Digital technologies have reshaped the inheritance ecosystem of intangible cultural heritage (ICH), and user demands serve as the core anchor for the digital cultural communication and market-oriented transformation of heritage. This study aims to analyze the value structure of user demands in the intelligent design transformation of Yingshan Winding Flower, a Jingchu intangible cultural heritage, and explore its innovative paths of digital cultural development and market application. Adopting the Grounded Theory, this paper conducts three-level coding on in-depth interview data from 32 users to construct a user demand value model for the intelligent design transformation of Winding Flower, and carries out targeted design practices based on the model. A theoretical user demand value model is established, which covers four dimensions: original intrinsic value, living heritage value, synaesthetic perceptual value, and production-consumption value. Corresponding to the four dimensions, four design strategies are proposed, namely, precise translation and in-depth internalization of cultural symbols based on the original intrinsic value, cross-scenario collaboration and cultural space construction based on the living heritage value, multimodal interaction and immersive experience design based on the synaesthetic perceptual value, and co-creation ecosystem construction and market closed-loop formation based on the production-consumption value. Centered on user demands, starting from aesthetic identity, and targeting cultural recognition and market acceptance, this research provides a reusable theoretical framework and practical approach for the intelligent design transformation of intangible heritage handicrafts.