Chris Pennycook is a REALTOR® with The Pennycook Team, a boutique real estate team operating under Royal LePage Burloak Real Estate Services in Burlington, Ontario, serving Burlington, Oakville, and Hamilton. As co-lead agent and principal of The Pennycook Team alongside his wife Melissa Pennycook, Chris brings nearly two decades of experience leading complex digital projects — and a deeply analytical mind — to every transaction he navigates on behalf of his clients.

The Pennycook Team is built around a structured, proactive client experience — anticipating what clients need before they ask, and protecting them at every stage of the process. For Chris, that structure is a natural extension of how he thinks. Born and raised in Oakville, now raising three boys in Burlington, he works in communities he genuinely knows at ground level. His background in software development and digital strategy gives him a specific ability: he reads contracts, negotiations, and market dynamics the way a developer reads code — looking for the logic, the dependencies, and the places where something could break before it does.

That instinct protects clients in ways they don’t always see coming. When buyers requested a structural engineer inspection on a listing over a flagged floor issue, Chris didn’t simply relay the request. He walked his sellers through every risk the inspection carried, brought in a reputable independent inspector to assess the same concern, received a written report confirming no structural issue existed — and then supported his clients in the decision to let the buyers walk rather than accept unnecessary risk. The deal didn’t close. The clients were protected. That is the distinction.

Chris works with buyers, sellers, investors, and landlords across Burlington, Oakville, and Hamilton — first-time buyers finding their footing, longtime homeowners ready for their next chapter, and everyone navigating the decisions that sit between where they are and where they want to be. He guides clients through decisions that are both financially significant and deeply personal — with clarity, calm, and a game plan always built around their best outcome.

The Pennycook Team | Royal LePage Burloak Real Estate Services | Burlington, Oakville, Hamilton