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.

Samuel Fielding House (1750)

The gambrel-roofed colonial cape-style house at 25 Marjorie Circle in Hebron was built c. 1745-1750 by Samuel Feilding. Soon after construction it was owned by Rev. Benjamin Pomeroy (1735-1784), a congregational minister who was influenced by the First Great Awakening. In 1791 the house was acquired by Amasa Gillett, whose widow later married Benjamin Phelps (the house was later called the Widow Polly Phelps Place). Gillett’s daughter Sibyl, who lived in the house until her death at the age of 95, made bonnets and had her shop in the house in the 1850s. Earlier, in 1835 the largest room in the house was used for Miss Bradford’s school for select young ladies. There is also a gambrel-roofed barn on the property.

Jonathan Warner House (1703)

Jonathan Warner House in Portland

The earliest part of the house at 613 Main Street in Portland was constructed in 1703 for Jonathan Warner. It was one room over one room with an end chimney (a style typical of Rhode Island). The house was enlarged over the years. Behind the northwest part was a section built in 1764 by sea captain Ithamar Pelton (1744-1806). The south part of the house was added in 1912 by William Gildersleeve.

Main House, Rectory School (1795)

Now comprising part of the “Main House” on the campus of the Rectory School in Pomfret is a house erected circa 1795 for Thomas Grosvenor (1744-1825), a lawyer who served in the Revolutionary War. Wounded in his right hand at the Battle of Bunker Hill, Grosvenor ended the was as a Lieutenant Colonel. The house was remodeled and greatly enlarged in about 1885 by Thomas Skelton Harrison, a Philadelphia industrialist. In 1925, Rev. Frank H. Bigelow and his wife, founders of the Rectory School in 1920, acquired the Harrison estate to become the school’s campus. In the ensuing years they erected a complex of wood-framed colonial revival buildings on the estate, which has been the school’s campus ever since.

Postcard of The Rectory School (Main House)

John Killbourne House (1740)

The house at 120 High Street in South Glastonbury is listed as 118 High Street in the 1978 Historical and Architectural Survey of Glastonbury, where it is described as the John Killbourne House, built in 1740. A plaque on the house reads “Spar Mill, Est. 1740.” Feldspar was quarried in the area in the early twentieth century and the nearby house at 9 Tryon Street is believed to have once been the mill’s office.