227 Real Estate Listings for Sale in Winnetka

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Living in Winnetka, IL


Tucked away north of Chicago, resting along the shores of Lake Michigan, lies Winnetka, a prosperous village offering superior schools, excellent recreation and luxurious estate homes. This exclusive community is characterized by its prominent estates nestled within its beautiful tree-lined streets, and carefully maintained natural areas. Aptly named after the Native American word meaning "beautiful land," the Village of Winnetka, IL is encompassed by breathtaking vistas and scenery that serves as backdrops to the esteemed Winnetka homes.


For a unique shopping experience, Elm Street and Green Bay Road in downtown Winnetka offer an array of charming retail stores and numerous local eateries. Hubbard Woods, another shopping district located in the far north end of the village, offers an unparalleled selection of local vendors selling high-end merchandise for your home and your wardrobe. Here sidewalk cafes and bakeries sit alongside local boutiques as well as a number of galleries showcasing some of the most exclusive works of art and antiques.


Having preserved much of its residential charm, Winnetka has remained untouched by major shopping malls or big box retail stores. The city’s peaceful streets are adorned by an eclectic blend of small local businesses contributing to the community as well as the culture. With a vivacious enthusiasm for their community, Winnetkans are highly active in their local organizations and are more than dedicated to upholding the prestige of their home town.


Widely known as one of the nation's wealthiest, most exclusive suburbs, Winnetka is home to an amalgamation of stately, picturesque estates. With many of the homes in Winnetka having been designed by leading architectural names, like George Washington Maher and John S. Van Bergen, the intricate details displayed in many of these homes continue to exude their elegance and grandeur today, giving the community the appeal it is well known for. In fact, the charm and beauty of this suburban community has caught the eyes of notable filmmakers over the years, which have made it the destination for blockbuster films such as Home Alone and Risky Business.


Families with children have the opportunity to discover the successful education program of Winnetka School District 36, which is comprised of five schools, including Crow Island, an architecturally significant National Historic Landmark. As a part of the New Trier Township, high school aged students will attend the high performing New Trier High School. Well recognized for its exceptionally high spend per student, New Trier High School provides top tier education for its pupils.


Located about 16 miles away from the bustling city of Chicago, Winnetka offers a tranquil atmosphere for its residents. The METRA commuter rail has two stops, one in downtown on Elm St. and one in Hubbard Woods, linking commuters to the downtown core of Chicago. You can also jump on I-94 or Lake Shore Drive to head into the city on your own.


With the vast majority of Winnetka, IL real estate consisting of single-family homes, the area is widely known for estates with classy architectural designs and monumental stature. Winnetka properties are among the most desired real estate in the state, with homes holding riparian rights being the most coveted of them all.


As a lakefront community boasting 23 acres of parkland directly on Lake Michigan, residents are provided with ample opportunity to enjoy a recreational paradise near the water. A dedicated dog beach also welcomes families with pets. Whether residents are swimming, boating or enjoying themselves at one of the expansive parks, the Winnetka Park District and its operations round out the benefits of living in this thriving Village of Winnetka, IL.


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