Combine strawberries and 1/4 cup sugar in a bowl. Toss to coat evenly. Let sit for 30 minutes at room temperature so the berries release their juices. Stir once midway.

Preheat oven to 425°F (220°C). Line or lightly grease a baking sheet.

In a large bowl, whisk together flour, 1/2 cup sugar, baking powder, and salt.

Cut the cold, cubed butter into the dry ingredients until the mixture looks like coarse crumbs with pea-sized bits of butter remaining.

Add the milk and stir gently until the dough just comes together. Do not overwork.

Turn the dough onto a lightly floured surface, pat into a 1-inch-thick circle, and use a biscuit cutter to cut rounds. Place them on the prepared sheet.

Bake for 12–15 minutes, until biscuits are golden on top and sound hollow when tapped. Remove and cool briefly on a wire rack.

While the biscuits bake, whip the heavy cream with powdered sugar and vanilla until soft peaks form.

Slice the biscuits in half. Spoon strawberries and their syrup over the bottom half.

Dollop or pipe whipped cream on top, crown with the biscuit top, and serve immediately.