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Brownfield regeneration to soft reuse such as recreation and amenity has become increasingly common due to the demand for the potential environmental, social and economic benefits that it can deliver. This has led in turn to an increased demand for improved tools to support decision-making for this style of regeneration: tools which are simple to use, based on robust scientific principles and preferably which can ultimately link to quantitative or semi-quantitative cost-benefit analyses. This work presents an approach to assessing and comparing different scenarios for brownfield regeneration to soft reuse and other end-points. A “sustainability linkages” approach, based on sustainability assessment criteria produced by the UK Sustainable Remediation Forum (SuRF-UK), is developed and used in a refined qualitative sustainability assessment, and applied to develop a conceptual site model of sustainability, for a specific case study site (Port Sunlight River Park, U.K., a public leisure park established and maintained on a capped and managed former landfill site). Ranking, on an ex post basis, highlighted the clear sustainability advantages that the establishment of the Port Sunlight River Park has compared with a hypothetical non-development scenario. The conceptual site model provides a clearer basis for understanding cause and effect for benefits and disbenefits and a rationale for grouping individual effects based on their ease of valuation, providing a road map for cost-benefit assessments by (1) being able to match specific linkages to the most appropriate means of valuation, and (2) transparently connecting the sustainability assessment and cost benefit assessment processes.