Own a piece of Playboy history–bunnies not included!

For those who have ever dreamed of living in one of Chicago’s most famous buildings, this is a rare opportunity to make that dream a reality. A stunning two-story penthouse in the historic Playboy Mansion is up for sale. The historic landmark building is located in Gold Coast at 1340 N. State Parkway. Once home to Hugh Hefner and the heart of Playboy Enterprises, the building is packed with history, glamour, and plenty of stories.

The mansion, which was built in 1889for Dr. George Swift Isham, a renowned Chicago surgeon, became a symbol of his status after he performed a life-saving tracheotomy on the son of a prominent Presbyterian minister. Dr. Isham, who was known formingling with the city's elite, hosted Theodore Roosevelt and Arctic explorer Robert Peary. After he died in 1929, the mansion was sold to a contractor, who adapted it to reflect the economic challenges of the Great Depression.

The mansion was converted into an apartment building but soon fell into disrepair due to neglect. In 1940, Chicago parking tycoon R.G. Lydy bought the property for $35,000 with plans to restore it. After Lydy had invested $175,000 in renovations, the home was returned to its former grandeur and became the talk of the town once again. It was later sold to the Pobliniak family, continuing its legacy as a prominent Chicago landmark.

In 1959, Hugh Hefner, founder of the Playboy empire, purchased the mansion for $370,000 and invested $400,000 to transform it into the ultimate "bunny burrow." In a 2016 WTTW documentary, “The Making of Playboy,” bunny Candace Collins recalled Hefner describing the mansion as a “Disneyland for adults.” With features like an indoor pool with a waterfall and underwater bar, sun and steam rooms, a bowling alley, a game room, offices, and dorms for the bunnies, Hefner hosted a parade of Hollywood stars and social elites.

In 1974, seeking to expand his empire, Hugh Hefner moved to California, leaving the mansion vacant for occasional use. In August 1984, he leased the property to the Art Institute for just $10 per year, allowing it to serve as a school and dormitory for students. According to a 1985 Chicago Tribune article, the lease lasted five years. The school hosted 300 students and 32 live-in residents until the mansion was sold in 1993.

Real estate developer Joseph W. Bunning purchased the building for $1.1 million and converted it to its current state.

The building at 1340 N. State Parkway features ten condominium units, with a three-story penthouse now on the market for $2.3 million. The unit boasts an “over-the-top chef’s kitchen with commercial-grade appliances and a central island with counter seating,” as noted by the listing agent. The top floor is dedicated to a spacious primary suite with two large walk-in closets, a marble spa bath, and a stunning private 1,000-square-foot roof terrace offering treetop views in every direction. The sale also includes a two-car garage. 

This triplex penthouse is a rare chance to live in one of the city's most iconic buildings, offering space, style, and stunning views. This exclusive triplex penthouse provides a rare opportunity to experience unparalleled luxury in one of the city’s most iconic buildings. For those seeking a home that blends sophistication, history, and modern comfort, this unique property is a once-in-a-lifetime chance to own a piece of Chicago’s architectural legacy.