Public School 158, 1920. This large school which fronts York Avenue from 77th to 78th Streets opened on Jan. 9, 1899. For more than four years, a school trustee, W. Horithal, had been advocating for a school building to education the rapidly growing population of immigrant children in the neighborhood. Today the school is named for Bayard Taylor, an American poet, literary critic, translator, travel author, and diplomat.

The four buildings of the former Shively Sanitary Tenements (a.k.a.East River Homes, Vanderbilt Model Tenements); 1911. Built in 1910-11, the Shively Sanitary Tenements, named for Dr. Henry Shively, were an experiment in housing for sufferers of tuberculosis and their families. Shively, architect Henry Atterbury Smith, and benefactor Anne Harriman Vanderbilt envisioned a housing development where poor tuberculosis patients could receive treatment in an environment replete with fresh air and sunlight — without being quarantined from their non-infected families. Smith's design prioritized features encouraging exposure to fresh air: open stairways, courtyards, rooftop recreation areas, and triple-hung windows were all thought to confer therapeutic benefits. The trustees were ultimately unable to provide meaningful help to poor New Yorkers with tuberculosis, though not for any failure of design or treatment — the apartments were simply too expensive for the communities they were intended to serve. In 1923, the trust governing the project was dissolved and the buildings sold for residential use. In 1986, the residential units were again turned over for condo conversion, with the new development dubbed the Cherokee apartments, after neighboring Cherokee Place.

FDR Drive, north of 78th Street, ca. 1979. The City and Suburban Homes Company was a firm established in 1896 whose goal was to create humanely designed tenements that produce a substantial profit. In 1901 they began filling the block between 78th and 79th and York and First Avenue. The block would eventually include 13 model tenements. The one outlier on the block was the building at the northwest corner of 78th Street and the East River. Constructed in 1910-1912 as a joint project with the Junior League of New York, the building was called the Junior League Hotel for Working Women, and was a residence specifically for single women. Designed by Philip Ohm, in a simple style with neo-Renaissance features. The original entrance was facing the water on what was then quiet Exterior Street (now elevated and noisy FDR Drive). In 1913, there were 317 residents including 40 stenographers, 32 dressmakers, 18 librarians, 14 milliners and 5 telegraphers. In 1978-1980 the building was converted into apartments and after threats of demolition in the 1980s, the building was lanmarked in 1990. Today the building remains residential, though the entrance now sits , safely, on East 78th Street.

Octagon Tower, ca. 1970. The Blackwell's Island Asylum opened in 1839. The first lunatic asylum in the city of New York and the first municipal mental hospital in the country, the facility on Blackwell's Island (later Welfare, now Roosevelt Island) was designed by Alexander Jackson Davis. Nearly from its opening the institution was plagued by overcrowding, under-funding, and scandals. In 1887 Nellie Bly, a reporter, entered the hospital under the guise of insanity on assignment from newspaperman Joseph Pulitzer. Her resulting report, later published as "Ten Days in a Mad-House," exposed and embarrassed the institution and was a major factor in its closure. Beginning in 1894, the institution slowly emptied, continuing until the final patients were moved to new facilities in 1901. The building was then taken over by Metropolitan Hospital, which remained on the island through 1955. The Octagon Tower is the only surviving structure of the original building. It was the main entrance to the Asylum. After the Metropolitan Hospital vacated the building in the 1950s it remained vacant and was left to deteriorate. The wings of the structure were demolished and the Octagon Tower was in rough shape (seen here) when it was placed on the National Register of Historic Places in 1972. In the early 2000s the building was restored and opened as the entrance to a pair of large adjacent apartment buildings.