The house at 2655 Long Hill Road in North Guilford was built c. 1730. The original owner was Joseph Chittenden, Jr. (died 1794), a cooper by trade. It was later owned by Benajah Stone III (1708-1757), who was married to Joseph’s sister, Mary. Benajah sold the house on March 3, 1746 to Samuel Fyler.
The Georgian Colonial house at 24 Main Street in Farmington dates to c. 1769, but it may incorporate the earlier home of John Hooker (1665-1745), son of Rev. Samuel Hooker, built around 1688. The house eventually passed to John Hooker‘s grandson, Roger Hooker, Jr. (1751-1830), who later sold it to Col. Isaac Cowles. It then passed to the Colonel’s son Maj. Timothy Cowles (1784-1858), who sold it in 1834 to store-owner William Gay.
Glimpsed through the trees in the image above is a house that was once the home of two of the most famous people of the twentieth century. Located at 232 Tophet Road in Roxbury, it has been much altered over the years. It was built for a Revolutionary War veteran and was later the residence of playwright Arthur Miller and his wife (from 1956 to 1961) Marilyn Monroe. The couple had originally planned to replace the old farmhouse with a new home designed by Frank Lloyd Wright, but they decided the plan produced by the famous architect was too impractical and expensive. According to Homes of Old Woodbury (1959), p. 247, the house was built about 1783 by Captain David Leavenworth. Sheldon Leavenworth sold it to Elliot Beardsley in 1847 and twenty years later it was acquired by Charles N. Ward. Frederick H. Leavenworth bought the house in 1888 and his son sold it to Miller in 1949, the year the playwright wrote Death of a Salesman at his first Roxbury home. Miller lived in Roxbury from 1947 until his death in 2005. The Leavenworth House has has remained in Miller’s family. Ten years after his death, his daughter donated a 100-acre parcel to the Roxbury Land Trust.
The house at 16 Barry Road in the Quaker Farms section of Oxford was once thought to have been built as early as 1680, but a date of 1740 is now considered more likely. In the early nineteenth century the house was owned by the Tomlinson family. It was used in the mid-nineteenth century by Preston Hinman for his shoemaking business. Greatly deteriorated by the early twentieth century, Ralph B. Pomeroy purchased it in 1947, removed a later dormer window and undertook the house’s restoration to a colonial appearance.
The house at 388 Amity Road in Bethany was built c. 1730. Its earliest known owner, c. 1780, is Ebenezer Dayton, a privateer of the Revolutionary War. A dramatic robbery took place in this house in 1780. The robbery was planned at the Turel Whittemore Tavern in Seymour. The incident is described by John Warner Barber in Connecticut Historical Collections (1836):
On the night following the 14th of March, 1780, the house of Capt. Ebenezer Dayton, then residing in this place, was broken into and robbed by seven men, who were tories, and headed by a British officer, from Long Island. Mr. Dayton’s house was situated nearly opposite where the first meeting house in Bethany was erected, about half a mile south of the present Congregational church, and about ten miles N. W. of New Haven.
The particulars of this robbery, were obtained from the Rev. Mr. Dayton, son of Capt. Dayton, mentioned above. Mr. Dayton, who belonged to Long Island, was on account of his attachment to the American cause, obliged to leave that island, and bring his effects with him to Bethany. A number of men, some of his neighbors, were obliged to leave the island for the same cause, and brought a considerable quantity of money with them, and for a while resided in Mr. Dayton’s house. With these facts, the robbers appear to have become acquainted. At the time of the robbery, Mr. Dayton was absent on business at Boston, and the men who had been staying in the house, had left the day before, so that there was no one in the house but his wife, Mrs. Phebe Dayton, three small children and two servant colored children. About midnight while they were all asleep, the window in the bedroom where Mrs. Dayton was sleeping, was burst in at once, seven armed men rushed in, passed through the room and immediately rushed into the chambers, expecting (it is supposed,) to find the men who had left the day before. While they were up stairs, Mrs. Dayton went to the front part of the house, raised the window and endeavored to alarm the neighbors. Mr. Hawley, the minister of the parish, and Dr. Hooker, the physician of the place, both lived within 20 rods distance; both had lights in their houses at the time, and both heard the alarm, but did not know from whence it proceeded. The robbers hearing Mrs. Dayton, came down, and tearing a sheet into strips tied her hands behind her, made her sit in a chair and placed her infant (about six months old,) in her lap, while one of the robbers placing the muzzle of his gun near her head, kept her in this position for about two hours, while the house was thoroughly ransacked from top to bottom. They found about 450 pounds in gold and silver, which belonged to Mr. Dayton, besides other valuable articles; what they could not conveniently carry off they wantonly destroyed, breaking in pieces all the crockery, furniture, &tc. The whole amount of property carried off and destroyed, including bonds, notes, &c. amounted to five thousand pounds.
The robbers left the house about 2 o’clock and went to a place in Middlebury, called Gunn town, where they were secreted in a cellar by a family who were friendly to the British cause. While they were on their way to Gunn town, they met a young man by the name of Chauncey Judd of Waterbury, on a bridge, who had been to see the young lady he afterwards married. Fearing he might discover them, they took him along with them. In the cellar kitchen where they were all secreted, there was a well. Into this well they talked of putting Mr. Judd; but the old lady of the house begged they would not think of it, as it would spoil the water. They stayed in this house a number of days: afterwards they went to Oxford, where they were secreted for several days longer in a barn; from thence they went to Stratford, took a whale boat and crossed over to Long Island. The people at Derby, having received information of their passing through that place two whale boats and crews, commanded by Capt. William Clarke and Capt. James Harvey, pursued them to the Island, and were fortunate enough to catch them all but one, just within the British lines. They were brought back, tried condemned and sent to Newgate; they however, broke prison and finally fled to Nova Scotia.
In the 1830s the house was owned by Colonel Elihu Sanford. In 1929 the house was moved 300 feet north of its original location to its current address.
The house at 1079 Main Street in Coventry is an example of a late eighteenth-century (certainly built by 1800) central-chimney residence that was later expanded and used as mill housing. In the late 1850s it was owned by the N. Kingsbury Company, manufacturers of satinet and by the late 1860s it was owned by the Mill Brook Woolen Company.
Deacon Joseph Ives (1674-1755) was one of the first settlers in what is now Cheshire. He built the house at 280 Fenn Road in Cheshire in 1724. As related in J. L. Rockey’s History of New Haven County, Connecticut, Vol. I (1892):
In the southeast portion of the town and near the residence of Mrs. Silas Ives, Joseph Ives settled in the year 1694; the same year of his marriage to Esther Benedict. He was one of the first, if not the first settler, in what is now Cheshire. He was chosen the first deacon of the Congregational church in 1724, and served the church in that capacity until the year 1739, at which time the second church edifice was erected. Deacon Ives was a very useful and devoted member of the infant parish. In this same house also his son Joseph and grandson Titus resided. The latter was a revolutionary soldier and was with Washington’s army at Harlem, N. Y., where he died in the year 1777. A letter written by his wife, and sent to him at Harlem, during his last sickness, and also the gun used by him in the colonial struggle for independence, are now extant and are preserved as precious memorials by the family of Mrs. Silas Ives, who are descendants, who reside within a few feet of the old Ives homestead, and who own and occupy the same property that has been in the possession of Deacon Joseph Ives and his descendants for about 200 years.