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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CONTINGENT Sophisticated Colonial On An Extra Wide Lot (72 Ft. Wide) On Coveted Walden Road In One Of Winnetka's Most Desirable Neighborhoods: Close To Both Downtowns, Schools, Parks, The Grand, Both Winnetka And Hubbard Woods Trains. This 5 Bedroom 4.1 Bath...
New Magnificent Transitional Home Situated On 1 Acre Picturesque Lot With Approximately 15,000 Square Feet Finished Space. Exterior Is Constructed Of Stone And Limestone With Slate Roof Which Represents Timeless Construction. The House Features 6...
Centrally Located In A Premiere "get To Everything" A+ Location, This Quintessential North Shore Coastal Shingle Home Delivers The Best Of Both Worlds. Thoughtfully Remodeled And Reimagined By Notable North Shore Architect Paul Konstant That Beau...
Beautifully Reimagined In 2023, This Custom Hemphill-designed Home Blends Modern Elegance With Timeless Craftsmanship. This Sophisticated Winnetka Home Is Completely Transformed, Including New Electrical And Plumbing, An Updated Floor Plan, Bay Wi...
Nestled On A Private Lane East Of Sheridan Road, This Distinguished Residence Combines Timeless Sophistication With Everyday Livability. With Over 6 Bedrooms (including An In-law/guest Suite) And 7.1 Baths, The Home Is Designed To Accommodate A Va...
CONTINGENT Built In 2003 By Greystone Builders, This Custom-designed Stucco French Tudor Residence Blends Timeless Old-world Craftsmanship With Modern Luxury. Offering 6 Bedrooms And 7 Baths, Every Detail Has Been Thoughtfully Curated To Evoke Warmth, Charac...
CONTINGENT This Meticulously Renovated And Turn-key Home Offers A Blend Of Exceptional Design And Tranquil Privacy. Completely Gutted And Renovated In 2022, Every Corner Of This Three-story Residence Has Been Thoughtfully Finished To Suit Modern Living. The ...
CONTINGENT Beautifully Renovated Lannon Stone Luxury Residence Steps From Town, Train And The Lake. Enter Through The Grand Center Hall That Leads To Both The Dining Room With Floor To Ceiling Windows And An Inviting Living Room With Wood Burning Fireplace A...
CONTINGENT Just Completed October 28th, This Breezy, Bright, And Beautifully Coastal New Construction By One Of The North Shore's Premier Builders Captures The Essence Of Modern Beachy Living. From The Moment You Arrive The Sea Salt Blue Shutters Set The Ton...
Gracefully Tucked Away On 1.55 Acres Of Lush Manicured Grounds, 62 Woodley Road Is A True Southern-inspired Masterpiece Reimagined For Today's Living. From The Moment You Approach The Iconic Black Lacquered Screen Door With Its Chippendale Detail,...
CONTINGENT Storybook Cape Cod Set On Enchanting Apple Tree Road Complete With That Magical Sidewalk To Crow Island School Offers Timeless Comfort In A Very Special Nook! Nestled On A Lush Half-acre Lot With Mature Trees, A Circular Drive & Attached 2-car Gar...
CONTINGENT 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...
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 December 16th, 2025 at 8:38pm CST.
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