Before US 27-301-441 enters Ocala, it veers off to the left at an intersection with County Road 464A (Southeast Lake Weir Avenue), a former segment of US 441 that eventually leads to Ocala Union Station. The first major intersection after this is 31st Street. Then it crosses under a railroad bridge before reaching the City Limits and the intersections with the northern terminus of CR 475 and crossing SR 464 (17th Street). US 27-301-441 intersects with SR 200 (becoming the new hidden state road until US 301 reaches US 1-23). The highway reaches the heart of Ocala at the intersection with SR 40 (West Silver Springs Boulevard). After this, the road crosses a railroad bridge west of Ocala Union Station. Five blocks later, it reaches the intersection of SR 492 (Northwest 10th Street) only to move in the opposite direction, leaving the US 301-441 overlap and taking SR 500 with it as they head northwest towards Williston, Perry, Tallahassee, and points north. Before US 301-441 leaves Ocala, it has an intersection with County Road 200A (Northwest 20th Street), which runs east and then north. This road was the former State Road 200A and decommissioned U.S. Route 301 Alternate.