Historic Gold Coast mansion with Playboy history for sale

Own a piece of Chicago history that blends the beauty and elegance of the Gilded Age with the legendary history of Playboy founder Hugh Hefner. 

This historic property at 1336 N. State Parkway is quietly tucked away in the Gold Coast. Built in 1914, the 9,000-square-foot mansion was originally constructed as a wedding gift for the daughter of prominent Chicago surgeon Dr. George Swift Isham. Designed as a 20-room townhouse, the residence was intentionally connected to the neighboring mansion at 1340 N. State Parkway, creating an elegant compound in the heart of the Gold Coast.

The stately home at 1340 later became part of Chicago pop culture history when Hugh Hefner purchased the property in 1959, transforming it into the original Playboy Mansion. In 1970, Hefner expanded the estate by acquiring 1336 N. State Parkway, using the additional space for offices, boardrooms and Bunny dormitory accommodations.

Designed by renowned architect James Gamble Rogers, the mansion reflected the grandeur of Chicago’s Gilded Age architecture. The connected properties became famous for their lavish details, including the legendary basement grotto with its indoor swimming pool and the iconic Latin phrase displayed at the entrance: “Si Non Oscillas, Noli Tintinnare,” translated as “If you don’t swing, don’t ring.”

By the mid-1970s, Hefner had permanently relocated to Los Angeles, later establishing the famed Playboy Mansion in Holmby Hills. In the 1980s, the Chicago properties found new life when they were leased to the School of the Art Institute of Chicago. Eventually, the main mansion at 1340 N. State Parkway was converted into luxury condominiums after the property was sold in 1993.

Today, 1336 N. State Parkway stands as an impeccably preserved single-family residence that blends historic elegance with modern luxury. This extraordinary 9,000 sq-ft. home features five bedrooms, nine bathrooms, an elevator, sauna and private two-car garage, offering a rare opportunity to own a residence deeply woven into Chicago’s architectural and cultural legacy. Many original details are still intact like ceiling details, crown moldings, fireplaces, rooftop and backyard space. 

(The listing is represented by Emily Sachs Wong , one of Chicago’s leading luxury real estate experts, for $8,990,000. [email protected], 312.613.0022) 

More from Chicago Star: 

Let’s help Navy Pier win its 4^th best fireworks title

Harry Potter Drone Art Show brings wizardry to Chicago’s night skies

‘Going Bacharach’ brings timeless hits to Chicago’s Apollo Theater

A mother’s love and a chance encounter: Patti Guzak’s ‘The Not-So-Exciting Adventures of Tuxedo Man’