Posted by Linda Shaughnessy on Wednesday, May 22nd, 2024 at 10:28pm.
Nestled on the North Shore of Chicago, just 16 miles from downtown, Winnetka is a picturesque community known for its diverse homes, beautiful beaches, and vibrant village life. With an array of historical lakefront estates, traditional village homes, and contemporary residences with dramatic ravine views, Winnetka offers something for everyone.
A Home for Every Taste
Winnetka’s real estate market is as varied as it is appealing. Home buyers can explore significant center hall brick Colonials, elegant English Tudors, majestic lakefront stone manor homes, charming Victorians, and modern classics by renowned architect Tony Grunsfeld. The architectural legacy of prominent figures such as David Adler, Howard van Doren Shaw, and George Maher is evident throughout the community, adding to its timeless appeal.
Embrace the Outdoors
Nature lovers will find much to enjoy in Winnetka. The community boasts 23 parks, a boating beach, and three public beaches—Lloyd Beach, Centennial Beach (a dog-friendly spot), and Tower Beach. The extensive Park District Program offers activities for all ages, while the A.C. Nielsen Tennis Center, Winnetka Public Golf Course, and Winnetka Ice Arena provide ample opportunities for recreation. Additionally, private golf and country clubs add to the area's allure, offering exclusive amenities and social events.
Education Excellence
Winnetka is served by two highly regarded public school districts. Winnetka School District 36 operates three elementary schools—Crow Island School, Greeley School, and Hubbard Woods School—and The Skokie School, a middle school. New Trier Township High School District 203, known for its academic excellence, serves high school students from Winnetka and surrounding communities.
Private education options are also plentiful. North Shore Country Day School offers a coeducational program from junior kindergarten through grade 12. Sacred Heart School and Faith, Hope & Charity School provide education from preschool through grade 8. The Hadley School for the Blind offers educational programs for individuals who are blind or visually impaired, while Winnetka Community Nursery School and Montessori School of Winnetka cater to younger children.
Convenient and Charming Village Life
Winnetka’s walkable village is home to three picturesque Tudor-style shopping areas filled with boutiques, cafes, and fine dining establishments. Commuters appreciate the convenience of Metra’s Union Pacific North Line, with stations at Elm Street, Indian Hill, and Hubbard Woods providing easy access to downtown Chicago.
Hubbard Woods: A Natural Haven
In the northeast section of Winnetka, Hubbard Woods is known for its natural beauty and stunning ravines. This area, located along Green Bay Road, features some of the finest antique shops on the North Shore, making it a destination for collectors and enthusiasts alike.
Golfing in Winnetka
Golf enthusiasts have excellent options in Winnetka. The Winnetka Golf Club, located at 1300 Oak St, offers a public 9-hole course that’s perfect for practice and recreation. Nearby, the private Indian Hill Club features a full range of amenities, including a golf course, tennis courts, swimming pools, and dining facilities. Although Skokie Country Club is not directly in Winnetka, it is close by and provides additional golfing opportunities.
A Lifestyle of Relaxation and Gracious Living
Winnetka offers a relaxed and gracious lifestyle that attracts North Shore home buyers. Whether you're looking for a historical estate, a modern home with breathtaking views, or a charming village residence, Winnetka has it all. The combination of natural beauty, educational excellence, and a vibrant community makes Winnetka a truly special place to call home.
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 Welcome To 611 Ash Street In East Winnetka! A True Classic On An Oversized 70x186 Lot. Greeted By The Large Inviting Porch, The Circular Floor-plan Gives The House A Wonderful Flow! Large Gracious Sun-filled Rooms Through Out. The Pretty Kitchen W...
CONTINGENT A Rare Opportunity In The Heart Of Winnetka, A Beautiful Newer-construction Brick And Stone Home Offering Timeless Design, Modern Comfort, And Impeccable Quality On Every Level. Built In 2005 And Freshly Updated For Today's Lifestyle, This Residen...
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,...
East Winnetka One-of-a-kind Home With Private Beach Access. Tucked Away On An Exclusive Private Lane, This Exceptional East Winnetka Residence Offers A Rare Opportunity To Enjoy Privacy And Luxury At Its Finest. Recently Renovated, 5 Bedrooms, 3...
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 4th, 2025 at 11:53pm CST.
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