Once-in-a-life time opportunity to own one of Chicago's iconic estates, showcasing over 25,000 Sq. Ft. of combined living spaces and situated on nearly a third of an acre on Gold Coast's most coveted Astor street. This palatial architectural masterpiece designed by Howard Van Doren Shaw for the Goodman Family graces the market for the first time in 40 years, promising to leave you speechless. A true hallmark of Chicago's rich history, Astor Court has long captivated passersby with its magnificent neo-classical/Georgian Revival architecture spanning an impressive 80' feet across. This distinguished estate is centered around a one-of-a-kind tremendous courtyard, meticulously landscaped with lush gardens and flowing fountains, transporting you to the tranquil Italian countryside, creating a peaceful sanctuary in the vibrant urban setting. The main residence of the estate features over 10,000 sq. ft. of exquisitely renovated grand spaces blending timeless elegance with modern luxury. No expense was spared in creating this treasure, presenting a rare opportunity to own a coveted piece of Chicago's history. Every inch of the home exudes sophistication and grandeur offering unparalleled living experience featuring 13' ceilings, venetian plaster walls, incredible intricate millwork and hardwood oak flooring throughout, fireplaces with magnificent original marble mantles, and gold plated fixtures. As you enter the home, you are immediately captivated by the grand sense of space, elegant design and a sweeping curved staircase that ascends to the expansive main living areas. Every room exudes scale and sophistication offering both beauty and functionality. There are five en-suite bedrooms, each with its own style and personality. The luxurious primary suite features beautiful lake views and a grand primary spa bath adorned with exquisite Italian marble. In addition to the main residence, Astor Court showcases six gorgeous unique rental units, each with its own distinct charm and character, generating significant income. The entire estate encompasses 45 rooms, 16 bedrooms, 17 baths and 18 fireplaces offering endless opportunities to expand the main residence or transform it into a sprawling multi-generational family compound. Currently, there are two parking spaces located directly behind the property with the option to convert the coach house into a garage for additional parking. This extraordinary estate is perfectly situated just steps from Michigan Avenue, the lakefront, parks, premier shops, favorite restaurants, and world-class entertainment.