Within peri-urban landscapes, this research investigated the complexity of the balance between urban development and green infrastructure preservation, with a specific focus on Harku municipality, Estonia. This study aimed to understand the interplay between cultural ecosystem services (CESs) and residents’ well-being. Aligned with the EU Nature Restoration Law, this research explored long-term dynamics in peri-urban areas’ CES conservation. The methodology included creating scenarios by combining new secondary data with the author’s prior studies, which covered landscape belts, CES values, and residents’ perceptions of satisfaction with the environment and recreation opportunities collected through a municipal survey. While residents expressed satisfaction in coastal and green spaces, a distinct decline was evident near villages with industrial and agricultural features, highlighting the landscape’s impact on well-being. This study identified case-study-specific threats related to rapid urbanisation and put forward constructive policy recommendations. The goal was to develop effective and sustainable strategies for preserving nature through ecosystem service-based frameworks, enhance community well-being, and account for landscape dynamics through scenario planning.