Winnetka has often been called the “crown jewel” of Chicago’s North Shore suburbs, located on the shores of Lake Michigan

approximately 19 miles north of Downtown Chicago. It’s bordered on the South by Kenilworth and Wilmette, on the West by Northfield, and on the North by Glencoe.
Winnetka was named number 4 on the list of America’s 25 Best Places To Live by CNN Money in 2007. According to Business Week, it is among the top 15 zip codes in America.
The town has nurtured a number of real-life headliners: Rock Hudson, former Defense Secretary Donald Rumsfeld and indie-rocker Liz Phair all spent formative years in this conservative Midwestern village.
Single-family homes account for nearly 90 percent of Winnetka’s housing stock, over 90 percent of which is owner-occupied. From multi-million dollar lakefront mansions to condominiums, townhomes and in-town cottages, there is something for everyone in this charming village.

Over half of Winnetka’s housing stock pre-dates World War II. In East Winnetka, nearly all of the homes are of pre-war vintage. Many grand estates are hidden from view east of Sheridan Rd, on sizable (by North Shore standards) parcels that drift down toward Lake Michigan. Winnetka’s downtown (actually three small districts anchored by Metra train stations), is a hub of rush-hour activity. Its beach-glass-and-driftwood shops mimic those in New York’s Hamptons, sans the celebrities.

The Hubbard Woods district, located near the Hubbard Woods Metra station creates a delightful “old world” atmosphere – one of the reasons many of the shops carry fine European imports. Residents will find home furnishings, accessories, antiques apparel and gift shops from local places like: Seagrass, Maze Home, and Sawbridge Studios.

Custom services include art frames, lampshades, window shades, wallpapers, paint, carpeting, and interior design. The Green Bay Trail, a hiking and bicycle trail, runs parallel to the train tracks at Hubbard Woods and is accessible from the platforms.

Winnetka has diverse selection of Greek, American, and casual restaurants. Favorite local spots include: Mirani’s, Avli, O’Neil’s, and Michael’s Restaurant.
The Winnetka Park District offers a rich array of parks, beaches and other recreational facilities, including a public golf course, an ice arena, boating facilities, and the renowned A.C. Nielsen Tennis Center.

The Grand Food Center is a pre-beach snack stop for Lovell and Kassine. The beach house on Lloyd Beach offers sailing programs including:

Jr. Sailing and Parent/Child Sailing classes.
Village services include an outstanding public library, a well-run, service-oriented municipal government, and highly professional police and fire departments.

A variety of restaurants, from casual to white tablecloth, are sprinkled throughout the village. Favorites include the white pizzas at the Trifecta Grill and the waffle cones at Love’s Yogurt.

The Winnetka Public Schools system serves around 2,000 students in the immediate area.The school district consists of three elementary schools and two middle schools: Hubbard Woods, Crow Island, and Samuel Sewall Greeley (est. 1912).

The Crow Island School has received other architectural recognitions from the Illinois School Board Association and the American Association of School Administration and the American Library Association. The school was named a national historic landmark by the Department of the Interior in 1990.

North Shore Country Day is a highly-acclaimed nonsectarian private school founded in 1919. With an active enrollment of 500 students, the school is divided into three levels: a lower school, middle, and upper school. Metra’s Union Pacific North Line makes three stops in Winnetka and reaches downtown Chicago in 35 to 40 minutes. Pace bus route 423 provides access to points north through Linden.

The Edens Expressway is also very accessible to residents. Much of Winnetka’s charm derives from its varied terrain, the size,variety and tastefulness of its architecture, its one-of-a-kind shops,restaurants and services, and the nearly 3 miles of shoreline, with both public and private beaches along Lake Michigan. What’s most distinctive about Winnetka, however, is the richness of its civic traditions, the quality of its public and private schools, and the intensity with which its citizens maintain and enhance its character.

Current Winnetka Homes for Sale

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