About Oak & Apple
Oak & Apple is a boutique property management firm committed to reinventing renting — by doing everything exceptional for our owners, tenants, and the communities we serve.
Our Philosophy
"Apple trees produce an immediate return. Oak trees have long-term payoff. Your investment should be managed with both in mind."
Real estate is a unique asset class — it pays you well today, and when managed appropriately, appreciates over time. Our job as your property manager is built right into the name of our company. We manage your property not just for the returns it produces today, but for the value it should generate over time.
Who we are
Oak & Apple was founded in Winnipeg with a straightforward premise: residential property owners deserve a management partner who treats their investment with the same care they would themselves.
We work with a select number of owners — by design. Staying boutique means every property gets real attention, every tenant gets a real response, and every owner gets a manager who actually knows their building.
Whether you own two units or two hundred, the standard doesn't change. Everything exceptional — that's not a tagline, it's the expectation we hold ourselves to every day.
Founder & Broker
"Great company to have manage your properties."
— Oak & Apple client
What we stand for
We don't manage properties to a minimum standard. Every interaction — with owners, tenants, and tradespeople — reflects the same commitment to doing things properly.
No hidden fees. No surprise charges. No decisions made without your knowledge. Our management agreements are built around your right to know exactly what's happening with your investment.
We manage your property not just for the returns it produces today, but for the value it should generate over time. Short-term decisions that compromise long-term value aren't in your interest — or ours.
We're not trying to be the biggest property management company in Winnipeg. We're trying to be the best one for the owners who choose us. That means staying small enough to care.
Our Promise
We stand behind our work. If you're not satisfied with how we're managing your property, we'll make it right — no questions asked. That's the standard we hold ourselves to, and the promise we make to every owner we work with.
Ready to get started?
Book a free consultation with Jamie. We'll be honest about whether we're the right fit for your property.
Book a free consultationProfessional Associations & Memberships
