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View All Winnetka Homes for Sale _ Updated Every 15 minutes

$250,000 - $500,000 $500,000 - $750,000 $750,000 - $1,000,000
$1,000,000 - $2,000,000 $2,000,000 - $3,000,000 $3,000,000 - $5,000,000
$5,000,000 - $10,000,000
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877 Tower Road, Winnetka, IL - $3,499,000

Residential, Detached Single
  • 5 Beds
  • 7 Baths
  • 8,402 SQFT
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A Unique And Special Custom Home From A Successful And Experienced North Shore Builder. A Plus Location Just Steps From The Lake On A Coveted Half-acre Home Site With Mature Trees Lining The Property. This Custom Design Makes This Move Up, Move Do...

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725 Walden Road, Winnetka, IL - $3,295,000

Residential, Detached Single
  • 5 Beds
  • 6 Baths
  • 7,800 SQFT
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Exceptional Custom Home On A Deep, Majestic Lot In The Heart Ofhubbard Woods On Idyllic Walden Road - Walk To Everything! This Spectacular Home Boasts Architectural Digest Quality And Design With Grand Entertaining Rooms, Private Office, Gorgeous ...

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921 Fisher Lane, Winnetka, IL - $2,999,000

Residential, Detached Single
  • 5 Beds
  • 7 Baths
  • 5,700 SQFT
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Feel The Lake Breezes From This Nantucket Style, Cedar Shake Home On .51 Acre In East Winnetka. Built In 2002, This Spectacular, Unique House Features Views Out Of Every Window. 5br X 4.3ba And Space For Everyone. First Floor Office/library, Dr, S...

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117 Woodley Road, Winnetka, IL - $2,750,000

Residential, Detached Single
  • 5 Beds
  • 6 Baths
  • 6,736 SQFT
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Superb One Owner Charles Paige Home Situated On Nearly An Acre On Sought After Woodley Road. Stunning Entry With Curved Staircase Opens To The Incredible Great Room With Volume Ceilings, Fireplace And Oversized Arched Windows. Handsome Paneled L...

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Photo of Listing #10973664

741 Prospect Avenue, Winnetka, IL - $2,750,000

Residential, Detached Single
  • 4 Beds
  • 6 Baths
  • 5,010 SQFT
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Sited On Nearly An Acre (.94) In A Prime East Winnetka Location This Glamorous White Brick Residence Was Designed By Renowned Architect Jerome Cerny And More Recently Rebuilt And Expanded. The Home Is Prominently Located On East Winnetka's Most D...

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744 Prospect Avenue, Winnetka, IL - $2,735,000

Residential, Detached Single
  • 6 Beds
  • 5 Baths
  • 6,820 SQFT
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The Essence Of Winnetka Is Beautifully Captured Within This Timeless, Stately Brick Georgian, Located In The Best East Winnetka "nook" With Winding Roads And Lake Breezes. Majestic In Its Own Right With A Curved Custom Carved Rotunda Centers The ...

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Photo of Listing #11087312

82 Woodley Road, Winnetka, IL - $2,625,000

Residential, Detached Single
  • 6 Beds
  • 6 Baths
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Classic Charm Meets Modern, Sophisticated Elegance. Welcome To 82 Woodley. This Beautiful Home Sits In Just Over 1.5 Professionally, Landscaped Acres And Sits Back Off Sought After Woodley Rd For Additional Privacy. Home Boasts 6 Bedrooms And 5.1...

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1040 Hubbard Place, Winnetka, IL - $2,599,000

Residential, Detached Single
  • 4 Beds
  • 5 Baths
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Spectacular East Winnetka Soft Contemporary On A Tranquil Lane In An Ideal Walk- To-everything Locale. Open, Expansive Rooms, Soaring Ceilings And A Fabulous Floor Plan Combine With Gorgeous Custom Renovations Throughout And An Exceptional 1/2 Acr...

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Photo of Listing #10988825

120 Evergreen Lane, Winnetka, IL - $2,595,000

Residential, Detached Single
  • 6 Beds
  • 9 Baths
  • 5,895 SQFT
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Classic Custom Built Charles Page Home Situated On Quiet Cul Du Sac Lane! Inviting Foyer Features Curved Staircase And Walls. Spacious Living Room Is Highlighted By Fireplace And Views Of The Landscaped Yard. Handsome Wood Paneled Library/office W...

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819 Humboldt Avenue, Winnetka, IL - $2,375,000

Residential, Detached Single
  • 5 Beds
  • 6 Baths
  • 6,500 SQFT
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Beautiful New Construction In The Heart Of Winnetka. Approx 6,500 Sq Ft Finished Space, 6 Bedrooms, 6.1 Baths, Special Features Include Gourmet Kitchen, Custom Built Library, Media Room, Wine Cellar, Terrific Lower Level With Exercise Room. State...

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508 Maple Street, Winnetka, IL - $2,295,000

Residential, Detached Single
  • 5 Beds
  • 6 Baths
  • 5,046 SQFT
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Stunning East Winnetka Georgian On Extra Wide .4 Acre Overlooking The Spectacular Sweeping Grounds Of The Village Green. Wonderful Renovation Of Classic Architecture With Kitchen/breakfast/family Room Across The Back & Addition Of A Additional 2 C...

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175 De Windt Road, Winnetka, IL - $2,275,000

Residential, Detached Single
  • 5 Beds
  • 6 Baths
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Privacy At It's Best! Stately English Home Tucked Away On One Of Winnetka's Most Beautiful Private Roads With It's Own Gated Entrance. This Incredible Sun Filled Home Lives Beautifully Inside And Outside! A Grand Reception Hall With Sweeping Stair...

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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 May 18th, 2021 at 9:31pm CDT.