Preheat oven to 400°F (204°C).
Wipe clean your pumpkin with a damp paper towel. Carefully cut it in half with a sharp knife and scoop out the seeds with a large spoon.
Drizzle the pumpkin with 1 tbsp of olive oil and season with salt and pepper to taste. Place the pumpkin skin side down on a baking sheet lined with parchment paper. Roast for about 40-60 minutes or until tender. You'll know it's done when you can easily pierce it with a knife or fork. Let the pumpkin cool for a few minutes and then peel off the skin. You will end up with about 4-4½ cups (2-2¼ lbs) of cooked pumpkin. Set aside.
Heat the remaining 2 tbsp of olive oil in a large Dutch oven or heavy pot over medium heat. Add the chopped onion and cook for about 3-5 minutes or until soft. Now, add the chopped garlic and cook for one more minute.
Add the cooked pumpkin, broth, water and season with salt and pepper to taste. Bring to a boil, then reduce the heat to medium-low and simmer for about 20 minutes.
Remove from the heat and then blend the soup either in a regular blender or with a hand-held blender until smooth. Return the pot of soup to the stove, add the heavy cream, season with more salt and pepper, if needed, and simmer for a few more minutes.
Serve immediately and drizzle with some more heavy cream. You can also serve it with your favorite bread or toppings.