Celebrating over 400 Years

At over 200 years old, with roots going back 400 years, the Bailey House is among the earliest buildings in Canada and rests on the estate of the Seigneurs of Port Royal.

In 1610, under the direction of Baron Jean de Poutrincourt, a small band of pioneers began the arduous task of transforming the Port-Royal trading post, began in 1605, into a permanent agricultural settlement. While the earliest chapters of the Seigneurial estate remain shrouded in the mist of the 17th century, the lineage of the land is undeniable. By 1610, Poutrincourt allotted 24 plots of land to the men in his company. We believe our estate was part of those original allocations. Our location was not only ideal for small scale farming, it is also in strategic location both in the town and along the river. We believe this estate is the most likely one that Jean Motin and Sir Charles De La Tour retreated to by 1654, when Emmanuel Le Borgne, and later the English, took possession of Port Royal.  By around 1688, Seigneur Alexandre Le Borgne de Belleisle (son of Emmanuel) and his wife Marie De La Tour (daughter of Jean and Charles) had established a formal manor along this scenic bend of the Annapolis River—a private domain that served as the seat of aristocratic and commercial life in the region for decades.

As the centuries turned, the manor and the estate changed hands many times starting with Francois Du Pont Duvivier, a Captain at the fort, whose son, also called Francois, would return in 1744 to lead an attack that very nearly recaptured the Fort for the French. Another owner was Samuel Douglass, whose wife is buried at Fort Anne and has the oldest gravestone in Canada. A later resident, Captain Edward How, Member of the Legislative Council of Nova Scotia, was assassinated in 1750. His widow, Marie Madeleine Winniet, has her own colourful story as the grand-daughter of “Baptiste” Maisonnat, a notorious French pirate. By 1783 the estate and manor was purchased by Joseph Totten, a British Loyalist originally from Westchester, New York. 

The manor eventually gave way to the grander architectural ambitions of the Georgian era. The villa we see today was likely commissioned circa 1817 by James Robertson, a prosperous merchant who seems to have amassed a fortune during the naval activity of the War of 1812. James’ wife, Charlotte Williams, was the sister of Sir Fenwick Williams, who almost certainly made some visits to the house. James himself also had interesting family connections as both his father and brother were Members of the Nova Scotia Assembly. James’ brother in-law was Simeon Ruggles, whose aunt, Bathsheba Ruggles was the first woman hanged in the newly independent United States. James and Charlotte had nine children in total and appear to have moved regularly between Annapolis Royal, Saint John and Halifax.  One of their grandsons,  James F Robertson, became a successful merchant in Sant John, New Brunswick, founding one of Canada’s largest department stores, and was also the primary benefactor of the Rothesay Netherwood School in that Province.

When James senior died, the house was acquired by the Elizabeth (Ward) Bailey, widow of Thomas Bailey and daughter in-law of Reverend Jacob Bailey. We know little of Elizabeth’s early story, but Thomas Bailey died young and led a colourful life, including being injured in a pistol duel on nearby Hog’s Island. Jacob Bailey was a prominent Loyalist clergyman who led a group of displaced parishioners from Maine to Annapolis Royal. Jacob attended Harvard and kept in touch with fellow classmate, 2nd President John Adams. Jacob also stayed at Benjamin Franklin’s house in London. Elizabeth,being a widow with three young daughter, transformed the residence into the town’s premier accommodation, hosting Nova Scotia’s most distinguished visitors for over half a century. We only have a glimpse of who we know stayed here such as the author Thomas Chandler Haliburton, Marquess and Marchioness Normanby,  the Earl Spencer and Bishop Inglis.

Like many great historic houses, the property faced a period of quiet decline in the early 20th century. By 1910, Elizabeth’s daughters had already sold off everything of value. The villa was divided into tenements and fallen into a state of near-dereliction. It remained in this precarious state until 1942, when it was rescued by Suzanne Haliburton. Her stewardship began a new era of preservation, ensuring that the home was maintained with respect.

The villa is exceptionally rare in its architectural integrity; unlike many of its contemporaries, no owner has ever significantly altered the core layout or added modern wings. The most notable update occurred around the year 2000, when ensuite bathrooms were discreetly integrated into each of the four principal bedrooms, seamlessly blending modern comfort with the home’s historic proportions.

Today, the residence is curated with a philosophy that honours both the Regency and Federal eras. The interior serves as a living gallery, furnished with a significant collection of original antiques and fine art dating from the early 1600s through the 1800s. This collection mirrors the dual history of the estate: reflecting both its origins as a Seigneurial sanctuary and its evolution into a premier Georgian villa.

Welcome to a house that does not merely remember the past, but lives within it.

 •  150 Saint George Street, Annapolis Royal, Nova Scotia

2026 Bailey House

Bailey House logo

150 Saint George Street,
Annapolis Royal, NS B0S 1A0

2026 Bailey House