Winnetka is a North Shore community of homes 16 miles to downtown Chicago. Winnetka homes for sale range from historical lakefront estates on Sheridan Road to traditional homes in the village, and new contemporary homes with dramatic views of the ravines. Winnetka is noted for its beaches and 23 community parks, a boating beach, an 18-hole public golf course, highly respected public and private schools, and a charming village that is home to many boutiques and cafes. Metra's UnionPacific North Line commuter trains to Chicago's downtown business district are found at Elm Street, Indian Hill, and Hubbard Woods stations. Read more
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An Extraordinary "boutique Hotel" Living Experience, Impeccably Situated In The Heart Of Winnetka. Beyond A Stately Solid-iron Gate Adorned With Gold Medallion Accents Lies A Private Sanctuary Just 18 Miles From Chicago And Less Than Half A Mile F...
A True Crown Jewel In Northfield Filled With Possibilities! This 2.4-acre Property Is At The End Of One Of The Village's Most Prestigious Lanes, Affording You All The Privacy You Could Desire Coupled With The Convenience Of Being Close To Blue Rib...
They Don't Build Them Like This Anymore, But They Should! This Solidly Built Custom Hemphill Home Is Ideally Located In Sought-after East Winnetka And Offers Timeless Character, Quality Craftsmanship, And Thoughtful Updates. Built In 1936 With Exc...
Brand New Roof Just Installed With Transferable Warranty!! Beautifully Maintained Home Offering Over 4,300 Square Feet Above Grade On A Rare 0.53-acre Corner Lot In A Sought-after Winnetka Location. The Centerpiece Of The Home Is The Dramatic M...
New Construction In 2010, Built By The Current Owner (only One Owner Since Completion). Beautiful Two-story Traditional Home With 6 Bedrooms (one In The Basement), 5 And 1/2 Baths (full Bathroom In The Basement), And Huge Finished Basement With L...
It Is Exceptionally Rare To Find A Privately Set Masterpiece With Sweeping Views Of The Winnetka Golf Course That Also Offers The Opportunity To Step Directly Into A Freshly Completed 2025/2026 Designer Showcase Renovation. Nestled On A Beautifull...
Welcome Home To 14 Winfield Circle, Where Effortless Ranch-style Living Meets An Extraordinary Outdoor Resort Lifestyle. Nestled On A Quiet, Low-traffic Circle, This Home Sits On A Massive .76 Acre Lot-providing A Private Paradise That Is Hard To ...
CONTINGENT Welcome To 870 Bryant Avenue, A Stunning Red Brick Georgian Just One Block From Lake Michigan In The Heart Of East Winnetka. Originally Built In 1919 And Thoughtfully Updated Over Time, This Remarkable Home Beautifully Blends Timeless Architecture...
Nestled On A Private Lane East Of Sheridan Road, This Distinguished Winnetka Residence Offers Privacy, Scale, Quality Craftsmanship, And Exceptional Everyday Livability In One Of The North Shore's Most Coveted East-side Locations. Designed For Ele...
2.3 Acre , 7 Bedroom, 6 Bathroom Single Family Available In Northfield! 18' Tall Living Room Greets You As You Enter This 7,600 Sq. Ft Home. It Overlooks 20' X 40' Pool And Accompanying Hot Tub. Gourmet Kitchen With New European Cabinets By Kinzi...
Generational Opportunity...the Chance Of A Lifetime Now Awaits In One Of Winnetka's Most Premier "off Lake" Enclave Neighborhood...936 Sunset Road With Two Golden Options For This Exclusive Real Estate Offering. This Extraordinary Ralph Lauren Vib...
Completely Rebuilt And Expanded In 2020, This Exceptional Northfield Residence Offers Approximately 4,500 Square Feet Of Thoughtfully Designed Living Space On A Rare Private Half-acre Lot, Plus Another 1000 Square Feet Of Garage And Basement Space...
Start discovering the diverse Winnetka homes for sale including significant center hall brick Colonials, English Tudors, lakefront stone manor homes, Victorians, and modern classics by Tony Grunsfeld.. Prominent architects who set the tone for this coveted community include David Adler, Howard van Doren Shaw, and George Maher,
North Shore home buyers will find Winnetka offers a relaxed and gracious lifestyle. There are three public beaches: Lloyd Beach and Centennial Beach (dog beach), Elder Beach, and Tower Beach, an extensive Park District Program, the A.C. Nielsen Tennis Center, Winnetka Public Golf Course, and the Winnetka Ice Arena., as well as a selection of historically significant private golf and country clubs A walkable community, Winnetka homes are convenient to commuter trains and three picturesque Tudor-style shopping areas featuring cafes, coffee houses, and fine dining.
Hubbard Woods in the northeast section of Winnetka is known for its natural beauty and ravines. Located along Green Bay Road you will find some of the finest antique shops on the North Shore.
Winnetka School District 36: This district operates three elementary schools and one middle school. The elementary schools in District 36 include Crow Island School, Greeley School, and Hubbard Woods School. The middle school is called The Skokie School.
New Trier Township High School District 203: This district operates New Trier High School, which is a highly regarded public high school serving the communities of Winnetka, Glencoe, Kenilworth, Northfield, and parts of Wilmette and Glenview.
Winnetka is home to a number of beautiful parks. These parks offer a variety of recreational opportunities, such as playing fields, walking trails, playgrounds, and more. Here are some of the parks you might find in or near Winnetka:
Crow Island Woods Park: This park offers natural beauty with walking trails and a natural woodland area.
Dwyer Park: A popular spot with a playground, seating areas, and open space.
Elder Lane Park: This park is located near the beach and offers a beach house and picnic area.
Hubbard Woods Park: This park features a playground, picnic area, and tennis courts.
Maple Street Park: A family-friendly park with playing fields, a playground, and tennis courts.
Tower Road Beach: Not a traditional park, but a great place for swimming and enjoying the lake.
Village Green Park: Located in the heart of Winnetka, this park offers a gazebo and is a popular spot for community events.
Skokie Playfield: This large park complex includes fields for various sports, tennis courts, a track, and even a golf course.
Lloyd Park: A beautiful place to enjoy Lake Michigan with a beach, playground, and boating opportunities.
West Elm Park: A smaller park with a playground and open space for relaxation.
These parks and others in the area provide plenty of opportunities for outdoor enjoyment, whether you're interested in sports, nature walks, or just spending time with friends and family.
Winnetka Golf Club: Located at 1300 Oak St, Winnetka, is a public golf course that offers 9 holes of golf. It's a popular spot for local golfers and provides a great opportunity for recreation and practice.
Indian Hill is a private golf and country club situated at 1 Indian Hill Rd, Winnetka. The club offers various amenities, including a golf course, tennis courts, swimming pools, and dining facilities.
Skokie Country Club: While not directly located in Winnetka, Skokie Country Club is nearby in Glencoe, IL. It is another private club with a well-regarded golf course and other amenities.
The North Shore Chicago listings on this page include Winnetka IL homes for sale. The property listings are updated as soon as they hit the market with new Winnetka homes for sale and rent. Start your home search and schedule showings online or, to learn more about Winnetka and Chicago's North Shore, call 312.961.6212
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 June 8th, 2026 at 1:29am CDT.
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