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

77 communities near Winsted

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Long Hill Village
$300Ks - $400Ks
Long Hill Village, Trumbull, CT
Resale Only | 55+ age-restricted | Built 1997 - 1999 | 71 homes
Regency at Woodbridge
$600Ks - $700Ks
Regency at Woodbridge, Woodbridge, CT
New Construction | 55+ age-restricted | Built 2023 - present | 70 homes
The Village at Hunt Glen
$300Ks
The Village at Hunt Glen, Granby, CT
Resale Only | 55+ age-restricted | Built 2003 - 2006 | 69 homes
Sonoma Woods
$300Ks
Sonoma Woods, Middletown, CT
Resale Only | 55+ age-restricted | Built 2005 - 2015 | 68 homes
Stoneleigh Woods at Carme...
$400Ks
Stoneleigh Woods at Carme..., Carmel, NY
Resale Only | 55+ age-restricted | Built 2012 - 2017 | 68 homes
Want to learn more about 55+ communities in Winsted? 55places can help!
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Hopmeadow Place
$200Ks - $300Ks
Hopmeadow Place, Simsbury, CT
Resale Only | 55+ age-restricted | Built 2005 - 2005 | 66 homes
Glassbury Court at Hunter...
$500Ks - $700Ks
Glassbury Court at Hunter..., Cortlandt, NY
Resale Only | 55+ age-restricted | Built 2007 - 2014 | 64 homes
Whitney Glen
$500Ks - $600Ks
Whitney Glen, Westport, CT
Resale Only | 55+ age-restricted | Built 1982 - 1982 | 62 homes
RiverWalk
$500Ks - $600Ks
RiverWalk, Branford, CT
New and Resale | 55+ age-restricted | Built 2007 - present | 60 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.
Woodcrest at Jacobs Hill
$300Ks
Woodcrest at Jacobs Hill, Cortlandt, NY
Resale Only | 55+ age-restricted | Built 2005 - 2006 | 58 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.
The Atrium of Portland
<$100k
The Atrium of Portland, Portland, CT
Resale Only | 55+ age-restricted | Built 2004 - 2004 | 56 homes
The Village at Buckingham
$500Ks - $600Ks
The Village at Buckingham, Avon, CT
Resale Only | 55+ age-restricted | Built 2002 - 2006 | 56 homes
Autumn Fields
$200Ks - $300Ks
Autumn Fields, Enfield, CT
Resale Only | 55+ age-restricted | Built 2004 - 2006 | 56 homes
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77 Sunset Lane
$400Ks - $700Ks
77 Sunset Lane, Ridgefield, CT
Resale Only | 55+ age-restricted | Built 2016 - 2018 | 54 homes
Evergreen
$500Ks
Evergreen, Cromwell, CT
New and Resale | 55+ age-restricted | Built 2005 - present | 52 homes
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Questions? Call us: (860) 909-8066
Regency Meadows
$500Ks
Regency Meadows, Trumbull, CT
Resale Only | 55+ age-restricted | Built 2003 - 2005 | 51 homes
Gloria Commons
$400Ks
Gloria Commons, Milford, CT
Resale Only | 55+ age-restricted | Built 2007 - 2015 | 50 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.
Villas at Seminary Hill
$400Ks
Villas at Seminary Hill, Carmel, NY
New Construction | 55+ age-restricted | Built 2018 - present | 50 homes
The Residences at Butterf...
$500Ks - $600Ks
The Residences at Butterf..., Cold Spring, NY
Resale Only | 55+ age-restricted | Built 2018 - 2023 | 49 homes
Bramble Ridge
$400Ks - $500Ks
Bramble Ridge, Suffield, CT
Resale Only | 55+ age-restricted | Built 2005 - 2015 | 47 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.
Chimney Hill
$500Ks - $700Ks
Chimney Hill, Farmington, CT
Resale Only | 55+ age-restricted | Built 2006 - 2013 | 44 homes
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Forest Mews
$300Ks - $400Ks
Forest Mews, Avon, CT
Resale Only | 55+ age-restricted | Built 2001 - 2004 | 40 homes
Bidwell Village
$300Ks - $400Ks
Bidwell Village, Coventry, CT
New Construction | 55+ age-restricted | Built 2020 - present | 37 homes
Billingsgate
$400Ks - $600Ks
Billingsgate, Simsbury, CT
Resale Only | 55+ age-restricted | Built 2003 - 2006 | 37 homes
Boulder Brook
$200Ks
Boulder Brook, Prospect, CT
Resale Only | 55+ age-restricted | Built 2004 - 2006 | 35 homes
Want to learn more about 55+ rental communities in Winsted? 55places can help!
Questions? Call us: (860) 909-8066
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.
Eden Park
$500Ks - $600Ks
Eden Park, Clarkstown, NY
Resale Only | 55+ age-restricted | Built 2011 - 2011 | 34 homes
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
Oak Meadow Estates
$400Ks
Oak Meadow Estates, Torrington, CT
New and Resale | 55+ age-restricted | Built 2013 - present | 31 homes
The Coach Homes at Ridgef...
$200Ks - $500Ks
The Coach Homes at Ridgef..., Ridgefield, CT
New Construction | 55+ age-restricted | Built 2019 - present | 30 homes
Autumn Estates
$500Ks - $600Ks
Autumn Estates, Farmington, CT
Resale Only | 55+ age-restricted | Built 2011 - 2017 | 30 homes
Want to learn more about 55+ communities in Winsted? 55places can help!
Questions? Call us: (860) 909-8066
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.
Bartlett Hollow
$200Ks - $400Ks
Bartlett Hollow, Middletown, CT
New Construction | 55+ age-restricted | Built 2015 - present | 25 homes
RiverBend Estates
$400Ks
RiverBend Estates, Oxford, CT
New and Resale | 55+ age-restricted | Built 2012 - present | 25 homes
Granite Woods
$600Ks - $700Ks
Granite Woods, Middlebury, CT
New Construction | 55+ age-restricted | Built 2020 - present | 24 homes
Summer Wind Estates
$300Ks - $400Ks
Summer Wind Estates, North Haven, CT
New Construction | 55+ age-restricted | Built 2015 - present | 18 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.
Park Glen
$600Ks
Park Glen, New Milford, CT
Resale Only | 55+ age-restricted | Built 2006 - 2015 | 17 homes
Want to learn more about 55+ rental communities in Winsted? 55places can help!
Questions? Call us: (860) 909-8066
Newington Ridge Preserve
$300Ks - $400Ks
Newington Ridge Preserve, Newington, CT
New Construction | 55+ age-restricted | Built 2014 - present | 16 homes
Cobblestone Court
$400Ks - $500Ks
Cobblestone Court, Essex, CT
New and Resale | 55+ age-restricted | Built 2017 - present | 8 homes
Overlook 1037 COTTAGE DR 18, CARMEL, NY, 10512, Carmel, NY 10512
$879,000

2 beds

|

3 baths

|

2,496 sq ft

|

Condo

1037 COTTAGE DR 18, CARMEL, NY, 10512
Community: Overlook
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
Overlook 4071 FAIRWAYS DR 136, CARMEL, NY, 10512, Carmel, NY 10512
$668,000

3 beds

|

3 baths

|

1,914 sq ft

|

Condo

4071 FAIRWAYS DR 136, CARMEL, NY, 10512
Community: Overlook
Heritage Hills 443 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589
$625,000

2 beds

|

2 baths

|

1,559 sq ft

|

Condo

443 HERITAGE HLS A, SOMERS, NY, 10589
Community: Heritage Hills
Jefferson Village 159 CARRIAGE CT C, YORKTOWN HEIGHTS, NY,..., Yorktown Heights, NY 10598
$560,000

2 beds

|

2 baths

|

1,300 sq ft

|

Condo

159 CARRIAGE CT C, YORKTOWN HEIGHTS, NY,...
Community: Jefferson Village
Want to learn more about 55+ communities in Winsted? 55places can help!
Questions? Call us: (860) 909-8066
Want to learn more about 55+ rental communities in Winsted? 55places can help!
Questions? Call us: (860) 909-8066
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
Heritage Hills 59 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589
$699,000

3 beds

|

2 baths

|

1,689 sq ft

|

Condo

59 HERITAGE HLS A, SOMERS, NY, 10589
Community: Heritage Hills
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
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
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 811 HERITAGE HLS, SOMERS, NY, 10589, Somers, NY 10589
$930,000

2 beds

|

2 baths

|

1,663 sq ft

|

Condo

811 HERITAGE HLS, 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.
Glassbury Court at Hunterbrook 2279 DALTON DR, CORTLANDT MANOR, NY, 105..., Cortlandt Manor, NY 10567
$925,000

2 beds

|

4 baths

|

3,500 sq ft

|

Condo

2279 DALTON DR, CORTLANDT MANOR, NY, 105...
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
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
Want to learn more about 55+ communities in Winsted? 55places can help!
Questions? Call us: (860) 909-8066
Glassbury Court at Cold Spring 43 YESTERDAY DR, COLD SPRING, NY, 10516, Cold Spring, NY 10516
$727,000

2 beds

|

3 baths

|

2,620 sq ft

|

Condo

43 YESTERDAY DR, COLD SPRING, NY, 10516
Heritage Hills 390 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589
$699,000

2 beds

|

2 baths

|

1,559 sq ft

|

Condo

390 HERITAGE HLS A, SOMERS, NY, 10589
Community: Heritage Hills
Want to learn more about 55+ rental communities in Winsted? 55places can help!
Questions? Call us: (860) 909-8066
Jefferson Village 156 CARRIAGE CT G, YORKTOWN HEIGHTS, NY,..., Yorktown Heights, NY 10598
$339,000

1 beds

|

1 baths

|

850 sq ft

|

Condo

156 CARRIAGE CT G, YORKTOWN HEIGHTS, NY,...
Community: Jefferson Village
Jefferson Village 108 VILLAGE RD B, YORKTOWN HEIGHTS, NY, ..., Yorktown Heights, NY 10598
$459,900

2 beds

|

2 baths

|

1,200 sq ft

|

Condo

108 VILLAGE RD B, YORKTOWN HEIGHTS, NY, ...
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.
Jefferson Village 141 FLINTLOCK WAY B, YORKTOWN HEIGHTS, N..., Yorktown Heights, NY 10598
$675,000

2 beds

|

2 baths

|

1,555 sq ft

|

Condo

141 FLINTLOCK WAY B, YORKTOWN HEIGHTS, N...
Community: Jefferson Village
Heritage Hills 593 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589
$1,100,000

3 beds

|

2 baths

|

1,905 sq ft

|

Condo

593 HERITAGE HLS B, SOMERS, NY, 10589
Community: Heritage Hills
Regency at Fishkill 423 REGENCY DR, FISHKILL, NY, 12524, Fishkill, NY 12524
$499,000

1 beds

|

2 baths

|

1,450 sq ft

|

Condo

423 REGENCY DR, FISHKILL, NY, 12524
Community: Regency at Fishkill
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.
Regency at Fishkill 326 REGENCY DR, FISHKILL, NY, 12524, Fishkill, NY 12524
$527,000

1 beds

|

2 baths

|

1,543 sq ft

|

Condo

326 REGENCY DR, FISHKILL, NY, 12524
Community: Regency at Fishkill
Want to learn more about 55+ communities in Winsted? 55places can help!
Questions? Call us: (860) 909-8066
Regency at Fishkill 145 REGENCY DR, FISHKILL, NY, 12524, Fishkill, NY 12524
$569,800

2 beds

|

2 baths

|

1,803 sq ft

|

Condo

145 REGENCY DR, FISHKILL, NY, 12524
Community: Regency at Fishkill
The Village at Oxford Greens 106 COUNTRY CLUB DR # 106, OXFORD, CT, 0..., Oxford, CT 06478
$580,000

2 beds

|

3 baths

|

1,590 sq ft

|

Condo

106 COUNTRY CLUB DR # 106, OXFORD, CT, 0...
Heritage Village 60 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$279,900

2 beds

|

2 baths

|

1,365 sq ft

|

Condo

60 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 623 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$535,000

3 beds

|

2 baths

|

1,716 sq ft

|

Condo

623 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Want to learn more about 55+ rental communities in Winsted? 55places can help!
Questions? Call us: (860) 909-8066
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 Village 568A HERITAGE VLG, SOUTHBURY, CT, 06488, Southbury, CT 06488
$409,900

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

568A HERITAGE VLG, SOUTHBURY, CT, 06488
Community: Heritage Village
Regency at Woodbridge 1 WHISPER RIDGE WAY # 51, WOODBRIDGE, CT..., Woodbridge, CT 06525
$749,000

3 beds

|

3 baths

|

2,180 sq ft

|

Condo

1 WHISPER RIDGE WAY # 51, WOODBRIDGE, CT...
Regency at Woodbridge 3 WHISPER RIDGE WAY # 50, WOODBRIDGE, CT..., Woodbridge, CT 06525
$699,000

3 beds

|

3 baths

|

Condo

3 WHISPER RIDGE WAY # 50, WOODBRIDGE, CT...
Regency at Woodbridge 8 WHISPER RIDGE WAY # 43, WOODBRIDGE, CT..., Woodbridge, CT 06525
$668,000

3 beds

|

3 baths

|

Condo

8 WHISPER RIDGE WAY # 43, WOODBRIDGE, CT...
Heritage Village 331 HERITAGE VLG E, SOUTHBURY, CT, 06488, Southbury, CT 06488
$275,500

2 beds

|

2 baths

|

1,365 sq ft

|

Condo

331 HERITAGE VLG E, SOUTHBURY, CT, 06488
Community: Heritage Village
Want to learn more about 55+ communities in Winsted? 55places can help!
Questions? Call us: (860) 909-8066
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 Village 917 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$225,000

1 beds

|

1 baths

|

928 sq ft

|

Condo

917 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Newbury Village 332 STILL WATER CIR # 332, BROOKFIELD, C..., Brookfield, CT 06804
$525,000

2 beds

|

2 baths

|

1,466 sq ft

|

Condo

332 STILL WATER CIR # 332, BROOKFIELD, C...
Community: Newbury Village
Oronoque Village 289 AGAWAM DR B, STRATFORD, CT, 06614, Stratford, CT 06614
$639,900

1 beds

|

3 baths

|

1,620 sq ft

|

Condo

289 AGAWAM DR B, STRATFORD, CT, 06614
Community: Oronoque Village
Oronoque Village 766 NYACK LN B, STRATFORD, CT, 06614, Stratford, CT 06614
$649,000

1 beds

|

3 baths

|

1,438 sq ft

|

Condo

766 NYACK LN B, 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.
Regency at Prospect 5 LILAC LN # 5, PROSPECT, CT, 06712, Prospect, CT 06712
$479,900

2 beds

|

3 baths

|

1,503 sq ft

|

Condo

5 LILAC LN # 5, PROSPECT, CT, 06712
Community: Regency at Prospect
Want to learn more about 55+ rental communities in Winsted? 55places can help!
Questions? Call us: (860) 909-8066
Regency at Woodbridge 12 WHISPER RIDGE WAY # 45, WOODBRIDGE, C..., Woodbridge, CT 06525
$679,000

3 beds

|

3 baths

|

Condo

12 WHISPER RIDGE WAY # 45, WOODBRIDGE, C...
Oronoque Village 183 APACHE LN A, STRATFORD, CT, 06614, Stratford, CT 06614
$499,900

2 beds

|

3 baths

|

1,426 sq ft

|

Condo

183 APACHE LN A, STRATFORD, CT, 06614
Community: Oronoque Village
Oronoque Village 87 CREEK LN A, STRATFORD, CT, 06614, Stratford, CT 06614
$420,000

1 beds

|

2 baths

|

1,454 sq ft

|

Condo

87 CREEK LN A, STRATFORD, CT, 06614
Community: Oronoque Village
Want to learn more about 55+ communities in Winsted? 55places can help!
Questions? Call us: (860) 909-8066
Oronoque Village 383 SEQUOIA LN A, STRATFORD, CT, 06614, Stratford, CT 06614
$635,000

1 beds

|

3 baths

|

1,360 sq ft

|

Condo

383 SEQUOIA LN A, STRATFORD, CT, 06614
Community: Oronoque Village
Bartlett Hill 9 PEAR ORCHARD RD # 9, PORTLAND, CT, 064..., Portland, CT 06480
$525,000

2 beds

|

3 baths

|

1,404 sq ft

9 PEAR ORCHARD RD # 9, PORTLAND, CT, 064...
Community: Bartlett Hill

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