Chronic pain is common in older people. However, little is known about how pain is experienced in residents of retirement villages (‘villages’), and how pain intensity and associations are experienced in relation to characteristics of residents and village living. We thus aimed to examine pain levels, prevalence and associated factors in village residents. The current paper is a cross‐sectional analysis of baseline data from the ‘Older People in Retirement Villages’ study in Auckland, New Zealand. Between July 2016 and August 2018, 578 village residents were interviewed face‐to‐face by gerontology nurse specialists, using interRAI Community Health Assessment (CHA) and customised survey. We used a validated pain scale and multivariable logistic regression analyses adjusted for pre‐specified confounders. Residents' median age was 82 years; 420 (73%) were female; 270 (47%) exhibited/reported daily pain, and in 11% this was severe. After controlling for confounders, daily pain was positively associated with self‐reported arthritis (OR = 3.88, 95% CI = 2.57–5.87), poor/fair self‐reported health (OR = 3.19, 95% CI = 1.29–7.93), having no health clinic on‐site (OR = 1.76, 95% CI = 1.10–2.83), and minimal fatigue (diminished energy but completes normal day‐to‐day activities) (OR = 1.77, 95% CI = 1.11–2.81). Similar associations were observed for levels of pain. We conclude that levels of pain and prevalence of daily pain are high in village residents. Self‐reported arthritis, self‐reported poor/fair health, no health clinic on‐site and minimal fatigue are all independently associated with a higher risk of daily pain and with levels of pain. This study suggests potential opportunities for villages to better provide on‐site support to decrease prevalence and severity of pain for their residents, and thus potentially increase wellbeing and quality‐of‐life, though as we cannot prove causality, more research is needed.