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Cheshire, CT 55+ active adult communities & homes for sale
Living in Cheshire
Residents of 55+ communities in Cheshire are loving this New Haven County town. Located in an area surrounded by greenscapes and plenty of interesting natural features, the town…
Residents of 55+ communities in Cheshire are loving this New Haven County town. Located in an area surrounded by greenscapes and plenty of interesting natural features, the town also has a suburban culture with quiet neighborhoods and many local amenities like clubs and facilities that make it easy to find new hobbies.
Climate & Geography
The climate in Central Connecticut is categorized as humid continental, which features four distinct seasons. Summers are generally hot and humid, while winters are cold and snowy. Residents can expect higher-than-average amounts of rain and snow, and approximately 198 sunny days throughout the year.
Recreation, Culture & Entertainment
Some of the top attractions in Cheshire include Barker Character Comic and Cartoon Museum, Roaring Brook Park, Bartlem Park, Drazen Orchards, Cheshire Hollow Farm, and Cheshire Historical Society. The town also offers various programs for the community including transportation services into and out of town.
There are plentiful parks and outdoor spaces within the town where residents can get outside and enjoy nature, and additional outdoor recreation activities such as hiking, fishing, and skiing, can be found at the nearby Naugatuck State Park.
Cheshire is also within driving distance of Hartford and New Haven, providing the perfect opportunity for day trips and weekend getaways to enjoy everything these cities have to offer.
Cost of Living & Taxes
The cost of living in Cheshire is higher than the state and national average. This is primarily due to the high cost of housing and homes, while other factors like groceries, utilities, and transportation are just slightly higher than the national average.
The effective income tax rate is as low as three percent and as high as 6.99 percent. Retirement income including Social Security benefits are fully exempt for taxpayers with limited income. Other retirement income like military pensions and railroad retirement benefits are fully exempt. Qualifying homeowners 65+Â can also receive property tax credits as well as additional municipality tax reliefs.
Health Care
Residents of 55+ communities in Cheshire have several area health care options to choose from. Among them are various hospitals recognized by U.S. News for high performance in many procedures and conditions. The closest hospital is St. Mary’s Hospital in Waterbury, about six miles away. Other choices include the Hospital of Central Connecticut, Middlesex Hospital, Yale New Haven Hospital, Hartford Hospital, and St. Francis Hospital and Medical Center, all within 20 miles.
Frequently Asked Questions
In Cheshire, there is 1 small community with less than 500 homes.
The smallest 55+ community in Cheshire has 88 homes, the largest has 88 homes, and the average community consists of 88 homes.
No, there are no gated 55+ communities in Cheshire.
132 communities near Cheshire
298 homes near Cheshire
Relevance
2 beds
|2 baths
|1,078 sq ft
|Condo
2 beds
|2 baths
|1,130 sq ft
|Condo
2 beds
|2 baths
|1,624 sq ft
|Manufactured Home
2 beds
|2 baths
|1,860 sq ft
|Condo
3 beds
|3 baths
|3,760 sq ft
|Condo
1 beds
|2 baths
|1,375 sq ft
|Condo
2 beds
|2 baths
|1,695 sq ft
|Condo
2 beds
|2 baths
|2,036 sq ft
|Condo
2 beds
|3 baths
|2,104 sq ft
|Condo
2 beds
|3 baths
|1,874 sq ft
|Condo
2 beds
|3 baths
|1,998 sq ft
|Condo
1 beds
|1 baths
|684 sq ft
|Condo
3 beds
|3 baths
|2,620 sq ft
|House
2 beds
|2 baths
|1,733 sq ft
|Condo
2 beds
|2 baths
|1,200 sq ft
|Condo
2 beds
|3 baths
|1,700 sq ft
|House
2 beds
|2 baths
|1,100 sq ft
|Condo
2 beds
|1 baths
|925 sq ft
|Condo
1 beds
|3 baths
|1,426 sq ft
|Condo
2 beds
|1 baths
|1,085 sq ft
|Condo
2 beds
|1 baths
|1,020 sq ft
|Condo
1 beds
|1 baths
|684 sq ft
|Condo
2 beds
|2 baths
|1,000 sq ft
|Condo
2 beds
|2 baths
|1,483 sq ft
|Condo
2 beds
|2 baths
|1,867 sq ft
|Condo
2 beds
|3 baths
|2,516 sq ft
|Condo
3 beds
|2 baths
|1,500 sq ft
|Condo
1 beds
|1 baths
|1,017 sq ft
|Condo
3 beds
|3 baths
|1,922 sq ft
|Condo
2 beds
|2 baths
|1,205 sq ft
|Condo
2 beds
|2 baths
|1,308 sq ft
|Condo
3 beds
|3 baths
|3,327 sq ft
|Condo
2 beds
|2 baths
|1,420 sq ft
|Condo
3 beds
|3 baths
|2,744 sq ft
|Condo
2 beds
|3 baths
|1,426 sq ft
|Condo
1 beds
|1 baths
|845 sq ft
|Condo
1 beds
|2 baths
|1,213 sq ft
|Condo
2 beds
|3 baths
|1,860 sq ft
|Condo
1 beds
|1 baths
|850 sq ft
|Condo
2 beds
|2 baths
|1,483 sq ft
|Condo
Frequently Asked Questions
In Cheshire, there is 1 small community with less than 500 homes.
The smallest 55+ community in Cheshire has 88 homes, the largest has 88 homes, and the average community consists of 88 homes.
No, there are no gated 55+ communities in Cheshire.
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REIN updates its listings on a daily basis. Data last updated: Sep 19, 2026.
This application does not include information on all of the properties available for sale at this time.
