Originally founded as L.B. Goodale in 1866, the company underwent three ownership changes with new partners added in the first two decades of the twentieth century. In 1925, sixteen year old Harry Helmsley graduated from Evander Childs High School in the Bronx and joined HelmsleySpear, then known as Dwight, Voorhis & Perry. Helmsley was soon elevated from a mail room clerk to the role of rent collector in the Hell's Kitchen district of Manhattan for the real estate brokerage firm, which specialized in leasing and managing buildings in low-rent neighborhoods. Around the time of the Great Depression, Helmsley began managing prime foreclosed properties on behalf of various banks, convincing them that the investments were sound. The firm benefited enormously from Helmsley's talents, and by 1938 he rose to become a partner, with the firm being renamed Dwight, Voorhis & Helmsley.

A turning point for the firm occurred in 1938 when Helmsley assumed ownership, rather than management of his first property—a ten-story office building on East 23rd Street that was scheduled for foreclosure. Foreseeing a postwar boom in the 1940’s, Helmsley began to seek out bargain properties located close to major commuter terminals. While he lacked the cash necessary to purchase properties outright, Helmsley discovered that by signing away his five percent commission and offering his real estate knowledge and experience, he could retain part-ownership in real estate properties. In 1949, Harry Helmsley partnered with Lawrence Wien, a highly successful real estate lawyer, who had become an expert at the tax and legal strategies of buying and selling properties. Through this partnership, Wien and his partners secured part ownership in exchange for funding the acquisition of Helmsley-identified projects. During the next 30 years, Wien and Helmsley created nearly 100 such partnerships, including the 1961 sale- and-leaseback of the Empire State Building.


This funding enabled the firm to engage in an active period of expansion, purchasing individual buildings and portfolios alike. In 1955, following the departure of Dwight and Voorhis (the two former partners in the firm), Mr. Helmsley acquired business competitor Spear & Company, and renamed the firm to HelmsleySpear. Helmsley later acquired Charles F. Noyes Company, expanding the firm's portfolio in Lower Manhattan under a new and separate company called Helmsley Noyes. His purchase of Brown Harris Stevens in 1961 added rental and cooperative
apartment sales and management to the firm’s scope of services. When coupled with nearly nine million square feet of office space and more than 5,000 apartments, HelmsleySpear grew to become one of the largest real estate management companies in the country.