SR 165 is a C-shaped route that connects Chesapeake and Norfolk in the Hampton Roads metropolitan area indirectly via Virginia Beach.

The highway's east–west segment connects the Chesapeake communities of Deep Creek and Great Bridge with the Princess Anne part of Virginia Beach.

SR 165 heads east through a forested area and crosses New Mill Creek before intersecting the eastern end of its old alignment, Cedar Road.

Pleasant Road, which is a four-lane divided highway until just east of its partial cloverleaf interchange with SR 168 (Great Bridge Bypass).

East of Centerville Turnpike, SR 165 enters a rural area in which it passes to the north of Naval Auxiliary Landing Field Fentress.

SR 165 continues past the Virginia Beach campus of Tidewater Community College and passes through the Salem area of the city, where the highway intersects Independence Boulevard and Lynnhaven Parkway.

In the Wards Corner area of Norfolk, the state highway has a partial interchange with I-64 that allows access to points to and from the direction of Virginia Beach.

SR 165 becomes a four-lane undivided highway at its grade crossing of Norfolk Southern Railway's rail line to Sewell's Point.