Henry Gildersleeve, Sr. (1817-1894) was a member of the prominent Gildersleeve shipbuilding family of Portland. In 1853 he erected his house, which has an Italianate-style cupola, at 625 Main Street. In 1932 the house was sold to Harold Randall, who is most likely the one who laid out the adjoining small street called Randall Place. As related in the History of Middlesex County, Connecticut, with Biographical Sketches of its Prominent Men (1884):
The eldest son of Sylvester and Rebecca Gildersleeve inherits from his father those rare traits of character that have distinguished the Gildersleeves, not only as a family of successful shipbuilders and merchants, but as a family who are noted for their public spirit and large hearted benevolence.
Henry was born in Portland, in that part of the town now known as Gildersleeve, on the 7th of April 1817. He enjoyed the limited educational advantages afforded by the district school, but acquired sufficient knowledge of the rudimental branches to fit him for the occupation he had chosen. At the age of 17, he commenced in his father’s yard to learn the business of shipbuilding, and soon acquired a thorough knowledge of the details of the business. At the age of 25, he was taken into partnership with his father, under the firm name of S. Gildersleeve & Son. In December 1872, he associated himself with the house of Bentley, Gildersleeve & Co., shipping and commission merchants, on South Street, New York. He retained his connection with the Portland shipbuilding firm and at the end of ten years he retired from the New York firm, resigning in favor of his son, Sylvester, who still continues the business in connection with his brother, Oliver, under the firm name of S. Gildersleeve & Co. Henry Gildersleeve, since retiring from his New York business, has devoted his whole time and attention to the shipbuilding and other interests with which he is connected in his native town.
Mr. Gildersleeve has been identified with many public enterprises outside of his shipbuilding interests. He was for a number of years a director in the Hartford Steamboat Company, and is now president of the Portland and Middletown Ferry Company, and a director in the Middlesex Quarry Company, also the First National Bank of Portland; and trustee of the Freestone Savings Bank. He has been for many years an active member and a liberal supporter of the Trinity Episcopal Church at Portland, was a large contributor to the fund for the erection of the building, and a member of the building committee.
In 1860, he represented the democratic party in the State Legislature, and sustained every measure for the vigorous prosecution of the war.
