Property development around transit stations has been viewed by many governments as a considerable way of financing public transportation. However, despite mounting evidence of the positive relationship between transport investment and proximate land value, the stakeholder relationship in enabling complex property–transit development has received relatively scarce attention. In this study, we analyze the railway financing strategies in two cities (Shenzhen and Hong Kong) connected by the first cross-border high-speed rail (HSR) network in China. Using a holistic power approach, this study presents power direction, power strength, and power mechanism as the critical factors for each case. The results reveal that different stakeholder relations arising from different social and institutional contexts have led to varying land value capture practices. The findings of this study contribute to sustainable railway financing in three phases: First, it unravels the relationship between railway financing and property development under the context of an intercity railway program, with the intervention of state power. Second, it sorts out critical elements in the implementation of the land value capture mechanism, especially institutional factors such as the role of the transit agency. Third, it directs a flexible development of the land value capture theory to cope with foreseeable problems such as land resource scarcity, institutional complexity, and interest divergence.