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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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...
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....
Beautiful, Classic Colonial With An Abundance Of Gracious, Oversized Rooms And An Exceptional Floor Plan - 67 Brandon Boasts 6 Bedrooms Above Grade And 5.1 Baths Total Including A First Floor Bedroom Option And Basement Bath. The Expansive Layout ...
Welcome To 78 Wagner Road, A Masterfully Crafted Estate Built By Heritage Luxury Homes And Nestled In The Heart Of Northfield. This Stunning Home Boasts 4-bedroom, 6.5-bathroom, And An Incredible Amount Of Refined Living Space, Seamlessly Blending...
This Estate Delivers The Ultimate Outdoor Summer Experience. It's Time To Sip 5pm Summer Cocktails In A True Country Club Setting With Gorgeous Vistas Of Precisely Manicured Grounds From The Tiered Entertaining Bluestone Patios With The Soothing ...
This Is The Quintessential All-american Beauty Nestled On Private Lane In Desirable Winnetka On A Half Acre With A Pool! This Home Was Completely Rebuilt And Redsigned For Today's Lifestyle In (2003-2004) - It Is Impeccable Inside And Out! Not ...
Nestled Privately Amidst The Prestigious Landscape Of Indian Hill Road, This Magnificent English Manor, Designed By Renowned Architect Edwin Clark, Presents An Unparalleled Opportunity To Immerse Yourself In The Epitome Of Understated Luxury Livin...
Timeless Elegance In The Heart Of East Winnetka! Set On An Expansive, Professionally Landscaped Lot, This East Winnetka Residence Exudes Timeless Elegance And Exceptional Curb Appeal. A Grand Foyer Welcomes You Into A Home Where Classic Architectu...
Luxurious Transitional Home That Sits An Almost 1acre, To Be Completed In July 2025.this 6 Bedroom ,6.1 Bathroom Masterpiece Is Thoughtfully Designed And Offers An Unparalleled Blend Of Elegance And Functionality.step Into The Grand Foyer That Is ...
Perfectly Positioned At The End Of A Quiet Cul-de-sac, This Striking Contemporary Home Rests On 3.14 Wooded Acres In Northfield, Within The Top-rated Sunset Ridge And New Trier School Districts. Solidly Constructed On An Extra-thick Concrete Slab,...
Better Than New! Impeccably Renovated 6br/5.2ba Center-entry Colonial Set On An Oversized (66 X 159) Professionally Landscaped Lot. This Four-level Home Features Abundant Natural Light, Oversized Windows, Wide Room Openings, Custom Millwork And Gl...
CONTINGENT Welcome To This Beautifully Maintained, Turn-key Home Nestled On Nearly An Acre At The End Of A Quiet Cul-de-sac-offering Privacy, Space, And Convenience. Enjoy Hard-to-find Ranch-style Living With A Grand First-floor Primary Suite Featuring A Spa...
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 19th, 2025 at 7:23pm CDT.
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