For sale Home

Listed Apr 24, 2026

$21,000,000 Est. $138,896/mo

1355 North Astor Street

  • 6

    Beds

  • 6

    Baths

  • 25,000

    Sq ft

The story

  • Basement

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 Astor Street. This is an exceptionally wide and long lot like no other. Originally designed by acclaimed architect Howard Van Doren Shaw for the Goodman Family, this extraordinary property is being offered for the first time in 40 years. A true masterpiece, this estate stands as a defining example of neo-classical and Georgian Revival design and spans an impressive 80 feet across and embodying Chicago's rich architectural heritage. At the center of the estate lies an exceptional private courtyard meticulously landscaped with formal gardens and fountains. This serene outdoor space evokes the tranquility of the Italian countryside, creating a private sanctuary within one of the city's most vibrant neighborhoods. Originally a single-family home, now an owner's home plus high end leased residences, is easily reverted back to a single-family home with a garage. The main residence encompasses more than 10,000 square feet of elegantly renovated interiors, combining timeless sophistication with modern luxury. Every detail reflects impeccable craftsmanship - from the soaring 13-foot ceilings and Venetian plaster walls to the intricate millwork, oak hardwood floors, and original marble fireplaces. A grand curved staircase welcomes you upon entry, setting the tone for the refined living spaces beyond. The home offers five en-suite bedrooms, each with its own unique design and character. The primary suite provides sweeping lake views and a luxurious spa-inspired bath finished with exquisite Italian marble. Complementing the main residence are six distinctive units that are currently leased -each offering individual charm and contributing significant income potential. In total, the estate comprises 45 rooms, 16 bedrooms, 17 baths, and 18 fireplaces, offering endless possibilities - from an expanded private residence to a magnificent multi-generational estate. Additional features include two parking spaces located directly behind the property, with the option of converting the existing coach house into a garage for further parking accommodations. Ideally positioned just steps from Michigan Avenue, the lakefront, parks, fine dining, luxury boutiques, and cultural attractions, this remarkable estate represents a rare opportunity to own a truly iconic piece of Chicago's history and architectural legacy.

Facts & features

Home type

Home

Year built

1914

Price per sq ft

$840

Included features

  • Fireplace

    9 fireplaces

  • Basement

    Yes

  • Cooling

    Central Air, Zoned

  • Heating

    Natural Gas, Forced Air, Zoned

  • Appliances

    Range, Microwave, Dishwasher, High End Refrigerator, Freezer, Washer, Dryer, Disposal, Wine Refrigerator

  • Flooring

    Hardwood

  • Roof

    Slate

  • Lot Information

    Landscaped, Garden, Views

  • Exterior

    Balcony, Lighting

  • Water Source

    Lake Michigan

  • Sewer

    Public Sewer

  • View

    Water

Mortgage calculator

Estimated monthly payment

$138,896 /mo

7% rate · 30-yr fixed · 20% down

  • Principal & interest $111,771
  • Property tax $21,000
  • Insurance $6,125

Includes principal, interest, taxes & insurance.

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Listing Broker

@properties Christie's International Real Estate

Broker Name

@properties Christie's International Real Estate

Agent

Emily Sachs Wong