St. Peter’s Roman Catholic Church and School, 1934. Designed by Patrick Charles Keeley, the Romanesque Revival church was dedicated in 1860. The St. Peter’s School at 101 Warren Street was added in 1866. The church closed in 1975 and was converted into condominiums, retaining much of its exterior features.

Commercial strip on the east side of Columbia Street, 1934. In the first half of the 20th century, prior to the construction of the Brooklyn-Queens Expressway's South Brooklyn segment, the docks to the west of Cobble Hill were a major employer and Columbia Street was one of a few vibrant commercial areas serving the community.

The name Cobble Hill came into use in the 1950s, likely an update from the name "Cobles Hill" which can be found on a 1766 map. Organized community groups fought against large housing projects, and advocated to make the area an historic district.

In 1878, the cornerstone was laid for the Pilgrim Chapel on the corner of Henry and Degraw Streets. The architect, J. Cleveland Cady, designed an Italianate-style building with a tall tower that had an exterior of Philadelphia pressed brick trimmed with Belleville stone and terra cotta. The auditorium had a high ceiling with open timbers, and was lighted by a continuous clear-story in which were windows filled with rolled cathedral glass of beautiful designs. There were 15 rooms grouped around the auditorium, all having direct light, ventilation and heat. When the Sunday-school rooms were opened into the auditorium, there was a capacity of 1,200 people.

By 1916, the Pilgrim Chapel had been decommissioned and was known as the Oriole Theater. Today's it's a MET supermarket.

Jenny Jerome, Winston Churchill's mother, was born in 1854 just a few blocks away at 197 Amity St. However it's the house on the corner at 426 Henry St., where Jenny later lived with her uncle that (inaccurately) bears a plaque to mark the event. In 1953 (seven years before this photo was taken) Churchill at the age of 74 made a visit to New York, and came to the house, to the delight of the neighborhood and city. He stood in front of the house and proclaimed “I am most grateful to those who have put up this tablet in commemoration of my mother, who was born here in Brooklyn.” The plaque has been there ever since.