The Town FilesWinchester, Connecticut
Town · population 10,224 (2020 Census)
- Median home
- $249,500
- Household income
- $66,519
- Jan low / Jul high
- 14° / 78°
- Snow a year
- 75 in
- Tornadoes ≤10 mi since 1950
- 10
- Median age
- 49.1
Winchester is a town of 10,224 people, Connecticut. The median home is worth $249,500, below the typical Connecticut town ($376,000). It ranks better for first-time buyers than 93% of Connecticut towns, better for a vacation home than 89% of Connecticut towns, easier by car than 85% of Connecticut towns.
How Winchester ranks
Percentile among Connecticut towns with at least 500 people on The Town Files lifestyle rankings. 50 is typical for the state; 90 means better than 90% of Connecticut towns.
Homes and cost of living
The median home in Winchester is worth $249,500, below the typical Connecticut town ($376,000). Homes cost about 3.8 times the median household income of $66,519, which is more affordable than 40% of Connecticut towns. Median rent is $1,174 a month. 65.8% of households own their home.
| Housing | Winchester | Typical Connecticut town |
|---|---|---|
| Median home value | $249,500 | $376,000 |
| Median rent | $1,174 | $1,462 |
| Median household income | $66,519 | $109,167 |
| Home value ÷ income | 3.8× | 3.6× |
| Homeownership | 65.8% | 80.3% |
| Median year built | 1955 | 1969 |
| Seasonal / vacation homes | 5.5% | — |
Who lives in Winchester
| People | Winchester | Typical Connecticut town |
|---|---|---|
| Median age | 49.1 | 45.0 |
| Age 65 and over | 27.4% | 20.6% |
| Under 18 | 15.4% | — |
| Bachelor's degree or higher | 27.8% | 45.8% |
| Below the poverty line | 12.8% | 5.7% |
| Veterans | 10.5% | — |
| Born outside the U.S. | 6.9% | — |
| Work from home | 6.9% | 16.8% |
| Average commute | 26.4 min | 27.6 min |
| Homes with broadband | 89.6% | 93.8% |
Weather in Winchester
July highs average 78.4°F and January lows 14.1°F. About 52.9 inches of rain and melted snow fall a year, with 74.9 inches of snow (typical Connecticut town: 39.0 in). Expect about 1 days a year at 90°F or hotter and 151 nights at or below freezing.
Tornadoes, storms and disasters
10 tornadoes have passed within 10 miles of Winchester since 1950, compared with 8 for the typical Connecticut town. 2 rated (E)F2 or stronger. The strongest, an F2, struck on June 23, 2001 about 8.8 miles from the town center. The most recent was on July 28, 2022.
Hail of 1 inch or larger has been reported within 10 miles 34 times; the largest was 1.75 inches on May 15, 2018.
Towns near Winchester
- Winsted, CT2.2 mi · 7,192 people · home $218,900
- Torrington, CT6.5 mi · 35,515 people · home $215,500
- Barkhamsted, CT7.0 mi · 3,647 people · home $368,000
- New Hartford, CT8.2 mi · 6,658 people · home $358,600
- Goshen, CT8.4 mi · 3,150 people · home $482,400
- Northwest Harwinton, CT10.5 mi · 3,158 people · home $330,500
- Canton, CT11.3 mi · 10,124 people · home $395,300
- North Canaan, CT11.6 mi · 3,211 people · home $267,300
Winchester questions
Is Winchester, Connecticut a good place to retire?
On The Town Files lifestyle rankings, Winchester scores better for retirees than 61% of Connecticut towns and quieter than 59%. 27.4% of residents are 65 or older (median age 49.1).
How much does a house cost in Winchester?
The median owner-occupied home in Winchester is valued at $249,500 (Census ACS 2020–2024), against a median household income of $66,519, so homes cost about 3.8 times income. Median rent is $1,174 a month.
What is the weather like in Winchester?
July highs average 78.4°F and January lows 14.1°F (NOAA 1991–2020 normals). It gets about 52.9 inches of precipitation a year and 74.9 inches of snow.
Does Winchester get tornadoes?
10 tornadoes have passed within 10 miles of Winchester since 1950 (NOAA Storm Events); the strongest was a F2 on June 23, 2001. The typical Connecticut town has had 8.
- U.S. Census Bureau, American Community Survey 5-year estimates (2020–2024)
- U.S. Census Bureau, 2020 Census and 2025 Gazetteer (2020 / 2025)
- NOAA NCEI U.S. Climate Normals (1991–2020)
- NOAA NCEI Storm Events Database (1950–2026)
- FEMA OpenFEMA Disaster Declarations (this product uses the FEMA OpenFEMA API but is not endorsed by FEMA) (1953–2026)
- NCES Common Core of Data (2023–24)
- BLS Quarterly Census of Employment and Wages; USDA ERS county unemployment (BLS LAUS) (2000–2024)
- The Town Files lifestyle rankings, built from federal demographic, school, crime and housing data (2025)