The fine house known as Hillcrest at 1 Neas Alley, was built on two early land grants. The 17th century home of widow Alice Finney stood on the northern half of the lot. To the south Daniel Jones erected a stone residence soon after it was granted in 1699. After Finney’s daughter married Jones, the two properties were joined to form one of the largest lots in the town. Ownership remains unclear after the Jones family died out in the 1750s, but a house was standing on the lot when Mary Leaycraft and Richard Minors sold the property to Richard Prudden in 1789. The deed to a neighbouring property reveals that Prudden was living there three years earlier as a tenant.

Originally from Southampton, Prudden was a highly successful merchant who channelled his profits into purchasing many of the lots surrounding Hillcrest. The symmetrical layout of this U-shaped building suggests that it was probably built shortly before Prudden acquired the house, although the quoins on the front of the house and the triple keystones over the windows, decorative elements dating to the late 1790s, raise the possibility that the merchant levelled an earlier structure and built afresh about 1800.

After Prudden’s death in 1814, his extensive landholdings were willed mostly to his two granddaughters, Ruth and Eliza. Hillcrest went to Eliza, who married William Richmond Higinbothom, a merchant from Baltimore, Maryland and the first commercial agent for the United States. Their daughter Elizabeth married William Tudor Tucker in 1832, and Tucker assumed the post of commercial agent after his father-inlaw died later that year. Thus, in the 1840s and 1850s, Hillcrest functioned as a place where Americans abroad could turn for aid.

Following an assassination attempt made during the dockworkers’ strike in 1863, William Tudor Tucker emigrated to Nebraska and the house was rented. In 1873 the Higinbothom heirs sold Hillcrest to Warwick merchant Samuel Chapman, who continued to let it to tenants. In 1900 Scottish Andrew Greig purchased it, perhaps to please his wife Anna, who was William Tudor Tucker’s daughter. Greig had come to Bermuda during the heyday of the American Civil War when he courted and wed Anna Tucker, but the couple departed when trade collapsed following the fall of the Confederacy. They returned in 1879 when Andrew took a less glamorous but more secure position as postal clerk.

John Wright, a later owner, replaced the house’s original wooden verandah with the present concrete one in 1920. Wright’s daughter Ellen Trew Robinson converted Hillcrest into a guesthouse called Aunt Nea’s Inn in 1961 and for many years Hillcrest offered visitors the rare opportunity to stay in an 18th century home in the heart of Bermuda’s oldest settlement. In 2025 it is being renovated but is intended to continue as a small hotel and spa.