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
| $1,000,000 - $2,000,000 | $2,000,000 - $3,000,000 | $3,000,000 - $5,000,000 |
| $5,000,000 - $10,000,000 | Over $10,000,000 |
This Is The Opportunity Buyers Wait For. An Architecturally Significant Hubbard Woods Georgian That Could Never Be Duplicated Today For Anywhere Near This Cost. Perfectly Positioned On One Of The Neighborhood's Most Coveted Cul-de-sac Streets, Thi...
Incredible Opportunity On Desirable Private Dorina Drive In Northfield's Award-winning New Trier School District! Breathtaking, Newly Reimagined Mansion On Nearly 1 Acre Lot, With 7800 Square Feet Of Living Space, Plus 3500 Square Foot Unfinished ...
The Quintessential White-painted Colonial Always Makes A Timeless Statement-but Set On One Of East Winnetka's Most Spectacular Blocks, Just Steps From Town, Train, Beach And Village Green, It Becomes Truly Exceptional. Welcoming In All The Most Be...
A Rare, Fully Renovated And Updated Home Offering Move-in-ready Luxury And Thoughtful Craftsmanship Throughout. The Primary Bath Was Renovated Down To The Studs, And Now Offers A Generous Shower, Private Water Closet, And All-new Fixtures, Plum...
CONTINGENT Set On Over Half An Acre On Private Indian Hill Road Within The Sought-after Greeley School District, This Exceptional 6-bedroom, 6.2-bath Home Offers The Perfect Blend Of Timeless Elegance And Everyday Livability. Striking Curb Appeal Sets The To...
If You've Been Looking For Room To Spread Out And Don't Want To Sacrifice Quality For Quantity, This Stately Brick Colonial Home Is The Answer. Blending Timeless Architecture With The Layout Families Want Today, This Home Has Over 10,000 Square Fe...
CONTINGENT 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 An Extraordinary Colonial Offering Timeless Elegance, Exceptional Estate-like Privacy, And Breathtaking Views Along The 12th Hole Of The Winnetka Golf Course. Set On Nearly One Acre Of Beautifully Landscaped Grounds And Positioned Approximately 25...
CONTINGENT Storybook Cape Cod In The Heart Of Winnetka...walk To Everything! Picture-perfect Curb Appeal, Timeless Character, And An Unbeatable In-town Location - This Home Has It All! Thoughtfully Expanded And Beautifully Updated, This Home Offers The Charm...
Beautifully Restored Idyllic Victorian Home Expanded For Today's Living Features A Flexible Floorplan With Easy Flow, Generously Sized Rooms, Dramatic Ceiling Heights, Detailed Millwork And Plaster Moldings, Inlaid Floors And An Abundance Of Tall ...
Regent Wood Homes Rarely Come To Market, And Once You See This One, You'll Understand Why Buyers Wait Years For A Chance Like This. As The Largest Home In This Maintenance Free Subdivision At Just Over 5,100 Total Square Feet, And The Only One Wit...
CONTINGENT **a Rare Offering On One Of Northfield's Most Desirable Streets.** Set On A Beautifully Landscaped One-acre Parcel, This Exceptional, Expanded Georgian Seamlessly Blends Timeless Architecture With Thoughtfully Curated Updates And Modern Amenities....
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 August 15th, 2026 at 7:29am CDT.
.jpg)
