This paper examines the materiality of digitally mapping eviction and landlord geographies, focusing on struggles and contradictions that critical GIS and counter-mapping collectives encounter in attempting to produce data, maps, and tools useful for housing justice organizing. I look at how public restrictions of parcel ownership and eviction data, along with limited accessibility of free and open source mapping software, often instantiate increased reliance upon technocapitalist data and infrastructure. Many of these systems are precipitative of gentrification geographies, thereby at odds with the politics of anti-displacement mapping. Meanwhile, there are a growing number of cartographic labs and companies that produce geospatial data related to evictions and property ownership, but that prioritize data accumulation and scalability over grounded housing justice. By exploring paradoxes within this space, I theorize the conjuncture of datafied property and propertied data landscapes.Homing in on San Francisco landscapes of the Tech Boom 2.0., I draw upon my own experience working with the Anti-Eviction Mapping Project and partner groups. I conclude by looking to housing justice and land rematriation practices based upon grounded relationalities–models that offer emancipatory trajectories for digitally mapping property and dispossession.