The Shelley House, at 248 Boston Post Road in Madison, dates to the late seventeenth/early eighteenth Century, with specific dates variously given that include 1709/1710 and 1730. This exceptionally well-preserved structure is a rare surviving example of a house that was clearly built in several stages, following a pattern believed to have been common at the time: starting with a one-room, two-story dwelling with a stone wall at one end (the east half), a second section added later (the west half) and finally a lean-to at the rear. Traditionally known as the William Shelley House and also known as the Stone-Shelley House, it underwent a controversial restoration c. 2008.
The large Italianate house with a cupola at 17-19 Wall Street in Madison was built in 1854. It was the home of Alva Orrin Wilcox (1799-1887). His entry in the 1893 book The Descendants of William Wilcoxson, Vincent Meigs, and Richard Webb, complied by Reynold Webb Wilcox, reads as follows:
Alva Orrin Wilcox, of Madison, Ct, son of Return of Madison, Ct., kept a hotel and ran a stage line from New Haven to New London, carrying the mail for thirty years, m. Sept. 27, 1826, Rachel, dau. of Billy Dowd, d. Aug. 21, 1889.
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 first meetinghouse in Madison was erected in 1705, on the southeast section of the town green. It had neither a bell nor a steeple and galleries were only added in 1715. A new meetinghouse was dedicated in May 1743, to which a steeple was added in 1799. The present First Congregational Church was built in the Federal style on the north part of the green in 1837-1838. As described in A Modern History of New Haven and Eastern New Haven County, Volume 1 (1918), by Everett G. Hill:
When the people built for the third time in 1838, they had the common struggle to break away from the green. There was a strong party that favored building on Deacon Hart’s lot north of the green, but so resolute was the minority that forty-seven members actually withdrew from the church in 1841, because of the change. The commanding site north of the green was chosen, and it and the building placed thereon have ever since been the pride of the people of Madison, the delight of all who visit the town. It is a building of notable architecture, acknowledged by all good judges to be one of the finest country churches of its type in New England. A handsome modern chapel was added to its equipment, on a plot just east of the green, in 1881.