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

134 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
3 rating (2 reviews) Heritage Hills
$400ks - $1Ms
Heritage Hills, Somers, NY
Resale Only | Age-targeted | Built 1974 - 2006 | 2,600 homes
Oronoque Village
$200ks - $400ks
Oronoque Village, Stratford, CT
Resale Only | 55+ age-restricted | Built 1971 - 1977 | 929 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
Overlook
$600ks - $900ks
Overlook, Carmel, NY
New Construction | 55+ age-restricted | 300 homes
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Spring Lake Village
$100ks - $200ks
Spring Lake Village, Southington, CT
Resale Only | 55+ age-restricted | Built 1970 - 2004 | 640 homes
Rivington
$300ks - $900ks
Rivington, Danbury, CT
New and Resale | Age-targeted | Built 2006 - present | 1,050 homes
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
The Retreat at Carmel
$300ks - $800ks
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.
5 rating (1 reviews) Newtown Woods
$300ks - $500ks
Newtown Woods, Newtown, CT
New and Resale | 55+ age-restricted | Built 2011 - present | 178 homes
South Pond Village
$300ks - $400ks
South Pond Village, Bloomfield, CT
Resale Only | 55+ age-restricted | Built 1999 - 2005 | 151 homes
Fairview at Oxford Greens
$400ks - $600ks
Fairview at Oxford Greens, Oxford, CT
New and Resale | 55+ age-restricted | Built 2019 - present | 125 homes
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
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Questions? Call us: (860) 909-8066
The Village at Whispering...
$400ks
The Village at Whispering...Rotterdam, NY
New Construction | 55+ age-restricted | Built 2025 - present | 85 homes
Regency at Woodbridge
$500ks - $700ks
Regency at Woodbridge, Woodbridge, CT
New Construction | 55+ age-restricted | Built 2023 - present | 70 homes
Baldwin Station
$400ks
Baldwin Station, Milford, CT
Resale Only | 55+ age-restricted | Built 2001 - 2003 | 82 homes
The Gardens of Wilbraham
$200ks - $400ks
The Gardens of Wilbraham, Wilbraham, MA
New and Resale | 55+ age-restricted | Built 2005 - present | 108 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.
Liberty at Newtown
$300ks - $400ks
Liberty at Newtown, Newtown, CT
Resale Only | 55+ age-restricted | Built 2003 - 2007 | 96 homes
Bartlett Hill
$300ks - $400ks
Bartlett Hill, Portland, CT
Resale Only | 55+ age-restricted | Built 2005 - 2011 | 82 homes
5 rating (1 reviews) Paris Square
$600ks - $900ks
Paris Square, Northvale, NJ
New and Resale | 55+ age-restricted | Built 2000 - present | 88 homes
Oak Meadow Estates
$200ks - $300ks
Oak Meadow Estates, Torrington, CT
New and Resale | 55+ age-restricted | Built 2013 - present | 31 homes
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Questions? Call us: (860) 909-8066
Park Glen
$300ks - $500ks
Park Glen, New Milford, CT
Resale Only | 55+ age-restricted | Built 2006 - 2015 | 17 homes
Meadow Brook Estates
$300ks - $400ks
Meadow Brook Estates, Oxford, CT
Resale Only | 55+ age-restricted | Built 2003 - 2020 | 246 homes
Villas at Seminary Hill
$200ks - $300ks
Villas at Seminary Hill, Carmel, NY
New Construction | 55+ age-restricted | Built 2018 - present | 50 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
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 Fishkill
$300ks - $400ks
Regency at Fishkill, Fishkill, NY
Resale Only | 55+ age-restricted | Built 2008 - 2020 | 164 homes
The Village at Hunt Glen
$300ks
The Village at Hunt Glen, Granby, CT
Resale Only | 55+ age-restricted | Built 2003 - 2006 | 69 homes
Granite Woods
$600ks - $700ks
Granite Woods, Middlebury, CT
New Construction | 55+ age-restricted | Built 2020 - present | 24 homes
Regency at Wappinger
$500ks
Regency at Wappinger, Wappingers Falls, NY
Resale Only | 55+ age-restricted | Built 2014 - 2020 | 225 homes
Evergreen
$400ks - $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
Newington Ridge Preserve
$300ks - $400ks
Newington Ridge Preserve, Newington, CT
New Construction | 55+ age-restricted | Built 2014 - present | 16 homes
Boulder Brook
$200ks
Boulder Brook, Prospect, CT
Resale Only | 55+ age-restricted | Built 2004 - 2006 | 35 homes
Gloria Commons
$200ks - $300ks
Gloria Commons, Milford, CT
Resale Only | 55+ age-restricted | Built 2007 - 2015 | 50 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.
Long Hill Village
$300ks - $400ks
Long Hill Village, Trumbull, CT
Resale Only | 55+ age-restricted | Built 1997 - 1999 | 71 homes
RiverBend Estates
$400ks
RiverBend Estates, Oxford, CT
New and Resale | 55+ age-restricted | Built 2012 - present | 25 homes
Summer Wind Estates
$300ks - $400ks
Summer Wind Estates, North Haven, CT
New Construction | 55+ age-restricted | Built 2015 - present | 18 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
Want to learn more about 55+ communities in Winsted? 55places can help!
Questions? Call us: (860) 909-8066
Regency Meadows
$500ks
Regency Meadows, Trumbull, CT
Resale Only | 55+ age-restricted | Built 2003 - 2005 | 51 homes
Bidwell Village
$300ks - $400ks
Bidwell Village, Coventry, CT
New Construction | 55+ age-restricted | Built 2020 - present | 37 homes
1...2
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
Overlook 3014 EASTVIEW LN # 110, CARMEL, NY, 1051..., Carmel, NY 10512
$779,000

2 beds

|

3 baths

|

2,466 sq ft

|

Condo

3014 EASTVIEW LN # 110, CARMEL, NY, 1051...
Community: Overlook
Meadow Brook Estates 215 MEADOW BROOK RD 215, OXFORD, CT, 064..., Oxford, CT 06478
$589,000

3 beds

|

3 baths

|

2,207 sq ft

|

Condo

215 MEADOW BROOK RD 215, OXFORD, CT, 064...
Heritage Village 915 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$275,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

915 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Oronoque Village 445 NORTH TRL A, STRATFORD, CT, 06614, Stratford, CT 06614
$644,900

1 beds

|

3 baths

|

1,620 sq ft

|

Condo

445 NORTH TRL 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
Jefferson Village 50 JEFFERSON OVAL A, YORKTOWN HEIGHTS, N..., Yorktown Heights, NY 10598
$475,000

2 beds

|

2 baths

|

910 sq ft

|

Condo

50 JEFFERSON OVAL A, YORKTOWN HEIGHTS, N...
Community: Jefferson Village
Heritage Village 968 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$249,000

2 beds

|

2 baths

|

1,071 sq ft

|

Condo

968 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
South Pond Village 162 THISTLE POND DR 162, BLOOMFIELD, CT,..., Bloomfield, CT 06002
$395,000

2 beds

|

2 baths

|

1,341 sq ft

|

Condo

162 THISTLE POND DR 162, BLOOMFIELD, CT,...
Community: South Pond Village
The Village at Oxford Greens 117 COUNTRY CLUB DR 117, OXFORD, CT, 064..., Oxford, CT 06478
$639,900

3 beds

|

3 baths

|

2,666 sq ft

117 COUNTRY CLUB DR 117, OXFORD, CT, 064...
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 Village at Oxford Greens 301 FAIRWAY DR 301, OXFORD, CT, 06478, Oxford, CT 06478
$619,000

2 beds

|

2 baths

|

2,080 sq ft

|

Condo

301 FAIRWAY DR 301, OXFORD, CT, 06478
Granite Woods 35 NUTMEG RD D1, MIDDLEBURY, CT, 06762, Middlebury, CT 06762
$229,000

1 beds

|

1 baths

|

889 sq ft

|

Condo

35 NUTMEG RD D1, MIDDLEBURY, CT, 06762
Community: Granite Woods
Oronoque Village 635 N TRL B, STRATFORD, CT, 06614, Stratford, CT 06614
$420,000

1 beds

|

3 baths

|

1,454 sq ft

|

Condo

635 N TRL B, STRATFORD, CT, 06614
Community: Oronoque Village
Heritage Village 73 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$195,000

2 beds

|

2 baths

|

1,032 sq ft

|

Condo

73 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 607 CHAMPIONSHIP DR # 607, OXFORD, CT, 0..., Oxford, CT 06478
$650,000

3 beds

|

3 baths

|

2,731 sq ft

|

Condo

607 CHAMPIONSHIP DR # 607, OXFORD, CT, 0...
Paris Square 5309 RIO VISTA LN, NORTHVALE, NJ, 07647, Northvale, NJ 07647
$479,000

1 beds

|

1 baths

|

Condo

5309 RIO VISTA LN, NORTHVALE, NJ, 07647
Community: Paris Square
The Summit at Bethel 12 BRIAR RIDGE DR # 12, BETHEL, CT, 0680..., Bethel, CT 06801
$619,900

2 beds

|

3 baths

|

2,023 sq ft

|

Condo

12 BRIAR RIDGE DR # 12, BETHEL, CT, 0680...
Oronoque Village 13 ALGONQUIN LN C, STRATFORD, CT, 06614, Stratford, CT 06614
$399,000

1 beds

|

2 baths

|

1,330 sq ft

|

Condo

13 ALGONQUIN LN C, 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 140 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589
$645,000

3 beds

|

2 baths

|

1,689 sq ft

|

Condo

140 HERITAGE HLS A, SOMERS, NY, 10589
Community: Heritage Hills
The Village at Oxford Greens 185 COUNTRY CLUB DR # 185, OXFORD, CT, 0..., Oxford, CT 06478
$645,000

3 beds

|

3 baths

|

2,595 sq ft

|

Condo

185 COUNTRY CLUB DR # 185, OXFORD, CT, 0...
The Village at Oxford Greens 185 COUNTRY CLUB DR 185, OXFORD, CT, 064..., Oxford, CT 06478
$645,000

3 beds

|

3 baths

|

2,595 sq ft

185 COUNTRY CLUB DR 185, OXFORD, CT, 064...
Heritage Village 423 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$320,000

2 beds

|

2 baths

|

1,365 sq ft

|

Condo

423 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
Regency at Woodbridge 3 EDGEWOOD WAY # 26, WOODBRIDGE, CT, 065..., Woodbridge, CT 06525
$629,000

3 beds

|

3 baths

|

Condo

3 EDGEWOOD WAY # 26, WOODBRIDGE, CT, 065...
Regency at Woodbridge 5 WHISPER RIDGE WAY 49, WOODBRIDGE, CT, ..., Woodbridge, CT 06525
$749,000

3 beds

|

3 baths

|

Condo

5 WHISPER RIDGE WAY 49, WOODBRIDGE, CT, ...
Heritage Village 405 HERITAGE VLG D, SOUTHBURY, CT, 06488, Southbury, CT 06488
$199,900

2 beds

|

2 baths

|

1,044 sq ft

|

Condo

405 HERITAGE VLG D, SOUTHBURY, CT, 06488
Community: Heritage Village
Oronoque Village 446 HAMMERSTONE LN B, STRATFORD, CT, 066..., Stratford, CT 06614
$635,000

3 beds

|

3 baths

|

1,426 sq ft

|

Condo

446 HAMMERSTONE LN B, STRATFORD, CT, 066...
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 182 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589
$475,000

2 beds

|

2 baths

|

1,205 sq ft

|

Condo

182 HERITAGE HLS A, SOMERS, NY, 10589
Community: Heritage Hills
Oronoque Village 151 S TRL B, STRATFORD, CT, 06614, Stratford, CT 06614
$460,000

1 beds

|

3 baths

|

1,426 sq ft

|

Condo

151 S TRL B, STRATFORD, CT, 06614
Community: Oronoque Village
The Retreat at Carmel 4 FROST CT, CARMEL, NY, 10512, Carmel, NY 10512
$759,900

2 beds

|

3 baths

|

2,035 sq ft

|

Condo

4 FROST CT, CARMEL, NY, 10512
Heritage Village 761 HERITAGE VLG D, SOUTHBURY, CT, 06488, Southbury, CT 06488
$339,900

2 beds

|

2 baths

|

1,063 sq ft

|

Condo

761 HERITAGE VLG D, SOUTHBURY, CT, 06488
Community: Heritage Village
Liberty at Newtown 79 SUZIE DR # 79, NEWTOWN, CT, 06470, Newtown, CT 06470
$575,000

2 beds

|

3 baths

|

2,317 sq ft

|

Condo

79 SUZIE DR # 79, NEWTOWN, CT, 06470
Community: Liberty at Newtown
Want to learn more about 55+ communities in Winsted? 55places can help!
Questions? Call us: (860) 909-8066
Heritage Village 891 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$310,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

891 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Rivington 85 WINDING RIDGE WAY # 85, DANBURY, CT, ..., Danbury, CT 06810
$825,000

3 beds

|

4 baths

|

1,794 sq ft

|

Condo

85 WINDING RIDGE WAY # 85, DANBURY, CT, ...
Community: Rivington
The Retreat at Carmel 2 BLAIR HEIGHTS 3317, CARMEL, NY, 10512, Carmel, NY 10512
$459,900

2 beds

|

2 baths

|

1,323 sq ft

|

Condo

2 BLAIR HEIGHTS 3317, CARMEL, NY, 10512
Heritage Hills 537 HERITAGE HLS D, SOMERS, NY, 10589, Somers, NY 10589
$600,000

2 beds

|

2 baths

|

1,470 sq ft

|

Condo

537 HERITAGE HLS D, 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.
The Summit at Bethel 32 HUNTING RIDGE LN # 32, BETHEL, CT, 06..., Bethel, CT 06801
$689,000

3 beds

|

4 baths

|

2,090 sq ft

|

Condo

32 HUNTING RIDGE LN # 32, BETHEL, CT, 06...
Spring Lake Village 1 COACH DR # 1, SOUTHINGTON, CT, 06489, Southington, CT 06489
$279,900

2 beds

|

2 baths

|

1,323 sq ft

|

Condo

1 COACH DR # 1, SOUTHINGTON, CT, 06489
Community: Spring Lake Village
The Retreat at Carmel 14 LANGDON GRV, CARMEL, NY, 10512, Carmel, NY 10512
$679,900

3 beds

|

3 baths

|

3,000 sq ft

|

Condo

14 LANGDON GRV, CARMEL, NY, 10512
Spring Lake Village 621 OVERLOOK PATH # 621, SOUTHINGTON, CT..., Southington, CT 06489
$340,000

2 beds

|

3 baths

|

1,133 sq ft

|

Condo

621 OVERLOOK PATH # 621, SOUTHINGTON, CT...
Community: Spring Lake Village
Want to learn more about 55+ communities in Winsted? 55places can help!
Questions? Call us: (860) 909-8066
Heritage Village 98 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$319,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

98 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 331 HERITAGE VLG E, SOUTHBURY, CT, 06488, Southbury, CT 06488
$265,000

2 beds

|

2 baths

|

1,365 sq ft

|

Condo

331 HERITAGE VLG E, SOUTHBURY, CT, 06488
Community: Heritage Village
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