Highmark’s Top 7 Most Gorgeous Buildings in Whitby, Ontario

Usually when we think of architecture, we imagine glorious castles, Gothic churches, stunning temples, and island oases; but Canada has its share of beautiful architecture from the iconic 19th and 20th centuries. Whitby is home to many antique homes and buildings, some almost two hundred years old.

We’ve put together a list of some of our favourite buildings in Whitby that you can check out! Whether it’s walking through scenic downtown or along Port Whitby, all of these buildings represent Canada’s history.

Note: all homes are visible from the street. Please do not enter private property without permission.

200 Colborne Street West

A ‘tour de force’ of the bricklayer’s art, this stylistically eclectic house was built for George Gross. After a period in the ownership of George Cormack, an important local lumber merchant and carpenter, the house was purchased by R.A. Hutchison, who was the Ontario South Public-School Inspector from 1913 to 1943. The house itself is one of only three Castle Style houses in Whitby, built in theGothic Revival style.

Via Whitby.ca

408 Byron Street South

This building was originally built as a Regency Cottage in 1853. Around 1875, while under the ownership of lawyer John Vandal Ham Jr., the building was transformed into a fashionable Second Empire style residence with the addition of themansard roof designed by Henry Langley.

Via Whitby.ca

416 Centre Street South

This important Classic Revivalstructure was designed by Frederick Cumberland and William Storm of Toronto and was constructed as the Ontario County Court House. Cumberland also worked on the designs for the centre portion of Osgoode Hall, University College, and St. James Cathedral, Toronto. The second floors on the wings were added in 1910 and the enlarged structure served as a courthouse until 1964. It became a Community Centre as Whitby’s Centennial project in 1967, with further restorations/renovations in 2003.

Via Whitby.ca

202 Byron Street North

This house was built by John Michael, a Scottish immigrant, around the year 1856. The structure is consistent with 1856 style architecture, but the brickwork is from a later period; other features of the house suggest an evolutionary development over time.

Via Whitby.ca

405 Dundas Street West Whitby Public Library & Celebration Square

In August 2003, construction began on a new modern library at the site of the old Whitby Municipal Building. Designed by Shore Tilbe Irwin and Partners of Toronto, it opened in May 2005 and was the recipient of several architectural awards. It is built in the International Modern style, featuring floor-to-ceiling windows and clean modern lines.

Via Whitby.ca


1450 Henry Street – Station Gallery

Whitby Junction Station was built at the foot of Byron Street for the Grand Trunk Railway (GTR) in 1903. Its turrets and bays were typical of train stations along the GTR which provided functional elements needed for telegraph operators to view incoming and outgoing trains. The low-hanging roof offered protection to passengers on the platforms. The station’s low and linear design layout is reminiscent of the Arts and Crafts style, the elements of which serve to blend and enhance the relationship between the landscape and architecture; the station’s many windows served to help bring the outside in. In 1970 the station was adapted into an art gallery.

Via Whitby.ca


301 Watson Street West – Port Whitby Marina

Located on Whitby’s natural harbour, the Port Whitby Marina is an award-winning, 420-slip marina operated by the Town of Whitby. The Marina offers fishing charters, sailing lessons, a clubhouse and lounge, and a public boat launch.

There are so many more homes, businesses, and landmarks throughout Whitby—these are just some of our favourites. We encourage you to explore Whitby by embarking on any of Whitby’s self-guided walking tours. Are you thinking about exploring Whitby and more? Make sure to follow us on Facebook and Instagram for more explorations of Whitby’s architecture!