Delray Beach has five local historic districts: Old School Square, Del-Ida Park, West Settlers, Nassau Park, and Marina. Permits there come with a Historic Preservation Building Permit Acknowledgement that speaks to windows directly.
The rule of thumb is repair first. If a historic window cannot be repaired, the replacement should match the original's trim, material, frame size and shape, and reveal. Exterior changes need a Certificate of Appropriateness from the board or staff, and the permit itself runs through the city's eServices portal.