Conventional methods of agriculture, especially tillage, are often accompanied by soil degradation in the form of erosion and organic matter depletion. Regenerative agricultural methods seek to repair soil ecosystems by building topsoil and soil organic matter (SOM), decreasing reliance on chemical fertilizers and increasing both water retention capacity and the diversity and quantity of soil microbial and fungal communities. The University of Washington (UW) student farm is an organic and regeneratively managed site on the UW Seattle campus. Over the past 20 years the farm gradually expanded so locations on the farm encompass both unimproved topsoil and soils managed regeneratively for periods of 5 to 20 years. This arrangement allows a time-trend analysis of soil development under regenerative methods. Measurements of topsoil thickness (defined as the distance from the ground surface to the base of the soil A horizon) and organic matter content were collected across 14 distinct plots on the farm to quantify trends over time and estimate net change in SOM (and soil organic carbon, or SOC). While SOM content weakly increased by 0.5% per year, topsoil thickness exhibited a significant linear increase of 0.86 cm per year. Over a twenty-year period under the management practices of the UW Farm total organic carbon storage in soils, determined using topsoil thickness, density, and SOC content, increased by between 4 and 14 t ha−1 yr−1. The general increases in topsoil thickness, SOM content, and total soil carbon demonstrate the potential of soil-health-focused practices to help maintain a productive and efficient urban growing space.