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.
Jonathan Bishop built the house at 191 State Street in Guilford in 1797. He farmed the family land with his brother, Jared, who lived at 205 State Street, the house built by their father. The farm was inherited by Jonathan Bishop, Jr., who was called “Captain” and shipped his produce to New York on a sloop he berthed at Jones Bridge. William E. Pinchbeck bought the property in 1928 and erected the longest iron-frame greenhouse ever constructed for his rose-growing business, which continues today as Roses for Autism.
The house at 107 State Street in Guilford was built in 1787 in the Federal style and has a later Greek Revival entryway. The house was built by two brothers, Samuel and Thomas Scranton, who were both farmers. It would become home to the brothers, their wives and their combined total of nine surviving children. It was inherited by Thomas Scranton, Jr.
Once thought to have been much older, the small house at 223 State Street in Guilford was probably built c. 1778 by Benjamin Hall. In 1803 he sold it to William Starr, whose family lived in it until 1995. A kitchen ell was added to the house around 1940.
The house at 101 State Street in Guilford was built in 1730 for Jabez Benton (1680-1756) and his wife Hannah Stone (1702-1773). They were married in 1726 and had seven children. In 1853 George Walter Hinckley, who would become a teacher and a minister, was born in the house. In 1889 he founded a farm school for homeless children in Fairfield, Maine called Good Will Farm. By the time Hinckley died in 1950, the school had a campus of 3,000 acres with 45 buildings and served more than 3,000 underprivileged and troubled youth.
Jonathan Starr, a tailor, erected the house at 133 State Street in Guilford in 1732 on land deeded to him by his father, Comfort Starr, also a tailor. He ended up deeding the property back to his father a year later and moved to East Guilford (now Madison). The house‘s hipped roof may not be original. The triple window and Federal-style doorway were probably added in the late eighteenth century. There is a preservation easement on the exterior of the house held by the Connecticut Trust for Historic Preservation. In recent decades the building has housed a series of businesses. It is currently home to Health Options, Center for Wellness.
The Italianate-style house at 72 Church Street in Guilford was built c. 1860. It has Queen Anne-style porches added later in the nineteenth century. This was the home of Deacon Eli Parmelee (1808-1882) who served in the state legislature and was a deacon of the First Congregational Church from 1852 until his death in 1882.