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.
The house at 620 Main Street, at the corner of Foote Road, in Glastonbury was built by Jehiel Goodrich (1741-1818) around 1760 (but traditionally dates to 1743) on land he had received from his father, William Goodrich (1697 or 1701-1787), in 1758. The ell was added later.
One of Connecticut’s oldest surviving houses is the Meigs-Bishop House, at 45 Wall Street in Madison. It is Madison’s second oldest house after the 1685 Deacon John Grave House. The Meigs-Bishop House was built in 1690 by Janna Meigs on land he had received from his father, Deacon John Meigs. As related in the Record of the Descendants of Vincent Meigs: Who Came from Dorsetchire, England, to America about 1635 (1901), by Henry B. Meigs:
Capt. Janna was evidently a man of education, as the importance of the many offices he filled would indicate; was deacon in the church; represented his district in the legislature of the Colony of Connecticut in 1716-’17-’18 and 1726; and was Justice of the Peace for New Haven Colony, annually from 1722 to 1733 inclusive, a position of greater importance then than now. In military life he was Captain of a Company in the Queen Ann wars.
He left the house to his son, Lt. Janna Meigs, who deeded it to his first cousin, Capt. Phineas Meigs. After serving in the Revolutionary War from 1777 to 1780, Capt. Meigs retired from the army and was named captain of the Guilford militia. On May 19, 1782, three British frigates tried to capture an American schooner that had run aground on a sand bar. Capt. Meigs set out from his Wall street home leading his men to battle British soldiers who had landed on shore. In the ensuing fight, Capt. Meigs was shot through the head. He is believed to be the last New Englander to be killed in an action against the British in the Revolutionary War. The green wool round hat he was wearing that night survives and is in the collection of the Connecticut Historical Society. It bears the entry and exit holes of the musket ball that killed Capt. Meigs.
Later owned by the Bishop family, the house has most recently been used for a succession of businesses.
The oldest surviving building in West Haven is the Ward-Heitmann House at 277 Elm Street. It may have been built as early as 1684 and was certainly on the site by 1725. The house was built by Ebenezer Clark, who sold it in 1730 to John Humphreville, who had married Clark’s sister Rebecca. The house remained in the Clark family until 1788, when it was purchased by sea captain Thomas Ward (d. 1839). It remained in the Ward family until George Ward sold it to Susan Perrin in 1861. She eventually sold it to Louisa Ward Heitmann, George Ward’s sister, in 1868. Her daughter, Henrietta Heitmann, inherited the house in 1897. She was engaged in various business ventures and also added the north wing to the house and used it as a dame school. The house passed out of the Ward-Heitmann family when Charles Elliott Pickett purchased it in 1910. In the twentieth century the house had a number of owners and for a time housed an antiques store and later a tearoom. The Milano family owned the house from 1949 to the early 1990s and left it to the National Trust for Historic Preservation, which sold it to the Ward-Heitmann House Museum Foundation in 1995. The house was then restored to become a museum.
The Abraham Scranton House, a Colonial saltbox at 548 Boston Post Road in Madison, opposite the Green, may have been built in 1703, 1720 or 1750. The latter date is when it came into the Scranton family.