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View All Winnetka Homes for Sale _ Updated Every 15 minutes

All Listings $400,000 - $500,000 $500,000 - $600,000
$600,000 - $700,000 $700,000 - $800,000 $800,000 - $900,000
$900,000 - $1,000,000 Over $1,000,000
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Photo of Listing #10681505

834 Boal Parkway, Winnetka, IL - $1,785,000

Residential, Detached Single
  • 6 Beds
  • Baths
  • 5,489 SQFT
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Golf Course Lifestyle Every Day! Solidly Built & Freshly Decorated Newer Red Brick Georgian Sited On 1/2 Acre Of Breathtaking Grounds On A Quiet Lane Across From The Golf Course. Every Room In The Right Place With Soaring Ceilings, Fine Millwork,...

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Photo of Listing #10705127

288 Auburn Avenue, Winnetka, IL - $849,000

Residential, Detached Single
  • 5 Beds
  • Baths
  • 4,514 SQFT
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Large Price Adjustment Makes This One Of Winnetka's Best Values For Size And Location.fabulous Five Bedroom 3+ 1/2 Baths In This Well Designed Contemporary. Vaulted Foyer Leads To Vaulted Ceiling Living Room With Massive Stone Fireplace, Recessed ...

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Photo of Listing #10701644

418 Ridge Avenue, Winnetka, IL - $1,115,000

Residential, Detached Single
  • 4 Beds
  • Baths
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Buyers Will Fall In Love With This Classic And Stately Winnetka Red Brick Colonial With Extra Wide And Deep Lot That Is Perfect For Children Of Any Age And Dogs. In Addition To Privacy Fences Lining Side And Back, There Is An Invisible Fence If Ne...

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Photo of Listing #10697978

922 Cherry Street, Winnetka, IL - $1,375,000

Residential, Detached Single
  • 5 Beds
  • Baths
  • 5,000 SQFT
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Masterfully Built, French Inspired Brick & Limestone Home Combines Exceptional, High-end Finishes With Fabulous Floor Plan Designed For Both Daily Living And Entertainment. Step Inside To A Dramatic 2 Story Foyer With Spiral Staircase And Flowing ...

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15 Woodley Road, Winnetka, IL - $4,090,000

Residential, Detached Single
  • 6 Beds
  • 7 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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Photo of Listing #10690033

695 Prospect Avenue, Winnetka, IL - $1,649,000

Residential, Detached Single
  • 7 Beds
  • Baths
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New Priorities In Housing Have Come From The Current "at Home" Lifestyle. Top Of The List For Families Are Rooms For Doing Your Job And Recreation Space. Privacy Is Another "must" When Everyone Is Together 24/7! The Solution Has Simply Become Floo...

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Photo of Listing #10674406

1141 Chatfield Road, Winnetka, IL - $1,349,000

Residential, Detached Single
  • 6 Beds
  • Baths
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Looking For An A+ Location Just Steps To The Hubbard Woods Downtown, School And Metra While Enjoying The Lifestyle And Feel Of A New Construction Home? A 2017 Down To The Studs Renovation And Expansion Of This Sunny 5+bedroom/5.1bath Home Created ...

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Photo of Listing #10661254

972 Pine Street, Winnetka, IL - $775,000

Residential, Detached Single
  • 3 Beds
  • Baths
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A Storybook Tudor W/slate Roof & Tudor-designed 2 Car Gar. A Solidly Built Brick Home, Family Rm W/fplc & Vaulted Ceilings, A Brick Patio Off Fam Rm W/sliders To Deep Wooded Yard. Charm & Character Throughout, W/ Gorgeous Liv Rm, Wood Moldings & F...

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Photo of Listing #10566791

1441 Tower Road, Winnetka, IL - $799,000

Residential, Detached Single
  • 5 Beds
  • Baths
  • 4,266 SQFT
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Gorgeous, Deep Lawn And Landscapes Surround This Spacious, Fabulous Home In Beautiful Hubbard Woods. Walk To Charming Hubbard Woods For Ice Cream, Lunch, Dinners And Parks! All The Conveniences For Today Are Included Under One Roof! Fantastic Ope...

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907 Oak Street, Winnetka, IL - $1,399,000

Residential, Detached Single
  • 5 Beds
  • 5 Baths
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Fantastic, Newer, Custom Build Home With Recent Updates And Large Scale Living Spaces On 4 Floors And Great Flow & Upgrades In A Coveted Location Close To Town, Train And Schools! 907 Oak Boasts A Super Sized Family Room With Fireplace And Wall ...

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560 Oak Street, Winnetka, IL - $3,175,000

Residential, Detached Single
  • 6 Beds
  • Baths
  • 4,900 SQFT
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New Construction In Prime East Winnetka. Walk To Beach, Greeley School, New Trier, Train And Town. Six Bedrooms, 5.1 Baths, Sport Court With 17' Ceiling, Gourmet Kitchen With Top Of The Line Appliances, Walnut Library, Timeless Elegance With Exqui...

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Photo of Listing #10633303

800 Green Bay Road, Winnetka, IL - $475,000

Residential, Detached Single
  • 3 Beds
  • 2 Baths
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Move In Ready Home In Beautiful Village Of Winnetka. Walking Distance To Shops, Restaurants, And Train. First Floor Features Formal Living Room, Dining Room, Family Room, Eat In, Newer Kitchen With Brand New Appliances And A Full Bathroom With Tub...

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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 August 5th, 2020 at 6:06pm CDT.