Houses - Historic Buildings of Connecticut

Henry Gildersleeve House (1853)

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.

Capt. Thomas Jefferson Sawyer House (1840)

Thomas Jefferson Sawyer was a sea captain who was born on Mason’s Island in Stonington in 1807 and moved to the coastal village of Noank in Groton circa 1840, where he built the Greek Revival-style house that still stands at 72 Main Street. He was an organizer and leading member of the Fort Hill Baptist Church in Groton. Among his children was a son who, like his father, was also named after the third president.

James N. Tibbals (1851)

The Greek Revival house at 9 Depot Hill Road in the village of Cobalt in East Hampton was built in 1851, with a rear ell that was added later. The house’s original owner was James N. Tibbals, whose father, Thaddeus Tibballs, had started a successful oakum manufactory on Great Hill Pond Brook. Nearby Middle Haddam was a center of ship-building and oakum was used for caulking wooden ships. James and his brothers continued operating the business after their father’s death. The brothers also owned a store nearby. As described in the Commemorative Biographical Record of Middlesex County, Connecticut (1903):

James N. Tibbals was born in the town of Middletown, September 20, 1824. When he was but ten years old, however, the family mover across the river, and settled in the town of Chatham. His earliest educational training was obtained by walking two miles to a district school, although later he and the children received instruction at home, from Miss Melinda Hurlbut. On reaching his majority he was taken into partnership by his father, and continued to conduct the business after the latter’s death until 1899, when as has been already said, he retired. The elder Tibbals conveyed to the son four hundred dollars’ worth of real property when he reached age of twenty-one, in order that the latter might possess the property qualification then prescribed by law for voters. He first exercised the right of suffrage by casting his ballot for the Whig candidates, and since the organization of the Republican party has been one its most loyal members. Under Mr. Tibbals’ sound business management the oakum manufacture has greatly prospered. Originally not more than eight or ten hands were employed, while at present (1902), during the busy season, as many as twenty find employment, and the annual output exceeds four hundred tons. The raw material used is obtained largely from ropes and rigging of dismantled vessels, although much of it is imported, a single purchase not infrequently reaching fifty tons. Mr. Tibbals’ entire life has been passed in Middlesex county, with the exception of a year spent at Roxbury, Mass., where he engaged in business, but was forced to abandon his enterprise because of a disastrous fire. As a citizen he is broad minded and public spirited, enjoying the affectionate esteem of the community. He has served the town as a selectman and has also held various minor offices. He is a devout, consistent member of the Congregational Church, and a liberal contributor to the cause of religion. He was one of the founders of the society of that denomination between Cobalt and Middle Haddam, among original members of which were no fewer than twenty-six of the Tibbals family, and of which he was a deacon for twelve years.

Capt. Giles Wilcox House (1786)

The center-chimney house at 455 East Street in the Westfield section of Middletown was built in 1786 by Giles Wilcox (1750-1838), a prominent citizen and militia captain, on land he had acquired from the estate of his father-in-law David Doud. The house, known as “Ashcroft,” remained in the Wilcox family until 1943, when it was acquired by the Brainard family. The house had to be repaired after an ash tree crashed through the roof during Tropical Storm Irene in 2011.

Moses Smith House (1850)

Built around 1850, the former house at 9 Maple Street in Kent is now used as offices. An example of a gable-fronted Greek Revival-style residence, in 1870 (according to the census) it was the home of Moses Smith, his wife Elvira and daughter Josie (he is also shown as the owner in the 1874 map of Kent). Smith, a wealthy businessman, was a partner in the commercial establishment of Smith & Page, which was located on North Main Street across from the railroad depot.

George Hopson House (1850)

The Italianate-style former house at 50 North Main Street in Kent was built circa 1850. It is associated with the prominent Hopson family, who were wealthy farmers and iron merchants in Kent in the nineteenth century. It is identified as the residence of George Hopson in an 1874 map of Kent. In more recent years, the house was converted to become a branch of the New Milford Savings Bank (which became NewMil Bank in 2000) and is now a branch of Webster Bank (which acquired NewMil Bankcorp in 2006).

Mildred C. Mallory Building (1963)

Designed to fit in with the many historical nineteenth-century buildings at Mystic Seaport, the museum’s MIldred C. Mallory Building was erected in 1963 using stone from a house in the Fort Rachel area of Mystic that had been destroyed in the 1938 hurricane. Serving as Mystic Seaport’s members’ lounge and membership office, the building named for Mildred C. Mallory (1897-1961) as a memorial to honor her efforts for the museum’s membership program. The first floor is covered with granite ashlar and the second floor with clapboards.

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