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.
Award Winning Home, Professionally Manicured Corner Lot, On One Of The Most Desirable Blocks In Winnetka (ash Street). Recipient Of The Prestigious Winnetka Preservation Award, Due To The Thoughtful Gut-renovation With Kip & Keeler Which Honored T...
Summer Is Right Around The Corner, And 139 Sheridan Is The Ultimate Lakefront Escape. Built Into The Bluff And Just Steps To The Water, This Turnkey Morgante Wilson Custom Home Is Designed For Effortless Lake Living. One Of The Last New Constructi...
Charming Red Brick Georgian Nestled In Highly Coveted East Winnetka Area Of Hubbard Woods, Just Steps To Schools, Shops, Restaurants, Train And Green Bay Trail. This Inviting Home On An Oversized Lot (62'x 297') Offers 5+ Bedrooms And 3.1 Bathroom...
Stunning Architectural Gem In East Winnetka, Where History Meets Modern Sophistication. This Magnificent 5+ Bedroom, 3.2-bath Classic, Set On An Expansive .4-acre Lot, Offers A Unique Blend Of Timeless Charm And Contemporary Luxury Overlooking The...
Come See This Classic Winnetka Beauty: Packed With Both Vintage Charm And All The Updates Of Today! 800 Lincoln Avenue Is A Beautiful Home Perfectly Situated In Sought After East Winnetka Location Where You Can Walk To Town And The Lake. Enter Thr...
Perfectly Situated In A Discreet Upscale Enclave East Of Sheridan Road. Beautifully Tucked Away Is Where You'll Find This Gorgeous Estate On A Professionally Landscaped .659 Acre. With Exceptional Quality, Elegance And Design Throughout There Are...
CONTINGENT Situated In The Most Charming Neighborhood Between Winnetka And Hubbard Woods, This Sunny, Meticulously Maintained 4+ Bedroom, 3 And A Half Bath Home Is The Perfect Combination Of Vintage Character And Modern Decor: Full Of Classic Architectural D...
Experience Unmatched Luxury In This Exceptional 10,000+ Sq. Ft. Private Estate Nestled On 1.2 Beautifully Landscaped Acres, This Extraordinary 7-bedroom, 6.5-bath Estate Offers The Perfect Blend Of Timeless Architecture And Modern Luxury. From ...
Stunning New Construction Transitional Home With Approximately 7,500 Square Feet Of Meticulously Finished Space, The Home Is Located On One Of The Most Picturesque Streets In East Winnetka In An Unbeatable Location. The Home Is Close To Town, Walk...
Architecturally Stunning Custom Contemporary On A Lush 1/2 Acre Private Lane With Lake Breezes. Designed To Maximize Natural Light And Indoor-outdoor Living, The Home Features Expansive Windows, Skylights, And Three Rooftop Decks. The Open Floor P...
Nestled On A Sprawling Tree Lined Lot In A Picturesque Setting, This Stunning 5-bedroom, 2.2 Bath Colonial Home Blends Elegance With Modern Convenience. From The Moment You Drive Down The Grand New Driveway That Was Recently Redone You Get An Und...
CONTINGENT Stunning 6-bed, 5.5-bath Classic Brick Georgian With Modern Elegance. Step Into Timeless Sophistication With This Newer-construction Classic Brick Georgian, Where Traditional Charm Meets Contemporary Luxury. Designed For Both Everyday Living And G...
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 April 23rd, 2025 at 6:38am CDT.
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