Large language models (LLMs) are rapidly assuming an intermediary role in housing search through the integration of listing platforms within conversational interfaces, mediating access to information, search, and recommendations within urban settings. We expand on prior work on racial steering in LLMs by conducting a behavioral audit of seven open-weight and closed-source LLMs across four U.S. cities, testing location recommendations across three iterative prompting conditions that progressively add lifestyle preference context and reflect fair housing paired-testing methodologies. We find that steering is an emergent behavior of the model's interpretive license rather than primarily a static property. Steering results from the interaction of a user's identity, preference articulation, and the spatial logic that a model has internalized about learned representations of place, preference, and opportunity in a given city, and how different types of users relate to it. While steering was present, it was not uniform in direction or magnitude across evaluated conditions. Preference-conditioned testing often increased or reconfigured the number of models that exhibited steering behaviors relative to baseline conditions, suggesting that LLMs may interpret what the same housing preference means differently depending on the racial identity of the user. Our findings also demonstrate that the city is not a neutral testing unit for LLM evaluation in place-based sectors, and results from one local market cannot be assumed to generalize to another. Local and domain expertise will be required in the housing sector to ensure that legal and institutional commitments to fair housing are not undermined while adopting AI tools that mediate spatial access.