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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
308 homes near Cheshire
Relevance
2 beds
|2 baths
|1,078 sq ft
|Condo
2 beds
|2 baths
|1,000 sq ft
|Condo
3 beds
|2 baths
|1,792 sq ft
|Manufactured Home
2 beds
|3 baths
|1,941 sq ft
|Condo
2 beds
|1 baths
|890 sq ft
|Condo
6 beds
|5 baths
|4,333 sq ft
|House
2 beds
|2 baths
|1,134 sq ft
|House
3 beds
|3 baths
|2,620 sq ft
|Condo
3 beds
|3 baths
|2,531 sq ft
|Condo
2 beds
|2 baths
|1,476 sq ft
|Condo
3 beds
|2 baths
|1,909 sq ft
|Condo
2 beds
|2 baths
|1,070 sq ft
|Condo
2 beds
|3 baths
|1,920 sq ft
|Condo
1 beds
|1 baths
|953 sq ft
|Condo
2 beds
|2 baths
|1,226 sq ft
|Condo
2 beds
|1 baths
|938 sq ft
|Condo
2 beds
|2 baths
|1,096 sq ft
|Condo
2 beds
|2 baths
|1,321 sq ft
|Condo
2 beds
|3 baths
|1,370 sq ft
|Condo
2 beds
|2 baths
|1,027 sq ft
|Condo
3 beds
|2 baths
|1,368 sq ft
|House
2 beds
|3 baths
|1,700 sq ft
|Condo
2 beds
|3 baths
|1,378 sq ft
|Condo
3 beds
|3 baths
|2,412 sq ft
|Condo
2 beds
|2 baths
|1,420 sq ft
|Condo
2 beds
|2 baths
|1,285 sq ft
|Condo
2 beds
|1 baths
|836 sq ft
|Condo
2 beds
|2 baths
|1,306 sq ft
|Condo
3 beds
|2 baths
|1,716 sq ft
|Condo
2 beds
|2 baths
|1,168 sq ft
|Condo
2 beds
|2 baths
|1,170 sq ft
|Condo
2 beds
|2 baths
|1,432 sq ft
|Condo
2 beds
|2 baths
|1,447 sq ft
|Condo
2 beds
|2 baths
|1,000 sq ft
|Condo
2 beds
|2 baths
|1,328 sq ft
|Condo
2 beds
|2 baths
|1,390 sq ft
|Condo
2 beds
|3 baths
|1,030 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: Oct 09, 2026.
This application does not include information on all of the properties available for sale at this time.
