Living in Cheshire, CT
Cheshire is a New Haven County town of 32.84 square miles on Route 10, with the Farmington Canal Heritage Trail, Lock 12, Roaring Brook Falls and the Barker Character, Comic and Cartoon Museum.
Cheshire at a glance
- Median sale price
- $550,000+4.2% vs last year 335 sales, last 12 months
- Property tax rate
- 31.36 mills town-wide, FY2027
- Estimated yearly tax
- ~$12,100 median-priced home
- Population
- 30,610 2024 Census estimate
- Land area
- 32.8 sq mi 932 per sq mi
What it is like in Cheshire
Cheshire is in New Haven County, 15 miles from New Haven and 25 miles from Hartford. It covers 32.84 square miles of land, has a population of 30,610, and borders Prospect, Meriden, Wallingford, Southington, Waterbury and Hamden.
The area was settled in 1694 as part of Wallingford and incorporated as a town in 1780. Prospect was part of Cheshire until 1829. Cheshire is nicknamed the Bedding Plant Capital of Connecticut, and the center of population of Connecticut is in town. Cheshire Academy was founded in 1794.
The Cheshire Historic District, listed on the National Register in 1986, includes the First Congregational Church, Town Hall and the Hitchcock-Phillips House on Church Street.
Lock 12 Historical Park on North Brooksvale Road preserves a section of the Farmington Canal, and the Farmington Canal Heritage Trail runs through town. Roaring Brook Falls, owned by the Cheshire Land Trust, is Connecticut's tallest single-drop waterfall. Town parks include Cheshire Park, Bartlem Park, Mixville Park and Roaring Brook Park, and Cheshire also has Fresh Meadows Wildlife Sanctuary and Cran Preserve.
The Barker Character, Comic and Cartoon Museum on Highland Avenue holds about 80,000 items. Sweet Claude's Ice Cream is in the Ball & Socket Arts building on West Main Street, and Cheshire Coffee is on Old Towne Road. First Congregational Church hosts an annual Strawberry Festival.
Getting around from Cheshire
| Drive to | Time | Miles |
|---|---|---|
| Hartford | 34 min | 25 |
| New Haven | 22 min | 15 |
| Stamford | 75 min | 54 |
| New York City (Midtown) | 128 min | 90 |
| Boston | 156 min | 126 |
| Providence | 128 min | 100 |
| Bradley Airport (BDL) | 58 min | 40 |
Rail stations nearby
- Wallingford 5.4 mi Amtrak
- Meriden 5.6 mi CTrail Hartford Line, Amtrak
- Naugatuck 7.8 mi Metro-North
Highways and routes
Route 10 is the main north-south road, Routes 42, 68 and 70 run east-west, Interstate 691 runs along the northern edge of town and Interstate 84 passes through the northwest. Drive times: New Haven 22 minutes (15 miles), Hartford 34 minutes (25 miles), Bradley Airport 58 minutes (40 miles), Stamford 75 minutes (54 miles) and New York City Midtown 128 minutes (90 miles).
There is no rail station in town. The nearest are Wallingford (Amtrak, 5.4 miles), Meriden (CTrail Hartford Line and Amtrak, 5.6 miles) and Naugatuck (Metro-North, 7.8 miles).
Schools in Cheshire
7 public schools in Cheshire School District. Which one serves an address depends on the district, so confirm with them.
Elementary 5
- Chapman
- Darcey
- Doolittle
- Highland
- Norton
Middle 1
- Dodd
High school 1
- Cheshire High School
Grades, number of students. Hover a school for its address.
For report cards, enrollment trends and spending per student, look up Cheshire School District on the state's EdSight site.
Source: National Center for Education Statistics, Common Core of Data. We do not rate or rank schools.
Eat, drink and explore in Cheshire
Open Cheshire in Google Maps →Eat and drink 4
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Coffee shop serving lattes, a wide tea selection, pastries, bagels and sandwiches.
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Pizzeria serving pizza and Italian dishes with a rotating draft beer list.
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Family-owned ice cream shop making its own ice cream, now in the Ball & Socket Arts building.
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Italian restaurant and banquet facility serving entrees, sandwiches and pizza.
Things to do and see 4
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Museum holding about 80,000 character toys, lunch boxes and cartoon collectibles.
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1785 Georgian house on the green that is home to the Cheshire Historical Society.
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Restored Farmington Canal lock from 1828 to 1848 with a museum, a helicoidal bridge and a paved trail.
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Seasonal farm market on South Meriden Road that its own site says reopened under new management on September 20, 2025.
Parks, preserves and trails 50
Show 36 more parks and conservation parcels
Parks and open space © OpenStreetMap contributors. Places to eat and visit last checked October 2026. These are not paid placements; they are simply our selection. Hours and menus change, so check before you go.
Cheshire housing market
Over the last 12 months, 335 homes sold in Cheshire with a median sale price of $550,000 and a median of 9 days on market. There are 34 homes for sale right now.
Homes sold for a median of $269 per square foot. The typical home sold for 102% of its list price, and the median sale price is up 4.2% from the year before. At the current pace of sales, the homes for sale would last about 1.2 months.
Cheshire's town-wide property tax rate is 31.36 mills (FY2027). Connecticut assesses homes at 70% of market value, so a median-priced home pays roughly $12,100 a year. Special taxing districts, such as fire districts, can add to this, and a home's actual assessment may differ from its sale price.
Source: SmartMLS, residential sales (single-family, condo and multi-family); mill rates: Connecticut Office of Policy and Management. Updated November 10, 2026.
Homes for sale in Cheshire
See all 34 →
Know before you move
Official and independent sources worth bookmarking if you are considering Cheshire.
Questions about Cheshire
What is the median home price in Cheshire, CT?
The median sale price in Cheshire is $550,000, based on 335 home sales in the last 12 months (SmartMLS). Updated November 10, 2026.
What is the property tax rate in Cheshire, CT?
Cheshire's town-wide property tax rate is 31.36 mills (fiscal year 2027). Connecticut assesses homes at 70% of market value, so a median-priced home pays roughly $12,100 a year. Special taxing districts can add to this.
How far is Cheshire, CT from Hartford?
Cheshire is about 25 miles and a 34-minute drive from downtown Hartford, measured from the town center without traffic.
How far is Cheshire, CT from New York City?
Cheshire is about 90 miles from Midtown Manhattan, roughly a 128-minute drive without traffic.
Is there a train station in Cheshire, CT?
The closest passenger rail station we have on record is Wallingford (Amtrak) about 5.4 miles from the center of Cheshire. Check the operator's schedule for current service.
What is the population of Cheshire, CT?
Cheshire has about 30,610 residents (U.S. Census Bureau estimate, 2024) and covers 32.8 square miles.
How many public schools are in Cheshire, CT?
Cheshire has 7 public schools in Cheshire School District. Which school serves an address depends on the district's boundaries, so confirm with the district.
How many homes are for sale in Cheshire, CT?
There are 34 homes for sale in Cheshire right now, per SmartMLS, as of November 10, 2026.
Which rail stations are closest to Cheshire?
Wallingford (Amtrak, 5.4 miles), Meriden (CTrail Hartford Line and Amtrak, 5.6 miles) and Naugatuck (Metro-North, 7.8 miles).
How far is Cheshire from New Haven and Hartford?
New Haven is 15 miles and about 22 minutes by car. Hartford is 25 miles and about 34 minutes.
What is the Farmington Canal Heritage Trail?
A non-motorized trail that runs through Cheshire along the old Farmington Canal route. Lock 12 Historical Park on North Brooksvale Road preserves a canal lock beside it.
What is Roaring Brook Falls?
A waterfall in the southwest of Cheshire, owned by the Cheshire Land Trust, and Connecticut's tallest single-drop waterfall.
Which towns border Cheshire?
Prospect, Meriden, Wallingford, Southington, Waterbury and Hamden.
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