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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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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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22 Country Lane, Northfield, IL - $1,550,000

Residential, Detached Single
  • 4 Beds
  • 4 Baths
  • 4,245 SQFT
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Sprawling Country Home With Four Fireplaces And Attached Garage Situated On 1.2+ Acres On A Highly Desirable Private Lane In Ideal Walk-to-everything Location. Thoughtfully Renovated And Lovingly Cared For With Spacious Floor Plan Featuring A Sun-...

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840 Lamson Drive, Winnetka, IL - $1,549,999

Residential, Detached Single
  • 5 Beds
  • 4 Baths
  • 6,736 SQFT
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Stunning Southern Colonial Situated On A Beautifully Landscaped Half Acre Less The A Block From Tower Beach And Two Blocks From Lloyd Beach. Exquisite Foyer Features A Curved Staircase And Appealing Wainscoting. Handsome Paneled Library With Firep...

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Photo of Listing #11085587

747 Ash Street, Winnetka, IL - $1,549,000

Residential, Detached Single
  • 4 Beds
  • 5 Baths
  • 2,784 SQFT
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Stylish Brick Colonial With Open Floor Plan And In Town Location! Fabulous Great Room With Fireplace Is Adjacent To The Kitchen And Opens The Expansive Deck. Bright White Updated Kitchen Includes Island, Eating Area, High-end Appliances And Gene...

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Photo of Listing #11087403

1140 Chatfield Road, Winnetka, IL - $1,499,000

Residential, Detached Single
  • 4 Beds
  • 3 Baths
  • 3,779 SQFT
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Remarkable Home With Space For Everyone In The Perfect Hubbard Woods Location. Thoughtfully Expanded And Continually Renovated Over The Course Of Ownership. Always Keeping The Classic Design Of The Original House In Mind While Incorporating Contem...

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Photo of Listing #11087153

846 Oak Street, Winnetka, IL - $1,495,000

Residential, Detached Single
  • 4 Beds
  • 5 Baths
  • 5,196 SQFT
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Fabulous Newer Construction 5 Bedroom Home With Recent Improvements Has The Features And Floor Plan Today's Buyers Seek. Beautiful Entry Foyer With Gracious Staircase Leads To The Living And Dining Rooms. The Newly Updated White Cabinet Kitchen W...

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140 Westview Road, Winnetka, IL - $1,495,000

Residential, Detached Single
  • 5 Beds
  • 4 Baths
  • 4,654 SQFT
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A Lush Half-acre In Winnetka's Most Ideal Location - Walk To The Award-winning Crow Island (k-4), Skokie (5/6), And Washburne (7/8) Schools. This 5 Bedroom Home Has Been Completely And Tastefully Renovated With Additions Designed By Paul Konstant....

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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.