As of the start of the 21st century, residents of Greenway are largely poor, and the neighborhood is characterized by multi-family homes and public housing projects.

[1] White settlers cleared much of the surrounding forest for farmland, however, and extensive soil erosion led to a heavy load of silt and effluent in the Anacostia.

The construction of the Pennsylvania Avenue, Benning, and other bridges and the diversion of inflowing streams to agricultural use also slowed the river's current, allowing much of the silt to settle and be deposited.

[3][5][6] The material dredged from the river would be used to build up the flats and turn them into dry land, eliminating the public health dangers they caused.

[7] In addition to this channel (which was meant to facilitate the passage of cargo ships) the McMillan Commission proposed building a dam across the Anacostia River at Massachusetts Avenue SE or at Benning Bridge to form a large lake for fishing and recreational boating.

In 1900, the United States Senate established the McMillan Commission, a body to advise the Congress and District of Columbia on ways to improve the parks, monuments, memorials, and infrastructure of the city as well as plan for urban renewal, economic growth, and expansion of the federal government.

[7][14] The D.C. government agreed in 1905,[8] and the United States Commission of Fine Arts (a federal advisory agency with review authority over the design and aesthetics of projects within Washington, D.C.) and the Army Corps of Engineers concurred in 1914.

[17] The Uniontown "suburb" was platted at the foot of the Navy Yard Bridge in 1854, and development slowly began to turn the agricultural land into businesses and residences.

As the bridge was being built in 1889, a consortium known as the Bliss-Havemeyer Syndicate (which included Representative Archibald M. Bliss, New York state bed manufacturer Erwin C. Carpenter, Representative Thomas J. Clunie, Senator and railroad attorney Chauncey Depew, Senator George Hearst, and sugar refining magnate John W. Havemeyer) purchased 800 acres (3,200,000 m2) of land in the former East Washington Heights development.

[25] On June 18, 1898, Congress chartered the East Washington Heights Traction Company to provide streetcar service in the new development.

[30] The Congress Heights development was wildly successful, and Randle invested heavily in the Belt Railway, a local streetcar company.

[31] In 1895, the Capital Railway Company extended its streetcar lines over the Navy Yard Bridge and down Nicholls Avenue to Congress Heights.

He made so much money that by 1905 he formed the development of "North Randle Highlands" (now the neighborhoods of Dupont Park, Penn Branch, and the lower portion of Greenway), which extended to Massachusetts Avenue SE.

[37] In October 1906, The Washington Post called Randle's developments "among the largest real estate enterprises ever successfully carried through in the District.

Built on 30 acres (120,000 m2) of land bounded by East Capitol Street, Minnesota Avenue SE, and Anacostia Park, the settlement consisted of 75 to 80 apartment buildings.

[42] As of the early 21st century, the Greenway neighborhood consisted of substandard or near-substandard multi-family homes and large and small public housing projects.

An unnamed stream (referred to as the "Fort Dupont tributary") exits the park and bisects the Greenway neighborhood to empty into the Anacostia River.