The Jacob Pledger House is located in northern Middletown, on the west side of Newfield Street at its junction with La Rosa Lane.

It is a 2+1⁄2-story masonry structure, built out of red brick and covered by a gabled roof with end chimneys.

The interior of the house has a number of original architectural features, most notably including its carved wooden staircase.

[2] The house was built in 1803 by Jacob Pledger, on 80 acres (32 ha) of land originally belonging to his father-in-law.

The property was roughly bisected by Newfield Street, and remained in agricultural use until after World War II.