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Browse All Homes for Sale Along Chicago's North Shore, $2,000,000 - $3,000,000

$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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Photo of Listing #12572807

331 East Witchwood Lane, Lake Bluff, IL - $2,095,000

Residential, Detached Single
  • 6 Beds
  • 6 Baths
  • 5,974 SQFT
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Set On A Quiet, Tree-lined Street In East Lake Bluff, This Landmark Home Is Recognized And Admired For Its Classic Tudor Charm. Built In 1929, The Brick-and-slate Residence Offers Nearly 6,000 Square Feet Of Living Space Across Three Finished Leve...

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Photo of Listing #12584903

697 Bluff Road, Lake Bluff, IL - $2,995,000

Residential, Detached Single
  • 4 Beds
  • 7 Baths
  • 6,822 SQFT
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Nestled In East Lake Bluff On A Beautiful Ravine With Seasonal Lake Michigan Views, This Exceptional Home Offers The Rare Luxury Of A Private Beach. A Dramatic Two-story Foyer With A Curved Staircase Sets The Tone For Timeless Elegance. At The Fro...

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Photo of Listing #12585208

1159 Chatfield Road, Winnetka, IL - $2,295,000

Residential, Detached Single
  • 4 Beds
  • 5 Baths
  • 4,390 SQFT
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Blending Timeless Elegance With Modern Sophistication, This Stunning 2016 Winnetka Home Feels Better Than New. Designed For Light, Flow, And Effortless Living, It Features 10-foot Ceilings, White Oak Floors, And Expansive Windows That Fill Each Ro...

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Photo of Listing #12482150

1423 Asbury Avenue, Winnetka, IL - $2,399,000

Residential, Detached Single
  • 6 Beds
  • 7 Baths
  • 5,350 SQFT
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Better Than New! This Artfully Restored & Renovated Home Has The Incredible Combination Of A Classic Center Entry Colonial Home With Sophisticated Formal Rooms And All The Current Amenities For Today's Modern Lifestyle. This Four-level Home Feat...

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Photo of Listing #12577928

875 Gordon Terrace, Winnetka, IL - $2,450,000

Residential, Detached Single
  • 6 Beds
  • 6 Baths
  • 5,687 SQFT
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Set On A Beautifully Landscaped .33 Acre Property In One Of Winnetka's Most Convenient Locations, 875 Gordon Terrace Is A Significant Historic Home Thoughtfully Reimagined Through A Recent Comprehensive Renovation And Expansion. An Elegant Wrough...

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Photo of Listing #12584824

2836 Blackhawk Road, Wilmette, IL - $2,550,000

Residential, Detached Single
  • 6 Beds
  • 6 Baths
  • 5,933 SQFT
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Just Listed! Welcome To 2836 Blackhawk Rd, A Beautiful And Elegant 6-bedroom, 5.1-bath Home In Highly Desirable Indian Hill Estates On An Oversized 80' X 182' Lot, Offering Exceptional Living Space Across Every Level! An Expansive Foyer Greets You...

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Photo of Listing #12578958

375 Washington Road, Lake Forest, IL - $2,500,000

Residential, Detached Single
  • 5 Beds
  • 5 Baths
  • 4,036 SQFT
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This Truly Exceptional East Lake Forest Residence, Masterfully Designed By Renowned Architect Stanley Anderson, Offers A Rare Blend Of Timeless Architectural Elegance And Sophisticated Modern Luxury. Meticulously Updated In 2022, The Home Received...

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Photo of Listing #12578721

626 Washington Avenue, Wilmette, IL - $2,295,000

Residential, Detached Single
  • 4 Beds
  • 5 Baths
  • 4,152 SQFT
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Remarkable Home Situated On A Desirable, Tree-lined Street In East Wilmette. Every Corner Of This 5 Bedroom, 4.1 Bathroom Home Has Been Impeccably Updated With A Blend Of Traditional Details And Modern Renovations To Meet Today's Buyer Lifestyle. ...

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Photo of Listing #12545046

380 Sterling Road, Kenilworth, IL - $2,000,000

Residential, Detached Single
  • 5 Beds
  • 4 Baths
  • 4,125 SQFT
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Set On A Half Acre In Kenilworth, This Beautifully Sunlit Home Seamlessly Blends Timeless Elegance With Effortless Everyday Living. A Gracious Living Room, Complete With A Fireplace And Oversized Picture Window, Frames Views Of The Expansive Manic...

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Photo of Listing #12575361 CONTINGENT

165 Fuller Lane, Winnetka, IL - $2,199,000

Residential, Detached Single
  • 5 Beds
  • 6 Baths
  • 4,994 SQFT
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Welcome To 165 Fuller Ln, Where Timeless Charm Meets Thoughtful, High-end Finishes In An Unbeatable East Winnetka Location Within The Coveted Greeley School District. Perfectly Positioned For Walkability To School, The Lake, Parks, And Everything ...

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85 Sunset Place, Lake Forest, IL - $2,899,000

Residential, Detached Single
  • 4 Beds
  • 5 Baths
  • 3,110 SQFT
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Accross From A Picturesque Park, This Designer-owned Home Is A Rare And Remarkable Find - Ideal As Either A Full-time Residence Or A Sophisticated Pied-a-terre. Meticulously Renovated For Effortless Living, It Offers 4,000 Square Feet Of Finished ...

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Photo of Listing #12579068 CONTINGENT

358 Winnetka Avenue, Winnetka, IL - $2,995,000

Residential, Detached Single
  • 4 Beds
  • 7 Baths
  • 5,900 SQFT
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Incredible Coveted Home With 5 Bedrooms, 5.2 Bathrooms, 3 Garages On 1/3 Acre Property Boasts Winnetka Address And Kenilworth School District. Built In 2004, This Beautiful Brick Home Feels Like New Construction With A Complete First Floor Renovat...

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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 March 8th, 2026 at 1:08am CST.

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.”

Chicago's Luxury Condos

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