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Browse All Homes for Sale Along Chicago's North Shore, $5,000,000 - $10,000,000

$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
Over $10,000,000
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139 Sheridan Road, Winnetka, IL - $9,499,900

Residential, Detached Single
  • 5 Beds
  • 8 Baths
  • 9,723 SQFT
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Summer Is Right Around The Corner, And 139 Sheridan Is The Ultimate Lakefront Escape. Built Into The Bluff And Just Steps To The Water, This Turnkey Morgante Wilson Custom Home Is Designed For Effortless Lake Living. One Of The Last New Constructi...

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2441 Woodbridge Lane, Highland Park, IL - $6,900,000

Residential, Detached Single
  • 9 Beds
  • 12 Baths
  • 10.8k SQFT
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Introducing An Exceptional Lakefront Residence On One Of Highland Park's Most Coveted Private Lanes. Set On A Masterfully Landscaped 1.85-acre Parcel, 2441 Woodbridge Lane Offers A Rare Combination Of Privacy, Scale, And Sophistication-backed By U...

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Photo of Listing #12275847 CONTINGENT

959 Sheridan Road, Highland Park, IL - $5,750,000

Residential, Detached Single
  • 5 Beds
  • 8 Baths
  • 7,800 SQFT
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Experience Coastal Elegance On Lake Michigan, Perfectly Situated On 1 Acre In East Highland Park With 100 Feet Of Private Sandy Beach. All Bluff Work Just Completed By Top North Shore Engineers! Wake Up To Breathtaking Sunrises And Unobstructed La...

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624 Pine Lane, Winnetka, IL - $5,995,000

Residential, Detached Single
  • 5 Beds
  • 8 Baths
  • 13.5k SQFT
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Welcome To This Stunning Custom Home Designed By Morgante Wilson, With Thoughtful Input From Discerning Owners. This Once In A Lifetime Home Is Nestled On A Picturesque 0.86-acre Lot On Private Pine Lane Near Schools, Town And Train. This Thoughtf...

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140 Sheridan Road, Winnetka, IL - $9,999,500

Residential, Detached Single
  • 5 Beds
  • 7 Baths
  • 13.2k SQFT
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This Is The North Shore's Most Regal Restoration To Ever Come On The Market With A Captivating, Majestic Presence Set On A Rare 1 Plus-acre Lot That Also Includes A Buildable Lot For A 2nd Structure To Create The Ultimate East Winnetka Estate. Thi...

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111 Mayflower Road, Lake Forest, IL - $6,250,000

Residential, Detached Single
  • 7 Beds
  • 7 Baths
  • 7,149 SQFT
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Rare Opportunity To Own This Beautiful Lakefront Home On 4.11 Acres W/ 300' Of Lake Michigan Shoreline On Coveted Mayflower Road. Located Down A Tree-lined Driveway At The End Of A Private Lane, This Stately Brick Home Was Built In 1914 And Featur...

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Photo of Listing #12263738

261 East Onwentsia Road, Lake Forest, IL - $7,250,000

Residential, Detached Single
  • 8 Beds
  • 13 Baths
  • 11.5k SQFT
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This Stunning East Lake Forest Estate Combines Elegant Architecture With Natural Beauty, Sitting On Nearly Three Gated Acres In The Heart Of Town. Designed In Collaboration With The Renowned Architect Darcy Bonner In 2010 It's A Perfect Blend Of S...

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147 Central Avenue, Highland Park, IL - $5,500,000

Residential, Detached Single
  • 4 Beds
  • 4 Baths
  • 4,600 SQFT
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Discover A Rare Gem On Central Ave-this Stunning Victorian Historic Landmark Sprawls Over 4 Picturesque Acres, Just Steps From The Pristine Shores Of Lake Michigan. This Unique Property, Once Called The Cornelius Field House, Features A Beautifull...

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794 Greenwood Avenue, Glencoe, IL - $5,275,000

Residential, Detached Single
  • 5 Beds
  • 8 Baths
  • 9,000 SQFT
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New Magnificent Transitional Home With Approximately 9,000 Square Feet Finished Space. Exterior Is Constructed Of Brick And Limestone With Slate Roof Which Represents Timeless Construction On One Of The Most Picturesque Streets In Glencoe. Close T...

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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 April 29th, 2025 at 1:23pm CDT.

CHOOSE YOUR LIFESTYLE

Linda Shaughnessy

In a city where the skyline is constantly reinventing itself, Linda Shaughnessy stands as a constant – a trusted luxury real estate advisor and confidante for her clients and a respected professional among her peers.

Linda approaches each client’s needs with care, dedication, and discretion. Her loyal clientele is a testament to her exceptional service, all of whom value her extensive knowledge of Chicago’s best buildings and cooperative boards.

A native New Yorker, Linda quickly adapted her discipline as a fashion buyer to excel in her new career as a luxury Chicago real estate broker. Her tenacity caught the eye of Jules Marling, chairman of Sudler Marling, a boutique Gold Coast brokerage and property management company. He hired Linda as senior vice president of brokerage to oversee the management of the company's three residential sales offices. In that role, Linda actively participated in Christie’s International Real Estate Network Great Estates.

Linda’s affiliations have also included membership in the Chicago Association of Realtors’ Top 1% Club, a past member of Who's Who in Luxury Real Estate board of governors, "LuxeHome 25" - the top 25 luxury real estate agents in Chicago, and she was included among the Megabrokers of the Midwest" by the luxury real estate publication Unique Homes. Currently, Linda is Senior Vice President of Sales at Jameson Sotheby’s International Realty..

Working seamlessly with a team of professionals, Linda is positioned to assist her clients with the highest level of personal service, ensuring that buyers and sellers have the information needed to make value-based real estate decisions.

REVIEW A SELECTION OF LINDA'S SIGNIFICANT SALES


“The location, the style, the feeling you get when you walk through the door – every aspect of your home should be a reflection of who you are, where you’ve been, and the life you aspire to live. Your best life begins with a home that inspires you.”

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