Around the Lake-Marion county border, US 27-441 enters a retirement community known as The Villages. Because of the frequent use of street-legal golf cars in the community, bridges and tunnels for these carts can be found throughout the road. US 27-441 leaves The Villages as it approaches County Road 42, a bi-county east-west scenic route through Central Florida. North of here, it serves as the eastern terminus of a newly constructed bypass to CR 484 in Summerfield. Within Belleview, the road encounters two somewhat important intersections; County Road 25A, and then State Road 35. SR 35 joins US 27-441 in a wrong-way concurrency with SR 500 as the road curves more to the west, until it reaches the intersection with US 301, where SR 35 turns south, and SR 500 becomes the hidden state road for US 27-301-441 for a few blocks. However SR 25 reunites with the triplex at the former eastern terminus of CR 484, and shares a concurrency with SR 25, and US 27-301-441's new secret route becomes SRs 25-500 once again. After that the road curves more to the north again. Near the right of way for the formerly proposed Cross Florida Barge Canal in Santos, the median for the road widens, as it contains supports for a bridge that was never completed once the Canal project was cancelled. Before the median narrows back down to normal again, it intersects CR 328, where a police station exists in the median. To the west of this intersection is the Santos Trail System trailhead of the Cross Florida Greenway.