Construction on the two properties that were to become the Homeport was started in 1856 and completed in 1858. George Roberts built the property at #80 and his brother David built the home at #60 Douglas Avenue on a choice hilltop of land overlooking the harbour and the shipyards where thier family fortunes were made. They maintained a close family association and built nearly identical houses in the rambling, informal, Italianate style popular at the time.

The Messrs. Roberts were grandsons of United Empire Loyalists from Central New Brunswick but the family's land grant was small and of poor quality and could not support a third generation growing family. David and George moved to Saint John, and joined the growing ranks of business, industry and the professions. They became successful merchants and lumbermen who turned to ship building as their fortunes grew and eventually established a large fleet of vessels. According to Esther Clark Wright in her publication, Saint John Ships and Their Builders, the Roberts Fleet was "more truly a Saint John fleet than any others operating in the last three decades of the 19th century". The Roberts prospered and maintained their Loyalist ties with a large volume of the family business carried on in England so in 1866 George relocated to Liverpool and David continued on in "The Colonies". It is from this rich maritime history and close ties to the sea Ralph and Karen have drawn inspiration for the Homeport Historic B&B/Inn.

The property at #80 was sold to a prominent local Druggist, Mr. T.B.Barker who ran a shop at #35 King Street. Several old bottles with the Barker family name are displayed in the house along with receipts and papers, dating back to the 1870's and 80's, that were found during renovations. This house had another brush with fame when, for a brief time, it became the family home of the celebrated Dentist Painless Parker. This dental renegade became a millionaire in New York in the 1890's with his carnival style painless dentistry medicine show. Several other long term owners keep the house as a single family home and in generally good repair until the 1980's.

The house at #60 did not fare as well. It was subdivided into several apartment units and suffered greatly from neglect and decay for many years. Both homes where acquired by a developer in the late 1980's with the intention of tearing them down and for a new development. In the process the #60 property was abandoned and left open to the elements for three years. The developer fortunately did not get to realize his destructive plan and the two houses where sold at auction to separate buyers in 1994. The #80 Douglas Ave. property was in good repair and was purchased, restored and converted to an Inn in 1997 by the current owners Ralph and Karen Holyoke. They then purchased the property at #60 Douglas Ave. in 2000 and spent over a year to complete restoration and join the two houses with a spectacular new entrance and Reception Hall.