Osborn House // 1772

This homestead in Fairfield, Connecticut is situated on the edge of what was formerly called Pequot Swamp, and was originally built by Stephen Osborn in 1772. It is said to be the third Colonial dwelling erected in this part of the town and was left undisturbed by the British when they burned Fairfield in 1779 and raided various sections of the country along the shore. The home was originally located a few blocks away, but was moved in the 1950s when the highway (I-95) was routed through this part of Fairfield. The saltbox Georgian home was documented prior to the move by the Historic American Buildings Survey (HABS).

DeForest House // c.1800

At the beginning of the 19th century, Fairfield, Connecticut was slowly recovering from its destruction by the British at the end of the Revolution. By around 1800, a member of the DeForest family appears to have built this home, across from the Town Common, overlooking the recently completed Fairfield County Courthouse. Before the American Civil War, the home was significantly altered, with a central pavilion, new round arch windows, and a full-length front porch, showcasing early Victorian-era desire for detail. The house changed hands several times over the next century, at one point becoming a boy’s school from 1891 to about 1909. In 1930, the house was renovated by architect Walter Bradnee Kirby, who restored the home back to its Colonial past, showing how the pendulum of architectural tastes can change back-and-forth with every passing generation.

Captain John Maltbie House // 1766

On July 7-8, 1779, the Red Coats marched through Fairfield torching houses to punish the locals for seeking independence. They killed locals, destroying anything they could find on their way out, setting fires to homes and civic buildings around the Green. This home was built by Isaac Tucker, later sold to Jonathan Maltbie, sea captain involved with East Indies trade. He later would fight against the British during the Revolution, and after the war, was hired as captain on one of the first cutter ships built, the Argus. During the British invasion of Fairfield, they attempted to set fire to this home three times, but it seemed to never go up in flames when they returned. The tradition holds that an elderly servant, hiding upstairs, put out the flames and saved the house from destruction, after the British Troops torched it. Burn marks apparently remain inside to this day. Since the home was built, the front door facing the street was relocated to the side, and a large multi-pane bay window was installed in its place.