College of Immaculate Conception, c. 1915. The College of Immaculate Conception was a preparatory school and seminary established by Bishop Charles E. McDonnell in 1914 in the Fort Greene neighborhood of Brooklyn. In the first year of the program, a class of 110 young men met in the vestry of Saint John's Chapel. Construction broke ground for their own school at 555 Washington Avenue in December of 1914. The program consists of a four-year high school program followed by a two-year college program. Students who wished to continue the priestly vocation were then assigned to a major seminary, where they would study for an additional six years. The program moved to a new Elmhurst campus in 1963.

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!

"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."

983 Fulton Street, ca. 1958 The northwest corner of Fulton Street and St. James Place featuring what was formerly a drugstore (no. 983) and candy-store (no. 985). Part of no. 983 (at left) was substantially redeveloped into a Met Food supermarket in 1964. The grocery, now a Key Food, has been something of a community landmark since its opening. Known for hiring youth from the community, the famous rapper, Biggie Smalls, was once a cashier there.

457 Clinton Avenue, a Second Empire villa, built in 1869. Originally owned by Nason B. Collins, a flour merchant, the house has a number of striking architectural features: a three-story tower, mansard roof, and front porch supported by fluted Doric columns.

Christoper Wallace, aka Biggie Smalls, aka Biggie, aka Notorious B.I.G., aka Big Poppa, was raised by his mom, Voletta Wallace, at 226 St. James Place. In front of 226 St James. Clarence Davis/NY Daily New He went on to become one of the greatest rappers of all time. Smalls was killed in a drive-by shooting in Los Angeles in 1997. He was just 24 years old. His only two LPs, whose titles eerily bookmarked his death, were Ready to Die and Life After Death, which came out just 16 days after his murder. In 2019, the corner of St. James Place and Fulton Street was named "Christopher Wallace Way." The Orient Temple Masonic Lodge, the site of some of Biggie’s first gigs In a sign of how the neighborhood has changed, the "one-room shack" that Biggie rapped about in his hit single "Juicy" was recently listed for rent at $5,100.

\#179-181-183 St. James Place, 1958. Designed in the Romanesque Revival and Queen Anne styles, ca. 1892 by William Tubby, no. 181 is the crowning centerpiece of three rowhouses designed and constructed as a trio. Both the exterior and the interior retain original design and details.

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.

489 Washington Avenue is a property that has worn many hats. Before it was a Pentecostal Church, this Second Empire mansion was a dance studio, a Grand Army Republic meeting hall, and a private family home to a descendant of the father of Irish Republicanism. With every new inhabitant, a piece of the building's architecture was changed. Lascelles and Grace Maxwell, the original owners of the home, raised their seven children in this house. The Maxwell's children sold the house in 1904 after both of their parents had died. It was then acquired by the Grant Chapter of the Grand Army of the Republic in 1906. The old boy's club was a fraternal organization that supported veterans of the Union Army who fought in the Civil War. The ground floor was converted into a museum to display military memorabilia, which touted all sorts of firearms, uniforms, and possessions of Ulysses S. Grant, whom the chapter was named for. The second story had its walls removed to be converted into a large meeting room, where a variety of social events were held. The groups' membership had dwindled by the late 1920s, and the Hall was sold. Weber Studio operated out of the space, teaching ballroom, Foxtrot, and the waltz led by A.J. Weber. The hall was still rented out for meetings and other events until 1940 when the property was sold to the Evergreen Church of God. The white stucco was removed and covered with a false brick facade, revealing the original brick in certain areas.

Lafayette Gardens Nursing Home, 447 Clinton Avenue,1958. This Italianate mansion is nearly 170 years old! It is one of the earliest structures of this style in New York City. Constructed circa 1850, the brick and brownstone was originally the home of a local auctioneer. After being owned by a furrier, the house was purchased by William Wade, a manufacturer of printing ink, in 1866. The Wade family owned the home until 1920. In the middle of the 20th century the building was owned and occupied by the Galilee Baptist Church; perhaps the Lafayette Gardens Nursing Home was a project of that institution (very little evidence of the history of the nursing home exists). The church occupied the home until the early 2000s, though during its tenure and after the building continued to deteriorate drastically. The windows were boarded up by plywood and cement blocks and the facade and interior were in terrible shape. The home was extensively renovated and restored in 2010 and now houses four rental units. In March of 2017, a 1,800 square foot unit was for rental market for $6,000.

941 Fulton Street, 1958. This four-story brick building was the home or workshop (it is unclear) of inventor Burton H. Cook from at least the 1890s until the 1910s. Cook invented and patented a number of mechanical products including a rotary ash sifter, a new and improved percolator, and a culinary grater and slicer. According to a search of his patents, he also worked on new types of suspenders and hair pins. The building listed on his advertisements still stands, though the twin double height projected bay windows, interestingly set back in the facade, have been removed. The ground floor commercial space has also converted into additional residential units.

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.

937 Fulton Street, ca. 1928. Originally home to the Rubel Coal and Ice Corporation, this building was erected in 1928 by architect Edward M. Adelsohn. The company was started by Samuel Rubel, who got his start selling ice and coal from a pushcart in East New York, Brooklyn. In its heyday, the company was very prosperous because coal and ice were two commodities that were in great demand. As the coal and ice business floundered, he invested in the Ebling Brewery of the Bronx. Rubel was said to be worth $8,000,000 at the time of his death – quite a considerable sum for that era.