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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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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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4 Indian Hill Road, Winnetka, IL - $2,149,000

Residential, Detached Single
  • 5 Beds
  • 7 Baths
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Now The Best Value On Indian Hill!! Tucked Off The Gold Course In An Exclusive Enclave On A Special Little Lane...it's All Here In This Custom Built Home W/first Floor Primary Bedroom, As The Open Floor Plan Is A Perfect Canvas For Those Who Want ...

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678 Sheridan Road, Winnetka, IL - $1,999,900

Residential, Detached Single
  • 6 Beds
  • 5 Baths
  • 4,826 SQFT
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Stunning East Winnetka Gem! Incredible Rehabbed Center Entry Colonial In A Fabulous Location. This Home Has Been Meticulously Redone From Top To Bottom With No Detail Missed. The Spacious And Warm First Floor Offers 3 Fireplaces, A Vast Living Roo...

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1161 Chatfield Road, Winnetka, IL - $1,999,000

Residential, Detached Single
  • 5 Beds
  • 7 Baths
  • 5,560 SQFT
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Stunning Newer Brick Colonial Home Situated On Special Dead End Street! This Three Story Custom Home Features Exceptional Millwork, Custom Cabinetry, Four Masonry Fireplaces, Hardwood Floors, Generator, And Superb Finishes Throughout. Inviting Foy...

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495 Ash Street, Winnetka, IL - $1,999,000

Residential, Detached Single
  • 6 Beds
  • 7 Baths
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East Winnetka! A Stunning Home On One Of East Winnetka's Premier Streets. Designed By Noted Architect Arthur Heun. Heun Also Designed The Adler Mansion, As In The Donor Of The Adler Planetarium. Architecturally Significant Italian Renaissance Home...

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250 Ridge Avenue, Winnetka, IL - $1,995,000

Residential, Detached Single
  • 5 Beds
  • 6 Baths
  • 5,558 SQFT
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Get In On The Ground Floor With A Unique Opportunity To Customize This East Winnetka New Construction 3 Story 5+1 Bedroom/5.1 Bath Home. This Free-flowing Floor Plan Offers Exactly What Today's Buyers Are Looking For. A Well-appointed White K...

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126 Bertling Lane, Winnetka, IL - $1,995,000

Residential, Detached Single
  • 5 Beds
  • 8 Baths
  • 5,827 SQFT
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Incredible Modern Farmhouse In East Winnetka With Attached Garage! Built By Winnetka's Most Well Known Custom Home Builder, This Home Features A Contemporary Design With Luxury Finishes And A Perfectly Laid Out Floor Plan With The Utmost Function...

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561 Orchard Lane, Winnetka, IL - $1,850,000

Residential, Detached Single
  • 5 Beds
  • 6 Baths
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Classically Styled Luxury Home With 6 Bedrooms And 5.1 Tiled Baths In East Winnetka Is Move In Ready With The Outstanding Amenities Discerning North Shore Buyers Require In A Home. Situated With An Amazing Location That Is Just Steps To Schools, T...

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1210 Lindenwood Drive, Winnetka, IL - $1,749,900

Residential, Detached Single
  • 4 Beds
  • 5 Baths
  • 3,841 SQFT
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Fresh & Transitional, This Magnificent Mid-century Modern Shines Bright After An Incredible Rehab On A Manicured, Private Half Acre Lot In One Of Winnetka's Exclusive Locations. Open Floorplan Living With Custom Built-ins, Light Oak Floors, And Fl...

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1015 Starr Road, Winnetka, IL - $1,650,000

Residential, Detached Single
  • 4 Beds
  • 4 Baths
  • 4,011 SQFT
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Amazing Property Located On The Beautiful And Private Starr Street. This Architecturally Significant Home Was Designed By John Van Bergen, The Student Of Frank Lloyd Wright. Work With The Team Of Award Winning Builder And Award Winning Architect T...

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989 Cherry Street, Winnetka, IL - $1,599,000

Residential, Detached Single
  • 4 Beds
  • 5 Baths
  • 3,717 SQFT
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Room To Breathe! Over 5,000 Sq. Ft. Of Living Space In This Fresh And Sophisticated Home On "tree Streets" In Winnetka! Located In The Crow Island/new Trier School System, This Home Has It All! This Exceptionally Upgraded Lannon Stone House, Built...

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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 1:17pm CST.