In the Hokkien dialect of the Chinese language, Chai Chee may be translated to mean Vegetable Market . Before the estate was built, the area was primarily farmland over a series of rolling hills. The kampong, or village, was located on a high hill around where the Singapore Anti-tuberculosis Association Clinic now stands. Before, one needs to go downhill to reach the clinic. Today the clinic sits much higher than the surrounding areas after the hills were levelled.
The area got its name as farmers would gather there daily to sell their produce. A thriving community soon evolved and Chai Chee became a focal point for the kampong residents there. When development began in the late 1960s, the estate was built originally with 40 blocks of flats, consisting mainly of rental units. It was the first Housing and Development Board estate to be built on the eastern part of Singapore. Community amenities were built, such as a market, food centre, shops, banks, library, community center, kindergarten and a bus terminus. To provide for employment, there were 3 factories built - Rollei Cameras, Varta Batteries and Nippon Miniature Bearing (NMB).
Chai Chee Estate quickly gained importance as it was then the only urban estate in the mainly rural part of eastern Singapore. In the early 1970s, the electoral division of Chai Chee stretches all the way southwards to Upper East Coast Road. This led to the naming of the school there as Chai Chee Secondary School , even though today that area is no longer part of Chai Chee Estate
