The goal of this study was to characterize the detection range of a near real-time baleen whale detection system, the digital acoustic monitoring instrument/low-frequency detection and classification system (DMON/LFDCS), equipped on a Slocum glider and a moored buoy. As a reference, a hydrophone array was deployed alongside the glider and buoy at a shallow-water site southwest of Martha’s Vineyard (Massachusetts, USA) over a four-week period in spring 2017. A call-by-call comparison between North Atlantic right whale upcalls localized with the array (n = 541) and those detected by the glider or buoy was used to estimate the detection function for each DMON/LFDCS platform. The probability of detection was influenced by range, ambient noise level, platform depth, detection process, review protocol, and calling rate. The conservative analysis of near real-time pitch tracks suggested that, under typical conditions, a 0.33 probability of detection of a single call occurred at 6.2 km for the buoy and 8.6–13.4 km for the glider (depending on glider depth), while a 0.10 probability of detection of a single call occurred at 14.4 m for the buoy and 22.6–27.5 km for the glider. Probability of detection is predicted to increase substantially at all ranges if more than one call is available for detection.