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.
***build Your Dream Home!!!*** Amazing Opportunity In The East Winnetka Neighborhood, Tear Down And Build Your Forever Home! Original 1913 Home Standing On 11,555 Sf 70x165 Corner Lot. Prime Winnetka Location, Walking Distance To Lake, Parks, Sc...
Completely Reimagined And Thoughtfully Designed, 1288 Sunview Is An Exceptional Winnetka Home Set On A Picturesque Half-acre Lot. The Property Has Been Transformed From Top To Bottom With A Focus On Design, Functionality And Quality, Creating A Ho...
Exceptional Newer Construction In An A+ Tree Streets Location, This French Provincial-inspired Brick And Limestone Home Offers Approximately 5,000 Square Feet Of Beautifully Finished Living Space, An Outstanding Floor Plan And An Extraordinary Lev...
Beautiful Brick Georgian In Sought-after Regent Wood, Offering Gracious Living Spaces And A Desirable First-floor Primary Suite. The Main Level Features Gorgeous Hardwood Floors, An Elegant Living Room With Soaring Cathedral Ceilings And Fireplace...
Rarely Available...the Luxury Of Wellness! Intentionally Rebuilt And Completely Renovated In 2020 (with 2026 Kitchen Refresh), This Pristine, Move-in Ready Greenguard Gold-certified Low/zero Voc Property Offers The Luxury Of A Newer, Health Consci...
Enjoy An East Winnetka Lifestyle On A Beautifully Landscaped Expansive .3 Acre All Brick Home In An Ideal Location, Only Blocks To Tower Road Beach, Hubbard Woods/winnetka Shops And Restaurants, Schools, Parks, And Train. This Sophisticated Georgi...
CONTINGENT Charming House In Winnetka With Timeless Appeal Welcome To This Charming Four-bedroom, 1 1/2 Bath Winnetka Home That Beautifully Blends Classic Character With Comfortable, Inviting Living Spaces. Warm And Welcoming From The Moment You Walk Past...
Phenomenal Value As This Finely Built Newer Construction Home Privately Set With Serene Panoramic Winnetka Golf Club Vistas Just Hit "elevated Luxury" Status With An Impeccable 2026 No Expense Spared Rehab. Starting Off With The New Stunning Chef'...
First Floor Signature Suite Luxury Living Awaits You In This Totally Rehabbed Brick French Country Manor Home Set On A Lushly Landscaped 1/2 Acre Lot In New Trier High School District Area Of Natty Northfield. Enjoy Living Large And Luxuriously In...
CONTINGENT Originally Custom-built As The Developer's Personal Residence, This Home Reflects A Level Of Craftsmanship And Intentional Design That Is Truly Second To None. Tucked Away At The End Of A Peaceful Cul-de-sac, The Property Offers A Sense Of Privacy...
**multiple Offers Received** Highest And Best Due Tuesday 9/15 By 9am** A Rare Expression Of Extraordinary North Shore Living, This Quintessential Red-brick Colonial Sits On A 100' X 175' Double Lot (.39 Of An Acre) On Coveted Hill Terrace, One Of...
Step Into A World Where Mid-century Charm Meets A Crisp, Modern Aesthetic. This Beautifully Updated Ranch In Northfield Offers A Seamless Blend Of Single-level Living And Sophisticated Design, Perfect For Those Who Appreciate Clean Lines And A Tho...
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 September 14th, 2026 at 9:59pm CDT.
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