Landscaping includes a large koi pond with an artificial stream, a small citrus orchard and two well-established forests of tree ferns and redwoods.

Hefner's personal suite occupies several rooms on the second and third floors, and is the most heavily renovated area of the building proper, with an extensive carved-oak decor dating to the 1970s.

The agreement protects the mansion from demolition, but still allows Metropoulos to make modernizations and substantial renovations and repairs to the property "following a long period of deferred maintenance while under Playboy ownership.

The compromise agreement reversed a move in November 2017 by Los Angeles City Councilmember Paul Koretz to seek landmark status for the mansion in the hope of protecting the architectural integrity of the estate for what he called "an excellent example of a Gothic-Tudor.

[24][27] The original Playboy Mansion was a 54-room[28] 30,000 sq ft (2,800 m2)[29] classical brick and limestone residence in Chicago's Gold Coast district at 1340 North State Parkway which had been built in 1899 (or 1903)[30] for $100,000 (equivalent to $3.07 million in 2024).

[31] Its original owner was Dr. George Swift Isham, a prominent surgeon whose social circle included Theodore Roosevelt and Robert Peary.

[33][34] The Chicago Mansion's basement, renovated upon occupancy as Hefner's original "grotto", had a swimming pool with a glass wall and attached bar.

[36] Located on the second floor of the building, Hefner's personal suite (containing a three-room apartment and bathroom) was prominently connected to the Roman Bath, an "elaborate bathing/sleeping area" designed for marathon group sex sessions that almost always encompassed Hefner, longtime friend/roommate John Dante and their respective paramours;[37] installed circa 1970[38], it contained "baroque gold spigots and faucets that sprayed and showered" alongside "a tub with chest-high water" and a mirrored alcove with an early (and mink-covered) waterbed.

[39] Hefner's suite also was connected to three additional rooms that were employed as the publisher's nominal office (notwithstanding his oft-publicized penchant for working in his bedroom's metonymous round rotating/vibrating bed).

[44] Although Playboy Enterprises remained headquartered in Chicago until 2012, Hefner designated the Mansion West as his full-time residence in 1975 following the criminal conviction and ensuing apparent suicide of Bobbie Arnstein, the culmination of an "investigation of drug use in Hefner's mansion" by U.S. Attorney for the Northern District of Illinois (and future Governor of Illinois) James R. Thompson that attracted significant publicity after Arnstein's March 21, 1974 indictment.

[50][51] Additionally, the December 1974 resignation of Robert J. Adelman (then chairman of the Rubloff Company, an influential Chicago real estate conglomerate) from Playboy Enterprises's board in the aftermath of the Arnstein conviction appears to have further estranged Hefner from the local business community, which was long circumspect of his lifestyle.

"Tom Bradley, the mayor, attended the opening of the Playboy Club and was a frequent guest at the parties and so was Jerry Brown, the governor.”[53] According to Hefner friend and fellow pornographer Suze Randall, the Chicago Mansion "had for some time been hired out for large business meetings" (such as a January 1975 convention for the Texas food industry that coincided with Arnstein's apparent suicide and a Randall business trip) "in an attempt to make it pay its way" as a profitable event facility.

[54] During a thwarted attempt to sell the property amid Playboy Enterprises' financial difficulties in July 1975, Senior Vice President Victor Lownes estimated that the publisher only spent three weeks at the Chicago Mansion (including several short business trips, a visit centered around Arnstein's funeral and a similar stay for a May 1975 backgammon tournament[55]) during the previous year.

[59] The contemporaneous sale of the Big Bunny (the company's McDonnell Douglas DC-9 business jet, which was almost exclusively employed for commutation purposes by Hefner and his immediate entourage after 1970) also rendered his previous lifestyle untenable due to his disdain of commercial aviation.

[60] Beginning in the summer of 1975, the Chicago Mansion was maintained with a "skeleton staff" of approximately 12 security and maintenance[61] employees[62] (having previously burgeoned to a height of 50 staff members during the facility's 1960s heyday, approximately 18 staffers remained when Lownes instituted layoffs in mid-1975) and primarily opened thereafter to the public for "occasional charity benefits and business functions" following the concomitant closure of the Bunny dormitory.

[64] During this period, Derick Daniels (who served as president and chief operating officer of Playboy Enterprises from 1976 to 1982) lived in a Chicago Mansion apartment throughout his first year with the company.

While Hefner vowed to "spend more time" in the city amid various meetings (and a lengthy press conference) at the Chicago Mansion following the controversial dismissal of Anthony Jackson (a recruiter then characterized as Playboy's highest-ranking Black executive) in August 1975,[65] his few documented visits to the Chicago Mansion thereafter consisted of October and November 1975 stays referenced in subsequent press reports,[66] a July 1976 trip centered around an awards luncheon for Elton John[67], a December 1978 holiday jaunt coinciding with one of the magazine's 25th anniversary parties (with a guest list that ran the gamut from Hefner's polyamorous Los Angeles circle to onetime Chicago Mansion stalwarts like Shel Silverstein)[68] and a November 1979 trip in conjunction with his longstanding support of the Chicago International Film Festival[69]; actor Harry Reems (alleged by contemporaneous Mansion butler Stefan Tetenbaum to have engaged in distinct sexual assignations during this period with both Hefner and his longtime executive assistant, Mary O'Connor) accompanied the publisher on the visit en route to a New York City theatrical engagement.

[71] When no buyers manifested, the main building was leased for $10 per year as a dormitory (under the imprimatur of Hefner Hall) for the School of the Art Institute of Chicago in August 1984; as part of the agreement, the School purchased 1336 North State Parkway[72] outright for $500,000 (equivalent to $1.5 million in 2024), while Playboy Enterprises formally deeded 1340 North State Parkway to the Art Institute when the agreement lapsed in 1989.

In February 2011, 123 people complained of fever and respiratory illness after attending a DomainFest Global conference event held at the Playboy Mansion.

After an investigation in response to the reported illnesses of the DomainFest attendees, epidemiologists from the Los Angeles County Department of Public Health disclosed their findings at a Centers for Disease Control conference.

[8] On June 21, 2022, a California civil trial jury found that comedian Bill Cosby sexually assaulted 16-year-old Judith Huth at the Playboy Mansion in 1975.

"[85] In 2024, Hefner's widow Crystal would publish a memoir backing allegations that the Mansion was an environment of sexual abuse, and also describing it as a place where she felt "imprisoned.