He owned the Walnut Tree Inn and other property in Southwark and became a wealthy merchant who supplied wagons to Oliver Cromwell’s army during the Civil War.
Caleb Lovejoy is primarily remembered in Guildford as a benefactor. In his will of 1676 he bequeathed property under lease in Southwark to form a charity for the benefit of the poor in Guildford. He appointed three guardians as trustees. Six pounds per annum was to be provided for “teaching of poor people’s children their letters until they could read their Testament.” The teaching to be undertaken, “by some honest poor woman.”
He stipulated that, after 45 years, four almshouses should be built in the parish of St Nicolas as accommodation for four poor persons of good character. However, it was not until 1839, after the sale of Caleb’s estate, that land was purchased in Bury Street Guildford and four almshouses were built.