Cut the strawberries in quarters and add to a shallow baking dish. Sprinkle with sugar and balsamic vinegar and toss to coat.
Roast for 20-25 minutes or until the strawberries have softened and the sauce has thickened slightly.
Remove from the oven and let cool.
Biscuits
In a small bowl, whisk together all the dry ingredients. Then use your hands to press the cold butter into the flour until it's fully incorporated but you still have pretty large chunks (about quarter sized).
Slowly drizzle buttermilk over top, combining as you go. Knead a few times in the bowl until you have a very dry, shaggy dough.
Turn the dough out onto a clean surface and press into a 1 inch thick rectangle. Cut into 4-5 even 2 ½ inch circles, then reshape the remaining dough and cut out 1-2 more. You should be able to get 6 biscuits.
Transfer the biscuits to a baking sheet and place in the freezer for 10-15 minutes before baking.
Remove the biscuits from the freezer and brush tops with melted butter (or a bit of heavy cream) and lightly sprinkle with sugar.
Bake biscuits at 400°F for 20-25 minutes or until golden brown on top.
Remove from the oven and let cool.
Whipped Cream
While the biscuits and strawberries are cooling, make the whipped cream. Add the heavy cream to a large bowl with the powdered sugar and vanilla extract. Beat on high with a hand mixer until thickened and medium peaks form.
Simply slice the biscuits in half and layer with roasted strawberries, whipped cream, and sliced fresh basil.
Notes
Once assembled, the shortcake is best when eaten immediately. However, you can store the biscuits at room temperature and the strawberries and whipped cream in the fridge, for up to 3 days.