Because of its location, Parallel to Pitt Street, which was the business hub of the city, and it's proximity to churches and schools, many families deemed it a very prime area to live. So in the late 1880s it quickly grew to become a beautiful and thriving residential neighbourhood. 

Sydney Street owners included merchants, teachers, physicians, tinsmiths, magistrates and postmasters. One of the earliest and more stately homes on the street was built for Dr. McDonald and his family. The property was purchased at 303 Sydney St. in 1846 and the house was built some time after. The doctor owned it until his death in 1882. The house looks much the same as it did more than 100 years ago, although the front wraparound porch was removed. 

Gordon R. Phillips built a home for his family at 229 Sydney St. in 1896. Not only was he a builder and contractor but he also owned a business on Pitt Street where he sold household furnishings. He was also active in city politics as a council member and even served as mayor. 

George Armstrong and his family built the brick Victorian home at 237 Sydney Street in 1887. He was a grocer and owned a spacious store in the Cline Block on Pitt Street. He too took an active part in public affairs and sat as a council member for several years. 

Many of these homes have managed to retain much of their original characteristics. A prime example is the McDonell home at 240 Sydney Street. Built between 1881 and 1885 in the Italian Villa Style, this house has retained all of its original beauty. George McDonell was a merchant and a postmaster. The home stayed in his family until 1914.