One of his daughters, Sita, married Business Magnate U. N. Gunasekera, considered to be Ceylon's most notable and influential civil engineer of the 20th century, having built many of the nation's largest buildings, including its first five star hotels, and a silent philanthropist himself.

Sir Ernest de Silva was, arguably, Ceylon's greatest philanthropist of the twentieth century, funding a vast number of charitable endeavours.

He and his wife, Senator Lady Evadne de Silva, funded the inaugural orphanage in Ceylon in the form of a donation of 9 acres (36,000 m2) in Katunayake.

Among Sir Ernest's numerous contributions to health care was the donation of the inaugural Radiology unit inclusive of the first X-ray machine in Ceylon to the National Hospital in memory of his father, A.E.

He gave away lands, buildings and funds to numerous orphanages, hospitals, schools, social service bodies, temples and hermitages without fanfare or publicity.

[1] He inherited and purchased thousands of acres of tea, rubber and coconut estates as well as land in the prominent areas of Colombo.

He owned 46 acres (7360 perches) of land mostly in the Cinnamon Gardens (Colombo 7) which, being one of the most expensive areas in Ceylon, would be worth approximately $600 million in the economy of the 2010s.

His company dealt in every description of Ceylonese produce, principally plumbago (graphite), desiccated coconut, fibre, cacao, rubber, cinnamon and tea.

In keeping with his charitable ways, he donated the stamp to his relative, Sir Cyril de Zoysa, for the construction of the YMBA headquarters building.

[13][14] In recognition of his services, Flower Road (where he resided) was renamed Sir Ernest de Silva Mawatha and a stamp was issued in his honour.

[1] Sir Ernest de Silva died at the age of 70, almost ten years after Ceylon gained independence, a cause he strived for.

Bandaranaike, who was the prime minister at the time, mentioned the loss the nation has to bear with and thanked the departed philanthropist for his services for Sri Lanka, saying that he was a "true gentleman in every sense of the word".