I think rather rare at least in the West. Except of course for anyone who is homeless for other reasons who is also Buddhist. It's going to be hard for anyone because we don't have this tradition of supporting homeless spiritual wandering truth seekers, and seeing this as a valued part of our society, in the West.
Of course only monks and nuns traditionally were homeless even at the times of the Buddha. And even when Buddha was alive, then the monks gathered together and stayed in one place in the rainy season when it became difficult to live as a wandering ascetic in India. And they often had wealthy patrons who provided places for them to stay at that time.
Which later developed into the Buddhist monasticism. In more recent times, many Buddhist monks live permanently in monasteries in traditional Buddhist countries, supported by donations from lay people.
In traditional Buddhist countries, then many Buddhist monks and nuns live permanently in monasteries. But some will wander through the countryside for a part of their life, as a wandering ascetic similarly to Buddhist monks and nuns at the time of the Buddha. For instance in the Thailand forest monks tradition, The Thai Forest Tradition
Also a Buddhist meditator (not necessarily a monk or nun) may go to meditate for many years in a cave, if that counts as homeless. In traditional societies, often supported by others who provide them with food.
A google search turns up a couple of examples of people in modern times following the same lifestyle in the West.