The morbidity and mortality experiences of people who are unhoused have been well-described, but much less is known about the overall well-being of these individuals. In this mixed methods study, housed and unhoused participants completed a multi-faceted 10 domain measure of well-being (the Stanford WELL Survey), and a subset of unhoused participants shared their experiences during qualitative interviews. Using propensity score matching, unhoused participants (n = 51) were matched at a ratio of 1:5 with housed participants (n = 255). The mean overall well-being score of the unhoused participants was significantly lower than that of the matched housed participants (B = −5.022, p = 0.013). Additionally, the two groups differed on some of the constituent domains of well-being, with unhoused participants reporting statistically significantly lower mean scores on social connectedness (B = −1.086, p = 0.000), lifestyle and daily practices (B = −1.219, p = 0.000), stress and resilience (B = −0.493, p = 0.023), experience of emotions (B = −0.632, p = 0.009), physical health (B = −0.944, p = 0.0001), and finances (B = −3.099, p = 0.000). The unhoused participants had a statistically significantly higher mean score for spirituality and religiosity (B = 2.401, p = 0.000) than their matched housed counterparts. The qualitative interviews further highlighted spirituality and religion as a coping mechanism for the unhoused. The results of this study highlight both unexpected strengths exhibited by the unhoused individuals and areas of challenge.