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Winsted, CT 55+ active adult communities & homes for sale - Page 5

Living in Winsted

Winsted is a town in Litchfield County, Connecticut, west of the capital city, Hartford. Its affordable cost of living and neighborly communities have made 55+ communities in…

Winsted is a town in Litchfield County, Connecticut, west of the capital city, Hartford. Its affordable cost of living and neighborly communities have made 55+ communities in Winsted an attractive option for retirees.

Climate & Geography

Winsted is located in western Connecticut, south of the Massachusetts border. Residents can expect four distinct seasons with an average temperature in the 80s during summer and 30s during winter. Winsted also experiences more rain and snow than the national average.

Recreation, Culture & Entertainment

Residents of Winsted can enjoy historical museums and landmarks such as the American Museum of Tort Law, Soldiers’ Monument and Memorial Park, Winchester Historical Society and the Whiting Mills Museum which centers around Winsted’s beginnings as a mill town.

Those in search of a small town atmosphere with friendly residents will find exactly that in Winsted. There are plenty of local businesses, cafes, and antique shops. The city is also home to a few outdoor adventures including Platt Hill State Park Scenic Reserve, where residents can take a hike, go sightseeing, fishing, and more.

Cost of Living & Taxes

Compared to the rest of the nation, the overall cost of living in Winsted is 10.5 percent lower than the U.S average. This is primarily due to the cost of housing which is well below the national median.

If a person’s gross income is below $75,000, then their Social Security benefits are exempt from taxation. Otherwise, there is a 25 percent tax rate applied to these benefits. Military pensions, however, are untaxed statewide. Residents of Winsted 55+ communities will be glad to know there are tax breaks available for residents who are 65 and older, including a property tax credit for homeowners who meet certain income criteria. Connecticut has a statewide sales tax rate of 6.35 percent.

Frequently Asked Questions


180 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 - $900ks
Heritage Hills, Somers, NY
Resale Only | Age-targeted | Built 1974 - 2006 | 2,600 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
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
Rivington
$300ks - $900ks
Rivington, Danbury, CT
New and Resale | Age-targeted | Built 2006 - present | 1,050 homes
Want to learn more about 55+ communities in Winsted? 55places can help!
Questions? Call us: (860) 909-8066
5 rating (2 reviews) Oronoque Village
$200ks - $400ks
Oronoque Village, Stratford, CT
Resale Only | 55+ age-restricted | Built 1971 - 1977 | 929 homes
Fairview at Oxford Greens
$400ks - $600ks
Fairview at Oxford Greens, Oxford, CT
New and Resale | 55+ age-restricted | Built 2019 - present | 125 homes
5 rating (1 reviews) Newtown Woods
$300ks - $500ks
Newtown Woods, Newtown, CT
New and Resale | 55+ age-restricted | Built 2011 - present | 178 homes
Meadow Brook Estates
$300ks - $400ks
Meadow Brook Estates, Oxford, CT
Resale Only | 55+ age-restricted | Built 2003 - 2020 | 246 homes
Regency at Fishkill
$300ks - $400ks
Regency at Fishkill, Fishkill, NY
Resale Only | 55+ age-restricted | Built 2008 - 2020 | 164 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 - $900ks
Overlook, Carmel, NY
New Construction | 55+ age-restricted | 300 homes
Spring Lake Village
$100ks - $200ks
Spring Lake Village, Southington, CT
Resale Only | 55+ age-restricted | Built 1970 - 2004 | 640 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
Regency at Woodbridge
$500ks - $700ks
Regency at Woodbridge, Woodbridge, CT
New Construction | 55+ age-restricted | Built 2023 - present | 70 homes
Granite Woods
$600ks - $700ks
Granite Woods, Middlebury, CT
New Construction | 55+ age-restricted | Built 2020 - present | 24 homes
Regency Meadows
$500ks
Regency Meadows, Trumbull, CT
Resale Only | 55+ age-restricted | Built 2003 - 2005 | 51 homes
Want to learn more about 55+ communities in Winsted? 55places can help!
Questions? Call us: (860) 909-8066
Regency at Prospect
$300ks - $400ks
Regency at Prospect, Prospect, CT
Resale Only | 55+ age-restricted | Built 2006 - 2020 | 379 homes
Liberty at Newtown
$300ks - $400ks
Liberty at Newtown, Newtown, CT
Resale Only | 55+ age-restricted | Built 2003 - 2007 | 96 homes
The Summit at Bethel
$500ks - $700ks
The Summit at Bethel, Bethel, CT
Resale Only | 55+ age-restricted | Built 2010 - 2021 | 235 homes
The Village at Buckingham
$300ks - $400ks
The Village at Buckingham, Avon, CT
Resale Only | 55+ age-restricted | Built 2002 - 2006 | 56 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.
Sonoma Woods
$300ks
Sonoma Woods, Middletown, CT
Resale Only | 55+ age-restricted | Built 2005 - 2015 | 68 homes
Pond Spring Village
$300ks
Pond Spring Village, Beacon Falls, CT
New and Resale | 55+ age-restricted | Built 2005 - present | 92 homes
1 rating (1 reviews) Beckley Farms
$300ks - $400ks
Beckley Farms, Berlin, CT
New and Resale | 55+ age-restricted | Built 2010 - present | 170 homes
5 rating (3 reviews) Founders Ridge
$300ks - $400ks
Founders Ridge, Middletown, CT
New Construction | 55+ age-restricted | Built 2017 - present | 75 homes
Billingsgate
$400ks - $600ks
Billingsgate, Simsbury, CT
Resale Only | 55+ age-restricted | Built 2003 - 2006 | 37 homes
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
Want to learn more about 55+ communities in Winsted? 55places can help!
Questions? Call us: (860) 909-8066
Bidwell Village
$300ks - $400ks
Bidwell Village, Coventry, CT
New Construction | 55+ age-restricted | Built 2020 - present | 37 homes
South Pond Village
$300ks - $400ks
South Pond Village, Bloomfield, CT
Resale Only | 55+ age-restricted | Built 1999 - 2005 | 151 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.
Woodcrest at Jacobs Hill
$200ks - $300ks
Woodcrest at Jacobs Hill, Cortlandt, NY
Resale Only | 55+ age-restricted | Built 2005 - 2006 | 58 homes
Founders Village
$400ks - $500ks
Founders Village, Southold, NY
Resale Only | 55+ age-restricted | Built 1981 - 1985 | 92 homes
The Village at Whispering...
$400ks
The Village at Whispering...Rotterdam, NY
New Construction | 55+ age-restricted | Built 2025 - present | 85 homes
The Cottages at Wire Mill
$1Ms
The Cottages at Wire Mill, Stamford, CT
New Construction | 55+ age-restricted | Built 2026 - present | 9 homes
Hopmeadow Place
$200ks - $300ks
Hopmeadow Place, Simsbury, CT
Resale Only | 55+ age-restricted | Built 2005 - 2005 | 66 homes
Clockmaker's Hill
$100ks
Clockmaker's Hill, Winsted, CT
Resale Only | 55+ age-restricted | Built 2005 - 2014 | 38 homes
Oak Meadow Estates
$200ks - $300ks
Oak Meadow Estates, Torrington, CT
New and Resale | 55+ age-restricted | Built 2013 - present | 31 homes
Newbury Village
$400ks - $500ks
Newbury Village, Brookfield, CT
New and Resale | 55+ age-restricted | Built 2005 - present | 120 homes
Want to learn more about 55+ communities in Winsted? 55places can help!
Questions? Call us: (860) 909-8066
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
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.
1...2
Heritage Village 191 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$574,900

3 beds

|

2 baths

|

1,716 sq ft

|

Condo

191 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
The Cottages at Wire Mill 16 WIRE MILL RD A, STAMFORD, CT, 06903, Stamford, CT 06903
$1,495,000

3 beds

|

4 baths

|

3,244 sq ft

16 WIRE MILL RD A, STAMFORD, CT, 06903
Jefferson Village 5 DEVON CT B, YORKTOWN, NY, 10598, Yorktown, NY 10598
$323,000

2 beds

|

1 baths

|

989 sq ft

|

Condo

5 DEVON CT B, YORKTOWN, NY, 10598
Community: Jefferson Village
Jefferson Village 27 WALDEN CT J, YORKTOWN, NY, 10598, Yorktown, NY 10598
$349,900

1 beds

|

1 baths

|

800 sq ft

|

Condo

27 WALDEN CT J, YORKTOWN, NY, 10598
Community: Jefferson Village
Billingsgate 14 BILLINGSGATE DR 14, SIMSBURY, CT, 060..., Simsbury, CT 06070
$750,000

2 beds

|

3 baths

|

2,729 sq ft

|

Condo

14 BILLINGSGATE DR 14, SIMSBURY, CT, 060...
Community: Billingsgate
Want to learn more about 55+ communities in Winsted? 55places can help!
Questions? Call us: (860) 909-8066
The Village at Oxford Greens 567 INVERNESS CT 567, OXFORD, CT, 06478, Oxford, CT 06478
$650,000

2 beds

|

2 baths

|

2,008 sq ft

|

Condo

567 INVERNESS CT 567, OXFORD, CT, 06478
Heritage Village 10 HERITAGE CIR A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$353,900

3 beds

|

2 baths

|

1,716 sq ft

|

Condo

10 HERITAGE CIR A, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 1 HERITAGE VLG C, SOUTHBURY, CT, 06488, Southbury, CT 06488
$225,000

2 beds

|

2 baths

|

1,044 sq ft

|

Condo

1 HERITAGE VLG C, SOUTHBURY, CT, 06488
Community: Heritage Village
Oronoque Village 93 SEMINOLE LN B, STRATFORD, CT, 06614, Stratford, CT 06614
$539,000

2 beds

|

3 baths

|

2,542 sq ft

|

Condo

93 SEMINOLE LN B, STRATFORD, CT, 06614
Community: Oronoque Village
Liberty at Newtown 25 FRANKLIN CT 25, NEWTOWN, CT, 06470, Newtown, CT 06470
$499,000

2 beds

|

2 baths

|

1,413 sq ft

|

Condo

25 FRANKLIN CT 25, NEWTOWN, CT, 06470
Community: Liberty at Newtown
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 527 PUTTING GREEN LN 527, OXFORD, CT, 06..., Oxford, CT 06478
$650,000

3 beds

|

3 baths

|

2,008 sq ft

|

Condo

527 PUTTING GREEN LN 527, OXFORD, CT, 06...
Regency Meadows 108 IMPERIAL CT 108, TRUMBULL, CT, 06611, Trumbull, CT 06611
$719,000

2 beds

|

3 baths

|

2,891 sq ft

|

Condo

108 IMPERIAL CT 108, TRUMBULL, CT, 06611
Community: Regency Meadows
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
Heritage Village 14 HERITAGE CIR B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$239,000

2 beds

|

2 baths

|

1,000 sq ft

|

Condo

14 HERITAGE CIR B, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 59 HERITAGE VLG F, SOUTHBURY, CT, 06488, Southbury, CT 06488
$209,000

2 beds

|

2 baths

|

1,308 sq ft

|

Condo

59 HERITAGE VLG F, SOUTHBURY, CT, 06488
Community: Heritage Village
Oronoque Village 638A ONONDAGA LN, STRATFORD, CT, 06614, Stratford, CT 06614
$499,900

1 beds

|

3 baths

|

1,175 sq ft

|

Condo

638A ONONDAGA LN, 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 51 JEFFERSON OVAL F, YORKTOWN, NY, 10598, Yorktown, NY 10598
$419,000

2 beds

|

2 baths

|

1,100 sq ft

|

Condo

51 JEFFERSON OVAL F, YORKTOWN, NY, 10598
Community: Jefferson Village
Heritage Village 930 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$419,900

2 beds

|

2 baths

|

1,398 sq ft

|

Condo

930 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 405 HERITAGE VLG D, SOUTHBURY, CT, 06488, Southbury, CT 06488
$159,999

2 beds

|

2 baths

|

1,044 sq ft

|

Condo

405 HERITAGE VLG D, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 73 HERITAGE VLG C, SOUTHBURY, CT, 06488, Southbury, CT 06488
$199,900

2 beds

|

2 baths

|

1,044 sq ft

|

Condo

73 HERITAGE VLG C, 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.

Frequently Asked Questions


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Want to learn more about 55+ communities in Winsted?

Call us: (860) 909-8066
180 homes
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