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North Shore Winnetka Homes for Sale

Posted by Linda Shaughnessy on Wednesday, May 22nd, 2024 at 10:28pm.

Discover the Charm and Elegance of Winnetka: A North Shore Gem

Winnetka

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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.

Browse All Winnetka Homes for Sale ~ Updated every 15 minutes

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Photo of Listing #12155965

54 Hibbard Road, Northfield, IL - $2,800,000

Residential, Detached Single
  • 5 Beds
  • 7 Baths
  • 8,450 SQFT
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A Dynamite Ranch Retreat...follow The Way Down The Long & Private Drive Set Off Hibbard Road That Only Takes A Split Second To Miss...and Arrive At One Of The North Shore's Most Well-kept Secrets Set On 1.33 Acres Of Maturely Landscaped Grounds Ac...

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Photo of Listing #12158709

1044 Happ Road, Northfield, IL - $1,650,000

Residential, Detached Single
  • 5 Beds
  • 6 Baths
  • 5,000 SQFT
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Impressive Two-story Home, Perfectly Nestled In A Serene And Private Setting. This Custom Built Property Boasts Beautifully Landscaped Grounds, Offering A Lush Oasis Of Tranquility And Seclusion. The Home Was Thoughtfully Constructed With Loads Of...

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Photo of Listing #12161453

803 Pine Street, Winnetka, IL - $2,450,000

Residential, Detached Single
  • 4 Beds
  • 4 Baths
  • 4,460 SQFT
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Absolute Perfection In The Heart Of East Winnetka! Completed In 2022, This Contemporary Two-story Masterpiece Offers The Perfect Combination Of Luxury And Convenience. Situated On A Beautifully Landscaped Lot, The Home Is Adorned With Brazilian I...

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Photo of Listing #12161150

1344 Edgewood Lane, Winnetka, IL - $2,099,000

Residential, Detached Single
  • 4 Beds
  • 6 Baths
  • 6,554 SQFT
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Much Bigger Than It Looks - Nestled In A Private Cul-de-sac, This Beautifully Renovated Cape Cod Home Offers A Perfect Blend Of Classic Architecture And Modern Amenities, Ideally Located To Enjoy All That Winnetka Has To Offer. The First Floor, Sp...

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Photo of Listing #12160709

17 Longmeadow Road, Winnetka, IL - $1,770,000

Residential, Detached Single
  • 7 Beds
  • 7 Baths
  • 6,000 SQFT
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Welcome To 17 Longmeadow, An Exceptional Retreat Set Upon Nearly One Acre Of Meticulously Manicured Grounds, Offering A Haven From The Urban Clamor. This Distinguished Residence Spans 6,000 Square Feet Across Two Main Levels, Augmented By An Addit...

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Photo of Listing #12151248

1080 Fisher Crescent Lane, Winnetka, IL - $3,580,000

Residential, Detached Single
  • 6 Beds
  • 5 Baths
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Stately Home Located In The Coveted East Winnetka Fisher Crescent Lane Neighborhood, This Elegant Residence Offers The Perfect Combination Of Luxury, Tranquility And Convenience. Situated On Over Half An Acre, The Home Is Nestled In A Nature-fille...

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Photo of Listing #12158346

624 Pine Lane, Winnetka, IL - $6,350,000

Residential, Detached Single
  • 5 Beds
  • 8 Baths
  • 13.5k SQFT
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Welcome To This Stunning Custom Home Designed By Morgante Wilson, With Thoughtful Input From Discerning Owners. This Once In A Lifetime Home Is Nestled On A Picturesque 0.86-acre Lot On Private Pine Lane Near Schools, Town And Train. This Thoughtf...

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Photo of Listing #12120075

36 Indian Hill Road, Winnetka, IL - $2,950,000

Residential, Detached Single
  • 4 Beds
  • 6 Baths
  • 5,638 SQFT
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First Time On Market Ever! Special Renovated Classic Set On 1 Acre, Nestled Within The Coveted Landscape Of Indian Hill Road Overlooking The 5th Fairway. A Timeless English Tudor, With A Major Renovation And Addition By The Current Owners (only Th...

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1492 Asbury Avenue, Winnetka, IL - $1,250,000

Residential, Detached Single
  • 4 Beds
  • 3 Baths
  • 3,254 SQFT
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1492 Asbury Is A Spacious And Charming Home Located In The Desirable Hubbard Woods Area Of Winnetka, Il. This Property Features Four Large Bedrooms And 2.5 Bathrooms, Providing Ample Space For Families Or Investors. The Recently Updated Kitchen In...

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104 Longmeadow Road, Winnetka, IL - $4,729,000

Residential, Detached Single
  • 7 Beds
  • 9 Baths
  • 13k SQFT
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An Extraordinary Testament To Luxury Living, This Home Has Been Completely Transformed From The Ground Up By Award-winning Architect Karl Straussburger. Every Detail Has Been Meticulously Curated To Cater To Athletes, Artists, Chefs, And Enthusias...

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917 Willow Road, Winnetka, IL - $1,785,000

Residential, Detached Single
  • 4 Beds
  • 5 Baths
  • 4,145 SQFT
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Introducing 917 Willow Road, Your Opportunity To Customize This Nearly 4200 Sq. Ft. Dream Home In The Heart Of Winnetka. This Is The Last Of Three Custom Homes In The Winnetka Trio, Conveniently Located Only Blocks From Local Favorite Boutiques An...

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838 Cherry Street, Winnetka, IL - $1,519,000

Residential, Detached Single
  • 4 Beds
  • 4 Baths
  • 3,510 SQFT
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Immaculate Move-in Ready, Elegant English Country Garden Family Home In Winnetka. Ideal "walk-to" Location To Metra, Library, Village Shopping & Dining, Schools, Parks, Playground & Beach. Ivy Covered Side Entrance With 2 Car Attached Garage With...

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Midwest Real Estate Data LLC Logo 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, 2024 at 10:53pm CDT.