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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
Of the 1 55+ community in Cheshire, it is for sale. By size, 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
309 homes near Cheshire
Relevance
2 beds
|2 baths
|1,123 sq ft
|Condo
2 beds
|2 baths
|1,592 sq ft
|Condo
2 beds
|1 baths
|1,085 sq ft
|Condo
2 beds
|2 baths
|1,078 sq ft
|Condo
2 beds
|2 baths
|1,000 sq ft
|Condo
1 beds
|1 baths
|684 sq ft
|Condo
2 beds
|2 baths
|1,234 sq ft
|Condo
2 beds
|3 baths
|1,452 sq ft
2 beds
|2 baths
|1,168 sq ft
|Condo
1 beds
|1 baths
|928 sq ft
|Condo
2 beds
|2 baths
|1,379 sq ft
|Condo
2 beds
|1 baths
|1,036 sq ft
|House
2 beds
|1 baths
|720 sq ft
|Mobile Home
2 beds
|3 baths
|1,988 sq ft
|Condo
2 beds
|1 baths
|1,085 sq ft
|Condo
2 beds
|2 baths
|1,500 sq ft
|Condo
3 beds
|3 baths
|2,500 sq ft
|Condo
2 beds
|2 baths
|1,386 sq ft
|Condo
2 beds
|3 baths
|2,164 sq ft
|Condo
1 beds
|3 baths
|2,660 sq ft
|Condo
2 beds
|2 baths
|1,313 sq ft
|Condo
2 beds
|3 baths
|1,426 sq ft
|Condo
2 beds
|3 baths
|2,184 sq ft
|Condo
2 beds
|2 baths
|1,247 sq ft
|Condo
2 beds
|3 baths
|1,328 sq ft
|Condo
2 beds
|2 baths
|1,248 sq ft
|Manufactured Home
2 beds
|2 baths
|1,370 sq ft
|Condo
Frequently Asked Questions
Of the 1 55+ community in Cheshire, it is for sale. By size, 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: Nov 14, 2026.
This application does not include information on all of the properties available for sale at this time.
