Condo

512 NARRAGANSETT VILLAS DR, LINDENHURST,...
Encore Atlantic Shores 177 MELODY CT, EASTPORT, NY, 11941, Eastport, NY 11941
$795,000

2 beds

|

2 baths

|

2,150 sq ft

|

Condo

177 MELODY CT, EASTPORT, NY, 11941
Greenwood Village 19 DOGWOOD LN, MANORVILLE, NY, 11949, Manorville, NY 11949
$155,000

2 beds

|

2 baths

|

871 sq ft

|

Condo

19 DOGWOOD LN, MANORVILLE, NY, 11949
Community: Greenwood Village
Warwick Grove 15 CROPSEY ST # 15-3A, WARWICK, NY, 1099..., Warwick, NY 10990
$625,000

2 beds

|

2 baths

|

1,823 sq ft

|

House

15 CROPSEY ST # 15-3A, WARWICK, NY, 1099...
Community: Warwick Grove
Want to learn more about 55+ communities in New Fairfield? 55places can help!
Questions? Call us: (959) 214-2391
Warwick Grove 2 SLY ST, WARWICK, NY, 10990, Warwick, NY 10990
$849,000

2 beds

|

3 baths

|

2,256 sq ft

|

House

2 SLY ST, WARWICK, NY, 10990
Community: Warwick Grove
Greenwood Village 23 LIMETREE DR, MANORVILLE, NY, 11949, Manorville, NY 11949
$235,000

2 beds

|

2 baths

|

1,000 sq ft

|

Condo

23 LIMETREE DR, MANORVILLE, NY, 11949
Community: Greenwood Village
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