Incorporated in 1896, Winnetka is home to New Trier High School. It is a classic North Shore town located 19 miles north of downtown Chicago. Elegant homes and grand estates line beautifully landscaped streets. The village covers about 4 square miles and features small business districts, downtown areas with restaurants and shops and small businesses. Students can attend elementary and middle school in District 36 and high school in District 203, at New Trier High School. The Winnetka Park District provides residents with programs including sports, camps, classes, performing arts, and waterfront activities. Winnetka’s stunning parks, green space, and beaches are perfect for residents who love biking, fishing, boating, and bird watching.
Winnetka Market Trends
Winnetka’s housing market remains highly competitive. Over the past six months, the median sale price was approximately $1.69 million, up 5.4% from 2025, while the median price per square foot reached $502, up 7.1%. Homes spent a median of just 5 days on the market, and buyers paid approximately 104% of the asking price on average..
