Highland Pines
Homes for Sale in Clearwater, FL

Highland Pines Add is a small, established Clearwater neighborhood of mid-century-era homes, mostly owner-occupied, where the value story is about the individual house rather than a uniform product type.

Stellar MLS sales records identify 291 homes in Highland Pines that have changed hands since 2004, built between 1950 and 2006 (median 1959), with a median living area of about 1,352 sq ft and a typical 3-bedroom, 2-bath layout; 100% are single-family homes. Source: Stellar MLS closed-sale history compiled by Momentum Research; counts reflect homes with a recorded MLS sale, not every home in the community.

County records show 7 qualified sales in Highland Pines across 2024–2025 (3 in 2024, 4 in 2025), median $322,500 — the last recorded sale per parcel on the Florida DOR 2025 assessment roll, independent of the MLS.

Pre-construction details are compiled from public records, builder announcements and builder listings, and are subject to change without notice; figures are deemed reliable but not guaranteed. Momentum Research figures are our own analysis. This page describes homes, pricing and community attributes, not residents.

Highland Pines is too small for its own price trend, so here is the market around it.

In ZIP 33755, 160 homes are on the market and 19% are under contract — a steady corner of Clearwater.

Across Pinellas County, 6,628 homes are active and 1,729 pending (21% under contract).

In ZIP 33755 (Clearwater), 513 homes closed in the last 12 months at a median of $280K ($242/sq ft), down 4.7% year over year, with a median 52 days on market. Right now 64 active and 23 pending listings put supply at about 3.5 months — a balanced market. See the live ZIP 33755 housing market and the Pinellas County market.

ZIP and county figures describe the wider market, not Highland Pines specifically. Momentum Research analysis of MLS records.

The build window runs from 1950 to 2001, but the median year built lands in 1958 — so most of what trades here carries mid-century bones. That is not a knock; it means block, layout, and lot character can be genuine, but it also means you underwrite roof age, electrical, plumbing, and any additions carefully. A median living area around 1,515 square feet points to compact, single-level-friendly footprints rather than sprawling floor plans.

A homestead share of about 65% tells you this is a hold-and-live community more than a rental play. Inventory tends to be thin, so when something updated comes to market it can move; when something dated lists, it sits until the price reflects the work it needs. Read every listing through that lens — the number on the sheet means little until you know what has and hasn't been touched.

In a small, older neighborhood like this, the difference between a good buy and an expensive mistake is knowing which homes have had real system and roof work and which are wearing cosmetic paint over deferred maintenance. We walk it with you, pressure-test condition against ask, and tell you plainly when a home is priced for its updates or priced on hope.

Confirm the current HOA dues, exactly what they cover, and any CDD bond or special assessment for a specific address before you offer.