The South End Historical Society maintains the Francis Dane House as a museum and archives dedicated to the preservation of one of the largest Victorian neighborhoods in the country. Luther Briggs's design is characteristic of much of the architecture of the South End in which the traditional Boston bowfront row house is embellished with Italianate brackets, window cornices, and a mansard roof with wide overhanging eaves. The more elaborate examples, such as the Francis Dane House, included oriel windows and window cornices of sandstone rather than cast iron. Architect John R. Hall designed a group of houses directly across the square at 529–533 Massachusetts Avenue in 1859. Briggs and Hall may have been responsible for other groups of houses on Chester Square as well.

Originally laid out in 1850 as an oval park similar to Union Park (SE7) and Worcester Square, Chester Square was conceived on a much grander scale. At the time this area constituted the outer reaches of the South End development. In 1891 Chester Street became an extension of Massachusetts Avenue, linking Dorchester to Cambridge, after which the road became a major cross-town artery.