In 1882 and 1883, Tom had led an overlanding party with his relatives, the Duracks and the Byrnes, and established Rosewood station, which extended from the eastern Kimberley region of Western Australia into the present Northern Territory.
Although he had lost the sight in one eye as the result of an insect bite that became infected, he proved an excellent athlete.
During the next 25 years, Kilfoyle built a reputation as a successful owner-manager on a medium-sized property of 734,000 acres (2,970 km2) on what was known as a "big man's frontier," increasingly dominated by companies and absentee proprietors.
A federal board of inquiry into land policy in 1937 praised Kilfoyle's thorough management and close supervision of Rosewood.
On 23 February 1939, Kilfoyle married Thelma Ada Hope Ryan at St. Mary's Catholic Cathedral in Perth.