Population aging increases the demand for home-based dental care, but access remains limited for older adults who are homebound. Although teledentistry is a strategy for overcoming mobility barriers, its feasibility within the routine of Primary Health Care (PHC) requires further investigation. This pragmatic pilot trial evaluated a teledentistry protocol for monitoring homebound older adults. Six homebound older adults in the Brazilian PHC system were assigned to receive either weekly remote monitoring via a telehealth platform or conventional home visits over a three-week period. Feasibility was assessed using the Acceptability, Adequacy, and Feasibility measures of the intervention (scale 1 to 5), along with diagnostic instruments (OFI-8, OHIP-14, Kihon Checklist). Teledentistry demonstrated moderate adequacy (3.5) and feasibility (3.3). However, acceptability was lower (3.0) due to severe digital literacy barriers that required caregiver mediation. Remote data collection proved technically stable, and the OFI-8 effectively tracked functional decline. In contrast, the intervention group showed a worsening of OHIP-14 scores, reflecting a likely increase in awareness of unmet needs without immediate physical relief. In conclusion, although continuous remote monitoring is technically feasible and safe, the low digital literacy of the target population suggests that a hybrid model—combining teledentistry with targeted in-person visits—appears to be more equitable.