Around 1990 Raymond began to hand over control of his empire to his daughter Debbie (Deborah Jane Raymond, born 28 January 1956), but she died accidentally from a heroin overdose on 5 November 1992. Debbie served as the editor-in-chief of the company's titles, as well as becoming involved in its property concerns.

He also circumvented the authority of the Lord Chamberlain's powers in 1958 when he opened the Raymond Revuebar strip club as a private club in the former Doric Ballroom in Soho's Walker's Court. He had been unimpressed with the first legal strip club in Soho, believing he could do better. Within two years, Raymond's Revuebar had 45,000 members. He also bought the freehold of his venue for £14,000 within a year or two, the beginnings of his property portfolio in Soho.

According to Raymond's biographer, Paul Willetts, Raymond's Revuebar initially attracted a "chic clientele", including the actor John Mills and Comedian Peter Sellers. The seedy reputation of the club led to regular clashes with the authorities about show content. In 1961, Raymond was fined £5,000 following a magistrate's decision that permitting members to ring the Ding Dong Girl's bells constituted an "unruly house". There was also the issue about an on stage performer swallowing a snake earning the club an official reputation as "filthy, disgusting and beastly".

Raymond first moved into publishing in 1964 when he launched the men's magazine King, but it ceased publication after two issues. In 1971, he took over the adult title Men Only; his other magazines eventually included Razzle and Mayfair. Among the Models featured in his magazines was Fiona Richmond, who became Raymond's girlfriend towards the end of his marriage to Jean Bradley (1951–74).

On 22 January 1967, Raymond was initiated into the Grand Order of Water Rats for his contribution to entertainment in the UK.

Raymond Diversified, investing millions into buildings and other property, especially in Soho starting in the 1970s, through his company, Soho Estates. During 1977, he was buying one Soho freehold each week, and also acquired property in Chelsea, Kensington and Hampstead. He was a frequent name on lists of the UK's wealthy reportedly with an estimated £650 million by the time of his death (one associate claimed the estate was worth billions), and Forbes placed him on its list of US dollar billionaires.

In 1974, he purchased the lease on the Windmill Cinema and returned it to the original name, the Windmill Theatre. Other theatres controlled by Raymond included the Whitehall Theatre where the sex comedy Pyjama Tops ran for more than five years along with several sequels, and the Royalty Theatre.

He was starting to hand over control to his daughter Debbie when she died of a heroin overdose in 1992, after which he became a recluse.

A recluse in his last years and living in a penthouse near the Ritz Hotel, he died of respiratory failure in 2008, age 82. His granddaughters Fawn and India James inherited his estate once estimated at £650m. Fawn announced her intention to commit to charity work in 2010. Their combined wealth was estimated as £454 million in The Sunday Times Rich List of 2015.

Often dubbed by the press 'King of Soho', he was the target of two extortion attempts, which was disclosed in the October 2010 release of Metropolitan Police papers. The second attempt was from decorators who threatened Raymond with bombing and shooting while pretending to be members of the IRA.

The Look of Love (released 26 April 2013) is about his life: Michael Winterbottom (director), Steve Coogan (Raymond), Anna Friel (wife, Jean), Imogen Poots (daughter, Debbie) and then-current Paul Raymond Publications employees and editors (extras or pseudo-cameos). The working title was The King of Soho, but this was changed as Howard Raymond had already trademarked it for another (as yet unmade) drama about his father's life; he stated that he had "never wanted or sought" to prevent Winterbottom's film being made.

The Lord Chamberlain's Office controlled what was allowed on theatre stages and ruled that nudes could not move, thus when Raymond toured with a show featuring nudes they were presented as statues, which moved about the stage on podiums. Raymond's preference, in this context, was for women between 18 and 30 years old, 5 feet 8 inches tall and with a chest measurement of no more than 36 inches. The reason for the latter provision, Raymond explained, was that "I wouldn’t like to embarrass my customers".