Cummings House (1855)

The Cummings House, located at 984 Main Street in Coventry, was built c. 1855. The house has a typical New England gable-roofed form that goes back to the Colonial period, but the detailing is distinctively Italianate in style. The 1857 map of Tolland County identifies the owner of the house as J. Cummings and the 1869 atlas of Hartford and Tolland Counties indicates it is owned by William M. Cummings.

Benjamin Bosworth House (1801)

Between 1791 and 1801, architect/builder Vini Goodell erected an imposing mansion for Benjamin Bosworth, a wealthy merchant and landowner. Also known as Squire Bosworth’s Castle, this grand Federal-style house is located on John Perry Road in Eastford, near the Congregational Church (Bosworth served on its building committee and removed the previous meeting house from the site). The Benjamin Bosworth House has a distinctive monitor roof. The monitor third floor was built as a Masonic meeting room and retains its built-in benches and has fireplaces at either end. As Janette Trowbridge, a later resident of the house, wrote about the house [included in A Modern History of Windham County, Connecticut, Vol. I (1920), edited by Allen B. Lincoln]:

The framing and sills were laid by the North Star. The hand carvings on the mantels, windows, and doors were elaborate for that time. They were cut with a jack knife by an employee who lived and worked in the house for an entire winter. Squire Bosworth desired a house which should be different from any other in the neighborhood. In this he succeeded, for the house has the appearance of a small gable-roofed house built on top of a larger square-roofed house.

Nathaniel Hall House (1770)

The Nathaniel Hall House (perhaps named for this Nathaniel Hall?), located at 48 State Street in Guilford, was built c. 1770 and has been much altered over the years. The second floor is thought to have been added around 1810, at which time the house probably acquired its current Federal-style detailing. An owner of the house in the 1980s removed the c. 1810 front porch and various later Victorian-era alterations.

Augustus Post House (1826)

The large Federal-style brick house at 4 Main Street (the corner of Routes 66 and 85) in Hebron was built c. 1820-1826 by Augustus Post. He soon sold the large residence and it passed through a series of owners that included Dr. John S. Peters and his business partner Abner Hendee. Peters was Governor of Connecticut from 1831 to 1833. In the late nineteenth century the house was acquired by W. S. Hewitt, who used it for his general store and post office. At some point the house was extended on the north side with a frame addition. The west side of the house has an entrance with a twentieth-century shed-roofed portico and the south side entrance was once altered to function as the storefront. The Hewitt family owned the house into the 1970s and it is commonly known as the Hewitt House. In 1978 the house was converted into office space. At that time the current Federal-style entrance on the south side was created.

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