Preheat the oven to 350°F (175°C).
Add the sugar to a small, heavy saucepan over medium-low heat. Cook, stirring occasionally, until the sugar melts and turns a deep golden caramel color.
Carefully pour the caramel into a 10-inch round baking dish. Tilt the dish gently so the caramel coats the bottom and sides. Set aside to cool slightly.
Beat the softened cream cheese in a large bowl until smooth and creamy.
Add the eggs one at a time, beating well after each addition.
Pour in the sweetened condensed milk, evaporated milk, and vanilla extract. Mix until the custard is smooth and evenly combined.
Pour the custard mixture over the caramel in the baking dish.
Place a damp kitchen towel in the bottom of a large roasting pan. Set the baking dish on top of the towel. Carefully place the roasting pan in the oven.
Pour boiling water into the roasting pan until it reaches about halfway up the sides of the flan dish. This water bath helps the Creamy Caramel Flan cook gently and evenly.
Bake for 50–60 minutes, or until the center is just set and has a slight jiggle when gently moved.
Remove the baking dish from the water bath and place it on a wire rack. Let it cool for about 1 hour.
Cover and refrigerate for at least 8 hours or overnight so the custard becomes completely chilled and firm.
To unmold, carefully run a thin knife around the edge of the flan. Place a rimmed serving platter over the baking dish, then quickly and carefully invert the dish. Lift the baking dish away and let the caramel sauce flow over the custard.
Slice and serve chilled.