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1355 N Astor Street, Chicago, IL - $21,000,000

Residential, Detached Single
  • 6 Beds
  • Baths
  • 25k SQFT
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Presenting An Unparalleled Opportunity To Acquire One Of Chicago's Most Distinguished Estates - An Historic Residence Offering Over 25,000 Square Feet Of Total Living Space, Set On Nearly One-third Of An Acre Along The Gold Coast's Prestigious Ast...

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915 N Dearborn Street, Chicago, IL - $18,500,000

Residential, Detached Single
  • 6 Beds
  • 6 Baths
  • 13.4k SQFT
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A Rare Piece Of Chicago's History, The Thompson House At 915 N. Dearborn Stands As One Of The Gold Coast's Original Architectural Treasures. Designed In 1888 By Cobb & Frost, The Renowned Architects Behind The Newberry Library And University Of Ch...

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451 E Grand Avenue Ph64, Chicago, IL - $12,250,000

Residential, Attached Single
  • 5 Beds
  • 6 Baths
  • 7,940 SQFT
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Introducing Penthouse 64 At One Bennett Park, A Robert A.m. Stern Building. A One-of-a-kind Full-floor Residence Defined By Exceptional Scale, Light, And Sweeping Lake And Skyline Panoramas. Encompassing Approximately 7,940 Square Feet, With 5 Bed...

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800 N Michigan Avenue Ph67, Chicago, IL - $12,250,000

Residential, Attached Single
  • 6 Beds
  • Baths
  • 8,690 SQFT
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The Last Raw Penthouse Available In The Gold Coast! An Amazing Opportunity To Transform This True Duplex Penthouse At Chicago's Esteemed Park Hyatt. Offering The Absolute Best Combination Of 360-degree Lake Michigan And City Skyline Views, 12-fo...

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800 N Michigan Avenue Ph64, Chicago, IL - $11,700,000

Residential, Attached Single
  • 5 Beds
  • 6 Baths
  • 8,500 SQFT
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An Oasis Above The Clouds, This One-of-a-kind Penthouse Comprises The Entire 64th Floor At The Prestigious Park Tower On North Michigan Avenue. Spanning 8,500 Sqft, This 15-room Apartment Was Meticulously Crafted By The Renowned Architectural Firm...

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159 E Walton Place Ph, Chicago, IL - $8,400,000

Residential, Attached Single
  • 4 Beds
  • Baths
  • 7,880 SQFT
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Own The Pinnacle Of Chicago Elegance In This 7880 Sq Ft Duplex Penthouse, Formerly Home To Vince Vaughn And The Original Headquarters Of Hugh Hefner's Playboy Enterprise. The Palmolive Building Is A True Art Deco Icon- Its Historic Beacon Once Lit...

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435 N Michigan Avenue 2203, Chicago, IL - $7,000,000

Residential, Attached Single
  • 3 Beds
  • Baths
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A Rare Turnkey 3 Bedroom + Den Residence With One Of The Most Architecturally Significant Private Outdoor Spaces In Chicago. The Terrace Is Framed By Original Gothic Limestone With Panoramic Views Of Lake Michigan, The Chicago River, And City Skyl...

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79 E Cedar Street, Chicago, IL - $6,900,000

Residential, Detached Single
  • 4 Beds
  • 7 Baths
  • 7,523 SQFT
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Welcome To 79 East Cedar Street. This Is A Rare Opportunity To Acquire A Home Of Significant Scale And Presence In The Gold Coast-one Of Chicago's Most Vibrant And Historic Neighborhoods. In 1884 Bertha Palmer Commissioned Architect Joseph Lyman S...

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451 E Grand Avenue 6111, Chicago, IL - $6,500,000

Residential, Attached Single
  • 3 Beds
  • Baths
  • 4,798 SQFT
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Perched 61 Stories Above Chicago's Lakefront, Residence 6111 At One Bennett Park Delivers Architectural Distinction By Robert A.m. Stern With Exquisite Custom Interiors And Commanding Citytolake Panoramas. A Private Foyer Introduces 4,800 Square ...

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1454 N Dearborn Street, Chicago, IL - $6,000,000

Residential, Detached Single
  • 6 Beds
  • Baths
  • 11k SQFT
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Nestled In The Heart Of Chicago's Prestigious Gold Coast, This Extraordinary Residence Commands Attention From Its Rare 30 X 150 Corner Parcel- A True Trophy Property On One Of The Neighborhood's Most Coveted Blocks. Listed On The National Registe...

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401 N Wabash Avenue 86a, Chicago, IL - $6,000,000

Residential, Attached Single
  • 4 Beds
  • Baths
  • 4,029 SQFT
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Spectacular Penthouse Unit On The 86th Floor, Designed By The World-renowned Architect Adrian Smith. This Super Upscale Residence Is Turn-key And Fully Furnished, Ready For Immediate Move-in. With 4 Bedrooms + Den And 5.1 Baths, Each Room Is Glamo...

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22 E Elm Street, Chicago, IL - $5,995,000

Residential, Detached Single
  • 11 Beds
  • Baths
  • 5,100 SQFT
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Currently Configured As Two Separate Residences, This Exceptional Property Offers The Flexibility To Function As A High-performing Luxury Investment Or Be Effortlessly Converted Into One Extraordinary Single-family Home. Built In 2016, 22 E. Elm S...

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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 July 10th, 2026 at 6:29am CDT.