Annual wintertime water-level drawdowns are a common management strategy in recreational lakes; however, few studies have estimated their relative impact on lake littoral habitat among a set of typically co-occurring anthropogenic stressors including lakeshore development and herbicide application. Within 21 Massachusetts, USA lakes that represented a drawdown magnitude gradient (0.07–2.26 m), we assessed depth-specific littoral habitat (coarse wood, sediment, macrophytes) at two sites adjacent to forested or developed shorelines. Using generalized linear mixed models, we found coarse wood abundance and branching complexity was not correlated with drawdown magnitude but was primarily explained by the presence of lakeshore development. Drawdown magnitude was negatively correlated with silt cover and positively correlated with coarse substrate cover, with effects further varying by depth (0.5 m vs. 1 m). Macrophyte biomass and biovolume were negatively correlated with drawdown magnitude with effects also varying by depth for biomass. Macrophyte taxa with annual longevity strategies (e.g., Najas flexilis) and amphibious growth forms increased in biomass proportions with drawdown magnitude. Distance-based redundancy analyses suggested macrophyte taxa composition was driven by drawdown magnitude, coarse substrate, alkalinity, water transparency, and herbicide use. These results suggest the importance of water quality and depth on macrophyte assemblage responses to winter drawdowns and the potential to develop drawdown-tolerant macrophyte assemblages. Altogether, understanding the unique impacts of anthropogenic stressors on littoral zone habitat across heterogeneous environmental lake conditions can help minimize impacts to lake ecological integrity while maintaining recreational value.