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.
The exact date that the house at 101 Fair Street in Guilford was built is uncertain. It was the site of a seventeenth-century home built by Thomas Cooke, one of the original settlers of Guilford and a signer of the 1639 Guilford Covenant that established the town while the colonists were still at sea. The current house on the site was possibly built by Miles Dudley around 1707, after his 1705/1706 marriage to Rachel Strong, but may contain sections built earlier. Dudley purchased the property in 1702. The Greek Revival doorway dates to the early 1830s.
The oldest house in Fairfield is the John Osbourne House at 909 King’s Highway, West. The oldest section consists of the original center-chimney block, which probably began as one-room and was then expanded. A lean-to added several decades after the house was built. The traditional date of construction is 1673, but the later date of 1734 is more likely. The house is traditionally associated with John Osborne, who married in 1673. His father Richard fought in the Pequot War and received a grant of land for his services. The last battle of the war was fought in 1637 in Pequot Swamp, which is located adjacent to the house. The colonial-era section of the house is flanked at both ends by two twentieth-century wings.
The Samuel Beach House in Branford (not to be confused with a later Samuel Beach House in Branford, built in 1875 as a summer cottage) is located at 94 East Main Street. The WPA Survey of Old Buildings in Connecticut dates the house to 1790. A twentieth-century owner, Samuel W. Beach, restored the house as closely as possible to a late eighteenth-century appearance.