This study proposes an AI approach for analyzing retail space transformation and quantifying retail gentrification at scale. Moving beyond survey and interview-based approaches that are limited in coverage and granularity, we leverage a large language model (GPT-4o) to perform semantic reasoning on shopping-mall point-of-interest (POI) data. The method innovates an LLM-enabled entity extraction and classification pipeline that operationalizes retail gentrification through interpretable indicators, including brand count, level, internationalization, and localization. It offers a novel framework for enabling systematic, citywide measurement of commercial restructuring. Theoretically, we extend the retail gentrification lens from streetscapes to shopping malls and develop a mall-oriented assessment framework that integrates GPT-4o outputs with POI attributes into an intelligent evaluation model. Using Shanghai as a case, we apply a dual time-slice comparison (2019 and 2024) and triangulate results with three empirical cases to validate the model’s ability to detect gentrification signals. Results reveal strong spatio-temporal polarization: intensified gentrification in central areas alongside peripheral downgrading, with high-value clusters shifting toward the northeast. This approach offers a scalable paradigm for cross-city comparative research and commercial planning.