Living in Middlebury, CT
Middlebury is a New Haven County town next to Waterbury, home to Quassy Amusement Park on Lake Quassapaug and the 1738 Josiah Bronson House.
Middlebury at a glance
- Median sale price
- $571,736+5.6% vs last year 118 sales, last 12 months
- Property tax rate
- 26.46 mills town-wide, FY2027
- Estimated yearly tax
- ~$10,600 median-priced home
- Population
- 8,025 2024 Census estimate
- Land area
- 17.8 sq mi 452 per sq mi
What it is like in Middlebury
Middlebury is in New Haven County in the Naugatuck Valley, bordering Naugatuck, Waterbury, Woodbury, Oxford, Watertown and Southbury. It covers 17.76 square miles of land and has a population of 8,025. It was incorporated as a town in 1807 and takes its name from its central position among Waterbury, Woodbury and Southbury.
The Josiah Bronson House, built in 1738, is on the National Register of Historic Places. Lake Quassapaug, a lake of about 296 acres, is in town. The former headquarters of Timex Group USA is also in Middlebury.
Quassy Amusement & Waterpark on Middlebury Road opened in 1908 as the Lake Quassapaug Amusement Park and is one of the oldest amusement parks still operating in the country. The Middlebury Historical Society on Library Road keeps a museum. Town outdoor places include Ledgewood Memorial Park, Meadowview Park, Tuttle Woods Preserve, Fenn's Pond and Turtle Pond.
Getting around from Middlebury
| Drive to | Time | Miles |
|---|---|---|
| Hartford | 47 min | 34 |
| New Haven | 38 min | 24 |
| Stamford | 73 min | 53 |
| New York City (Midtown) | 120 min | 86 |
| Boston | 171 min | 136 |
| Providence | 145 min | 111 |
| Bradley Airport (BDL) | 72 min | 50 |
Rail stations nearby
- Naugatuck 4.3 mi Metro-North
- Waterbury 4.4 mi Metro-North
- Beacon Falls 6.6 mi Metro-North
Highways and routes
Interstate 84 Exit 17 is near the Straits Turnpike, and Route 64 (Middlebury Road) runs through town. Drive times: New Haven 38 minutes (24 miles), Hartford 47 minutes (34 miles), Bradley Airport 72 minutes (50 miles), Stamford 73 minutes (53 miles) and New York City Midtown 120 minutes (86 miles).
There is no rail station in town. Naugatuck station (4.3 miles), Waterbury station (4.4 miles) and Beacon Falls station (6.6 miles) all have Metro-North service.
Schools in Middlebury
3 public schools in Regional School District 15. Which one serves an address depends on the district, so confirm with them.
Elementary 2
- Long Meadow
- Middlebury
Middle 1
- Memorial
Grades, number of students. Hover a school for its address.
For report cards, enrollment trends and spending per student, look up Regional School District 15 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 Middlebury
Open Middlebury in Google Maps →Eat and drink 4
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Brewery and sports bar pouring house-brewed beer alongside a menu of bar food.
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Pizzeria in a strip mall serving New Haven-style thin-crust pies, one of three Waterbury-area locations.
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Casual restaurant and bar serving lunch, dinner and Sunday brunch, with takeout and catering.
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Restaurant with a modern Mediterranean menu leaning Italian, plus cocktails and wines from a family vineyard.
Things to do and see 2
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Local history museum open most Monday afternoons and by appointment.
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Amusement park on Lake Quassapaug that opened in 1908, with rides, the Splash Away Bay waterpark and a beach.
Parks, preserves and trails 43
Show 29 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.
Middlebury housing market
Over the last 12 months, 118 homes sold in Middlebury with a median sale price of $571,736 and a median of 26 days on market. There are 27 homes for sale right now.
Homes sold for a median of $256 per square foot. The typical home sold for 100% of its list price, and the median sale price is up 5.6% from the year before. At the current pace of sales, the homes for sale would last about 2.7 months.
Middlebury's town-wide property tax rate is 26.46 mills (FY2027). Connecticut assesses homes at 70% of market value, so a median-priced home pays roughly $10,600 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 Middlebury
See all 27 →
Know before you move
Official and independent sources worth bookmarking if you are considering Middlebury.
Questions about Middlebury
What is the median home price in Middlebury, CT?
The median sale price in Middlebury is $571,736, based on 118 home sales in the last 12 months (SmartMLS). Updated November 10, 2026.
What is the property tax rate in Middlebury, CT?
Middlebury's town-wide property tax rate is 26.46 mills (fiscal year 2027). Connecticut assesses homes at 70% of market value, so a median-priced home pays roughly $10,600 a year. Special taxing districts can add to this.
How far is Middlebury, CT from Hartford?
Middlebury is about 34 miles and a 47-minute drive from downtown Hartford, measured from the town center without traffic.
How far is Middlebury, CT from New York City?
Middlebury is about 86 miles from Midtown Manhattan, roughly a 120-minute drive without traffic.
Is there a train station in Middlebury, CT?
The closest passenger rail station we have on record is Naugatuck (Metro-North) about 4.3 miles from the center of Middlebury. Check the operator's schedule for current service.
What is the population of Middlebury, CT?
Middlebury has about 8,025 residents (U.S. Census Bureau estimate, 2024) and covers 17.8 square miles.
How many public schools are in Middlebury, CT?
Middlebury has 3 public schools in Regional School District 15. Which school serves an address depends on the district's boundaries, so confirm with the district.
How many homes are for sale in Middlebury, CT?
There are 27 homes for sale in Middlebury right now, per SmartMLS, as of November 10, 2026.
What is Quassy?
Quassy Amusement & Waterpark is an amusement park on Lake Quassapaug that opened in 1908, with rides, a waterpark called Splash Away Bay and a beach.
Where is the nearest train station?
Naugatuck station is 4.3 miles away and Waterbury station is 4.4 miles away. Both have Metro-North service.
How far is Middlebury from New Haven?
New Haven is 24 miles and about 38 minutes by car.
What is the Josiah Bronson House?
A house built in 1738 that is listed on the National Register of Historic Places.
Which towns border Middlebury?
Naugatuck, Waterbury, Woodbury, Oxford, Watertown and Southbury.
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