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

163 homes near Winsted

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3.6 rating (7 reviews) Heritage Village
$200ks - $500ks
Heritage Village, Southbury, CT
Resale Only | 55+ age-restricted | Built 1967 - 2005 | 2,580 homes
Oronoque Village
$200ks - $400ks
Oronoque Village, Stratford, CT
Resale Only | 55+ age-restricted | Built 1971 - 1977 | 929 homes
3 rating (2 reviews) Heritage Hills
$400ks - $800ks
Heritage Hills, Somers, NY
Resale Only | Age-targeted | Built 1974 - 2006 | 2,600 homes
Overlook
$600ks - $900ks
Overlook, Carmel, NY
New Construction | 55+ age-restricted | 300 homes
4 rating (1 reviews) Jefferson Village
$100ks - $500ks
Jefferson Village, Yorktown Heights, NY
Resale Only | 55+ age-restricted | Built 1967 - 1982 | 1,000 homes
Want to learn more about 55+ communities in Winsted? 55places can help!
Questions? Call us: (860) 909-8066
The Village at Oxford Gre...
$400ks - $500ks
The Village at Oxford Gre..., Oxford, CT
New and Resale | 55+ age-restricted | Built 2004 - present | 835 homes
Fairview at Oxford Greens
$400ks - $600ks
Fairview at Oxford Greens, Oxford, CT
New and Resale | 55+ age-restricted | Built 2019 - present | 125 homes
Spring Lake Village
$100ks - $200ks
Spring Lake Village, Southington, CT
Resale Only | 55+ age-restricted | Built 1970 - 2004 | 640 homes
Regency at Fishkill
$300ks - $400ks
Regency at Fishkill, Fishkill, NY
Resale Only | 55+ age-restricted | Built 2008 - 2020 | 164 homes
Liberty at Newtown
$300ks - $400ks
Liberty at Newtown, Newtown, CT
Resale Only | 55+ age-restricted | Built 2003 - 2007 | 96 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.
Rivington
$300ks - $900ks
Rivington, Danbury, CT
New and Resale | Age-targeted | Built 2006 - present | 1,050 homes
5 rating (1 reviews) Newtown Woods
$300ks - $500ks
Newtown Woods, Newtown, CT
New and Resale | 55+ age-restricted | Built 2011 - present | 178 homes
The Gardens of Wilbraham
$200ks - $400ks
The Gardens of Wilbraham, Wilbraham, MA
New and Resale | 55+ age-restricted | Built 2005 - present | 108 homes
Regency at Prospect
$300ks - $400ks
Regency at Prospect, Prospect, CT
Resale Only | 55+ age-restricted | Built 2006 - 2020 | 379 homes
Oak Meadow Estates
$200ks - $300ks
Oak Meadow Estates, Torrington, CT
New and Resale | 55+ age-restricted | Built 2013 - present | 31 homes
South Pond Village
$300ks - $400ks
South Pond Village, Bloomfield, CT
Resale Only | 55+ age-restricted | Built 1999 - 2005 | 151 homes
Want to learn more about 55+ communities in Winsted? 55places can help!
Questions? Call us: (860) 909-8066
The Powder Forest Homes
$500ks - $700ks
The Powder Forest Homes, Simsbury, CT
Resale Only | 55+ age-restricted | Built 2006 - 2016 | 182 homes
Regency Meadows
$500ks
Regency Meadows, Trumbull, CT
Resale Only | 55+ age-restricted | Built 2003 - 2005 | 51 homes
The Village at Whispering...
$400ks
The Village at Whispering...Rotterdam, NY
New Construction | 55+ age-restricted | Built 2025 - present | 85 homes
Newbury Village
$400ks - $500ks
Newbury Village, Brookfield, CT
New and Resale | 55+ age-restricted | Built 2005 - present | 120 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.
Applegate Estates
$500ks - $400ks
Applegate Estates, Southington, CT
New and Resale | 55+ age-restricted | Built 2010 - 2025 | 94 homes
The Summit at Bethel
$500ks - $700ks
The Summit at Bethel, Bethel, CT
Resale Only | 55+ age-restricted | Built 2010 - 2021 | 235 homes
Billingsgate
$400ks - $600ks
Billingsgate, Simsbury, CT
Resale Only | 55+ age-restricted | Built 2003 - 2006 | 37 homes
Stoneleigh Woods at Carme...
$400ks
Stoneleigh Woods at Carme..., Carmel, NY
Resale Only | 55+ age-restricted | Built 2012 - 2017 | 68 homes
The Retreat at Carmel
$300ks - $800ks
The Retreat at Carmel, Carmel, NY
Resale Only | 55+ age-restricted | Built 2008 - 2018 | 312 homes
Pond Spring Village
$300ks
Pond Spring Village, Beacon Falls, CT
New and Resale | 55+ age-restricted | Built 2005 - present | 92 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 Winsted? 55places can help!
Questions? Call us: (860) 909-8066
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
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.
Park Glen
$300ks - $500ks
Park Glen, New Milford, CT
Resale Only | 55+ age-restricted | Built 2006 - 2015 | 17 homes
Bidwell Village
$300ks - $400ks
Bidwell Village, Coventry, CT
New Construction | 55+ age-restricted | Built 2020 - present | 37 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
O'Meara Farm
$400ks
O'Meara Farm, Farmington, CT
Resale Only | 55+ age-restricted | Built 1998 - 2005 | 104 homes
Evergreen
$400ks - $500ks
Evergreen, Cromwell, CT
New and Resale | 55+ age-restricted | Built 2005 - present | 52 homes
Shaker Heights
$400ks - $500ks
Shaker Heights, Enfield, CT
New Construction | 55+ age-restricted | Built 2018 - present | 77 homes
Bramble Ridge
$300ks
Bramble Ridge, Suffield, CT
Resale Only | 55+ age-restricted | Built 2005 - 2015 | 47 homes
Want to learn more about 55+ communities in Winsted? 55places can help!
Questions? Call us: (860) 909-8066
Autumn Fields
$200ks - $300ks
Autumn Fields, Enfield, CT
Resale Only | 55+ age-restricted | Built 2004 - 2006 | 56 homes
Regency at Wappinger
$500ks
Regency at Wappinger, Wappingers Falls, NY
Resale Only | 55+ age-restricted | Built 2014 - 2020 | 225 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.
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Regency at Fishkill 811 REGENCY DR 802, FISHKILL, NY, 12524, Fishkill, NY 12524
$161,450

2 beds

|

2 baths

|

1,100 sq ft

|

Condo

811 REGENCY DR 802, FISHKILL, NY, 12524
Community: Regency at Fishkill
Newtown Woods 1011 BROOKSIDE CT 1011, NEWTOWN, CT, 064..., Newtown, CT 06470
$500,000

2 beds

|

2 baths

|

1,483 sq ft

|

Condo

1011 BROOKSIDE CT 1011, NEWTOWN, CT, 064...
Community: Newtown Woods
Heritage Village 18 HERITAGE CRST D, SOUTHBURY, CT, 06488, Southbury, CT 06488
$434,981

3 beds

|

2 baths

|

1,735 sq ft

|

Condo

18 HERITAGE CRST D, SOUTHBURY, CT, 06488
Community: Heritage Village
Fairview at Oxford Greens 1131 ST ANDREWS DR 50, OXFORD, CT, 06478, Oxford, CT 06478
$713,775

2 beds

|

3 baths

|

2,536 sq ft

|

Condo

1131 ST ANDREWS DR 50, OXFORD, CT, 06478
The Village at Oxford Greens 1131 ST ANDREWS DR 50, OXFORD, CT, 06478, Oxford, CT 06478
$713,775

2 beds

|

3 baths

|

2,536 sq ft

|

Condo

1131 ST ANDREWS DR 50, OXFORD, CT, 06478
Want to learn more about 55+ communities in Winsted? 55places can help!
Questions? Call us: (860) 909-8066
Heritage Village 28 HERITAGE CRST E, SOUTHBURY, CT, 06488, Southbury, CT 06488
$615,000

3 beds

|

2 baths

|

1,735 sq ft

|

Condo

28 HERITAGE CRST E, SOUTHBURY, CT, 06488
Community: Heritage Village
Paris Square 1302 RIO VISTA LN, NORTHVALE, NJ, 07647, Northvale, NJ 07647
$750,000

3 beds

|

2 baths

|

Condo

1302 RIO VISTA LN, NORTHVALE, NJ, 07647
Community: Paris Square
Jefferson Village 51 JEFFERSON OVAL E, YORKTOWN, NY, 10598, Yorktown, NY 10598
$455,000

2 beds

|

2 baths

|

1,100 sq ft

|

Condo

51 JEFFERSON OVAL E, YORKTOWN, NY, 10598
Community: Jefferson Village
Heritage Village 29 HERITAGE VLG D, SOUTHBURY, CT, 06488, Southbury, CT 06488
$305,000

2 beds

|

2 baths

|

1,076 sq ft

|

Condo

29 HERITAGE VLG D, SOUTHBURY, CT, 06488
Community: Heritage Village
Oronoque Village 513 OPA LN A, STRATFORD, CT, 06614, Stratford, CT 06614
$584,900

2 beds

|

3 baths

|

1,620 sq ft

|

Condo

513 OPA 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.
Heritage Hills 900 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589
$742,000

2 beds

|

3 baths

|

1,552 sq ft

|

Condo

900 HERITAGE HLS B, SOMERS, NY, 10589
Community: Heritage Hills
Oronoque Village 778 QUINNIPIAC LN A, STRATFORD, CT, 0661..., Stratford, CT 06614
$480,000

1 beds

|

3 baths

|

1,175 sq ft

|

Condo

778 QUINNIPIAC LN A, STRATFORD, CT, 0661...
Community: Oronoque Village
Heritage Village 411 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$469,000

2 beds

|

2 baths

|

1,398 sq ft

|

Condo

411 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Hills 33 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589
$565,000

2 beds

|

2 baths

|

1,320 sq ft

|

Condo

33 HERITAGE HLS A, SOMERS, NY, 10589
Community: Heritage Hills
Heritage Hills 101 HERITAGE HILLS DR A, SOMERS, NY, 105..., Somers, NY 10589
$649,000

2 beds

|

2 baths

|

1,500 sq ft

|

Condo

101 HERITAGE HILLS DR A, SOMERS, NY, 105...
Community: Heritage Hills
Heritage Village 132 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$424,900

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

132 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Want to learn more about 55+ communities in Winsted? 55places can help!
Questions? Call us: (860) 909-8066
Jefferson Village 113 VILLAGE RD C, YORKTOWN, NY, 10598, Yorktown, NY 10598
$420,000

2 beds

|

2 baths

|

1,200 sq ft

|

Condo

113 VILLAGE RD C, YORKTOWN, NY, 10598
Community: Jefferson Village
Oronoque Village 13 ALGONQUIN LN B, STRATFORD, CT, 06614, Stratford, CT 06614
$396,000

1 beds

|

2 baths

|

1,480 sq ft

|

Condo

13 ALGONQUIN LN B, STRATFORD, CT, 06614
Community: Oronoque Village
Heritage Village 877 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$284,000

2 beds

|

2 baths

|

1,365 sq ft

|

Condo

877 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
The Summit at Bethel 6 LOCKWOOD CIR 6, BETHEL, CT, 06801, Bethel, CT 06801
$619,000

3 beds

|

3 baths

|

1,771 sq ft

|

Condo

6 LOCKWOOD CIR 6, BETHEL, CT, 06801
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.
Pond Spring Village 37 SEPTEMBER LN 37, BEACON FALLS, CT, 06..., Beacon Falls, CT 06403
$450,000

2 beds

|

3 baths

|

1,328 sq ft

|

Condo

37 SEPTEMBER LN 37, BEACON FALLS, CT, 06...
Community: Pond Spring Village
Meadow Brook Estates 223 MEADOW BROOK RD 223, OXFORD, CT, 064..., Oxford, CT 06478
$589,900

2 beds

|

2 baths

|

1,480 sq ft

|

Condo

223 MEADOW BROOK RD 223, OXFORD, CT, 064...
Oronoque Village 261 AGAWAM DR A, STRATFORD, CT, 06614, Stratford, CT 06614
$525,000

2 beds

|

3 baths

|

1,620 sq ft

|

Condo

261 AGAWAM DR A, STRATFORD, CT, 06614
Community: Oronoque Village
Heritage Village 899 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$479,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

899 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Oronoque Village 209 ACORN LN B, STRATFORD, CT, 06614, Stratford, CT 06614
$599,000

1 beds

|

3 baths

|

1,438 sq ft

|

Condo

209 ACORN LN B, STRATFORD, CT, 06614
Community: Oronoque Village
The Powder Forest Homes 9 ASHTON CIR, SIMSBURY, CT, 06070, Simsbury, CT 06070
$650,000

2 beds

|

2 baths

|

1,809 sq ft

|

Condo

9 ASHTON CIR, SIMSBURY, CT, 06070
Applegate Estates 90 APPLE GATE 190, SOUTHINGTON, CT, 0648..., Southington, CT 06489
$450,000

2 beds

|

2 baths

|

1,350 sq ft

|

Condo

90 APPLE GATE 190, SOUTHINGTON, CT, 0648...
Community: Applegate Estates
Want to learn more about 55+ communities in Winsted? 55places can help!
Questions? Call us: (860) 909-8066
Regency Meadows 108 IMPERIAL CT 108, TRUMBULL, CT, 06611, Trumbull, CT 06611
$739,000

2 beds

|

3 baths

|

2,891 sq ft

|

Condo

108 IMPERIAL CT 108, TRUMBULL, CT, 06611
Community: Regency Meadows
Heritage Village 139 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$409,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

139 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Regency at Fishkill 246 REGENCY DR, FISHKILL, NY, 12524, Fishkill, NY 12524
$469,999

1 beds

|

2 baths

|

1,543 sq ft

|

Condo

246 REGENCY DR, FISHKILL, NY, 12524
Community: Regency at Fishkill
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 738 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$355,000

2 beds

|

2 baths

|

1,398 sq ft

|

Condo

738 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 69 HERITAGE VLG D, SOUTHBURY, CT, 06488, Southbury, CT 06488
$279,900

2 beds

|

2 baths

|

1,044 sq ft

|

Condo

69 HERITAGE VLG D, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 122 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$354,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

122 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 69 HERITAGE VLG C, SOUTHBURY, CT, 06488, Southbury, CT 06488
$260,000

2 beds

|

2 baths

|

1,044 sq ft

|

Condo

69 HERITAGE VLG C, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 170 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$349,900

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

170 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Oronoque Village 488 COMMANCHE LN A, STRATFORD, CT, 06614, Stratford, CT 06614
$575,000

2 beds

|

3 baths

|

1,438 sq ft

|

Condo

488 COMMANCHE LN A, STRATFORD, CT, 06614
Community: Oronoque Village
Jefferson Village 80 C INDEPENDENCE CT, YORKTOWN, NY, 1059..., Yorktown, NY 10598
$359,000

1 beds

|

1 baths

|

850 sq ft

|

Condo

80 C INDEPENDENCE CT, YORKTOWN, NY, 1059...
Community: Jefferson Village
Heritage Village 2 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$350,000

2 beds

|

2 baths

|

1,572 sq ft

|

Condo

2 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Want to learn more about 55+ communities in Winsted? 55places can help!
Questions? Call us: (860) 909-8066
The Village at Oxford Greens 505 TRADITIONS CT 505, OXFORD, CT, 06478, Oxford, CT 06478
$755,000

3 beds

|

3 baths

|

2,652 sq ft

|

Condo

505 TRADITIONS CT 505, OXFORD, CT, 06478
Heritage Village 916 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$379,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

916 HERITAGE VLG A, 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.
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