Highland Pines is an established single-residential neighborhood in central Clearwater, in Pinellas County, laid out across mid-century plat additions off South Highland Avenue near Belleair Road. Local neighborhood guides describe the housing stock as built largely between the early 1950s and 2000, ranging from modest mid-century homes to larger updated properties (neighborhoods.com and Homes.com Clearwater guides, 2026).
The Highland Pines 5th Addition is one of the recorded plat additions that make up the broader neighborhood, so the name on a deed reflects the plat the lot was filed under rather than a separate community. The result is varied lot sizes and home ages within a single walkable area, which is why condition and the specific parcel matter more than the headline.
The location is the pitch: Highland Pines is centrally placed in Clearwater, close to the Largo line, with quick access to downtown Clearwater, the US 19 and Gulf-to-Bay retail corridors, and the Gulf beaches a short drive west. It is inland rather than waterfront, which generally keeps it away from the most severe coastal storm surge, though parcel-level flood checks still apply.
The work in Highland Pines is sorting condition: roof age, systems, and insurability on an older home, plus the FEMA flood zone and the fee picture for the exact parcel, before you let a central-Clearwater price tempt you.
