[2] He was educated at the Scotch College, Melbourne, and was brought up to pastoral pursuits, in which his father achieved very great success.
In 1857 he, with his brothers, purchased Colbinabbin and other stations in the Rodney district at a cost of about £200,000; and in 1868, on a friendly dissolution of partnership, the Stanhope estate fell to his share.
[2] In 1874, in conjunction with J. Ettershank, of East Loddon, Winter visited England and successfully conducted the appeal to the Privy Council against the Crown, relative to the five shilling per acre penalty sought to be enforced against the holders of certificated lands.
[2] In 1871 Winter stood for the Eastern Province against Sir Francis Murphy, but ultimately retired in that gentleman's favour.
His brother, James Winter, of Toolamba, Murchison, who died at Norwood, near London, in 1886, was also a well-known pastoralist.