The Henry Connell House is designated a Local Historic Place for its location, its Second Empire-style architecture, and its connection to Henry Connell, mayor of Woodstock from 1885 to 1890.

The Henry Connell House was erected in 1885 on a large, sloping lot. The block of Union Street where the house is located was historically known as "Victoria Terrace." This area was home to many of Woodstock's wealthiest citizens and contains some of the most elaborate and aesthetically pleasing homes in the town, including several heritage sites.

The house itself is notable for its high quality and serves as a prime example of the Second Empire style. Though the Second Empire was popular in the region during the 1880s, this house is one of only a few examples of the style in Woodstock itself. This style can be seen in the steep mansard roof (built by family friend Alexander Dunbar) and extensive wrought iron cresting, including locally made iron windows in an Austrian pattern. Its excellent craftmanship is accentuated by its operational plumbing and electrical wiring, both considered luxuries at the time.

Lastly, the house is recognized for its eponymous occupant, Henry Connell. In his youth, Connell was a regular traveler, spending a long time working in river navigation in Argentina and Uruguay and serving as a soldier in the Paraguayan War. Following his return to Woodstock in 1870, Connell acted as a proponent of electric power and began a career in politics. He was elected the town's mayor from 1885 to 1890 and served as a MLA from 1892 to 1895.