1355 N Astor Street
Chicago, IL, 60610
$21,000,000
6 Beds
6 Baths
25,000 SqFt
0 Acres
Add
Add
$21,000,000
1355 N Astor Street
Chicago, IL, 60610
MLS #MRD12628484 image #0MLS #MRD12628484 image #1MLS #MRD12628484 image #2MLS #MRD12628484 image #3MLS #MRD12628484 image #4MLS #MRD12628484 image #5MLS #MRD12628484 image #6MLS #MRD12628484 image #7MLS #MRD12628484 image #8MLS #MRD12628484 image #9MLS #MRD12628484 image #10MLS #MRD12628484 image #11MLS #MRD12628484 image #12MLS #MRD12628484 image #13MLS #MRD12628484 image #14MLS #MRD12628484 image #15MLS #MRD12628484 image #16MLS #MRD12628484 image #17MLS #MRD12628484 image #18MLS #MRD12628484 image #19MLS #MRD12628484 image #20MLS #MRD12628484 image #21MLS #MRD12628484 image #22MLS #MRD12628484 image #23MLS #MRD12628484 image #24MLS #MRD12628484 image #25MLS #MRD12628484 image #26MLS #MRD12628484 image #27MLS #MRD12628484 image #28MLS #MRD12628484 image #29MLS #MRD12628484 image #30MLS #MRD12628484 image #31MLS #MRD12628484 image #32MLS #MRD12628484 image #33MLS #MRD12628484 image #34MLS #MRD12628484 image #35MLS #MRD12628484 image #36MLS #MRD12628484 image #37MLS #MRD12628484 image #38MLS #MRD12628484 image #39MLS #MRD12628484 image #40MLS #MRD12628484 image #41MLS #MRD12628484 image #42MLS #MRD12628484 image #43MLS #MRD12628484 image #44MLS #MRD12628484 image #45MLS #MRD12628484 image #46MLS #MRD12628484 image #47MLS #MRD12628484 image #48MLS #MRD12628484 image #49MLS #MRD12628484 image #50MLS #MRD12628484 image #51MLS #MRD12628484 image #52MLS #MRD12628484 image #53
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.

Property Details

Price:
$21,000,000
MLS #:
MRD12628484
Status:
Active
Beds:
6
Baths:
6
Type:
Single Family
Neighborhood:
chinearnorthside
Listed Date:
Apr 24, 2026
Finished Sq Ft:
25,000
Year Built:
1914
OtherChi – Near North SideChinearnorthsideOgden ElementaryOgden InternationalWater

Schools

School District:
299
Elementary School:
Ogden Elementary
Middle School:
Ogden International

Interior

Appliances
Range, Microwave, Dishwasher, High End Refrigerator, Freezer, Washer, Dryer, Disposal, Wine Refrigerator
Bathrooms
5 Full Bathrooms, 1 Half Bathroom
Cooling
Central Air, Zoned
Fireplaces Total
9
Flooring
Hardwood
Heating
Natural Gas, Forced Air, Zoned
Interior Features
Dry Bar, Wet Bar, Elevator, Built-in Features, Walk-In Closet(s), Historic/Period Mlwk, Special Millwork, Paneling, Pantry
Laundry Features
In Unit

Exterior

Architectural Style
Other
Community Features
Curbs, Gated, Sidewalks, Street Lights, Street Paved
Construction Materials
Brick, Limestone, Slate
Exterior Features
Balcony, Lighting
Lot Features
Landscaped, Garden, Views
Parking Features
Brick Driveway, Off Alley, Yes, Other
Parking Spots
2
Parking Total
2
Patio And Porch Features
Deck, Patio
Roof
Slate
View
Water
Window Features
Screens

Financial

HOA Fee Frequency
Not Applicable
HOA Includes
None
Tax Year
2024
Taxes
$197,887
Need more info?
Ask a Question
Ready to go see it?
Schedule a Showing

Debra Dobbs is one of Chicago’s top realtors with more than 41 years in the real estate business.

More About Debra

Mortgage Calculator

 

Map

Current real estate data for Single Family in Chicago as of Apr 25, 2026
2,774
Single Family Listed
69
Avg DOM
234
Avg $ / SqFt
$579,105
Avg List Price

Community

Similar Listings Nearby

broker reciprocity
MLS# MRD12273547broker reciprocity
915 N DEARBORN Street
Chicago, IL

$18,500,000

Property Summary

    1355 N Astor Street Chicago IL is a Single Family for sale in Chicago, IL, 60610. It is listed for $21,000,000 and features 6 beds, 6 baths, and has approximately 25,000 square feet of living space, and was originally constructed in 1914. The current price per square foot is $840. The average price per square foot for Single Family listings in Chicago is $234. The average listing price for Single Family in Chicago is $579,105. To schedule a showing of MLS#mrd12628484 at 1355 N Astor Street in Chicago, IL, contact your Compass | Debra Dobbs | The Dobbs Group agent at 3123074909.
1355 N Astor Street
Chicago, IL