The growing digitization of business has revolutionized marketing practices in various areas, e.g., in the real estate sector. This research aims to understand how digital marketing strategies influence sales in the real estate sector. To this end, a mixed methodology was used, combining an observation table of real estate agencies in Portugal (N = 20), supported by statistical analysis, and semi-structured interviews with stakeholders in the real estate sector (N = 5). The results reveal that despite awareness of digital technology, the adoption of more advanced tools, e.g., technical SEO, automation, virtual reality, and personalization, is still scarce, especially in smaller agencies. It was found that digital marketing can significantly increase lead generation, optimize customer relationships, and mitigate market seasonality, but it requires investment, training, and a data-driven mindset. The study reinforces the need for integration between technology and human contact as a critical factor for success and proposes strategic paths for digital evolution in the sector.