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Winsted, CT 55+ rental communities & homes for rent

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


1 communities near Winsted

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Want to learn more about 55+ rental communities in Winsted? 55places can help!
Questions? Call us: (860) 909-8066
Sylvan Woods Westchester
$3,031.06 - $4,811.06 / mo
Base rent from $2,895
Sylvan Woods Westchester, Buchanan, NY
New Construction | 55+ age-restricted | Built 2025 - present | 148 rental 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.
Jefferson Village 39 SUSSEX DR B, YORKTOWN, NY, 10598, Yorktown, NY 10598
$333,000

2 beds

|

2 baths

|

1,000 sq ft

|

Condo

39 SUSSEX DR B, YORKTOWN, NY, 10598
Community: Jefferson Village
New Long Hill Village 71 CIDER MILL LN, TRUMBULL, CT, 06611, Trumbull, CT 06611
$595,000

1 beds

|

3 baths

|

2,660 sq ft

|

Condo

71 CIDER MILL LN, TRUMBULL, CT, 06611
Community: Long Hill Village
New Spring Lake Village 504 CARRIAGE DR 504, SOUTHINGTON, CT, 06..., Southington, CT 06489
$319,900

2 beds

|

2 baths

|

1,313 sq ft

|

Condo

504 CARRIAGE DR 504, SOUTHINGTON, CT, 06...
Community: Spring Lake Village
New Heritage Village 425 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$200,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

425 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
New Oronoque Village 161 BISON LN A, STRATFORD, CT, 06614, Stratford, CT 06614
$575,000

2 beds

|

3 baths

|

1,426 sq ft

|

Condo

161 BISON 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
New Chatfield Farms 6 FIELDSTONE LN 6, BEACON FALLS, CT, 064..., Beacon Falls, CT 06403
$639,000

2 beds

|

3 baths

|

2,184 sq ft

|

Condo

6 FIELDSTONE LN 6, BEACON FALLS, CT, 064...
Community: Chatfield Farms
New Pond Spring Village 127 PONDVIEW CIR 127, BEACON FALLS, CT, ..., Beacon Falls, CT 06403
$465,000

2 beds

|

3 baths

|

1,328 sq ft

|

Condo

127 PONDVIEW CIR 127, BEACON FALLS, CT, ...
Community: Pond Spring Village
New Jefferson Village 36 SUSSEX DR A, YORKTOWN, NY, 10598, Yorktown, NY 10598
$350,000

1 beds

|

1 baths

|

725 sq ft

|

Condo

36 SUSSEX DR A, YORKTOWN, NY, 10598
Community: Jefferson Village
New Heritage Hills 343 HERITAGE HLS C, SOMERS, NY, 10589, Somers, NY 10589
$520,000

2 beds

|

2 baths

|

1,435 sq ft

|

Condo

343 HERITAGE HLS C, SOMERS, NY, 10589
Community: Heritage Hills
New Long Hill Village 36 CIDER MILL LN, TRUMBULL, CT, 06611, Trumbull, CT 06611
$525,000

2 beds

|

2 baths

|

1,370 sq ft

|

Condo

36 CIDER MILL LN, TRUMBULL, CT, 06611
Community: Long Hill 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.
New Heritage Hills 39 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589
$699,000

2 beds

|

2 baths

|

1,427 sq ft

|

Condo

39 HERITAGE HLS B, SOMERS, NY, 10589
Community: Heritage Hills
New Rivington 79 WINDING RIDGE WAY 79, DANBURY, CT, 06..., Danbury, CT 06810
$1,112,000

3 beds

|

4 baths

|

2,596 sq ft

|

Condo

79 WINDING RIDGE WAY 79, DANBURY, CT, 06...
Community: Rivington
New Heritage Hills 254 HERITAGE HLS C, SOMERS, NY, 10589, Somers, NY 10589
$829,000

3 beds

|

2 baths

|

1,780 sq ft

|

Condo

254 HERITAGE HLS C, SOMERS, NY, 10589
Community: Heritage Hills
New Spring Lake Village 261 CARRIAGE DR 261, SOUTHINGTON, CT, 06..., Southington, CT 06489
$375,000

2 beds

|

2 baths

|

1,207 sq ft

|

Condo

261 CARRIAGE DR 261, SOUTHINGTON, CT, 06...
Community: Spring Lake Village
New Heritage Hills 314 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589
$490,000

2 beds

|

2 baths

|

1,138 sq ft

|

Condo

314 HERITAGE HLS A, SOMERS, NY, 10589
Community: Heritage Hills
New The Powder Forest Homes 4 ASHTON CIR 4, SIMSBURY, CT, 06070, Simsbury, CT 06070
$729,000

2 beds

|

4 baths

|

2,381 sq ft

4 ASHTON CIR 4, SIMSBURY, CT, 06070
Want to learn more about 55+ communities in Winsted? 55places can help!
Questions? Call us: (860) 909-8066
Heritage Village 399 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$275,000

2 beds

|

2 baths

|

1,076 sq ft

|

Condo

399 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Hills 788 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589
$749,900

2 beds

|

2 baths

|

1,764 sq ft

|

Condo

788 HERITAGE HLS B, SOMERS, NY, 10589
Community: Heritage Hills
Jefferson Village 116 VILLAGE RD D, YORKTOWN, NY, 10598, Yorktown, NY 10598
$529,000

2 beds

|

2 baths

|

1,200 sq ft

|

Condo

116 VILLAGE RD D, YORKTOWN, NY, 10598
Community: Jefferson Village
Overlook 4052 FAIRWAYS DR 293, CARMEL, NY, 10512, Carmel, NY 10512
$699,000

3 beds

|

3 baths

|

2,274 sq ft

|

Condo

4052 FAIRWAYS DR 293, CARMEL, NY, 10512
Community: Overlook
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.
Meadow Brook Estates 107 MEADOW BROOK RD 107, OXFORD, CT, 064..., Oxford, CT 06478
$569,900

3 beds

|

3 baths

|

1,922 sq ft

|

Condo

107 MEADOW BROOK RD 107, OXFORD, CT, 064...
Jefferson Village 172 LONG HILL DR B, YORKTOWN, NY, 10598, Yorktown, NY 10598
$675,000

2 beds

|

2 baths

|

1,550 sq ft

|

Condo

172 LONG HILL DR B, YORKTOWN, NY, 10598
Community: Jefferson Village
Heritage Hills 897 HERITAGE HLS C, SOMERS, NY, 10589, Somers, NY 10589
$749,900

2 beds

|

3 baths

|

1,666 sq ft

|

Condo

897 HERITAGE HLS C, SOMERS, NY, 10589
Community: Heritage Hills
Heritage Village 27 HERITAGE CRST C, SOUTHBURY, CT, 06488, Southbury, CT 06488
$390,000

2 beds

|

2 baths

|

1,447 sq ft

|

Condo

27 HERITAGE CRST C, SOUTHBURY, CT, 06488
Community: Heritage Village
Regency at Prospect 146 SYCAMORE DR, PROSPECT, CT, 06712, Prospect, CT 06712
$529,900

2 beds

|

3 baths

|

1,850 sq ft

|

Condo

146 SYCAMORE DR, PROSPECT, CT, 06712
Community: Regency at Prospect
Regency at Wappinger 20 AVONDALE LN, WAPPINGER, NY, 12590, Wappinger, NY 12590
$745,000

3 beds

|

3 baths

|

2,056 sq ft

|

Condo

20 AVONDALE LN, WAPPINGER, NY, 12590
Whitney Glen 39 WHITNEY GLN 39, WESTPORT, CT, 06880, Westport, CT 06880
$925,000

2 beds

|

2 baths

|

1,600 sq ft

|

Condo

39 WHITNEY GLN 39, WESTPORT, CT, 06880
Community: Whitney Glen
Want to learn more about 55+ communities in Winsted? 55places can help!
Questions? Call us: (860) 909-8066
Heritage Village 809 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$329,900

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

809 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Sonoma Woods 2 SONOMA LN 2, MIDDLETOWN, CT, 06457, Middletown, CT 06457
$549,900

2 beds

|

3 baths

|

1,903 sq ft

2 SONOMA LN 2, MIDDLETOWN, CT, 06457
Community: Sonoma Woods
Heritage Village 45 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$289,900

2 beds

|

2 baths

|

1,032 sq ft

|

Condo

45 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.
Heritage Village 198 HERITAGE VLG B, SOUTHBURY, CT, 06488, Southbury, CT 06488
$325,000

2 beds

|

2 baths

|

1,432 sq ft

|

Condo

198 HERITAGE VLG B, SOUTHBURY, CT, 06488
Community: Heritage Village
Heritage Hills 449 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589
$630,000

2 beds

|

2 baths

|

1,472 sq ft

|

Condo

449 HERITAGE HLS B, SOMERS, NY, 10589
Community: Heritage Hills
Jefferson Village 149 FLINTLOCK WAY D, YORKTOWN, NY, 10598, Yorktown, NY 10598
$325,000

1 beds

|

1 baths

|

835 sq ft

|

Condo

149 FLINTLOCK WAY D, YORKTOWN, NY, 10598
Community: Jefferson Village
Heritage Village 62 HERITAGE VLG A, SOUTHBURY, CT, 06488, Southbury, CT 06488
$186,000

2 beds

|

2 baths

|

1,032 sq ft

|

Condo

62 HERITAGE VLG A, SOUTHBURY, CT, 06488
Community: Heritage Village
Oronoque Village 638 ONONDAGA LN A, STRATFORD, CT, 06614, Stratford, CT 06614
$485,000

1 beds

|

3 baths

|

1,175 sq ft

|

Condo

638 ONONDAGA LN A, STRATFORD, CT, 06614
Community: Oronoque Village
Pond Spring Village 41 PONDVIEW CIR 41, BEACON FALLS, CT, 06..., Beacon Falls, CT 06403
$485,000

2 beds

|

2 baths

|

1,501 sq ft

|

Condo

41 PONDVIEW CIR 41, BEACON FALLS, CT, 06...
Community: Pond Spring Village
Rivington 19 WARRINGTON ROUND 19, DANBURY, CT, 068..., Danbury, CT 06810
$749,000

3 beds

|

3 baths

|

2,196 sq ft

|

Condo

19 WARRINGTON ROUND 19, DANBURY, CT, 068...
Community: Rivington
Heritage Village 786 HERITAGE VLG C, SOUTHBURY, CT, 06488, Southbury, CT 06488
$295,000

2 beds

|

2 baths

|

1,000 sq ft

|

Condo

786 HERITAGE VLG C, SOUTHBURY, CT, 06488
Community: Heritage Village
Want to learn more about 55+ communities in Winsted? 55places can help!
Questions? Call us: (860) 909-8066
Overlook 4103 FAIRWAYS DR 152, CARMEL, NY, 10512, Carmel, NY 10512
$649,000

3 beds

|

3 baths

|

1,914 sq ft

|

Condo

4103 FAIRWAYS DR 152, CARMEL, NY, 10512
Community: Overlook
Overlook 4101 FAIRWAYS DR 151, CARMEL, NY, 10512, Carmel, NY 10512
$749,000

3 beds

|

4 baths

|

2,141 sq ft

|

Condo

4101 FAIRWAYS DR 151, CARMEL, NY, 10512
Community: Overlook
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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