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Winnetka Homes for Sale , $1,000,000 - $2,000,000

$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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Photo of Listing #12507234 CONTINGENT

611 Ash Street, Winnetka, IL - $1,649,000

Residential, Detached Single
  • 4 Beds
  • 4 Baths
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Welcome To 611 Ash Street In East Winnetka! A True Classic On An Oversized 70x186 Lot. Greeted By The Large Inviting Porch, The Circular Floor-plan Gives The House A Wonderful Flow! Large Gracious Sun-filled Rooms Through Out. The Pretty Kitchen W...

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Photo of Listing #12499816

520 Provident Avenue, Winnetka, IL - $1,950,000

Residential, Detached Single
  • 4 Beds
  • 5 Baths
  • 3,800 SQFT
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A Rare Opportunity In The Heart Of Winnetka, A Beautiful Newer-construction Brick And Stone Home Offering Timeless Design, Modern Comfort, And Impeccable Quality On Every Level. Built In 2005 And Freshly Updated For Today's Lifestyle, This Residen...

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1350 Westmoor Trail, Winnetka, IL - $1,595,000

Residential, Detached Single
  • 5 Beds
  • 5 Baths
  • 4,925 SQFT
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Charming 5-bedroom Stone & Brick Home On A Serene 1/2-acre Lot. Tucked Away On A Quiet Cul-de-sac In A Highly Sought-after Neighborhood, This Beautifully Maintained Multi-level Residence Offers Over 4,500 Square Feet Of Comfortable Living Space. A...

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Photo of Listing #12499401 CONTINGENT

305 Poplar Street, Winnetka, IL - $1,250,000

Residential, Detached Single
  • 3 Beds
  • 3 Baths
  • 3,128 SQFT
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One Of East Winnetka's Most Coveted Locations! Handsome Brick Colonial With Separate Studio Perfectly Blends Timeless Character With Modern Updates. Fresh And Bright With A Circular Floor Plan And Hardwood Floors. Wonderful Living And Entertaining...

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1370 Sunview Lane, Winnetka, IL - $1,995,000

Residential, Detached Single
  • 4 Beds
  • 5 Baths
  • 4,632 SQFT
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Exquisitely Crafted For Luxurious Living And Effortless Entertaining, This Exceptional Residence, Custom Designed By The Homeowner And Noted Local Architectural Firm W.d. Murphy Associates, Backs Onto The Serene Golf Course, Offering Picturesque V...

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Photo of Listing #12465665 CONTINGENT

455 Sunset Ridge Road, Northfield, IL - $1,100,000

Residential, Detached Single
  • 4 Beds
  • 3 Baths
  • 3,202 SQFT
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Welcome To 455 Sunset Ridge - A Rare 4-bed/3-full-bath North Shore Home That Offers Ranch-like Living. Extensive Renovation In 2014 Included New Tear Off Roof, New Hardie Exterior, Updated Kitchen And Baths, New Front Porch, And More. The Home Off...

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1295 Sunview Lane, Winnetka, IL - $1,299,000

Residential, Detached Single
  • 2 Beds
  • 3 Baths
  • 2,316 SQFT
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Exciting Chance To Refashion This Light-filled Ranch Home To Your Personal Vision. Large Windows Throughout The Home Offer Beautiful Views And Light. The Spacious Kitchen Opens To The Vaulted Family Room. The Master Bedroom And Second Bedroom Ar...

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Photo of Listing #12451416

764 Boal Parkway, Winnetka, IL - $1,550,000

Residential, Detached Single
  • 3 Beds
  • 4 Baths
  • 3,146 SQFT
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Set Amidst A Stunning Wooded Backdrop Between The Tranquil Skokie Lagoons And The Lush Winnetka Golf Club, This Remarkable Home Offers Three Bedrooms And 3.1 Baths Across More Than 3,000 Square Feet Of Thoughtfully Designed Living Space. Situated ...

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Photo of Listing #12402232 CONTINGENT

1288 Sunview Lane, Winnetka, IL - $1,050,000

Residential, Detached Single
  • 5 Beds
  • 4 Baths
  • 2,714 SQFT
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Discover An Incredible Opportunity To Either Construct A Brand-new Home Or Renovate This Charming Traditional Residence Situated On A Picturesque Half-acre Lot. Step Into The Welcoming Entrance Hall, Complete With A Guest Powder Room And Closet, L...

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Photo of Listing #12331764

1492 Asbury Avenue, Winnetka, IL - $1,099,000

Residential, Detached Single
  • 4 Beds
  • 3 Baths
  • 2,380 SQFT
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Rehabbers-opportunity Awaits! Have You Been Searching For A Home On One Of Hubbard Woods' Most Cherished Streets? A Place Where Your Family Can Grow, In A Community Known For Its Charm And Friendly Community? This Is That Rare Opportunity. Thi...

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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 November 6th, 2025 at 9:08pm CST.