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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
$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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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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Photo of Listing #10980400

27 Indian Hill Road, Winnetka, IL - $4,799,000

Residential, Detached Single
  • 6 Beds
  • 9 Baths
  • 8,800 SQFT
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Outstanding Georgian Home Situated On A Secluded 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 Se...

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47 Indian Hill Road, Winnetka, IL - $4,795,000

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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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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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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150 Meadow Lane, Winnetka, IL - $3,999,900

Residential, Detached Single
  • 5 Beds
  • 6 Baths
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Idyllic & Rare Winnetka Estate Set On Picturesque Grounds Of 1.5 Acres Right In The Heart Of Winnetka & In Crow Island District! A Special Renovated Gem That Offers Serenity And Privacy Unlike Any Thing Else This Close To Town. Organically Set At ...

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Photo of Listing #11052334

246 Sheridan Road, Winnetka, IL - $3,559,900

Residential, Detached Single
  • 6 Beds
  • 9 Baths
  • 5,850 SQFT
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With Breathtaking, Unobstructed Views Of The Lake, This Ideally Positioned Beauty Directly Across From Centennial Park & Elder Beach Is The Ultimate Winnetka Retreat With A Fantastic Pool & Outdoor Oasis. Incredibly Solid Commercial Grade Built Es...

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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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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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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 9:16pm CDT.