Architects and real estate developers whose works are in the district include George S. Cooper, Thomas Franklin Schneider, B. Stanley Simmons, Harry Wardman, and Frank Russell White.

[2] The present-day historic district was envisioned as part of the capital city by Pierre Charles L'Enfant's 1791 plan, but the area remained rural and undeveloped for several decades.

[3] By 1852, plans were drawn up for 11 squares subdivided by streets and alleys, but the rural landscape remained largely uninhabited except for scattered frame houses and shanties occupied by working-class people.

Seeing the potential for real estate in close proximity to the streetcar line, developers purchased parcels of land in the area which at the time was owned by one person.

One of these early residents was writer and statesman Frederick Douglass, who purchased three Second Empire-style homes on the corner of 17th and U Streets in 1877 as a real estate investment.

The earnings Frederick Douglass received from these real estate ventures, along with his writings and speaking engagements, ensured his financial security during retirement at Cedar Hill.

Inhabitants included the city's Recorder of Deeds James C. Dancy and Howard University faculty member Joseph Lealand Johnson, the second African American to earn both a Ph.D. and an M.D.

But the term Strivers' Section was reclaimed as a positive description by people including social historian William Henry Jones, who praised "negro pioneers" that didn't limit themselves to segregated areas of the city.

[3] White residents on the neighborhood's southern border created a racially restrictive covenant that blocked African Americans and Jews from living on their streets.

Many of the African Americans who continued to live in Strivers' Section during this period were prominent members of their community, but in certain areas such as Seaton Street, poor residents struggled.

[3][9] After racial covenants were ruled unconstitutional in the 1948 Supreme Court case Shelley v. Kraemer, African American residents of Strivers' Section were no longer limited to which neighborhoods they could live in and began to move to other areas of the city.

Although some historic buildings were demolished in the following decades, including ones on U Street that were replaced with the DC Police's Third District headquarters in 1974, most of the urban renewal plans that would have dramatically changed the neighborhood's appearance did not take place.

[2] Prominent African Americans who lived just beyond the historic district's boundaries included poets Langston Hughes and Georgia Douglas Johnson, educator Lucy Diggs Slowe, military officer Benjamin O. Davis Sr., opera singer Todd Duncan, attorney Charles Hamilton Houston, civil rights activist Dutton Ferguson who challenged segregation on U Street, and ophthalmologist Arthur Curtis and his wife Helen who were the subjects of the Corrigan v. Buckley Supreme Court case that involved racially restrictive covenants.