Rough terrain traversability is often estimated through point-wise roll, pitch, or force-angle margins along a planned path. However, these metrics are often inaccurate and overly conservative because they ignore how terrain disturbances and low-level controller corrections can affect the vehicle's motions. To overcome these limitations, we introduce Execution-Grounded Traversability (EGT), defined as the probability that a vehicle-controller pair can execute a candidate path while meeting trajectory-level tracking and progress requirements. We estimate EGT by predicting the distribution of closed-loop trajectories using a latent-space flow matching (FM) model conditioned on multi-resolution terrain features and 3D vehicle attitude and wheel-ground contact points prior. Across 650 simulated trials on unseen terrains, EGT reduces safe-path rejection to 2.2% (versus 11.4%-39.5% for pose-margin and force-angle baselines) and unsafe acceptance to 7.7%. Integrated into a receding-horizon sampling-based planner, EGT reduces navigation failure rates by 24-42 and 30-44 percentage points over [1] and [2], respectively, while cutting goal-reaching time by up to 20.5% and 45%. Finally, we demonstrate zero-shot transfer of our simulation-trained model to real-world outdoor experiments.