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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 #12121925

139 Sheridan Road, Winnetka, IL - $10,699,900

Residential, Detached Single
  • 5 Beds
  • 8 Baths
  • 12.7k SQFT
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Beautifully Perched In The Bluff With Incredible Panoramic Lake Views From All Rooms, This Newly Built Crisp Navy, Blue Cedar Shake Nantucket Accented With White Trim Brings Home The Best In Class To Winnetka Lakefront Living. Custom Built By Morg...

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Photo of Listing #12119089

950 Westmoor Road, Winnetka, IL - $2,265,000

Residential, Detached Single
  • 5 Beds
  • 6 Baths
  • 5,260 SQFT
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Stunning New Construction Home By Local Builder With Over 30 Years Of Custom Home Building! Best Value For New Construction In Winnetka! First Floor Includes An Open Floor Plan Including A Chef's Kitchen With High End Appliances, Custom Cabinetry ...

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Photo of Listing #12106751

681 Lincoln Avenue, Winnetka, IL - $4,195,000

Residential, Detached Single
  • 6 Beds
  • 7 Baths
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Amazing Opportunity To Own One Of Winnetka's Most Incredible Properties! This Benjamin Marshall Beauty Sits On 2/3rds Of An Acre In The Heart Of The Village. Professionally Landscaped With An Oversized Pool, Putting Green And 1/2 Basketball Cour...

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Photo of Listing #12118505

747 Walden Road, Winnetka, IL - $2,490,000

Residential, Detached Single
  • 6 Beds
  • 7 Baths
  • 4,970 SQFT
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Step Into This Bright And Airy Modern Farmhouse New Construction In Coveted Hubbard Woods, And Call It Home. Situated Between Hubbard Woods And Winnetka Metra Stations, This Charming Light-filled 7 Bed 6.5 Bath Home Is Situated On Walden Road, A S...

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Photo of Listing #12109883

269 Locust Road, Winnetka, IL - $1,695,000

Residential, Detached Single
  • 5 Beds
  • 5 Baths
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Set Back From The Street, This 5 Bedroom, 4.5 Bath Meticulously Maintained Cape Cod Sits On A Picturesque, Private Half Acre. There Are Two Primary Bedroom Suites, One On Main Floor And The Other On The Second Floor. As You Enter Through The Front...

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542 Meadow Road, Winnetka, IL - $1,299,000

Residential, Detached Single
  • 4 Beds
  • 4 Baths
  • 3,384 SQFT
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Welcome To This Spectacular 4 Bedroom, 3.1 Bath Home In Sought After Winnetka Location On An Oversized Lot 50 X 190 With The Benefits Of Joseph Sears School In Kenilworth. Charm Abounds When You Step Into This Beautiful Brick Tudor Home. With Ove...

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597 Oak Street, Winnetka, IL - $2,250,000

Residential, Detached Single
  • 5 Beds
  • 8 Baths
  • 5,193 SQFT
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A Rare Opportunity To Own This Masterful Renovation Of A French Provincial Revival Home In East Winnetka. The Most Classic Old World Feel, And Completely Rebuilt And Expanded In 2011 To 3 Floors, 5 Bedrooms, And 5.3 Bathrooms. Winner Of The 2014 W...

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1201 Lindenwood Drive, Winnetka, IL - $4,350,000

Residential, Detached Single
  • 5 Beds
  • 7 Baths
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Welcome To Your Dream Home At 1201 Lindenwood Dr. This Stunning Residence Seamlessly Blends Timeless Elegance With Modern Luxury, Offering The Perfect Blend Of Comfort And Sophistication. No Detail Has Been Left Untouched. As You Step Through The ...

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302 Walnut Street, Winnetka, IL - $1,150,000

Residential, Detached Single
  • 3 Beds
  • 3 Baths
  • 2,883 SQFT
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East Winnetka Home Combines The Charm Of An Arts And Crafts Bungalow W/all The Modern Luxuries Of A 2013 Gut Renovation. Inviting Screened-in Porch Opens To Stylish Foyer, Oversized Living Room With Gas Fireplace And Formal Dining Room With Built-...

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332 Elder Lane, Winnetka, IL - $2,775,000

Residential, Detached Single
  • 7 Beds
  • 6 Baths
  • 8,626 SQFT
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Rare Opportunity To Own A House Steps To Lake Michigan In The Heart Of Winnetka On An Almost Half Acre Lot. Grand 7 Bed 4.2 Bath Full Masonry Home Built In 1916 With 5753 Sqft Above Grade Living Space In The Prairie School Style, Exudes Elegance, ...

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1000 Vernon Avenue, Winnetka, IL - $1,399,000

Residential, Detached Single
  • 4 Beds
  • 3 Baths
  • 3,277 SQFT
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Welcome To This English-style Home In The Heart Of Hubbard Woods! Situated On A Spacious Corner Lot, This Home Boasts An Abundance Of Natural Light And A Serene Private Backyard, Providing The Perfect Blend Of Elegance And Tranquility. Step Throug...

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2245 Drury Lane, Northfield, IL - $1,695,000

Residential, Detached Single
  • 3 Beds
  • 3 Baths
  • 3,300 SQFT
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Rarely Available! A Very Special 3-bedroom Ranch Home Situated On 1+ Beautiful Acres On A Highly Desirable Private Lane. A Magnificent And Loving Redesign Of Both Interior & Exterior Has Recently Been Completed. Renovations Are Too Many To Be...

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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 July 27th, 2024 at 5:53am CDT.