Intertidal reefs of Crassostrea virginica (eastern oyster) provide ecologically valuable habitat in estuaries along the Atlantic coast of North America. In Mosquito Lagoon, a shallow-water estuary on the east coast of central Florida, USA, historical aerial imagery was used to document a 24% decline in the live C. virginica reef area between 1943 and 2009. Using 2021 imagery, every living and dead reef in the same region was manually digitized to identify changes during the intervening 12 years. Positive impacts of C. virginica reef restoration that took place between 2007 and 2021 were also digitized to quantify long-term restoration impact. Natural, live C. virginica reef coverage throughout the system was found to have decreased by 50.6% between 2009 and 2021 and, thus, 62.6% between 1943 and 2021. This was attributed to reef fragmentation, reef footprint loss, boating activity, and mangrove expansion. Of the 2542 live reefs identified using 2009 imagery, 219 reefs fragmented, 988 reefs no longer had an identifiable footprint, and 598 reefs contained visible mangroves with non-continuous canopies. Conservatively, 63.6% of directly restored reef area was classified as living reef in 2021, and 74.5% of restoration projects were more than 50% live reef. Dead reef area decreased by 57.9% throughout the system. Understanding changes in C. virginica reef acreage, reef numbers, and mangrove expansion is essential for resource management, restoration practices, and tracking climate change impacts on publicly protected estuaries.