In 1796, John Pelton, Jr. erected a one and a half-story gambrel-roofed house at what is now 64 Indian Hill Avenue in Portland. At a later date the house was raised to a full two stories, with the second story having a hewn overhang above the first story.
The house at 598 Main Street in Portland was built circa 1840. It was originally the home of ship carpenter Luther Savage, who married Mary Jane Buck in 1850. In 1927, the house was still occupied by Savage’s descendants, who estimated the house had been built 81 years earlier (1846).
In 1888, Henry Gildersleeve, Jr. (1858-1944) erected a grand Victorian-era residence at 624 Main Street in Portland, across the street from the 1853 house erected by his father, the prominent shipbuilder Henry Gildersleeve, Sr. (1817-1894). The career of Henry Gildersleeve, Jr. is described in Gildersleeves of Gildersleeve, Conn. and the Descendants of Philip Gildersleeve, by Willard Harvey Gildersleeve:
Henry Gildersleeve, Jr., graduated in 1875 from Middletown High School and received the degree of B. A, from Wesleyan University in 1879 where he was a member of the football team and of the baseball team. He was also a member of the "Waverleys," a famous old ball club of Portland. In 1881, he received the degree of LL. B., from Columbia University. He spent his vacations and the following year in Hartford, Ct., in the law office of Judge Hammersley of Connecticut Supreme Court. Shortly after he was admitted to the bar in N. Y. City and entered the law office of Messrs. Huntley & Bower. After another year of constant work and study his health was affected, resulting in a serious attack of brain fever. Recovering from the attack, he took chaise of the schooner "Ruth Robinson," and made a trip with it. He then entered the store of S. Gildersleeve & Sons as clerk and becoming interested, was made partner in 1885. He was also part owner of the Gildersleeve and Cromwell Ferry. He organized the Gildersleeve Coal Co. in 1885, was notary public and secretary of the Portland Water Co. In 1900 he sold his interest in the store, having been employed by the Tonawanda Iron & Steel Co., of Tonawanda, N. Y,, on their whaleback steamers. In 1901 he sold the large mansion which he built in 1888 at 624 Main street, Gildersleeve, Ct., to his brother, Oliver, and after working in the Gildersleeve shipyard until 1907, devoted his attention to tobacco raising. Episcopalian. Resides in Gildersleeve, Ct.
The house was later the residence of Oliver’s son Walter Gildersleeve (1874-1949).
The house at 32 Indian Hill Avenue in Portland was built circa 1799. It was originally the home of Elijah Shepard, a master carpenter who alternated between working at the nearby Gildersleeve shipyard and the shipyard in Middle Haddam. Sylvester Gildersleeve later used the house as an office for the Gildersleeve steam saw mill, which was built in 1868.
589 Main Street in Portland was the site of the c. 1720 house of Thomas White. It seems to have been replaced c. 1740 by a house constructed for Jeremiah Goodrich (1709-1793), who was part of Portland’s shipbuilding industry and active in town affairs. The house was originally a single-chimney residence that was later enlarged to have two chimneys. It was later owned by his son Hezekiah Goodrich (1745-1817). Hezekiah was a Jeffersonian Republican who was one of five men removed from office as Justice of the Peace in by the Federalist state government due to his attendance at an August 29, 1804 general meeting of Republican delegates from 97 Connecticut towns held in New Haven. At the time Connecticut was still operating under the 1662 Royal Charter, but the delegates favored the drafting of a constitution, declaring it “the unanimous opinion of this meeting that the people of this state are at present without a constitution of civil government.” Federalists were outraged at what they considered a radical and dangerous position, and they succeeded in revoking Goodrich’s commission, as described in Historical Notes on the Constitutions of Connecticut, 1639-1818 (1901) by J. Hammond Trumbull:
The result of the October election in an increased federal majority showed that the popular mind was not yet prepared for a radical change. When the General Assembly met, the leaders of the dominant party, elated by success, resolved to administer a signal rebuke to the revolutionary designs of the minority. Five justices of the peace, who had attended the republican meeting at New Haven and taken part in its proceedings, were cited to appear before the Assembly, “to shew reasons why their commissions should not be revoked,” since “it is improper,” as the preamble of the resolution sets forth, “to entrust the administration of the laws to persons who hold and teach that the government is an usurpation.”
Connecticut would finally hold a constitutional convention in 1818.
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.
The house at 618 Main Street in Portland was erected in 1807 for Jeremiah Gildersleeve (1781-1857), a ship carpenter and navigator who was a member of the famous Gildersleeve shipbuilding family. He married Lucy Ann Cone in 1804.
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