Hull and slice the strawberries into a bowl, then sprinkle with sugar and gently mash with a fork or muddler until juicy and slightly broken down. Let sit for 10-15 minutes to macerate and release their juices.
In a chilled mixing bowl, whip the heavy cream with sugar until soft peaks form. The cream should be silky and hold gentle folds when lifted. Keep refrigerated until ready to assemble.
Preheat your oven to 425°F (220°C). In a large bowl, whisk together flour, baking powder, and salt. Add the cold, cubed butter and cut it into the dry ingredients with a pastry cutter or fork until the mixture resembles coarse crumbs with some pea-sized bits.
Pour in the buttermilk and vanilla extract, then gently fold the mixture with a spatula or spoon just until combined. Do not overmix to keep the biscuits tender.
Turn the dough out onto a lightly floured surface and gently knead it a few times to bring it together. Pat the dough into a 1-inch thick rectangle and cut out rounds with a biscuit cutter or glass.
Place the biscuits onto a baking sheet lined with parchment paper. Bake in the preheated oven for 12-15 minutes, or until golden brown and slightly crisp at the edges.
Remove the biscuits from the oven and let them cool slightly on a wire rack. They should be warm and crumbly, perfect for layering.
Once cooled, slice the biscuits horizontally if desired, or serve whole. Spoon a generous amount of mashed strawberries onto the biscuit base, then top with a dollop of whipped cream and the biscuit top if sliced.
Finish by spooning more strawberries and whipped cream over the top for a luscious, juice-soaked finish. Serve immediately to enjoy the contrast of warm, flaky biscuit and cool, creamy topping.