Winnipeg, Manitoba
Property ownership, your way.
Whether you want to stay hands-on with professional backup, or hand everything over completely — Oak & Apple has a membership built for how you want to own.
Serving residential landlords across Winnipeg.
Our memberships
Choose the level of support that fits.
Every landlord is different. We built three memberships so you can get exactly the support you need — nothing more, nothing less.
01
Landlord Membership
"Own it yourself — with a professional team behind you."
Best for
- DIY landlords
- Owners just getting started
- Investors who want access to professional resources
Includes
- Treetop Telegraph newsletter
- Educational resources
- Landlord pricing on services
- Access to Oak & Apple when professional assistance is needed
02
Manager Membership
"You remain in control. We provide the professional systems."
Best for
- Owners who still want to manage their property
- Those who want professional infrastructure
Includes
- Everything in Landlord Membership
- Core Services
- Owner Portal & Tenant Portal
- Rent Collection & Monitoring
- Document Vault
- Mailing Address
- Emergency Contact Infrastructure
- Vendor Network
- Administrative support
Additional services available as needed.
03
Investor Membership
"Own the investment. We'll manage the rest."
Best for
- Owners who want complete professional management
Includes
- Everything in Manager Membership
- Full tenancy administration
- Leasing
- Maintenance administration
- Financial administration
- Ongoing property management
- Day-to-day management by Oak & Apple
Single family home pricing shown. Pricing varies by property type. Contact us for a custom quote.
Getting started
Simple to start. Easy to stay.
Pick your membership.
Start with the membership that fits where you are today. You can always move up as your needs change — or as you decide you'd rather spend your weekends differently.
We get you set up.
We onboard your property, set up your portals, and make sure everything is in order. Whether you're staying hands-on or handing over the keys, we make the transition smooth.
Own on your terms.
Stay as involved as you want. Log into your owner portal anytime, call us when you need us, or let us handle everything end-to-end. Your property, your call.
Why us
Not your typical property management company.
"Property management should be there at every step of the landlording journey; not just the finish line."
Boutique
We deliberately stay small. Every owner gets a dedicated point of contact who knows their property, their tenants, and their goals. You're never a ticket number.
Tech-forward
Our owner portal, digital lease signing, and maintenance tracking mean you always know what's happening — without having to ask. Technology handles the routine so people can handle the rest.
Human
When a tenant has a hard month, or a repair needs a judgment call, or you want to talk through a decision — there's a real person on the other end. That's not a feature. It's the whole point.
Not sure where to start?
Let's find the right fit together.
A free, no-obligation conversation about your property and which membership makes sense for you. We'll be honest — even if that means recommending you start with the free tier.
