The role of orthostatic hypotension (OH) in the continuum of cognitive aging remains to be clarified. We sought to investigate the associations of OH with dementia, cognitive impairment, no dementia (CIND), and CIND progression to dementia in older adults while considering orthostatic symptoms. This population-based cohort study included 2532 baseline (2001–2004) dementia-free participants (age ≥60 years; 62.6% women) in the SNAC-K (Swedish National Study on Aging and Care in Kungsholmen) who were regularly examined over 12 years. We further divided the participants into a baseline CIND-free cohort and a CIND cohort. OH was defined as a decrease by ≥20/10 mm Hg in systolic/diastolic blood pressure upon standing and further divided into asymptomatic and symptomatic OH. Dementia was diagnosed following the international criteria. CIND was defined as scoring ≥1.5 SDs below age group-specific means in ≥1 cognitive domain. Data were analyzed with flexible parametric survival models, controlling for confounding factors. Of the 2532 participants, 615 were defined with OH at baseline, and 322 were diagnosed with dementia during the entire follow-up period. OH was associated with an adjusted hazard ratio of 1.40 for dementia (95% CI, 1.10–1.76), 1.15 (0.94–1.40) for CIND, and 1.54 (1.05–2.25) for CIND progression to dementia. The associations of dementia and CIND progression to dementia with asymptomatic OH were similar to overall OH, whereas symptomatic OH was only associated with CIND progression to dementia. Our study suggests that OH, even asymptomatic OH, is associated with increased risk of dementia and accelerated progression from CIND to dementia in older adults.