Winchester is a town in Litchfield County, Connecticut, home to about 11,823 people across 33 square miles. Its ZIP code is 06098.
Homes sold for a median of $216 per square foot in the three months ending August 2026, a seller’s market.
Each card is that ZIP code’s whole market, including any part outside Winchester. Seller’s market: under 4 months of supply; buyer’s market: over 6. Methodology
We’re writing up Winchester’s story and what everyday life there is like, for people thinking about moving in.
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| Nearest major airport | Bradley International Airport (BDL)19 miles away |
|---|---|
| Nearest city of 250,000+ | New York, NY98 miles away |
Straight-line distances from the center of Winchester; driving is longer.
Source: Airports from OurAirports (scheduled passenger service); city centers and populations from the U.S. Census Bureau.
Source: Members of Congress from the congress-legislators project; districts from the Census Bureau’s relationship files; governor and mayor from Wikidata.
Winchester had 10,224 residents in the 2020 census, down 4% since 2000.
It’s the 87th largest of 169 towns in Connecticut by population.
Litchfield County grew from 63,672 residents in 1900 to 185,186 in 2020.
Litchfield County, 1900–2020
Source: U.S. Census Bureau decennial censuses (counties 1900–1990 from the Bureau’s historical county file).
Average highs peak around 84°F in summer, and winter lows average 14°F. About 51.3 inches of rain and melted snow fall in a typical year, with about 51 inches of snow.
Source: NOAA 1991–2020 climate normals, Barkhamsted, CT weather station (5 miles away).
51 doctors and other health care providers list an office in Winchester.
Nearest hospitals
Providers with an office here
| Primary care doctors | 9 |
|---|---|
| Specialist doctors | 4 |
| Dentists | 8 |
| Nurse practitioners and physician assistants | 1 |
| Mental health providers | 17 |
| Physical and occupational therapists | 8 |
| Optometrists | 1 |
| Chiropractors | 3 |
| Pharmacies | 6 |
Source: Hospitals from CMS Hospital General Information (ratings are CMS overall star ratings); straight-line distances; providers from the CMS National Plan and Provider Enumeration System (NPPES), by practice address and primary specialty.
Parks (9 nearby)
Grocery stores (1 nearby)
Pharmacies (1 nearby)
Libraries (2 nearby)
Museums (3 nearby)
Counts are within about 4 miles of the center of town.
Source: Map data © OpenStreetMap contributors (openstreetmap.org/copyright), as mapped by volunteers; it can miss places or include closed ones.
Public schools here are run by Winchester School District, Regional School District 07, The Gilbert School District and others. Check each district’s attendance zones for a specific address.
| School | Grades | Students | Type | Distance |
|---|---|---|---|---|
| Mary P. Hinsdale SchoolWinsted | Pre-K–2 | 263 | Public | 0.5 mi |
| Pearson SchoolWinsted | 2–6 | 318 | Public | 0.1 mi |
| Northwestern Regional Middle SchoolWinsted | 7–8 | 218 | Public | 1.3 mi |
| The Gilbert SchoolWinsted | 7–12 | 452 | Public | 0.5 mi |
| ExplorationsWinsted | 9–12 | 77 | Charter | 0.6 mi |
| Northwestern Regional High SchoolWinsted | 9–12 | 536 | Public | 1.3 mi |
Source: U.S. Department of Education, NCES: Common Core of Data (2024-2025) for public schools. Listed by address; we don’t rate schools.
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Town boundaries don’t always match ZIP codes: a ZIP code can cross into neighboring towns, and a town can share a ZIP code with its neighbors. Facts describe the town itself; market figures describe whole ZIP codes.