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Why Winnetka?

Long considered one of the best North Shore suburbs to settle down in, Winnetka was ranked number two on a recent 24/7 Wall St. list of America’s best cities to live in. Here, there’s a little bit of something for everyone in the family – from a welcoming community and affordable housing, to a high concentration of restaurants and parks.

Within Winnetka’s borders, you’ll find various award-winning school options, a fine dining scene that rivals downtown’s, theaters and tons of green space and recreational parks. It’s a village-style suburb, with the same quaint shops and neighborhood feel you would expect.

In the guide:

  • Parks & Schools
  • Restaurants & Shopping
  • Attractions & Entertainment
  • Transportation & more

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Winnetka Homes For Sale

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Winnetka, Illinois

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.

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.

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.

Leslie Glazier | Real Estate Broker

Leslie Glazier | Broker


Ali Erie-Murphy | Real Estate Broker

Ali Erie-Murphy | Broker