CDL began in a small, rented office in Amber Mansions on 7 September 1963, staffed by only eight employees, to acquire, develop and sell property. The Company went public in November 1963 and its shares were listed on what was known then as the Malayan Stock Exchange.

In 1965, CDL completed its first housing project, Fresh Breezes in Johor Bahru, and pioneered the "show house" concept. Subsequently, CDL launched its first condominium in Singapore, Clementi Park. This was followed by the launch of its first high-rise residential development in Singapore, City Towers, which was completed in 1966.

In 1972, the Hong Leong Group, under the guidance and leadership of founder, the late Mr Kwek Hong Png, acquired a controlling interest in CDL and embarked on a strategic diversification into commercial and industrial developments, launching its first residential cum shopping development, City Plaza. CDL then acquired more investment and development properties such as Tanglin Shopping Centre, Katong Shopping Centre, Woh Hup Complex (now known as Golden Mile Complex), Queensway Shopping Centre and The Arcade.

With the late Mr Kwek’s aspiration and strong business acumen, CDL emerged as a major property developer in Singapore. In the 1980s, CDL launched 21 residential properties and completed 12 investment properties. In 1983, it completed the construction of City House in the heart of the Central Business District, which became CDL's headquarters.

CDL's foray into the hotel business began with the acquisition of King's Hotel and soon after, Orchid Inn, now known as Copthorne King's Hotel Singapore and Copthorne Orchid Hotel Singapore respectively. This was followed by rapid expansion and regionalisation.

Today, CDL's hospitality arm, Millennium & Copthorne Hotels plc (M&C) is Singapore's largest international hotel group and one of the largest hotel owners and operators in the world.