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View All Winnetka Homes for Sale _ Updated Every 15 minutes

$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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Photo of Listing #11997017

44 Woodley Road, Winnetka, IL - $2,799,000

Residential, Detached Single
  • 4 Beds
  • 6 Baths
  • 4,327 SQFT
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Casual Elegance Is Beautifully Interwoven Throughout This Classic Estate Set On An Acre Of Mature Grounds Professionally Landscaped By Scott Byron. Recent Renovations And Enhancements Of Approximately $1.5 Million. The Fenced-in Property Also Feat...

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Photo of Listing #12014972

607 Willow Road, Winnetka, IL - $1,999,999

Residential, Detached Single
  • 5 Beds
  • 6 Baths
  • 4,620 SQFT
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Exquisitely Situated In Highly Sought-after East Winnetka, This Captivating Winn Colonial Home Boasts Timeless Charm And Modern Comforts. Nestled On An Expansive 55 X 187 Lot Just A Short Walk Away From The Serene Shores Of Lake Michigan, This Res...

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256 Woodlawn Avenue, Winnetka, IL - $1,375,000

Residential, Detached Single
  • 4 Beds
  • 3 Baths
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East Winnetka Classic! You Will Love Everything This 4 Bedroom, 2.5 Bath Brick Home Has To Offer. A Center Entry Leads You To A Sun-filled First Floor Featuring A Spacious Living Room With Fireplace, Private Office With French Doors, Separate Dini...

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747 Walden Road, Winnetka, IL - $2,690,153

Residential, Detached Single
  • 6 Beds
  • 7 Baths
  • 4,970 SQFT
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Step Into This Bright And Airy Modern Farmhouse New Construction In Coveted Hubbard Woods, And Call It Home. Situated Between Hubbard Woods And Winnetka Metra Stations, This Charming Light-filled 7 Bed 6.5 Bath Home Is Situated On Walden Road, A S...

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315 Woodland Avenue, Winnetka, IL - $1,775,000

Residential, Detached Single
  • 5 Beds
  • 4 Baths
  • 5,510 SQFT
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This Is The One You've Been Waiting For. Located In Highly Desirable East Winnetka, This Home Combines The Charm Of Years Past With Every Amenity For Today's Lifestyle. With Its Impeccable Design, Spacious Rooms, And Fantastic Location, This Prope...

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807 Bryant Avenue, Winnetka, IL - $2,799,000

Residential, Detached Single
  • 5 Beds
  • 7 Baths
  • 6,589 SQFT
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Feel Lake Breezes In Outstanding Full Gut Renovation And Expansion Of An Exceptional Architectural Home Reimagined By Michael Abraham On Idyllic .4 Acre Just Steps From The Beach, Town, Train & Parks! Stunning, Professionally Landscaped Grounds By...

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1149 Cherry Street, Winnetka, IL - $1,895,000

Residential, Detached Single
  • 5 Beds
  • 5 Baths
  • 3,761 SQFT
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Classic 5 Bedroom 4.5 Bathroom Center Entrance Colonial With Terrific Layout And Extra Wide Lot (75 X180). The Circular Flow Of The House Will Delight Buyers. Late 1990s Addition Off The Back Of The House Allowed For An Open Concept Kitchen/family...

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1234 Westmoor Road, Winnetka, IL - $3,499,000

Residential, Detached Single
  • 4 Beds
  • 8 Baths
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Welcome To Your Dream Home On Idyllic Westmoor Road! This Exceptional Custom Residence Blends Sophistication With California Flair, Offering An Incredibly Livable Space Designed For Easy First-floor Living And Gracious Entertaining. Step Into The...

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1044 Elm Street, Winnetka, IL - $1,795,000

Residential, Detached Single
  • 4 Beds
  • 5 Baths
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You Will Feel The Home's High Quality Of Its Construction, Built In 2004. The Hardwood Floors Don't Creak, The Deep Baseboards, Ceiling Trim, Door And Window Trims Add Luxury To Every Room Including The Basement. This Solid Brick Home With Soarin...

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950 Westmoor Road, Winnetka, IL - $2,439,000

Residential, Detached Single
  • 5 Beds
  • 6 Baths
  • 5,260 SQFT
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Stunning New Construction Home By Local Builder With Over 30 Years Of Custom Home Building! First Floor Includes An Open Floor Plan Including A Chef's Kitchen With High End Appliances, Custom Cabinetry & Massive Island. Kitchen Flows Into The Fa...

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Photo of Listing #11983496

260 Woodlawn Avenue, Winnetka, IL - $3,250,000

Residential, Detached Single
  • 5 Beds
  • 7 Baths
  • 5,392 SQFT
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Simply Beautiful! The Contemporary Home 2024 Is Ready For Occupancy! A Corner Lot Is Across From A Park With A Playground, Only A Few Blocks Away From Lake Michigan. The Exterior Finish Is A Combination Of Stucco And Limestone. Open Concept First ...

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745 Sheridan Road, Winnetka, IL - $3,399,000

Residential, Detached Single
  • 6 Beds
  • 8 Baths
  • 9,930 SQFT
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Welcome To 745 Sheridan Road, A Luxurious And One-of-a-kind Modern Custom-built French Chateau! 745 Features 7 Bedrooms All Of Which Have Their Own Full Bathrooms. Located On The East Side Of The Coveted Sheridan Road And Just Steps Away From The ...

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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 28th, 2024 at 5:53pm CDT.