The residential choices of seniors are an important issue to be considered in both social sciences and in urban planning. In this study, we aimed to analyze how the young-elderly in the Montreal metropolitan area deal with the duality opposing a dwelling's characteristics with those of the neighborhood in their residential choices. Therefore, those who move need to make choices within the constraints of both dwelling and neighborhood characteristics. We employed a statistical approach combining both dwelling and neighborhood characteristics from the 2011 National Household Survey (2011 NHS) and geospatial data, first in separate models and then in a joint model. Our results revealed that the general characteristics of an ideal home of retirees are 3 to 4 rooms, a high-rise building, and a low-density neighborhood. We noted that the geographical location of the previous dwelling is an important determinant of the geographical location of the new one, suggesting a strong territorial attachment among the young-elderly. By stratifying the model with the income quintile, we noted that choices varied widely according to the socioeconomic profile. Thus, for the lower-class of young-elderly, housing costs are a predominant factor, while condos are the preferred housing tenure of the upper class, who also sought to live in a wealthy neighborhood. This segregation dynamic may lead to territorial segmentation, where the upper class seeks to live apart from the rest of the population.