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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 #12217284

139 Sheridan Road, Winnetka, IL - $9,750,000

Residential, Detached Single
  • 5 Beds
  • 8 Baths
  • 9,723 SQFT
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Sailing Into 2025 At This Ultimate All-american Beach House, Where Nantucket-inspired Style Meets The Thrill Of Lakefront Living-your Perfect Waterside Escape Awaits! Incredible Opportunity To Own On The Lake In Winnetka For Under 10 Million With ...

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Photo of Listing #12269095

880 Willow Road, Winnetka, IL - $1,100,000

Residential, Detached Single
  • 5 Beds
  • 4 Baths
  • 3,100 SQFT
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Rare Opportunity In Today's Market To Find An Almost-new, Move-in-ready Home Offering Comfort, Convenience And A Contemporary Vibe. This Spacious 5-bedroom, 3.5-bath Home Features A Bright, Open Layout With Natural Oak Floors And A Designer Kitche...

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Photo of Listing #12267764

1166 Cherry Street, Winnetka, IL - $1,350,000

Residential, Detached Single
  • 4 Beds
  • 4 Baths
  • 3,611 SQFT
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Longtime Homeowners Have Meticulously Maintained (and Added Onto) This Exceptionally Large 3600 Square Foot Home. It's So Much Bigger Than It Looks! Get Ready To Have Your Homebuyer Wish List Boxes Checked. Fabulous Winnetka Location On A Favorite...

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Photo of Listing #12271657

625 Thornwood Lane, Northfield, IL - $2,195,000

Residential, Detached Single
  • 5 Beds
  • 7 Baths
  • 7,751 SQFT
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This House Checks All The Boxes For Suburban Paradise! Fun House For Entertaining And Plenty Of Room To Stay Forever! Nestled On A Serene 1/2-acre Lot At The End Of A Peaceful Cul-de-sac, This Beautifully Updated Georgian-style Home Offers The Per...

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1087 Cherry Street, Winnetka, IL - $2,199,000

Residential, Detached Single
  • 4 Beds
  • 5 Baths
  • 3,700 SQFT
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Spectacular New Construction In The Heart Of Winnetka's Picturesque "tree Streets" & Minutes To Winnetka's Vibrant Downtown & Award-winning Schools. Unparalleled Design & Craftsmanship Featuring 4 Bedrooms / 4.1 Baths Expanding 3700 Square Feet. E...

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538 Meadow Road, Winnetka, IL - $1,325,000

Residential, Detached Single
  • 4 Beds
  • 4 Baths
  • 2,907 SQFT
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Fall In Love With The Curb Appeal And All-american Charm Of This Beautiful Home In Kenilworth's Award-winning Joseph Sears School District! 4 Bedrooms, 3 1/2 Baths - This Beauty Boasts A Surprisingly Deep Lot For The Area (50 X 190!) The First Flo...

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870 Heather Lane, Winnetka, IL - $3,599,000

Residential, Detached Single
  • 5 Beds
  • 7 Baths
  • 7,500 SQFT
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Spectacular Opportunity To Customize This Beautiful Proposed New Construction Property On A Half Acre In Gorgeous Winnetka. Featuring 6-bedrooms, 6.1-bathrooms, And Over 7,000 Square Feet Of Total Living Space, Every Detail In This Program Has Bee...

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765 Sheridan Road, Winnetka, IL - $14,900,000

Residential, Detached Single
  • 7 Beds
  • 8 Baths
  • 15.8k SQFT
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Prepare To Be Captivated By This Exceptional Chicago Brick And Limestone Estate, A True Masterpiece Nestled Along The Serene Winnetka Lakefront. Spanning An Impressive 15,784 Square Feet Across Four Levels, This Custom-built Home, Completed In 200...

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115 Dickens Road, Northfield, IL - $2,219,000

Residential, Detached Single
  • 5 Beds
  • 7 Baths
  • 7,678 SQFT
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Resort Style Living Is The Key To This 2.3 Acre Property! *** Builders/developers *** You May Be Able To Subdivide This Property Into Two Buildable Lots! 18' Tall Living Room Greets You As You Enter This 7,600 Sq. Ft Home. It Overlooks 20' ...

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93 Coventry Road, Northfield, IL - $1,350,000

Residential, Detached Single
  • 4 Beds
  • 4 Baths
  • 3,317 SQFT
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A Great Home In The Estate Zoned Area Of Northfield. This House Has Two Double Size Bedrooms A Smaller Bedroom Plus A Master Bedroom With Its Own Bathroom. There Are Two Fireplaces With A Large Living Room, Dining Room And Family Room As Well As...

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351 Ridge Avenue, Winnetka, IL - $1,150,000

Residential, Detached Single
  • 4 Beds
  • 5 Baths
  • 3,040 SQFT
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Step Into This Exquisite 4-bedroom, 4.1-bathroom Gem, Nestled In A Coveted In-town Location Just Moments From The Train, Top-rated Schools, And Lush Parks. This Elegant Home Boasts A Circular Floor Plan Awash With Natural Light, Featuring A Sophis...

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2136 Drury Lane, Northfield, IL - $2,699,000

Residential, Detached Single
  • 5 Beds
  • 6 Baths
  • 6,450 SQFT
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Welcome To 2136 Drury Lane In Northfield -a Stunning Custom-built Contemporary Residence By Power4company That Exemplifies The Pinnacle Of Luxury Living In Northfield. This Exquisite New Construction Features 6 Bedrooms, 5.1 Baths, And An Expansiv...

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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 January 20th, 2025 at 4:38pm CST.