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

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 Hills 512 HERITAGE HLS C, SOMERS, NY, 10589, Somers, NY 10589
$610,000

2 beds

|

2 baths

|

1,265 sq ft

|

Condo

512 HERITAGE HLS C, SOMERS, NY, 10589
Community: Heritage Hills
Heritage Hills 569 HERITAGE HILLS DR B, SOMERS, NY, 105..., Somers, NY 10589
$599,999

2 beds

|

2 baths

|

1,470 sq ft

|

Condo

569 HERITAGE HILLS DR B, SOMERS, NY, 105...
Community: Heritage Hills
Beckley Farms 91 SCENIC DR 91, BERLIN, CT, 06037, Berlin, CT 06037
$679,900

3 beds

|

3 baths

|

2,068 sq ft

|

Condo

91 SCENIC DR 91, BERLIN, CT, 06037
Community: Beckley Farms
Heritage Village 162 HERITAGE VLG D, SOUTHBURY, CT, 06488, Southbury, CT 06488
$249,000

2 beds

|

2 baths

|

1,076 sq ft

|

Condo

162 HERITAGE VLG D, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Hills 823 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589
$750,000

2 beds

|

3 baths

|

1,531 sq ft

|

Condo

823 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
Heritage Village 397 KRUEGER CIR A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$439,700

3 beds

|

2 baths

|

1,716 sq ft

|

Condo

397 KRUEGER CIR A, SOUTHBURY, CT, 06488
Community: Heritage Village
The Village at Oxford Greens 1073 AUGUSTA DR 1073, OXFORD, CT, 06478, Oxford, CT 06478
$629,900

2 beds

|

3 baths

|

2,232 sq ft

|

Condo

1073 AUGUSTA DR 1073, OXFORD, CT, 06478
Fairview at Oxford Greens 1073 AUGUSTA DR 1073, OXFORD, CT, 06478, Oxford, CT 06478
$629,900

2 beds

|

3 baths

|

2,232 sq ft

|

Condo

1073 AUGUSTA DR 1073, OXFORD, CT, 06478
Oronoque Village 55 BLACKHAWK LN B, STRATFORD, CT, 06614, Stratford, CT 06614
$639,000

2 beds

|

3 baths

|

1,360 sq ft

|

Condo

55 BLACKHAWK LN B, STRATFORD, CT, 06614
Community: Oronoque Village
Oronoque Village 209 ACORN LN B, STRATFORD, CT, 06614, Stratford, CT 06614
$554,000

2 beds

|

3 baths

|

1,438 sq ft

|

Condo

209 ACORN 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.
Heritage Village 633 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$400,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

633 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Village 626 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$289,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

626 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Hills 593 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589
$995,000

3 beds

|

2 baths

|

1,905 sq ft

|

Condo

593 HERITAGE HLS B, SOMERS, NY, 10589
Community: Heritage Hills
Heritage Hills 154 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589
$525,000

2 beds

|

2 baths

|

1,396 sq ft

|

Condo

154 HERITAGE HLS B, SOMERS, NY, 10589
Community: Heritage Hills
The Village at Buckingham 3 CAVENDISH PL 3, AVON, CT, 06001, Avon, CT 06001
$689,000

3 beds

|

3 baths

|

2,730 sq ft

3 CAVENDISH PL 3, AVON, CT, 06001
Jefferson Village 45 JEFFERSON OVAL G, YORKTOWN, NY, 10598, Yorktown, NY 10598
$429,900

2 beds

|

2 baths

|

1,100 sq ft

|

Condo

45 JEFFERSON OVAL G, YORKTOWN, NY, 10598
Community: Jefferson Village
Want to learn more about 55+ communities in Winsted? 55places can help!
Questions? Call us: (860) 909-8066
Heritage Hills 446 HERITAGE HLS D, SOMERS, NY, 10589, Somers, NY 10589
$679,000

2 beds

|

2 baths

|

1,559 sq ft

|

Condo

446 HERITAGE HLS D, SOMERS, NY, 10589
Community: Heritage Hills
Rivington 11 MERCY ST 11, DANBURY, CT, 06810, Danbury, CT 06810
$600,000

2 beds

|

4 baths

|

1,572 sq ft

|

Condo

11 MERCY ST 11, DANBURY, CT, 06810
Community: Rivington
Jefferson Village 18L HASTINGS CT, YORKTOWN, NY, 10598, Yorktown, NY 10598
$340,000

2 beds

|

1 baths

|

1,000 sq ft

|

Condo

18L HASTINGS CT, YORKTOWN, NY, 10598
Community: Jefferson Village
Heritage Village 149 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$198,000

1 beds

|

1 baths

|

928 sq ft

|

Condo

149 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.
Bidwell Village 94 STONEHOUSE RD 13, COVENTRY, CT, 06238, Coventry, CT 06238
$365,000

3 beds

|

4 baths

|

1,810 sq ft

|

Condo

94 STONEHOUSE RD 13, COVENTRY, CT, 06238
Community: Bidwell Village
Overlook 2011 SUMMIT LOOP 86, CARMEL, NY, 10512, Carmel, NY 10512
$936,000

2 beds

|

3 baths

|

2,873 sq ft

|

Condo

2011 SUMMIT LOOP 86, CARMEL, NY, 10512
Community: Overlook
Overlook 2037 SUMMIT LOOP 92, CARMEL, NY, 10512, Carmel, NY 10512
$899,000

2 beds

|

2 baths

|

2,102 sq ft

|

Condo

2037 SUMMIT LOOP 92, CARMEL, NY, 10512
Community: Overlook
Overlook 2055 SUMMIT LOOP 95, CARMEL, NY, 10512, Carmel, NY 10512
$905,000

2 beds

|

2 baths

|

2,102 sq ft

|

Condo

2055 SUMMIT LOOP 95, CARMEL, NY, 10512
Community: Overlook
Heritage Village 13 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$223,000

2 beds

|

2 baths

|

1,032 sq ft

|

Condo

13 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Sonoma Woods 35 SONOMA LN 35, MIDDLETOWN, CT, 06457, Middletown, CT 06457
$589,000

2 beds

|

3 baths

|

1,798 sq ft

|

Condo

35 SONOMA LN 35, MIDDLETOWN, CT, 06457
Community: Sonoma Woods
Heritage Village 955 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$269,900

2 beds

|

2 baths

|

1,398 sq ft

|

Condo

955 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
Spring Lake Village 28 COACH DR 28, SOUTHINGTON, CT, 06489, Southington, CT 06489
$230,000

2 beds

|

1 baths

|

985 sq ft

|

Condo

28 COACH DR 28, SOUTHINGTON, CT, 06489
Community: Spring Lake Village
The Village at Oxford Greens 155 COUNTRY CLUB DR 155, OXFORD, CT, 064..., Oxford, CT 06478
$659,000

3 beds

|

3 baths

|

2,908 sq ft

155 COUNTRY CLUB DR 155, OXFORD, CT, 064...
Heritage Village 616 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$375,000

2 beds

|

2 baths

|

1,398 sq ft

|

Condo

616 HERITAGE VLG B, 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.
Spring Lake Village 102 TIMBER RDG 102, SOUTHINGTON, CT, 064..., Southington, CT 06489
$210,000

1 beds

|

1 baths

|

920 sq ft

|

Condo

102 TIMBER RDG 102, SOUTHINGTON, CT, 064...
Community: Spring Lake Village
Heritage Village 886 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$414,900

2 beds

|

2 baths

|

1,398 sq ft

|

Condo

886 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Regency Meadows 17 REGENCY CIR, TRUMBULL, CT, 06611, Trumbull, CT 06611
$765,000

3 beds

|

4 baths

|

2,597 sq ft

|

Condo

17 REGENCY CIR, TRUMBULL, CT, 06611
Community: Regency Meadows
Heritage Hills 606 HERITAGE HLS F, SOMERS, NY, 10589, Somers, NY 10589
$874,900

2 beds

|

2 baths

|

1,860 sq ft

|

Condo

606 HERITAGE HLS F, SOMERS, NY, 10589
Community: Heritage Hills
Oronoque Village 71 DAKOTA LN A, STRATFORD, CT, 06614, Stratford, CT 06614
$600,000

1 beds

|

2 baths

|

1,375 sq ft

|

Condo

71 DAKOTA LN A, STRATFORD, CT, 06614
Community: Oronoque Village
Founders Village 2555 YOUNGS AVE 11A, SOUTHOLD, NY, 11971, Southold, NY 11971
$605,000

2 beds

|

2 baths

|

1,200 sq ft

|

Condo

2555 YOUNGS AVE 11A, SOUTHOLD, NY, 11971
Community: Founders Village
Jefferson Village 52 JEFFERSON OVAL A, YORKTOWN, NY, 10598, Yorktown, NY 10598
$430,000

2 beds

|

2 baths

|

1,100 sq ft

|

Condo

52 JEFFERSON OVAL A, YORKTOWN, NY, 10598
Community: Jefferson Village
Jefferson Village 27 WALDEN CT F, YORKTOWN, NY, 10598, Yorktown, NY 10598
$399,000

2 beds

|

1 baths

|

925 sq ft

|

Condo

27 WALDEN CT F, YORKTOWN, NY, 10598
Community: Jefferson Village
Want to learn more about 55+ communities in Winsted? 55places can help!
Questions? Call us: (860) 909-8066
Heritage Village 751 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$215,000

2 beds

|

2 baths

|

1,000 sq ft

|

Condo

751 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Regency at Fishkill 621 REGENCY DR, FISHKILL, NY, 12524, Fishkill, NY 12524
$499,000

1 beds

|

2 baths

|

1,499 sq ft

|

Condo

621 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.
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