St. Paul's Episcopal Church was erected in 1834. The parish moved to a new building in 1866. The new brick structure was constructed just to the north on St. Pauls Avenue.

Public School 15, September 9, 1937. Completed in 1898 as the Middletown Township District School No. 1, the stately building with prominent clock tower was constructed on a plot occupied by a school since 1855. Designed by Staten Island resident and architect Edward Alfred Sargent, the later named Public School 15 is rendered in a rough-textured red brick with terra cotta and stone trim. Though Sargent is best known for his Queen Anne, Shingle, and Colonial Revival home design, he completed three schools on Staten Island. With two of the other schools lost, Public School 15 remains Sargent's educational legacy in the borough. The school building was designated a New York City landmark in 1996 and after a number of decades as administrative offices (the school functions ceased in 1965) the building has returned to education use as Public School 65.

199 St. Pauls Avenue, October 22, 1926. According to the photographer's notes for this photograph, this home was, for a time, the residence of Richard Adams Locke. Locke, a British journalist who wrote for the New York newspaper The Sun, was said to be the author of a newspaper hoax in 1835. Called the "Great Moon Hoax," a series of articles which described the discovery of an animal civilization on the moon by astronomer Sir John Herschel. Herschel supposedly observed bison, goats, unicorns, bipedal tail-less beavers, bat-like winged humanoids, and the structures they had built. Herschal was not involved in the hoax and in fact did not know until longer after the fact that these discoveries were attributed to him. Likely undertaken to boost the circulation of the newspaper, the hoax was an undeniable success, eclipsing a similar hoax story published by Edgar Allan Poe a few months earlier, and launching The Sun into dramatically increased distribution and reputation.