Founded by Maria Bowen Chapin, Miss Chapin's School for Girls and Kindergarten for Boys and Girls opened in 1901 at 12 West 47th Street with 78 students and 7 teachers. Eventually expanding and occupying a couple of buildings, the school moved to its current location in 1928. Delano and Aldrich, a New York architecture firm, designed and built the neoclassical building that the school still occupies at 100 East End Avenue. It was at this location that the school's name was changed to the Chapin School at Ms. Chapin's request.

St. Stephen’s parish was founded in 1902 to serve the Hungarian immigrant population of the Lower East Side. With the upward migration of the Hungarian population to Yorkville, in 1928 the congregation constructed a new church, parochial school, community center, and adjoining rectory on 408 East 82nd Street. The Romanesque Revival-style building was designed by Hungarian architect Emil Szendy. The building’s inventive design combines the school and church into one structure. The church was an important and central place for the Hungarian community, and after World War II it became the center for actions directed against the Soviet Union’s occupation of Hungary. Today, the parish of St. Stephen’s has been relocated to St. Monica’s on East 79th Street, but the School is still active and popular for families in Yorkville.

Webster Branch, November 20, 1928. Constructed in 1906 to the designs of the architectural firm of Babb, Cook & Willard, the Webster Branch of the New York Public Library became an important community hub for the neighborhood's large Czech population. The library provided Czech newspapers and magazines, children’s story hours in Czech, a location for Bohemian Club meetings, and exhibition space for cultural displays.

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.

St. Monica Roman Catholic Church, ca. 1905. Founded in 1879, St. Monica's was the fourth Catholic parish established on the Upper East Side. While the first services were conducted in a small second-story store space, the church moved into its first new church building in 1883. In 1906 the firm of Schickel & Ditmars, well known for their Catholic church architecture completed the current church. The Gothic Revival building opened for services on Thanksgiving Day.

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.

10 Gracie Square ca. 1945 One of the most exclusive and prestigious addresses in New York 10 Gracie Square on 84th street and the east river overlooking Carl Schurz Park was designed by Pennington and Lewis in 1930. Vincent Astor the developer of Gracie Square wanted to create a new upper class residential district. Gloria Vanderbuilt, conductor Andre Kostelanetz, critic Alexander Woolcott, publishers John Fairchild and Horace Havemayer III were a few of the residents of the 42 large duplex apartments. The exterior is red brick except for the main façade in limestone with an "asymmetrical fenestration" pattern. The intriguing rooftop loggia made from square columns and chimneys sets it apart as the grandest and most desirable residence.

The Church of St. Monica was founded in 1879 by the same pastor that had founded St. Joseph’s. St. Monica’s grew out of humble beginnings, with the mission to serve the expanding Irish Catholic population of the neighborhood. The current building at 413 East 79th Street, shown here at the year of its completion, 1905, was designed in a Gothic Revival style by the firm Schickel & Ditmars. Its facade on East 79th Street remains nearly unchanged since construction.