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Winnetka Homes for Sale , $3,000,000 - $5,000,000

$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 #12525471

213 Linden Street, Winnetka, IL - $3,199,900

Residential, Detached Single
  • 6 Beds
  • 7 Baths
  • 5,338 SQFT
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Centrally Located In A Premiere "get To Everything" A+ Location, This Quintessential North Shore Coastal Shingle Home Delivers The Best Of Both Worlds. Thoughtfully Remodeled And Reimagined By Notable North Shore Architect Paul Konstant That Beau...

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1015 Sheridan Road, Winnetka, IL - $3,750,000

Residential, Detached Single
  • 6 Beds
  • 8 Baths
  • 8,303 SQFT
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Nestled On A Private Lane East Of Sheridan Road, This Distinguished Residence Combines Timeless Sophistication With Everyday Livability. With Over 6 Bedrooms (including An In-law/guest Suite) And 7.1 Baths, The Home Is Designed To Accommodate A Va...

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Photo of Listing #12505224 CONTINGENT

889 Cherry Street, Winnetka, IL - $3,295,000

Residential, Detached Single
  • 5 Beds
  • 7 Baths
  • 5,339 SQFT
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Just Completed October 28th, This Breezy, Bright, And Beautifully Coastal New Construction By One Of The North Shore's Premier Builders Captures The Essence Of Modern Beachy Living. From The Moment You Arrive The Sea Salt Blue Shutters Set The Ton...

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Photo of Listing #12489209 CONTINGENT

2202 Martin Lane, Northfield, IL - $3,999,999

Residential, Detached Single
  • 8 Beds
  • 11 Baths
  • 21k SQFT
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Experience The Ultimate In Luxury Living At 2202 Martin Ln In Northfield, Where Everyday Life Feels Like A Dream Vacation. An Exceptional Masterpiece On A Private Cul-de-sac Street. Large Home, Aprx 21,000 Sf, With Spectacular Architecture & Sett...

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Photo of Listing #12447231 CONTINGENT

640 Hill Road, Winnetka, IL - $4,560,000

Residential, Detached Single
  • 6 Beds
  • 7 Baths
  • 8,549 SQFT
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Greeley And Winnetka Schools!! Welcome To Meadowpool - A Distinguished Tudor Residence Nestled On A Meticulously Landscaped And Wooded One Acre Lot. Built In 1923, The Home's Design Exudes Classic Tudor Charm With Stucco And Stone Exterior And A S...

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32 Woodley Road, Winnetka, IL - $4,950,000

Residential, Detached Single
  • 5 Beds
  • 7 Baths
  • 9,908 SQFT
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Nestled Down A Winding, Private Road On 1.9 Meticulous Park-like Acres, This Grand, Almost 10,000 Square Foot Residence Exudes Luxury And Timeless Elegance. The Front Entrance Is Set Apart From The Road By A Sweeping Circular Drive Bordered By Pri...

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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 December 4th, 2025 at 11:08pm CST.