Guilford Academy (1794)

For sixty years the First and Fourth Congregational Societies in Guilford each maintained their own schoolhouse, located next to each other on the Green. These were then combined into one building of two stories, erected in 1794. The building was moved from the Green to its current location, at 19 Church Street, in 1827. It then housed a secondary school, called the Guilford Academy (aka high school), on the upper floor. As related in A History of the Plantation of Menunkatuck and of the Original town of Guilford, Connecticut (1897), by Bernard Christian Steiner:

In 1837 the [town’s center school] district was divided into four parts and school houses built in the northeast and southwest districts, the northwest district occupying a part of the academy, the upper part of which building was occupied in 1838 by Mr. Dudley as a high school.

The academy closed in 1856, after the Guilford Institute (which would later become the high school) opened. The former Academy building then became a private residence. The front porch was most likely added around that time.

Deacon Darius Knight House (1825)

The house at 93 Chaplin Street in Chaplin has been dated variously to 1840, 1832 and 1825. It was the home of Deacon Darius Knight. The house next south on Chaplin Street, just past the intersection with Tower Hill Road (87 Chaplin Street), was the home of E. W. Day, so the intersection became known as Knight and Day Corner. The Knight House was later home to a minister and a doctor.

Orrin and Electa Hale House (1817)

The house at 181 Main Street in South Glastonbury was originally the home of Orrin Hale (died 1870) of Portland and his wife Electa Taylor Hale (died 1865) of South Glastonbury. The date of their marriage is unknown, but their first child was born in 1817 and they were likely living in their new home by then. The house, which town assessors dated to 1770, combines elements of the Federal and Greek Revival styles.