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View All Winnetka Homes for Sale _ Updated Every 15 minutes, $2,000,000 - $3,000,000

$250,000 - $500,000 $500,000 - $750,000 $750,000 - $1,000,000
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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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Photo of Listing #10911400

856 Sheridan Road, Winnetka, IL - $2,950,000

Residential, Detached Single
  • 5 Beds
  • 6 Baths
  • 8,600 SQFT
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Welcome To 856 Sheridan Road! Perfection Through And Through In This Stately East Winnetka Brick Home Just Steps From Lake Michigan And The Beaches. Incredible Space Throughout, From The Moment You Walk Into The Two Story Marble Entry. This Home...

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741 Prospect Avenue, Winnetka, IL - $2,950,000

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 - $2,850,000

Residential, Detached Single
  • 6 Beds
  • 6 Baths
  • 6,820 SQFT
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Luxury And Elegance Of 1918 Updated With The Magnificence Of Today's Standards And Luxury! The Home You Have Been Dreaming Of Is Available Now! Your Search For Perfection Lives At 744 Prospect Avenue And You Can Too. Incredible Neighborhood, Pa...

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Photo of Listing #10273000

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

Residential, Detached Single
  • 7 Beds
  • 12 Baths
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Completely Renovated, Expanded & Enhanced This Spectacular Woodley Road Residence Is Situated On Nearly An Acre Of Sweeping Lawns, Manicured Hedges & Mature Trees. The 3-story Georgian Home Boasts Well Over 10,000 Sq Ft Of Living Space Highlighte...

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120 Evergreen Lane, Winnetka, IL - $2,675,000

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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175 De Windt Road, Winnetka, IL - $2,599,999

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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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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1225 Spruce Street, Winnetka, IL - $2,345,000

Residential, Detached Single
  • 5 Beds
  • 6 Baths
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One-of-a-kind Private Oasis With Completely Renovated Four Season Outdoor Lifestyle Amenities, Including Swimming Pool, Spa, Pool-house And Outdoor Kitchen, On A Beautifully Landscaped Half-acre In The Heart Of Winnetka! Stunning Home Expansion D...

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467 Sheridan Road, Winnetka, IL - $2,150,000

Residential, Detached Single
  • 5 Beds
  • 4 Baths
  • 4,400 SQFT
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Rare Opportunity To Own This Custom Home In Desirable East Of Sheridan Road With Private Beach Rights! The 4400sf, 5bd/3.5 Bath, Open Floor Plan Home Is Flooded With Natural Light And Perfect For Entertaining. All Rooms Are Generously Sized In Th...

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679 Hill Road, Winnetka, IL - $2,150,000

Residential, Detached Single
  • 4 Beds
  • 8 Baths
  • 7,559 SQFT
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Sensationally Revamped Sun-filled, Newer Construction Home On Almost One Half Acre Fenced Property Blending Classic Bones, Transitional Decor And New Updates Making It A Perfect Lifestyle Home For Today. Brick Paver Circle Drive Directs You To ...

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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 March 4th, 2021 at 12:01am CST.