The property that now houses 205-209 Orange street was originally a two story home, first recorded on . That structure was torn down on April 16, 1913 and replaced soon after with a four story mixed use brick building constructed by Hubbell and Merwin. In the first half of the twentieth century the building housed a bakery, stationer, paint company, the Connecticut Savings Bank of New Haven, several lawyers and unions. An article in 1946 found in the Dana Collection reports the sale of the building from the Grand Lodge of the Ancient Order of United Workmen of North Dakota to the newly formed 207 Orange Realty Company, headed by Robert L. Sykes of Sykes and Libby Jewelry. Tenants listed at that time included chapters of the United Steel Workers, United Mine Workers, International Ladies’ Garment Union, War Relief Committee, and the United Rubber Workers of America, the abundance of unions likely due to the building’s proximity to city hall.



The building was not part of the State Street Redevelopment and Renewal Area. Price & Lee directories report prolonged periods of vacancy in much of the building and high turnover of tenants. Storefronts were removed, a new façade was added, and the entrance was moved to the corner of the building between 1951 and 1973, as revealed in Sanborn maps, and the neighboring buildings were replaced with parking. A bank was later constructed on one of the neighboring lots, 245 Orange St, but now sits vacant.



The building’s most recent occupant is The Connection, Inc., a human services and development agency, which arrived in the past two years.