A merchant, from 1439 or earlier Sylvester regularly arranged for imported commodities to be carted to Winchester from Southampton, notably, quantities of wine and victuals such as herring, salt fish, garlic, onions, oil and fruit, but also black soap, wax, alum and madder. On occasion, too, he sent cartloads of goods to be sold in Andover and even in the capital.
In 1439 Sylvester had been elected a member of the 24, the body chosen to advise the mayor, and began a term as their bailiff, but on 18 Feb. following the mayor and his brethren granted him exoneration from office.
Robert Colpays*, the Winchester lawyer who died in 1446, asked Sylvester to be a feoffee of his property in Calpe Street, to fund obits in the church of St. Thomas the Martyr for the good of his soul and prayers for members of his family. Similarly, he agreed to take on the trusteeship of buildings in Minster Street, including those next to his own tenement on the lane leading to Calpe Street, which the Wiltshire esquire Robert Erle* formally conveyed to him and others in November 1450, during the first session of the Parliament to which he had just been elected.
On 11 June 1460 the mayor and council granted that Sylvester might have a stip of land two feet wide adjacent to the King’s highway so that he might build an extension to a house he had recently purchased, and also relinquished to him the city’s title to a lane on the east side of the property.
