Preheat the oven to 350°F. Grease an 8-inch round cake pan and line the bottom with parchment paper.
In a large bowl, whisk together the flour, baking powder, salt, and sugar.
Add the cold cubed butter to the dry ingredients. Use a pastry cutter, fork, or your fingers to work the butter into the flour mixture until crumbly.
Add the milk and vanilla extract. Stir gently until just combined. Be careful not to overmix.
Spread the batter evenly into the prepared cake pan. Sprinkle coarse sugar on top if using.
Bake for 30–35 minutes, or until the shortcake is golden and a toothpick inserted into the center comes out mostly clean.
Let the shortcake cool in the pan for about 15 minutes, then remove it from the pan and transfer it to a wire rack to cool completely.
While the shortcake cools, add the sliced strawberries and granulated sugar to a bowl. Stir and let sit until the strawberries become juicy.
To make the whipped cream, add the cold heavy whipping cream, powdered sugar, and vanilla to a mixing bowl. Beat until soft peaks form.
Once the shortcake is completely cool, spread the homemade whipped cream over the top.
Spoon the fresh strawberries and their juices over the whipped cream.
Slice and serve right away.