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 Chicago Luxury Real Estate for Sale

 

Browse Chicago Luxury Real Estate l See New MLS Listings

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

Residential, Detached Single
  • 6 Beds
  • 7 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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Photo of Listing #12511518 CONTINGENT

800 North Michigan Avenue Ph67, Chicago, IL - $12,500,000

Residential, Attached Single
  • 6 Beds
  • 7 Baths
  • 9,250 SQFT
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A Rare Opportunity To Create A One-of-a-kind Residence Atop Chicago's Premier Address - 800 N. Michigan Avenue. This Full-floor Duplex Penthouse, The Crown Jewel Of Park Tower, Is Now Offered As Raw Space, Ready For Your Custom Design, With 12-foo...

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

Residential, Attached Single
  • 5 Beds
  • 7 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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2026 North Kenmore Avenue, Chicago, IL - $9,995,000

Residential, Detached Single
  • 10 Beds
  • 10 Baths
  • 13.4k SQFT
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Unique Opportunity For The Luxury Homeowner Who Wants To Provide An Opportunity For An Extended Family Habitat, Live In Nanny, Or Even Business Associates To Be Close In The Huge Coach House Over The Attached 5 Car Garage. The Coach House Also Cou...

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1853 North Burling Street, Chicago, IL - $9,450,000

Residential, Detached Single
  • 7 Beds
  • 6 Baths
  • 8,691 SQFT
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Set On An Expansive 44-ft-wide Lot On The Most Coveted Block Of One Of Chicago's Most Prestigious Streets, 1853 N Burling Is An Exceptional Custom-built Estate. Situated In The Heart Of Lincoln Park, This Architectural Tour De Force Seamlessly Com...

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Photo of Listing #11954424

159 East Walton Place Ph, Chicago, IL - $8,900,000

Residential, Attached Single
  • 4 Beds
  • 5 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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363 East Wacker Drive 9101, Chicago, IL - $7,999,000

Residential, Attached Single
  • 4 Beds
  • 5 Baths
  • 5,734 SQFT
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Perched Atop The Iconic St. Regis Chicago, This Full-floor Penthouse Is The Highest Residential Customizable Home In The City And The Midwest! Spanning The Entire 91st Floor, This Raw Space Offers A Rare Chance To Create A One-of-a-kind Residence...

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1878 North Orchard Street, Chicago, IL - $7,995,000

Residential, Detached Single
  • 5 Beds
  • 8 Baths
  • 9,512 SQFT
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Stunning Beyond Words, This East Lincoln Park Masterpiece Redefines Luxury At Every Turn. Set On A 36x131 On Coveted Orchard Street, This 9,500 Square Foot Home Speaks To A Most Discerning Buyer Seeking The Ultimate Blend Of Superior Craftsmanship...

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14 West Superior Street 6900, Chicago, IL - $7,995,000

Residential, Attached Single
  • 4 Beds
  • 5 Baths
  • 6,085 SQFT
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Astonishing Full Floor Home With Breathtaking 360 Degree Views, Outdoor Space, Direct Elevator Access And Bespoke Finishes! Still Time To Customize Your Home To The Caliber You Have Come To Expect From Jdl Development!! Completion Slated For Secon...

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189 East Lake Shore Drive Ph18, Chicago, IL - $7,250,000

Residential, Attached Single
  • 5 Beds
  • 6 Baths
  • 7,462 SQFT
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Amazing, Dramatic Penthouse In A Classic Vintage Building On East Lake Shore Drive! This Home Has Been Completely Renovated With Over 7400 Square Feet Of Luxurious Finishes And Offers Expansive Lake & City Views Plus 2 Terraces With 550 Square Fee...

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451 East Grand Avenue Ph66, Chicago, IL - $6,995,000

Residential, Attached Single
  • 4 Beds
  • 6 Baths
  • 7,147 SQFT
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One Bennett Park Has Taken Its Place Among Chicago's Most Elite Residences. Designed By Robert A.m. Stern Architects And Developed By Related Midwest, This World Class Building Was Designed From The Top Down. Gracing The Crown Of This Iconic Lakef...

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800 North Michigan Avenue 63ph, Chicago, IL - $6,950,000

Residential, Attached Single
  • 5 Beds
  • 6 Baths
  • 8,400 SQFT
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Remarkable Opportunity To Acquire Full Floor Park Tower Penthouse At A Truly Outstanding Value. Delivering Panoramic 360 Degree Views Of Chicago's World-class Architecture And Lake Michigan, Plus Captivating Sunrise To Sunset Views. This 5 Bedroom...

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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 7th, 2025 at 7:23am CST.