Prepare the strawberries by hulling and slicing them. In a medium bowl, combine the sliced strawberries with 1/4 cup granulated sugar. Toss gently and let sit for about 30 minutes to create a syrup.

Preheat your oven to 425°F (220°C). In a large bowl, whisk together the flour, 1/4 cup sugar, baking powder, and salt. Add the cold, cubed butter and mix until the mixture resembles coarse crumbs.

Pour in the heavy cream and vanilla extract. Stir until just combined, being careful not to overmix. Turn the dough onto a floured surface, knead gently, and pat into a 1-inch thick rectangle. Cut out rounds using a biscuit cutter and place on a baking sheet lined with parchment paper.

Bake for 12-15 minutes or until golden brown. Let cool slightly.

While the shortcakes are baking, prepare the whipped cream by combining 1 cup heavy cream, powdered sugar, and 1 teaspoon vanilla extract in a mixing bowl. Whip until soft peaks form.

To assemble, slice each shortcake in half horizontally. Spoon a generous amount of macerated strawberries onto the bottom half, add a dollop of whipped cream, and place the top half on top. Repeat for remaining shortcakes and serve immediately.