Preheat the oven to 450 degrees F.

Snap the dry stem ends off of each asparagus and place on a heavy baking sheet. Drizzle with olive oil, sprinkle with salt and pepper, and toss. Roast until the asparagus is slightly caramelized, about 15 - 25 minutes (depending on the thickness of the spears). Cool slightly.

Wrap each asparagus with 1 piece (about 1/2 a slice) of prosciutto, exposing tips. Arrange on a platter and drizzle with balsamic vinegar.  Serve at room temperature.