About Oak & Apple
Built for owners at every stage of the journey.
Whether you're a first-time landlord figuring it out, or a seasoned investor ready to step back — Oak & Apple was built to meet you where you are.
Our Philosophy
The oak and the apple.
"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
A Winnipeg firm, built on relationships.
Most landlords don't start out wanting to be landlords. They inherit a property, buy a second home, or make an investment — and suddenly they're fielding maintenance calls at 10pm and chasing rent on the first of the month.
Oak & Apple was founded because that story is too common. Rental property ownership should be a genuine asset — something that works for you, not the other way around. We built a firm that supports owners at every stage: from the DIY landlord who just needs a little guidance, to the investor who wants to hand everything off and never think about it again.
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.
Founder & Broker
Jamie Buhler
"Great company to have manage your properties."
— Oak & Apple client
What we stand for
The principles we manage by.
Everything Exceptional
We don't manage properties to a minimum standard. Every interaction — with owners, tenants, and tradespeople — reflects the same commitment to doing things properly.
Transparent by Default
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.
Long-Term Thinking
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.
Boutique on Purpose
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
The Peace of Ownership Guarantee.
If you don't feel your life is easier within the first 30 days, we'll cancel the agreement and refund your management retainer. No fine print, no hard feelings — just a straightforward promise that we earn your trust before we keep it.
Ready to get started?
Book a free consultation with Jamie. We'll be honest about whether we're the right fit for your property.
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