Living in Chester, CT
Chester is a Middlesex County town on the lower Connecticut River, with a village center along Main Street and a ferry landing on Route 148.
Chester at a glance
- Median sale price
- $549,000−7.9% vs last year 43 sales, last 12 months
- Property tax rate
- 27.78 mills town-wide, FY2027
- Estimated yearly tax
- ~$10,700 median-priced home
- Population
- 3,748 2024 Census estimate
- Land area
- 16.1 sq mi 234 per sq mi
What it is like in Chester
Chester is in Middlesex County, in the lower Connecticut River Valley. It covers 16.05 square miles of land and had a population of 3,748 in the figures used for this guide.
The area was the site of a Native American village called Pattaquonk, and English settlement began in 1692. Chester was formed from the northern part of Saybrook and incorporated in 1836. A ferry across the Connecticut River has run from the town since 1769.
The village center is built around Main Street, where restaurants, galleries, a brewery and shops sit close together. The town borders Deep River, Killingworth, Haddam, East Haddam and Lyme. Whelen Engineering, a maker of warning lights and sirens, is headquartered in town.
Chester has a long list of open spaces, including the Village Green, North Quarter Park, Town Park at Jennings Pond, the Pattaconk Lake Boat Launch and the Connecticut Valley Railroad State Park Trail. Preserves include Constance Baker Motley Preserve, Scudder Preserve, Wood Preserve, Chester Creek Preserve and Carini Preserve.
Main Street has Grano Arso, River Tavern, OTTO Pizza, The Village Bistro and Little House Brewing Company, and Marker 37 sits on the waterfront at Chester Point Marina. The Chester Historical Society runs the Chester Museum at the Mill at 9 West Main Street. Goodspeed Musicals operates a second theatre, the Norma Terris Theatre, in town. Shops and galleries on Main Street stay open late for the First Friday Night Art Stroll.
Getting around from Chester
| Drive to | Time | Miles |
|---|---|---|
| Hartford | 47 min | 34 |
| New Haven | 50 min | 29 |
| Stamford | 105 min | 73 |
| New York City (Midtown) | 159 min | 109 |
| Boston | 164 min | 134 |
| Providence | 104 min | 83 |
| Bradley Airport (BDL) | 69 min | 48 |
Rail
No passenger rail station within 8 miles.
Highways and routes
Route 148 runs through Chester to the ferry landing. Drives are of 47 minutes (34 miles) to Hartford and 50 minutes (29 miles) to New Haven. Stamford is 105 minutes (73 miles) away and Midtown Manhattan is 159 minutes (109 miles). Bradley Airport is 69 minutes (48 miles) away.
The town has no rail station of its own. The Estuary Transit District runs its 9 Town Transit bus service through Chester and nearby towns, and a connection to the Old Saybrook train station is available by bus.
Schools in Chester
1 public school in Chester School District. Which one serves an address depends on the district, so confirm with them.
Elementary 1
- Chester
Grades, number of students. Hover a school for its address.
For report cards, enrollment trends and spending per student, look up Chester 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 Chester
Open Chester in Google Maps →Eat and drink 8
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Italian restaurant serving house-made pasta and bread, a tasting menu, wine and cocktails, with phone takeout.
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Scoop shop selling craft ice cream by the cone, plus pints, sundaes and ice cream cakes.
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Brewery and taproom in a nearly 200-year-old building with a rotating tap list and a beer garden.
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Waterfront restaurant at Chester Point Marina with a raw bar, indoor and patio seating, and a function space upstairs.
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Wood-fired pizzeria with salads, Italian-style dishes, craft beer and takeout or delivery.
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Restaurant with a daily-changing farm-to-table menu, cocktails and a wine list, open for lunch and dinner.
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Thai restaurant serving curries, noodle dishes and stir-fries for dine-in, takeout and delivery.
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Bistro serving New American dishes for dinner, with weekend brunch, a bar and a lounge.
Things to do and see 1
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Local history museum run by the Chester Historical Society in a former mill shop, with seasonal weekend hours.
Parks, preserves and trails 13
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.
Chester housing market
Over the last 12 months, 43 homes sold in Chester with a median sale price of $549,000 and a median of 11 days on market. There are 11 homes for sale right now.
Homes sold for a median of $294 per square foot. The typical home sold for 100% of its list price, and the median sale price is down 7.9% from the year before. At the current pace of sales, the homes for sale would last about 3.1 months.
Chester's town-wide property tax rate is 27.78 mills (FY2027). Connecticut assesses homes at 70% of market value, so a median-priced home pays roughly $10,700 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 Chester
See all 11 →
Know before you move
Official and independent sources worth bookmarking if you are considering Chester.
Questions about Chester
What is the median home price in Chester, CT?
The median sale price in Chester is $549,000, based on 43 home sales in the last 12 months (SmartMLS). Updated November 10, 2026.
What is the property tax rate in Chester, CT?
Chester's town-wide property tax rate is 27.78 mills (fiscal year 2027). Connecticut assesses homes at 70% of market value, so a median-priced home pays roughly $10,700 a year. Special taxing districts can add to this.
How far is Chester, CT from Hartford?
Chester is about 34 miles and a 47-minute drive from downtown Hartford, measured from the town center without traffic.
How far is Chester, CT from New York City?
Chester is about 109 miles from Midtown Manhattan, roughly a 159-minute drive without traffic.
What is the population of Chester, CT?
Chester has about 3,748 residents (U.S. Census Bureau estimate, 2024) and covers 16.1 square miles.
How many public schools are in Chester, CT?
Chester has 1 public school in Chester 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 Chester, CT?
There are 11 homes for sale in Chester right now, per SmartMLS, as of November 10, 2026.
What is there to do in Chester?
Main Street has restaurants, a brewery, galleries and shops, the Chester Museum at the Mill, and the Norma Terris Theatre. The Connecticut Valley Railroad State Park Trail and several town preserves are open for walking.
How far is Chester from Hartford and New Haven?
Hartford is 47 minutes (34 miles) by car and New Haven is 50 minutes (29 miles).
Is there a train station in Chester?
No. The 9 Town Transit bus service from the Estuary Transit District serves Chester, and the Old Saybrook station is reached by bus.
Is there a ferry in Chester?
The Chester-Hadlyme Ferry crosses the Connecticut River from the Route 148 landing and has run since 1769. It operates seasonally and was suspended for repairs in September 2026, so check the CTDOT ferry page for current status.
Which towns border Chester?
Deep River, Killingworth, Haddam, East Haddam and Lyme.
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Towns that border Chester
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