Miles Dudley House (1707)

101 Fair St., Guilford

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. (more…)

John Osborne House (1673)

John Osborne House

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.