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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A Large 5br Home With A 4 Car Garage, A Corner Lot, And An Amazing Location! This Home Welcomes You With Great Curb Appeal, Starting With The Front Porch Overlooking Elm. The Main Level Has A Separate Dining And Living Room, And A Large Family Ro...
Blending Timeless Elegance With Modern Sophistication, This Stunning 2016 Winnetka Home Feels Better Than New. Designed For Light, Flow, And Effortless Living, It Features 10-foot Ceilings, White Oak Floors, And Expansive Windows That Fill Each Ro...
Timeless Winnetka Colonial On Private Hill Terrace. Set On Coveted Hill Terrace, A Charming Private Street Just Moments From The Indian Hill Metra Station, This Beautifully Maintained Winnetka Colonial Offers An Exceptional Combination Of Classic ...
Better Than New! This Artfully Restored & Renovated Home Has The Incredible Combination Of A Classic Center Entry Colonial Home With Sophisticated Formal Rooms And All The Current Amenities For Today's Modern Lifestyle. This Four-level Home Feat...
Set On A Beautifully Landscaped .33 Acre Property In One Of Winnetka's Most Convenient Locations, 875 Gordon Terrace Is A Significant Historic Home Thoughtfully Reimagined Through A Recent Comprehensive Renovation And Expansion. An Elegant Wrough...
Step Into A Beautifully Transformed Hemphill Home In Winnetka With Private Access To The Forest Glen Neighborhood. Modern Updates Meet Classic Character Following Extensive 2023 Renovations, Including New Electrical And Plumbing, An Improved Floor...
Beautiful And Tastefully Updated Multi-level Home In Picturesque Landscape Offering 4 Bedrooms And 4 Baths With A Second Lower Level Kitchen. The First Floor Includes A Vaulted-ceiling Living Room With Gas Fireplace, Modern Kitchen, Lovely Large F...
Nestled In The Heart Of One Of Winnetka's Most Coveted Neighborhoods, This Handsome Tudor Seamlessly Blends Timeless Architecture With Today's Luxury Finishes And Amenities. Enter Through The Arched Doorway To Find Beauty At Every Turn With New Wi...
CONTINGENT Welcome To 165 Fuller Ln, Where Timeless Charm Meets Thoughtful, High-end Finishes In An Unbeatable East Winnetka Location Within The Coveted Greeley School District. Perfectly Positioned For Walkability To School, The Lake, Parks, And Everything ...
CONTINGENT Incredible Coveted Home With 5 Bedrooms, 5.2 Bathrooms, 3 Garages On 1/3 Acre Property Boasts Winnetka Address And Kenilworth School District. Built In 2004, This Beautiful Brick Home Feels Like New Construction With A Complete First Floor Renovat...
CONTINGENT Classic Brick Dutch Colonial On A Picturesque, Tree-lined Street In The Heart Of Hubbard Woods, Offering An Unbeatable Walk-to-everything Location Just Steps To The Metra, Shops, Parks, Dining, And Top-rated Schools. Originally Built In 1924 And E...
Welcome To This Margaret Mccurry Designed 5 Bedroom, 6 Bathroom Home With A Primary Suite On The First Floor And Golf Simulator And Extensive Lower Level Recreation Area. Tucked Off Indian Hill Golf Course On A Special Little Lane, It's All Here I...
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 March 8th, 2026 at 12:38am CST.
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