Built prior to 1830
At one time inhabited by a family of Flys.
The earliest record for 1227 Westbrook Street is from 1830. There is little doubt the home predates that by 35+ years.
The main block is a post colonial standard 3 bays wide by one deep. It’s 2 stories high with a garrett.
There is a rear ell but it is attached to the northeast end and projecting off the north gable. It’s an uncomfortable connection.
The aforementioned 1830 document is a deed in which Charles Bartlett purchased the property from one Isaac Fly. Isaac was the son of James Fly who had been involved in the masting trade prior to the Revolution. Perhaps James built the house.
Myrtle Lovejoy’s ‘This Was Stroudwater’ quotes the local historian, Leonard Bond Chapman, as stating Fly had married Sally Bailey in 1804 and they had:
“moved into a house presumably built for Colonel Westbrook’s workers… standing now on the original site at Stroudwater… it having been turned to front the street, a story added and an ell also”.
Although I think it would be fascinating to see if in fact there are remnants of a much earlier structure, Westbrook having died in 1744, I suspect the house dates from the early postcolonial period. Somewhere around 1785-1790.