To prepare syrup, in a large saucepan combine trimmed and halved strawberries, sugar, and 1/2 cup water. Bring just to boiling, stirring to dissolve sugar. Remove from heat. Cover; cool to room temperature.
Press mixture, a little at a time, through a mesh sieve; discard solids. In a 2-quart pitcher, stir together the syrup, wine, and 1/2 cup water. Pour into ice pop molds, filling each 1/4 full. Add some of the sliced strawberries. Repeat until each pop mold is full, alternating adding wine mixture and strawberries. Cover with lid and insert ice pop sticks. Freeze for at least 5 hours or overnight.
Remove ice pops from mold. Freeze unmolded ice pops for at least 20 minutes before serving.