Beginning in 1890 and extending through the first half of the 20th century, the district’s history is associated with the development of politics and government, commerce, and transportation within Littleton’s commercial core. 

The circa 1925 Knight-Wood House, a one-and-a-half-story, side-gabled residential building with its associated garage, are excellent local examples of Craftsman style architecture. 

From 1927 until 1973, the home was operated by an international association of hotel workers as a recuperative care facility for its members from throughout the United States.  The International Geneva Association was founded in 1877 in Geneva, Switzerland and spread to the United States during the early 20th century.  Additions, in 1941, to the wood frame Craftsman style building reflected the need for more space and the evolution in health care practices, while retaining the overall residential appearance of the property.

The Arapaho Hills subdivision, constructed between 1955 and 1964, reflects new patterns in the post-World War II period and their influence on the development of new forms of suburban residential subdivisions.  

This 1914 brick schoolhouse served children in the Greenwood Village area until 1967 and now houses a center for the arts.  It became the focus of local community life and reflects the era before school district consolidation.  The school retains its original brick walls, decorative wooden shingles in the gable ends, and stone trim. The property is associated with the Rural School Buildings in Colorado Multiple Property Submission.

The 1967 Key Saving and Loan Association building represents the transformation of the previously conservative American banking industry into a consumer-oriented service business in the post-Depression and post-World War II period.  

The Hopkins House, part of the Hopkins Farm, is an excellent local example of the high style Classic Cottage subtype. The house exhibits the various elements defining the high style variant, such as 1½-story height, multiple dormers, a Palladian style window with classical columns on the facade dormer, Tuscan porch columns, and bay windows on two sides. 

The 1937 Englewood Post Office is significant in the area of Politics / Government, Community Planning and Development, architecture, and for its national significance in the area of Art for its 1940 mural by important American artist Boardman Robinson. 

Built in 1924 as part of the developing South Broadway commercial corridor in downtown Englewood, the two-storefront, single-story Dransfeldt Building was the long-time home (1924-53) of The Englewood Herald and Enterprise, the prominent local newspaper that emerged from the 1923 consolidation of The Englewood Enterprise(founded 1910) and The Englewood Herald (1920). 

The 1915 depot is the last remaining wood framed and stuccoed Mission Revival style depot formerly operated by the Santa Fe Railroad in Colorado.  The City of Englewood relocated the depot to its present site in 1994.