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View All Winnetka Homes for Sale _ Updated Every 15 minutes, $3,000,000 - $5,000,000

$250,000 - $500,000 $500,000 - $750,000 $750,000 - $1,000,000
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27 Indian Hill Road, Winnetka, IL - $4,999,000

Residential, Detached Single
  • 6 Beds
  • 9 Baths
  • 8,800 SQFT
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Outstanding Georgian Home Situated On 1.6 Acres Overlooking Spring Fed Lake. This Classic Home Was Built In 2005 With Exquisite Millwork, Generously Scaled Rooms And Eleven Foot Ceilings On The First Floor And 9 Foot Ceiling On The Second Floor....

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Photo of Listing #10857430

47 Indian Hill Road, Winnetka, IL - $4,950,000

Residential, Detached Single
  • 6 Beds
  • 8 Baths
  • 12.2k SQFT
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Magnificent Winnetka Estate Featured In Sheridan Road Magazine And The Rush Hospital's Coveted 2018 Cooks' Tour. Set Upon An Expansive 1.3-acre Lot, This Incredible Home Offers Views Of Indian Hill Club's 4th Green. Completed In 2016, This 12,200 ...

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745 Sheridan Road, Winnetka, IL - $4,890,000

Residential, Detached Single
  • 6 Beds
  • 8 Baths
  • 7,568 SQFT
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This Magnificent French Chateau, Custom Private Real Estate Is Situated On East Of Sheridan Rd, Luxury Mentions Surrounded Winnetka's Glorious Lakefront. This 7 Bed/7.5 Bath Home Welcomes You With A Circle Drive And Meticulous Landscaping And Has ...

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885 Private Road, Winnetka, IL - $4,499,000

Residential, Detached Single
  • 5 Beds
  • 5 Baths
  • 10.5k SQFT
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Extraordinarily Rare New Construction On Over A Half Acre (.6) Of A Beautiful Wooded Lot On One Of Winnetka's Most Coveted Locations. Fantastic In-town Country Living On A Private Retreat Artfully Crafted By One Of The North Shores Premier Builder...

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Photo of Listing #10935023

150 Meadow Lane, Winnetka, IL - $4,449,900

Residential, Detached Single
  • 5 Beds
  • 6 Baths
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As If You Were Set In The Famous Movie "the Holiday" This Picture Perfect Cotswolds Country Estate Rolls Right Of A Movie Set. Organically Set Down The End Of Private Meadow Lane Set On Glorious Lush 1.4 Acres Of Mature Grounds With Cascades Of En...

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738 Tower Road, Winnetka, IL - $3,999,999

Residential, Detached Single
  • 6 Beds
  • 11 Baths
  • 10k SQFT
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Outstanding Beautiful Lakefront Red Brick Georgian Nestled Between Tower & Lloyd Beaches In The Heart Of East Winnetka! Spectacular Lake Views From All 4 Floors Of Phenomenal Space. Watch The Sunrise & Set. Gated Entrance - A Stunning Grand Foyer ...

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460 Ash Street, Winnetka, IL - $3,999,999

Residential, Detached Single
  • 5 Beds
  • 8 Baths
  • 8,400 SQFT
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Proposed New Construction Located In A Great A+ East Winnetka Location Just A Block From Lake Michigan, Close To Schools And Train. This Home Will Be Built With All Of The Top Level Materials And Designer Finishes. 5 En-suite Bedrooms Above Grade ...

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1005 Mount Pleasant Road, Winnetka, IL - $3,899,900

Residential, Detached Single
  • 5 Beds
  • 7 Baths
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Incredible One Of A Kind Offering As This Home Isn't Just Newer Impeccable Construction... It's A Spectacular Designer Showcase Home Delivers Over 8,000 Sq. Ft. Of Perfection. The Finest Finishes & Design In An Equally Amazing Location At The End ...

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265 White Oak Lane, Winnetka, IL - $3,695,000

Residential, Detached Single
  • 5 Beds
  • 8 Baths
  • 8,105 SQFT
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This Is It... A+ Location One Of Winnetka's Most Special Lanes A One Of A Kind New Construction Home That Delivers The Ultimate Living & Entertaining Experience W/the Finest Details & Features. City Dwellers This Is Your House As It's Hip & Trans...

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1095 Fisher Lane, Winnetka, IL - $3,500,000

Residential, Detached Single
  • 5 Beds
  • 7 Baths
  • 7,400 SQFT
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This Fisher Lane House Chooses Timeless Over Trendy... Always. Incorporating Classic Finishes And Custom European Detailing Throughout 7,400 Sf Above Grade, This Magnificent Home Exudes Style And Comfort On 3/4 Of An Acre In Coveted East Winnetka!...

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977 Sheridan Road, Winnetka, IL - $3,495,000

Residential, Detached Single
  • 4 Beds
  • 7 Baths
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Timeless And Modern....classical Inspired Architecture! Privacy In A Winnetka Property Encircled With Mature Trees And Tucked Away On A Quiet Private Road East Of Sheridan Road! This Spectacular Home Has Exceptional Quality And Design Throughout W...

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Photo of Listing #10917574

15 Woodley Road, Winnetka, IL - $3,400,000

Residential, Detached Single
  • 6 Beds
  • 8 Baths
  • 6,057 SQFT
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Majestic In Its Own Right, This One-of-a-kind Woodley Road Estate Was Carefully Crafted To Withstand The Test Of Time And Impeccably Maintained By The Current Owners For Over Forty Years. Stately Gated Entrance Upon Arriving At This Private Stone ...

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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.