Prepare the Strawberries: In a bowl, combine the sliced strawberries and 1/4 cup of granulated sugar. Toss gently to coat, then refrigerate for at least 30 minutes to let the flavors meld.
Preheat the Oven: Preheat your oven to 425°F (220°C). Line a baking sheet with parchment paper.
Make the Biscuits: In a large bowl, whisk together the flour, 1/4 cup of granulated sugar, baking powder, and salt. Add the cold, cubed butter and use a pastry cutter or your fingers to work it into the dry ingredients until the mixture resembles coarse crumbs.
Add Wet Ingredients: Pour in the milk and vanilla extract, stirring until just combined. Be careful not to overmix; the dough should be slightly sticky.
Shape the Biscuits: Turn the dough out onto a floured surface and gently knead it a few times. Pat the dough into a 1-inch thick rectangle. Use a round biscuit cutter to cut out biscuits, reusing scraps until all the dough is used. Place the biscuits on the prepared baking sheet.
Bake the Biscuits: Bake in the preheated oven for 12-15 minutes or until the biscuits are golden brown. Remove from the oven and let them cool.
Whip the Cream: In a separate bowl, whip the heavy cream, powdered sugar, and vanilla extract until stiff peaks form.
Assemble: Split the biscuits in half horizontally. Spoon some of the macerated strawberries onto the bottom half of each biscuit, followed by a dollop of whipped cream. Place the top half of the biscuit over the cream.