One of the five oldest houses in Connecticut is the Bushnell Farm house at 1445 Boston Post Road in Old Saybrook. It began as a two room, one story, thatch roofed post and beam house built by the Elder Joshua Bushnell. It is listed in the National Register of Historic Places as the Elisha Bushnell House and J. Frederick Kelly, in his classic Early Domestic Architecture of Connecticut (1924), calls it the Older Bushnell House. The house was expanded over the two centuries that the Bushnell family owned it. The property has a number of outbuildings, including an early eighteenth-century barn, a loom house (the Bushnells were both farmers and weavers) and a building referred to as the slave house. Maintained as a private residence in an excellent state of preservation, the property is often opened to schools, historical societies and the Connecticut River Museum Summer Camp.
At the northwest corner of the Boston Turnpike at 21 Bread & Milk Street in Coventry is a house built circa 1735 by John Wilson (1702-1773). After his death in 1773, the house passed to his son William (1729-1819), who married Sarah Rust, and his grandson Jacob (1749-1826), who married Hannah Dimmock in 1771. Jacob Wilson operated a tavern at the house from 1773 until 1817, when he sold the property to Joshua Frink.
The saltbox house at 566 Boston Post Road in Madison was long thought to have been built by John Dudley in 1675, making it the oldest house in town. The nomination for the Madison Green Historic District instead attributes it to Gilbert Dudley with a date of c. 1740. A plaque by the Madison Historical Society gives a date of c. 1720. On April 11, 1776, while on his way from Cambridge to New York, George Washington stopped to dine at the house, which was then a tavern run by Captain Gilbert Dudley.
The Keeney Homestead is a colonial saltbox house located at 1026 Forbes Street in East Hartford. Associated with the Keeney family, the house was built around 1750-1780 and was possibly moved to its current address c 1805 from an unknown original location. After a fire damaged the house in the 1940s, it was restored with the interior of an eighteenth-century house from Glastonbury.
Built in 1752, the saltbox house at 1174 Windsor Avenue in Windsor was the home of Capt. Nathaniel Loomis. This may be Capt. Nathaniel Loomis III (1719-1784). A Windsor Historical Society House Tour in 2010 included the Loomis House, where visitors could hear Harriet Loomis (1784-1876) describe the hardships of the Revolutionary War. I don’t know her relationship to Capt. Nathaniel Loomis.