Notice of intention to designate 376 Chartwell Road

On October 20, 2025, Oakville Town Council resolved to pass a Notice of Intention to Designate the following property under Section 29 of the Ontario Heritage Act, R.S.O. 1990, c. O.18, as amended, as a property of cultural heritage value and interest:

Hillside Farmhouse
376 Chartwell Road
PCL 3-1, SEC M198; LT 3, PL M198; OAKVILLE

The property at 376 Chartwell Road is located on the northwest corner of the intersection of Chartwell Road and Macdonald Road. The property contains a circa 1891 two-storey brick Queen Anne farmhouse known as Hillside Farmhouse.

Statement of cultural heritage value or interest

Design and physical value

The Hillside Farmhouse has design and physical value as a representative example of a Queen Anne brick farmhouse from the Victorian era. The house was built in 1891 with elements of these styles, including its tall massing, asymmetrical design and intersecting hip and gable roofs. Built on a lakestone foundation and clad in red brick, the house has a stately look and includes many of the whimsical details typically found on a Queen Anne house. These include the tall, narrow, flat, and arched windows, large arched window opening on front elevation with stained glass, large front entrance with arched transom window with stained glass, and decorative wood cornice with brackets and vergeboard throughout. The house retains many of its historic features and is a good example of the architectural style.

Historical and associative value

The Hillside Farmhouse has cultural heritage value for its direct associations with its original owner who had the house constructed, John Macdonald and his family. Macdonald was a local butcher and well-known cattle rancher, who was also deputy reeve of Oakville, a town councillor and a local magistrate. His wife, Janet, was the daughter of Peter Morrison, one of three brothers who moved to Oakville from Scotland and started a successful cattle ranching business. The Morrisons and Macdonalds were large landowners in this area northeast of the town of Oakville in the 1800s and early 1900s. Macdonald Road is named after the family. The property is also directly associated with the theme of ranching and farming in the 19th and early 20th century in what is now southeast Oakville.

Contextual value

The property is physically and historically linked to its surroundings. This historic farmhouse stands in its original location from its build date of circa 1891 and is one of the oldest houses in the area. It contributes to the understanding of the local community, and its growth from a cattle farming sector to an urban town subdivision. It is integrally linked to the farming history of the area – Oakville’s agricultural economy was mainly run by the Morrison family and their relative through marriage, John Macdonald, who was the owner of the property when the house was built. The road to the south of the house, Macdonald Road, is named after the family who built this house and mature trees from the original farmstead can be found throughout the area.

Description of heritage attributes

Key heritage attributes of the property at 376 Chartwell Road that exemplify its cultural heritage value as a Queen Anne brick house, as they relate to the north, east, south and west elevations of the historic two-and-a-half storey brick house, include its:

• Tall massing and asymmetrical form with articulated elevations;
• Hip roof with intersecting gables;
• Red brick cladding in a running bond pattern with fanned brick voussoirs over doors and windows;
• Fenestration of original window and door openings;
• First storey ‘picture window’ on east elevation, including wood windows and stained-glass transom window and wood trim;
• Stained-glass transom window above front entrance on east elevation;
• The presence of narrow Queen Anne style one-over-one windows with wood trim throughout the house;
• Stone window sills;
• Decorative wood cornice with brackets; 
• Wood fish-scale shingles and decorative wood vergeboard in gables; and
• Lakestone foundation above grade.

Any objection to this designation must be filed no later than November 21, 2025. Objections must be directed to the Town Clerk at townclerk@oakville.ca or 1225 Trafalgar Road, Oakville, Ontario L6H 0H3. The objection must include the reasons for the objection and all relevant facts.

Further information respecting this proposed designation is available from the Town of Oakville. Any inquiries may be directed to Carolyn Van Sligtenhorst, Heritage Planner at 905-845-6601, ext. 3875 (TTY 905-338-4200), or by email at carolyn.van@oakville.ca. 

Issued at the Town of Oakville on October 22, 2025.