Living in Winchester, CT
Winchester is a Litchfield County town of 32.52 square miles around Winsted, Highland Lake and Crystal Lake, where Route 8 and US 44 meet.
Winchester at a glance
- Median sale price
- $330,000+13% vs last year 117 sales, last 12 months
- Property tax rate
- 30.00 mills town-wide, FY2027
- Estimated yearly tax
- ~$6,900 median-priced home
- Population
- 10,309 2024 Census estimate
- Land area
- 32.5 sq mi 317 per sq mi
What it is like in Winchester
Winchester is in northeastern Litchfield County, bordering Colebrook, Torrington, Barkhamsted and New Hartford. It covers 32.52 square miles of land and has a population of 10,309. Winsted, in the eastern part of town, is the largest community, and Winchester Center is the other principal community.
Winchester was incorporated on May 21, 1771 and is named after Winchester, England. Highland Lake, Crystal Lake and Winchester Lake are in town, and the Still River, a tributary of the Farmington River, flows through the eastern side. Northwestern Connecticut Community College is in Winsted.
Town outdoor places include Highland Lake Boat Launch, Resha Beach, Laurel Park, Club Island Park, Platt Hill State Park, Silas Hall Pond Preserve and the Ruez Trail. The American Mural Project on Whiting Street is an indoor mural installation in a former mill.
Winsted's Main Street has Railway Cafe at 580 Main Street, and Little Red Barn Brewers is on Lake Street in the former Lambert Kay building, now called Winsted Edgeworks.
Getting around from Winchester
| Drive to | Time | Miles |
|---|---|---|
| Hartford | 57 min | 31 |
| New Haven | 81 min | 51 |
| Stamford | 116 min | 81 |
| New York City (Midtown) | 165 min | 112 |
| Boston | 178 min | 131 |
| Providence | 155 min | 105 |
| Bradley Airport (BDL) | 65 min | 31 |
Rail
No passenger rail station within 8 miles.
Highways and routes
Connecticut Route 8 and US Route 44 meet in Winsted, and Route 263 connects Winchester Center and Winsted. Drive times: Hartford 57 minutes (31 miles), Bradley Airport 65 minutes (31 miles), New Haven 81 minutes (51 miles), Providence 155 minutes, Boston 178 minutes and New York City Midtown 165 minutes (112 miles). Northwestern Connecticut Transit District provides bus service.
Schools in Winchester
6 public schools in Winchester School District, Regional School District 07, Explorations District and The Gilbert School District. Which one serves an address depends on the district, so confirm with them.
Elementary 2
- Mary P. Hinsdale
- Pearson
Middle 1
- Northwestern Regional
High school 3
- Explorations
- Northwestern Regional High School
- The Gilbert School
Grades, number of students. Hover a school for its address.
For report cards, enrollment trends and spending per student, look up Winchester School District, Regional School District 07, Explorations District and The Gilbert 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 Winchester
Open Winchester in Google Maps →Eat and drink 8
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Chinese restaurant on Main Street serving lunch and dinner.
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Dairy Queen ice cream and soft-serve shop on Main Street.
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Domino's pizza store on Main Street that held its opening ribbon-cutting on October 21, 2025.
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Pizzeria on Main Street serving pizza, grinders and sandwiches.
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Brewery and taproom in the former Lambert Kay building with rotating food trucks, live music and trivia nights.
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Italian restaurant serving steak, pasta and seafood, with a separate takeout counter for pizza.
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Cafe on Main Street serving breakfast and lunch, with a separate ice cream bar.
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Casual American restaurant and taproom serving burgers, entrees and beer from local breweries.
Things to do and see 2
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Indoor mural installation in a former mill building celebrating American workers, made with contributors from all fifty states.
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Museum in a 1925 former bank building on Main Street, with exhibits on landmark tort cases; open Tuesday through Sunday.
Parks, preserves and trails 49
Show 35 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.
Winchester housing market
Over the last 12 months, 117 homes sold in Winchester with a median sale price of $330,000 and a median of 13 days on market. There are 24 homes for sale right now.
Homes sold for a median of $193 per square foot. The typical home sold for 100% of its list price, and the median sale price is up 13% from the year before. At the current pace of sales, the homes for sale would last about 2.5 months.
Winchester's town-wide property tax rate is 30.00 mills (FY2027). Connecticut assesses homes at 70% of market value, so a median-priced home pays roughly $6,900 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 Winchester
See all 24 →
Know before you move
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Questions about Winchester
What is the median home price in Winchester, CT?
The median sale price in Winchester is $330,000, based on 117 home sales in the last 12 months (SmartMLS). Updated November 10, 2026.
What is the property tax rate in Winchester, CT?
Winchester's town-wide property tax rate is 30.00 mills (fiscal year 2027). Connecticut assesses homes at 70% of market value, so a median-priced home pays roughly $6,900 a year. Special taxing districts can add to this.
How far is Winchester, CT from Hartford?
Winchester is about 31 miles and a 57-minute drive from downtown Hartford, measured from the town center without traffic.
How far is Winchester, CT from New York City?
Winchester is about 112 miles from Midtown Manhattan, roughly a 165-minute drive without traffic.
What is the population of Winchester, CT?
Winchester has about 10,309 residents (U.S. Census Bureau estimate, 2024) and covers 32.5 square miles.
How many public schools are in Winchester, CT?
Winchester has 6 public schools in Winchester School District, Regional School District 07, Explorations District and The Gilbert 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 Winchester, CT?
There are 24 homes for sale in Winchester right now, per SmartMLS, as of November 10, 2026.
What is Winsted?
Winsted is the largest community in the Town of Winchester, in the eastern part of town, where Route 8 and US Route 44 meet.
Which highways serve Winchester?
Connecticut Route 8 and US Route 44 meet in Winsted, and Route 263 connects Winchester Center with Winsted.
Which lakes are in Winchester?
Highland Lake, Crystal Lake and Winchester Lake. Highland Lake has a town boat launch and Resha Beach.
Is Riverton in Winchester?
No. The Riverton village with the Hitchcock Chair Company is in neighboring Barkhamsted.
Which towns border Winchester?
Colebrook, Torrington, Barkhamsted and New Hartford.
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