Posted by Linda Shaughnessy on Wednesday, May 22nd, 2024 at 10:28pm.
Nestled on the North Shore of Chicago, just 16 miles from downtown, Winnetka is a picturesque community known for its diverse homes, beautiful beaches, and vibrant village life. With an array of historical lakefront estates, traditional village homes, and contemporary residences with dramatic ravine views, Winnetka offers something for everyone.
A Home for Every Taste
Winnetka’s real estate market is as varied as it is appealing. Home buyers can explore significant center hall brick Colonials, elegant English Tudors, majestic lakefront stone manor homes, charming Victorians, and modern classics by renowned architect Tony Grunsfeld. The architectural legacy of prominent figures such as David Adler, Howard van Doren Shaw, and George Maher is evident throughout the community, adding to its timeless appeal.
Embrace the Outdoors
Nature lovers will find much to enjoy in Winnetka. The community boasts 23 parks, a boating beach, and three public beaches—Lloyd Beach, Centennial Beach (a dog-friendly spot), and Tower Beach. The extensive Park District Program offers activities for all ages, while the A.C. Nielsen Tennis Center, Winnetka Public Golf Course, and Winnetka Ice Arena provide ample opportunities for recreation. Additionally, private golf and country clubs add to the area's allure, offering exclusive amenities and social events.
Education Excellence
Winnetka is served by two highly regarded public school districts. Winnetka School District 36 operates three elementary schools—Crow Island School, Greeley School, and Hubbard Woods School—and The Skokie School, a middle school. New Trier Township High School District 203, known for its academic excellence, serves high school students from Winnetka and surrounding communities.
Private education options are also plentiful. North Shore Country Day School offers a coeducational program from junior kindergarten through grade 12. Sacred Heart School and Faith, Hope & Charity School provide education from preschool through grade 8. The Hadley School for the Blind offers educational programs for individuals who are blind or visually impaired, while Winnetka Community Nursery School and Montessori School of Winnetka cater to younger children.
Convenient and Charming Village Life
Winnetka’s walkable village is home to three picturesque Tudor-style shopping areas filled with boutiques, cafes, and fine dining establishments. Commuters appreciate the convenience of Metra’s Union Pacific North Line, with stations at Elm Street, Indian Hill, and Hubbard Woods providing easy access to downtown Chicago.
Hubbard Woods: A Natural Haven
In the northeast section of Winnetka, Hubbard Woods is known for its natural beauty and stunning ravines. This area, located along Green Bay Road, features some of the finest antique shops on the North Shore, making it a destination for collectors and enthusiasts alike.
Golfing in Winnetka
Golf enthusiasts have excellent options in Winnetka. The Winnetka Golf Club, located at 1300 Oak St, offers a public 9-hole course that’s perfect for practice and recreation. Nearby, the private Indian Hill Club features a full range of amenities, including a golf course, tennis courts, swimming pools, and dining facilities. Although Skokie Country Club is not directly in Winnetka, it is close by and provides additional golfing opportunities.
A Lifestyle of Relaxation and Gracious Living
Winnetka offers a relaxed and gracious lifestyle that attracts North Shore home buyers. Whether you're looking for a historical estate, a modern home with breathtaking views, or a charming village residence, Winnetka has it all. The combination of natural beauty, educational excellence, and a vibrant community makes Winnetka a truly special place to call home.
Rarely Available 2013 New Construction In Avoca/new Trier School District! Don't Miss This Exceptional Opportunity To Own A Beautifully Updated Home In A Prime Location-just Steps From Playgrounds, Shops, Restaurants, And The Forest Preserve. Thou...
Move Right Into This 4 Bedroom Home Located In Prime East Winnetka Location- Walkable To Greeley, New Trier, Indian Hill Train Stop, Beach, And Parks! A Thoughtful And Functional Main Level Features Living Room, Dining Room, Powder Room And Kitche...
Step Into This Elegantly Appointed Colonial Home In The Highly Sought Northfield Community. Enter This Beautifully Maintained And Updated Residence Through A Gracious Foyer Anchored By Rich Hardwood Flooring, Crown Moldings, And An Effortless Flo...
CONTINGENT Beautiful Traditional Colonial On A Corner Lot In A Great Walk To Everything Location In Winnetka! A True Family Home With Amazing Curb Appeal That Greets You With A Pretty Brick And Bluestone Entry. A Lovely Living Room With A Fireplace And A Lar...
CONTINGENT Welcome To This Quintessential Winnetka Home, Perfectly Designed For Gracious Entertaining And Comfortable Family Living. As You Approach The Home, You Are Beckoned To Sit On The Fabulous Front Porch, Share An Ice Tea Or A Glass Of Wine And Watch ...
CONTINGENT Welcome To 570 Happ Rd - A Completely Reimagined Four-bedroom Plus Office, Five-bath Home On A Spacious 1/3-acre Lot. Every Inch Of This Home Has Been Updated Since 2023 With High-end Finishes And Modern Conveniences, Including All-new Dual-zoned ...
Discover An Incredible Opportunity To Either Construct A Brand-new Home Or Renovate This Charming Traditional Residence Situated On A Picturesque Half-acre Lot. Step Into The Welcoming Entrance Hall, Complete With A Guest Powder Room And Closet, L...
Experience The Ultimate In Luxury Living At 2202 Martin Ln In Northfield, Where Everyday Life Feels Like A Dream Vacation. An Exceptional Masterpiece On A Private Cul-de-sac Street. Large Home, Aprx 21,000 Sf, With Spectacular Architecture & Sett...
CONTINGENT Opportunity To Own And Enhance A Once-in-a-generation Architecturally Rich East Winnetka Home Built In 1894 And Set On A Beautifully Landscaped .42-acre Corner Lot Just Steps From Town, Train, Schools, Lake Michigan Beaches And The Village Green. ...
Custom Built By Notable Architect Paul Konstant In 2017, 305 Maple Row Truly Is A Masterpiece Sitting On A Breathtaking 1.22 Acre Property. This Stunning 7,024 Square Ft Home Lives Like A Ranch And Is Situated On One Of Northfield's Most Sought-af...
CONTINGENT Stunningly Updated And Maintained 4 Bedroom/3.1 Bath Home In The Ideal Tree Streets Location! Perfect Brick Georgian Has Been Extensively Upgraded By The Current Owners! Classic Main Level Floorplan With Formal Living Room With Fireplace, Complete...
CONTINGENT Introducing A Stunning Blend Of Timeless Sophistication And Modern Functionality In The Heart Of Winnetka. This Sun-drenched 5-bedroom, 4.1-bathroom Home Spans 3,440 Square Feet Of Thoughtfully Designed Living Space, Perfect For Today's Lifestyle....
The data relating to real estate for sale on this website comes in part from the Broker Reciprocity program of Midwest Real Estate Data LLC. Real Estate listings held by brokerage firms other than Sotheby's International Realty are marked with the Broker Reciprocity logo or the Broker Reciprocity thumbnail logo (a little black house) and detailed information about them includes the names of the listing brokers. Some properties which appear for sale on this website may subsequently have sold and may no longer be available. The information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed. Many homes contain recording devices, and buyers should be aware they may be recorded during a showing.
Listing information last updated on July 17th, 2025 at 10:53am CDT.
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