Three of these are National Historic Landmarks: St. John's Episcopal Church, the Carnegie Institution of Washington Administration Building, and the Robert Simpson Woodward House.

Significant contributing properties in the historic district include the Embassy of Kazakhstan, Hay–Adams Hotel, House of the Temple, and the Russian ambassador's residence.

[1][2][3] The federal government owns the right-of-way between the building lines while the road, sidewalks, and planted areas such as tree boxes are under the jurisdiction of the District of Columbia Department of Public Works.

The street continues north past the historic district for another 5.25 miles (8.45 km) to the city's boundary with Montgomery County, Maryland.

Commercial structures including office buildings and hotels comprise most of the properties south of Scott Circle, but there are also a dozen houses still standing.

Due to mosquito-infested streams that flowed south from Meridian Hill, building a house between the area of Scott and Dupont Circle was considered unfashionable.

[15] During the 1880s a number of expensive and ornate homes were finally built along lower 16th Street and around Scott Circle, an area that at the time was racially integrated and included simple frame houses.

[16] A large home built south of Scott Circle in 1886 was for Lucius Tuckerman, whose Richardsonian Romanesque house on the southwest corner of 16th and I Streets was designed by Hornblower & Marshall.

[2] During the 1890s, as the city continued to quickly grow, 16th Street became a fashionable place to live and many of the surviving homes north of Scott Circle were built during this period.

[16] The Gothic Revival Church of the Holy City, also designed by Pelz, at 1611 16th Street was built in 1896 and features a 158-foot (48 m) tower and several Tiffany stained glass windows.

[1][3] South of Scott Circle a large house designed by Rotch & Tilden was built in 1891 for Senator Eugene Hale and located on the northeast corner of 16th and K Streets.

The couple had purchased dozens of lots in the area and were vocal advocates of the City Beautiful movement, encouraging politicians and foreign governments to build monuments, houses, and embassies near present-day Meridian Hill Park.

The Beaux-Arts Warder Apartment House on the southeast corner of 16th and M Streets was built in 1905 and designed by Jules Henri de Sibour and Bruce Price.

[13][16] This decade also saw the construction of an institutional building, the National Geographic Society's (NGS) Hubbard Memorial Hall at 1156 16th Street, built in 1902 and designed by Hornblower & Marshall.

[1][25] In an effort to have a prestigious address in the nation's capital, institutional organizations selected noted architects to design their impressive buildings on 16th Street.

Carrère and Hastings designed the neoclassical Carnegie Institution of Washington Administration Building, completed in 1910, which sits on the southeast corner of 16th and P Streets.

Naval commander Richard T. Mulligan chose de Sibour to construct a five-story Colonial Revival mansion on the northwest corner of 16th and R Streets that was completed in 1910.

[1] Construction of luxury apartment buildings continued though, including The Hadleigh at 2101 16th Street, designed in the Renaissance Revival style by Clark Jr. and completed in 1920.

He chose Mesrobian to design the Renaissance Revival building and with permission from John Hay's daughter, Wardman named the new hotel The Hay-Adams.

Scott Circle was considered especially dangerous and a city guidebook from the time stated: "with its inner and outer rings of surging traffic, this is for pedestrians probably the most hazardous ground within the District."

In 1941 a tunnel was built beneath Scott Circle, allowing passengers traveling on 16th Street to avoid the intersections of Massachusetts and Rhode Island Avenues.

The Pall Mall at 1112 16th Street NW was constructed in 1940 and architect Robert O. Scholz designed the building to reflect a combination of the Art Deco and Renaissance Revival styles.

[1] The First Baptist Church congregation demolished their imposing building in 1953 and replaced it with a Gothic Revival sanctuary designed by Walter Horstmann Thomas and Harold E.

[1][12][40] The former home of Supreme Court Justice Horace Gray, which replaced John Adams II's circa 1829 house, was demolished to make way for the church building.

[1] Coinciding with a growing national interest in historic preservation, local activists and historians advocated for the protection and rehabilitation of remaining buildings on 16th Street.

Three of the buildings that were previously considered intrusions, The General Scott, the Sixteen Hundred Apartments, and the Washington House, were redesignated as contributing properties.

[1] For many years the Third Church of Christ, Scientist congregation had dealt with high maintenance costs, structural defects, and a decrease in the number of attendees in their 1971 building.

[50][51][52] A two-block stretch of 16th Street in the historic district was renamed Black Lives Matter Plaza in 2020, following protests after the murder of George Floyd.

This allure of location has ensured the prestigious viability of 16th Street throughout its history and has encouraged the varied and high quality collection of building types.

Three of these are further designated as National Historic Landmarks (NHL): St. John's Episcopal Church, the Carnegie Institution of Washington Administration Building, and the Robert Simpson Woodward House.