Henry Holland, Jr. was born in Albany in 1704. He was the second son of garrison officer and sheriff, Henry Holland and Irish-born Jenny Seeley.

By the time he was five, he was accompanying his soldier father. In 1709, he was identified on a duty roster as a "boy" and unfit for the Canadian expedition." He continued to serve in his father's company until 1719, when he was apprenticed for seven years to learn business in New York under merchant Thomas Kearney.

At the end of that term, he returned to Albany to tend to some of the administrative aspects of his father's operations. In 1727, he was elected assistant alderman for the first ward. A year later, he married Alida Beekman - daughter of a successful Albany merchant. The marriage produced but one daughter. Settling in Albany, he purchased a lot on the Plain in 1730. Later, he would erect a substantial house on a riverside lot along Market Street.

Over the next two decades, Henry Holland, Jr. lived in Albany but acted to solidify his image as a loyal adherent among provincial authorities in New York. He was rewarded with royal appointments as justice of the peace, master of the chancery court, and sheriff of Albany County in 1739. He held that post through some local controversy until 1746. By that time, Albany leaders openly resented the appointment of royal placemen to the sheriff's office. Native son but still British-identified, Henry Holland Jr. was a compromise appointee. He also was able to participate in frontier land patents - an initiative that left him with valuable acreage in the Mohawk country and to the north of Albany. During that period, he began to conduit cargoes out to frontier developer William Johnson.

During the hostilities with the French in 1744-48, Holland served as a commissary - procuring provisions and supplies on behalf of the British war effort. Still the sheriff, he came under fire in Albany for his tactics in securing materials from Albany storehouses. He was replaced as sheriff in September 1746.

By the 1750s, Henry Holland, Jr. had relocated to New York City to pursue business opportunities. During the Great War for Empire, he was an owner of at least two privateers. He also acquired an estate on Staten Island and represented Richmond County in the provincial Assembly from 1761 to 1769.

In March 1777, he filed a will calling himself a New York merchant and in good health. No wife nor children were named. His executors were instructed to sell his real estate for the education of his grandchildren. His slave Dinnah, was to be freed within a year of his death. And the remainder of his estate was to be divided among his three living grandchildren. The will cleared probate in May 1782.