1355 N Astor Street

$21,000,000

 

A Once-in-a-Lifetime Opportunity: One of Chicago’s Iconic Estates


This palatial architectural masterpiece spans over 25,000 sq. ft. of combined living space, situated on nearly one-third of an acre on Astor Street, the Gold Coast’s most coveted address. Designed by the renowned Howard Van Doren Shaw for the Goodman Family, this estate is hitting the market for the first time in 40 years, offering an unparalleled opportunity to own a piece of Chicago’s rich history.


A true hallmark of neo-classical/Georgian Revival architecture, Astor Court commands attention with its impressive 80-foot-wide façade. At its heart lies a one-of-a-kind courtyard, meticulously landscaped with lush gardens and flowing fountains, creating a tranquil Italian countryside ambiance in the middle of the city.


Main Residence: Timeless Elegance & Modern Luxury

The main residence offers over 10,000 sq. ft. of exquisitely renovated grand spaces, where no expense was spared in blending classic elegance with modern luxury. Every inch of this home exudes sophistication and grandeur, featuring:

  • 13’ ceilings
  • Venetian plaster walls
  • Intricate millwork and oak hardwood flooring throughout
  • Fireplaces with original marble mantles
  • Gold-plated fixtures

Upon entering, you’re immediately captivated by the grand sense of space, a sweeping curved staircase, and a seamless flow between rooms that balance beauty and functionality.


The estate includes five en-suite bedrooms, each uniquely designed. The luxurious primary suite boasts breathtaking lake views and a grand spa bath adorned with exquisite Italian marble.


Additional Residences & Income Potential

Beyond the main residence, Astor Court includes six stunning rental units, each uniquely designed, providing significant income potential.


Unmatched Space & Flexibility

With 45 rooms, 16 bedrooms, 17 baths, and 18 fireplaces, the possibilities for this estate are endless. It offers opportunities to:

  • Expand the main residence
  • Create a sprawling multi-generational family compound

Parking & Prime Location

  • The property includes two parking spaces behind the estate, with the option to convert the coach house into a garage for additional parking.
  • Located just steps from Michigan Avenue, the lakefront, parks, premier shops, fine dining, and world-class entertainment, this estate provides the best of Chicago’s Gold Coast lifestyle.

This extraordinary residence is a rare opportunity to own an iconic piece of Chicago’s history, where timeless elegance meets modern luxury in one of the city’s most prestigious neighborhoods.

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