I've had it for many years and it's too leggy? How can I encourage new growth? Cut back? Repot? Fertilize? And when is best time of year? Thanks!

Its a Dracaena marginata. And that is exactly what they look like. In fact, your's is a lot bushier than most. You can cut them back - they will grow new branches just below where you cut. And you can replant the cut off pieces to grow more plants.

I endorse what Daisy has advised. In addition, I strongly recommend that you NOT repot or fertilize. Increased light will enhance new growth, but it seems to be doing fine where it is.

Hi & welcome! Agree, Dracaena marginata:
Dragon Tree (Dracaena reflexa var. angustifolia)

This plant looks more bushy because it has more branches. It's normal for the foliage to be in a "poof" at the tip of each branch. I agree, your plant looks great! To get more branches, existing ones can be cut in the hopes that more than 1 branch will replace it, which is often the case, but there are no guarantees. I usually do trimming in late spring through summer, when growth is most vigorous.

A brighter spot can cause the foliage to be upright for a longer period, resulting in a more perky appearance, like this plant:


I repot all of mine every 1-2 yrs. I do it at any time of year except the shortest days of winter. If you find a pancake of roots at the bottom of the root ball, cutting that off will make removing the old soil easier & give roots a chance to grow normally again. This is how bonsai masters are able to keep trees alive for hundreds of years in small pots.

There's a house plant forum here, if you'd like to browse other discussions about Dracaena trees. You can also move this discussion to that forum if you want to by clicking 'suggest a change' in this discussion, in the links between the last post & the box to type a reply.
Dragon Tree (Dracaena reflexa var. angustifolia)