Yes, that worked. Forgot that when pulling low, LED is still connected and causing current to flow. The circuit is Vdd->LED->current-limiting resistor (Rc)->pin->R->GND so a voltage divider is formed between Rc and R.
With LED forward voltage of ~3V, Rc of 220ohms and Vdd = 5V, if I see 440mV at my measurement point, R ~ 64ohms. This is close to what I actually measure. Will use this as the value in my circuit.
Thanks!