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Winnetka has established a reputation as one of the most desirable communities in the greater Chicago area.

Properties In This Neighborhood

Welcome to Winnetka

Small-town Illinois treasure with an intimate community and quaint, quiet streets.

Nestled 16 miles north of downtown Chicago in Cook County and adjacent to Lake Michigan, Winnetka is an enchanting and beloved village with beautiful houses and a down-to-earth community. Winnetka is small enough that the village is cozy and tight-knit but just large enough to boast a dazzling shopping scene. With its parks and town events, Winnetka offers a desirable lifestyle for its residents. There is a dynamic array of homes, from lakefront mansions to luxury condominiums and single-family Victorian, Colonial, Tudor, and contemporary homes all built by distinguished architects. Residents enjoy being active outside, whether at the community center, on nature trails, or on the water. They take advantage of the easy access to Chicago but enjoy Winnetka’s quiet and residential nature. The gorgeous, peaceful, tree-lined streetscapes are the perfect place to live, play, and make memories. Welcome to Winnetka.

What to Love

  • Active and close-knit community
  • Upscale shopping destinations
  • Exciting neighborhood events
  • Beautiful and charming parks

​​​​​​​People & Lifestyle

Winnetka is a fabulous place to live. Between the open green spaces, the picturesque downtown, the breathtaking beaches, and the lovely homes, the Chicago suburb draws attention from all over due to its residential yet exciting atmosphere. There are many small-town things to do in Winnetka, and the community is neighborly and affectionate, where close bonds are formed between residents at the town’s parades, barbecues, and gatherings. Residents like having the option to commute or work in town, and they revel in the town’s unrivaled selection of unique shops, stores, and excellent schools.

Dining, Entertainment & Shopping

You can’t go wrong popping into any store, restaurant, or cafe in Winnetka. There’s plenty of upscale boutique shopping, including Neapolitan Collection, Athene, Bunny & Babe, and Marcus. For a white tablecloth dinner, make reservations at Tocco for an incredible evening of ambiance and delicious Italian food. Mino's is another tasty, authentic Italian spot, with a high-end restaurant and cool bar. French fare never looked better than it does at George Trois and Aboyer, where it’s eloquently plated and satisfying to the last bite. Spirit Elephant is the first fully plant-based restaurant and bar on Chicago’s North Shore. The swanky yet relaxed sit-down eatery is overflowing with fresh, healthy fare. Everything is seasonal, and the globally influenced cocktails come highly recommended.

Things to Do

In addition to its restaurants and shops, there are both upbeat and laid-back things to do in Winnetka. The Winnetka Music Festival is an awesome place to be each summer, especially when you get to witness top national and international emerging artists in their element. Winnetka Children’s Fair is a long-running, popular community event, with rides, food, games, and every inch of fun you can imagine. The Village Green is a 3.36-acre neighborhood park complete with benches, a playground, and open space, and is anchored by a World War I memorial. Hubbard Woods Park has an icy-cool splash pad, as well as bocce ball courts (good news: balls are available for rent!), picnic tables, a playground, and even ice-skating outdoors in the winter! Looking to fish, play, or get in the water? Elder Lane Park is a scenic lakefront park where you can frolic in the sand, and Tower Road Beach is Winnetka’s main swimming beach. The Community House is a neighborhood recreation center with classes, events, and activities. Adults can get active at the A.C. Nielsen Tennis Center, a dream facility with eight indoor and twelve outdoor courts (five with lights), a nursery, and a complete pro shop.


Winnetka has several highly rated schools and educational facilities of note, including the public high school, New Trier High School.


We offer the highest level of integrity, expertise, and service. The Dawn McKenna Group is the #1 leading real estate team in the Midwest, Southwest Florida and Park City for Coldwell Banker. With offices in Chicago’s Gold Coast and Lincoln Park, Hinsdale, Lake Forest and Winnetka, Lake Geneva, New Buffalo, and on 5th Avenue in Naples, and Park City, the Dawn McKenna Group agents are ready to serve you everywhere you call home. Whether buying, selling or renting, you can count on our Local Expertise and Global Reach.

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