ca. 1938 This two-story, wood-frame school was Public School 3, later known as Old Public School 3. The school was founded in 1855. The Board of Education was able to replace the school and move it to the site of Public School 3 on Jefferson and Hancock Avenues. The Old Public School was converted into a library in 1897 through a contribution of $1.6 million from Andrew Carnegie.

Clinton Hill's namesake avenue was once known as the Gold Coast of Brooklyn. Oil tycoons and baking powder magnates built lavish mansions here in the late 1800s. Charles Pratt, who kicked off the architectural gold rush, founded the Pratt Institute just a few blocks from his home. Clinton Hill was also home to Mollie Fancher, AKA “The Brooklyn Enigma,” who was famous for spending 50 years in bed. The Enigma was said to see through walls, read books by touching them, and survive on minuscule amounts of food. During one seven-month period, she reportedly consumed only “four teaspoons of milk, two teaspoons of wine, one small banana, and one cracker.” In 1967, Patti Smith and Robert Mapplethorpe moved into an apartment on the second floor of a townhouse on 160 Hall Street with walls smeared with blood and psychotic scribbling, an oven crammed with discarded syringes, and a refrigerator overrun with mold. They paid $80 a month. Today, that same townhouse rents for $8,000 a month—used syringes not included. Clinton Hill was also where Biggie Smalls, one of the greatest rappers of all time, grew up. He was raised in a “one-room shack” by his mom at 226 St. James Place.

Church of the Nativity, ca. 1941. The Church of the Nativity was built in 1915 by Raymond Almirall who, over the course of his career, designed many hospitals, libraries, and buildings for the Catholic Church in Brooklyn. The building's design references those of the early churches of Italy, with running arches, classical columns, and a very early Christian basilica style interior. In its earliest days, the Church of the Nativity served the area's large Irish Catholic population. While there was little mixing with Germans and Italians, the church was known to turn other ethnic Catholics groups away. In 1921, Rev. Bernard Quinn, who had spent his career petitioning for a church where black and white Catholics could worship together, built St. Peter Claver Church only three blocks away. His service became so popular that it drew people from all over Brooklyn, including the Church of the Nativity. With time, St. Peter Claver continued to grow and the Church of the Nativity began to shrink. Finally, in 1973, the diocese closed the Nativity and merged its congregation with St. Peter Claver. By the turn of the twenty-first century, the parish sold the church to a Pentecostal church, Elim Gospel Tabernacle, which still occupies the space today. The Elim congregation considered the Catholic iconography in the building to be a "heathen," and tore down anything that was overtly Catholic. As such, the Almirall Church that stands today is only Catholic on the exterior!

Bedford Branch, August 24, 1941. The Bedford Library was the first branch of the Brooklyn Public Library system, which opened in 1897. It was originally housed in a series of non-purpose built structures, including the old P.S. 3 on Bedford Avenue. Between 1904 and 1905 a new Carnegie Library building was constructed to the designs of the architectural firm of Lord & Hewlett, who designed seven of the Carnegies in total. Similar to other "suburban" style libraries, Bedford is set back from the street, surrounded by a small lawn, and rendered in a Classical Revival style of red brick with simple limestone ornamentation. The lampposts visible flanking the entrance in this 1941 photograph have been restored.

"The building formerly housing the exclusive Lincoln Club of Brooklyn is a striking Queen Anne style structure designed in 1889 by Brooklyn based architect Rudolph L. Daus. The club is located in the Clinton Hill area, once the home of some of Brooklyn’s wealthiest citizens. It is one of a number of large, sumptuous clubhouses erected in Brooklyn in the last two decades of the 19th century, and it is one of the few to retain its architectural integrity. Founded in 1878 by a small group of men who banded together for social purposes and to further the interests of the Republican Party, the Lincoln Club was dissolved in 1931 as many of Brooklyn’s elite moved away."

Bedford Y.M.C.A. ca. 1923 In 1853 the first YMCA in Brooklyn opened its doors. Back then, the mission of the Young Men’s Christian Association was more evangelical than anything – but they did have a swimming pool and other such facilities. The Bedford Avenue branch opened in 1888 at its original location of 420 Gates Avenue in the Brooklyn neighborhood of Bedford-Stuyvesant. As the population of the area expanded in size, so did the need for an even larger space to accommodate everyone and by the turn of the century in 1901, construction was underway for a new space at 1115 Bedford Avenue. The new location (as seen above) officially opened its doors in 1905 offering amenities such as a state-of-the-art (at the time) gymnasium and swimming pool. Over the next several decades, the neighborhood’s changing demographics along with the continued segregation of YMCA facilities through the mid-1940s caused the Bedford Avenue YMCA’s visitors and memberships to dwindle. As a result, classes were permanently canceled, funding was reduced, and the property fell into a state of neglect. In 2007, instead of receiving much-needed renovations, the building was demolished and a new building was erected in its place. Now residing at 1121 Bedford Ave on the corner of Monroe Street, it has become one of the busiest locations in Brooklyn, with a membership roster of over 8,000 people.

186 Quincy Street, 1913. J. C. Hoagland, Civil War veteran, wholesale grocer, and baking powder mogul, built this home circa 1874. Designed by an unknown architect, the Second Empire residence housed the Hoaglands for less than 20 years. By 1909 the home was occupied by a music school, and within the next decade, it became a multi-family residence. Today the once single family house has 11 units. The building has been maintained very well, though the owners removed the iron cresting at the roofline during renovations in 2015.

The Vendome is Brooklyn’s oldest surviving multi-unit apartment building. When it opened in 1887, the building’s 17 apartments were serviced by an elevator and had access to the billiard room, a caterer, and a shoeshine. Eventually, the building fell into decline, and after being abandoned for several years, it was taken by the city for failure to pay taxes. In 1980 a fire gutted the building and its demolition was imminent. At the last minute, thanks to local efforts, state and city grants were secured for rebuilding the apartment.

218 Gates Avenue, 1919. In the late 1860s, the wealthy lace merchant John Gibb built is massive Second Empire mansion for his growing family (he would eventually have 13 children by two wives). He also owned much of the surrounding land, so for its first few decades, no other buildings stood between this house and Classon Avenue. (Gibbs was a bit of a curmudgeon who did not wish to be bothered on his quiet property.) In the late 1880s, Gibb and two of his sons got even richer when they went into business with Frederick Loeser. Frederick Loeser & Company became one of the largest department stores in Brooklyn. Gibb moved out to his Long Island estate at the turn of the century, and the large house cycled through several well-heeled owners. Owing to its enormous square footage, the house was converted into a convalescent home following the first World War. Later it was the Long Island Motor Club, a social club before becoming Hopewell House, a residential space for underprivileged women and children. In the second half of the 20th century, the homes became Plaza North Hotel, a hotel and event venue. This use ended in the 1980s after the activities here and in the more recently constructed outer building devolved in the illegal sphere. It then sat empty and in ruins. The Pratt Area Community Council bought the house from the city in 2000. They restored and reworked the mansion offices, meeting rooms and public spaces, while demolishing the outbuildings and constructing new edifices with studio apartments on the Monroe Street side of the lot. Today the complex includes more than 70 units of affordable housing.