New Haven County · Updated September 26, 2026
Cheshire, CT real estate
Cheshire borders Southington, and it’s where many of my Southington clients look when they want more land.
The Cheshire market right now
Cheshire by the numbers
What I’m seeing
- Homes listed right now carry a median asking price of $559,900, well above the $467,500 median that homes actually sold for over the past year. Part of that is the mix of homes on the market today, and it’s the reason I price from closed sales rather than from other listings.
- Well-priced homes are moving fast. The typical listing has been on the market about 13 days.
- Inventory is tighter than a year ago: 66 single-family listings now versus 97 in October.
Sources: RentCast, from public sale records and current listing data, updated September 26, 2026. Sale records cover October 2025 to July 2026 and can trail the market by a few months. For an exact number on your home, request a Home Value Report.
Living in Cheshire
About Cheshire
Cheshire sits between Waterbury and New Haven, with quick access to I-691, I-84 and Route 10.
The town calls itself the Bedding Plant Capital of Connecticut, and the Farmington Canal Trail runs through it.
Most homes are single-family colonials and contemporaries on larger lots, with condo communities such as Copper Hill for buyers who want less upkeep.
A tip from Stanley
Cheshire homes often sit on an acre or more. Well, septic and lot condition can move value as much as the kitchen, so I check the town record for those before we set a price.
Thinking about a move in Cheshire?
Call or text 860-329-4820, or send me a note. I’m happy to talk through timing, price or anything else, with no pressure.
More town guides: SouthingtonWallingfordMeridenPlantsvilleBerlinPlainvilleBristolEast LymeAll towns