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View All Winnetka Homes for Sale _ Updated Every 15 minutes, $1,000,000 - $2,000,000

$250,000 - $500,000 $500,000 - $750,000 $750,000 - $1,000,000
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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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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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533 Hawthorn Lane, Winnetka, IL - $1,939,000

Residential, Detached Single
  • 4 Beds
  • 5 Baths
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Stunning Home In East Winnetka! No Detail Spared In This Exceptional 5 Bedroom, 4.1 Bath Home With Spacious, Open Rooms That Flow Seamlessly For Today's Lifestyles. First Floor Features A Large Entrance Hall That Opens To A Living Room (with Firep...

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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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532 Oak Street, Winnetka, IL - $1,799,000

Residential, Detached Single
  • 5 Beds
  • 6 Baths
  • 4,200 SQFT
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Perched On A Lovely 100' Wide Property On One Of East Winnetka's Prettiest Streets, This Grandly-scaled 5 Br/4.2 Ba Classic Feels Like New (whole House Gut Renovation In Early 2000s & Many Recent Updates). Lofty Ceilings, Large Open Rooms & Thick,...

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899 Oak Street, Winnetka, IL - $1,775,000

Residential, Detached Single
  • 5 Beds
  • 6 Baths
  • 5,322 SQFT
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The Best Possible Walk To Everything Location. Just A Couple Blocks To Town, Train, Park, Schools Restaurants And Shopping. Meticulously Maintained And Updated "like" New Construction. With 4 Floors Of Living Space, 6 Bedrooms 5 1/2 Baths, The Lig...

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554 Orchard Lane, Winnetka, IL - $1,775,000

Residential, Detached Single
  • 5 Beds
  • 5 Baths
  • 4,968 SQFT
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Ideally Located In East Winnetka, This Newer Construction Home Features An Open Concept 1st Floor With High End Finishes, Oversized Windows, A Large Backyard And An Attached Garage. The House Is Close To Multiple Parks, Schools, Beaches, 2 Metra ...

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137 Sheridan Road, Winnetka, IL - $1,749,000

Residential, Detached Single
  • 7 Beds
  • 6 Baths
  • 4,981 SQFT
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California And Connecticut Come Together In The East Winnetka Cape Cod Home Sitting On .45 Of An Acre And Steps From The Beach. Terrific Living Space With 7 Bedrooms And 5.1 Baths. Perfect Transitional Layout With 3 Of The Bedrooms (all With En ...

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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, Who Worked With Frank Lloyd Wright. Work With The Team Of Award Winning Builder And Award Winning Architect ...

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1144 Tower Road, Winnetka, IL - $1,649,000

Residential, Detached Single
  • 5 Beds
  • 5 Baths
  • 5,500 SQFT
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**sold While In Private Listing Network**located In The Heart Of Hubbard Woods, Near Town, Train And Schools, This Home Displays The Finest All Brick Construction With Slate Roof, Limestone Quoining And Windowsills. A Dramatic Two-story Foyer With...

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669 Walden Road, Winnetka, IL - $1,599,000

Residential, Detached Single
  • 4 Beds
  • 4 Baths
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Fabulous In Town Winnetka Location! Freshly Painted & Decorated 4+br/3.1 Ba Colonial With Spectacular Recent Improvements Since 2016. Private Retreat On 100'wide Lot In The Heart Of Town. Breathtaking 1/3 Acre On One Of Winnetka's Most Premier S...

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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 9:46pm CDT.