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In the United States and across Europe, research on second—and multiple—homeownership for vacation and leisure use has traditionally focused on the in-migration of urban residents into rural locales. Indeed, this line of inquiry has been warranted for many years because of the very high concentration of urban dwellers who have sought out second homes in natural amenity-rich rural destinations. However, drawing on interviews with sixty-one second homeowners who purchase property for vacation or leisure use, this paper unravels an empirical puzzle. While previous research treats second homeownership as a primarily urban-to-rural phenomenon, this analysis uncovers a preponderance of second homeowners who purchase secondary residences in urban locales, as well as suburbanites who purchase secondary residences in rural and urban destinations, respectively. To makes sense of these findings, I suggest that empirical and theoretical attention to second homeownership requires a twenty-first century reappraisal to account for both the heterogeneity of second homeownership as well as the larger socio-economic conditions under which it materializes.