Cheshire, CT
Buying or selling a home in Cheshire
Cheshire is one of the most popular towns in the area for families, and it's easy to see why: a highly rated school district, a walkable town center, and homes set back on tree-lined streets. I work with buyers and sellers in Cheshire throughout the year, from first-time buyers to families trading up.
About the town
What Cheshire is like
Cheshire is a town of about 29,000 in New Haven County, settled in 1694 and known as the Bedding Plant Capital of Connecticut for its long greenhouse and nursery history. It's a bedroom community with a strong school system and easy access to both New Haven and Hartford.
Market note
Cheshire homes sell steadily, and the good schools keep demand strong. The right price depends on your street, your condition, and what's sold nearby in the last six months. I'll put together the comps before we set a number.
Population
About 29,000 residents (2020 U.S. Census)
Commute
About 20 to 25 minutes to New Haven via Route 10 and roughly 30 to 35 minutes to Hartford via I-84. It works well for commuters to either city.
Schools
Cheshire Public Schools are consistently rated among the top districts in Connecticut. Cheshire High School is well regarded, and the district includes highly rated elementary and middle schools.
Homes for sale
Browse current listings in Cheshire on my Berkshire Hathaway site , or tell me what you're looking for and I'll send you homes as they come up.
Local favorites
Places Cheshire residents actually go
A few spots worth knowing when you're checking out the town.
A local spot for coffee and lunch on West Main Street.
A roastery and cafe on South Main Street.
A neighborhood coffee stop on Old Towne Road.
A craft brewery on Diana Court pouring hop-forward IPAs, including its flagship Headway, in a popular taproom.
An 80-foot waterfall in the southwestern hills with a short, rewarding hike to a lookout.
A flat, paved rail trail that runs right through Cheshire, popular with walkers, runners, and cyclists.
A beloved local homemade ice cream spot since 1988, now at 493 W Main St at Ball & Socket Arts.
Want more ideas? See what’s happening in Cheshire.
Thinking about Cheshire?
I know Cheshire street by street. Whether you're buying, selling, or just getting oriented, let's talk.