Albert Barnes Commentary Zechariah 14:10

"All the land shall be made like the Arabah, from Geba to Rimmon south of Jerusalem; and she shall be lifted up, and shall dwell in her place, from Benjamin`s gate unto the place of the first gate, unto the corner gate, and from the tower of Hananel unto the king`s wine-presses." — Zechariah 14:10 (ASV)

All the land shall be turned as a plain from Rimmon to Gebah - Kimchi: "All the land around Jerusalem, which is now mountainous, as it is said, The mountains are round about Jerusalem (Psalms 125:2), shall become as level as a plain, but Jerusalem itself shall be exalted, and high above all the earth." The dignity of the Church, as a city set upon a hill, which cannot be hid (Matthew 5:14), is symbolized here by the sinking of all that is around it and its own rising up; as in Micah and Isaiah: The mountain of the Lord’s house shall be established on the top of the mountains, and shall be exalted above the hills (Isaiah 2:2; Micah 4:1).

Gebah (literally, "hill"), now "Jeva," was a frontier garrison, once held by the Philistines (1 Samuel 14:5) and fortified by Asa (1 Kings 15:22). It was on the northern boundary of Benjamin, together with Michmash (1 Samuel, in the place cited) (now Mukhmas), commanding an important pass by which Jerusalem was approached (Isaiah 10:28–29).

"Rimmon, south of Jerusalem" is mentioned in Joshua among the southern towns of Judah (Joshua 15:32), given to Simeon (Joshua 19:7; 1 Chronicles 4:32). Both survived the Captivity.

They mark then the north and south of the kingdom of Judah, a long mountain chain, which is pictured as sinking down into a plain, so that Jerusalem alone might be exalted.

From Benjamin’s gate unto the place of the first gate - Benjamin’s gate must obviously be a gate to the north, and doubtless the same as "the gate of Ephraim," as the way to Ephraim lay through Benjamin. This too probably refers to the prophecy of Jeremiah, that the city shall be built to the Lord from the tower of Hananeel unto the gate of the corner (Jeremiah 31:38). Jehoash, king of Israel, broke down the wall of Jerusalem from the gate of Ephraim to the corner-gate, four hundred cubits (2 Kings 14:13; 2 Chronicles 25:23), after the war with Amaziah.

Zechariah seems to speak of Jerusalem as it existed in his time. For the tower of Hananeel (Nehemiah 3:1) still existed; the "first gate" was probably destroyed, since he does not speak of it, but of its "place;" the gate of Benjamin and the corner-gate probably still existed, since Nehemiah (Nehemiah 3:1, 3, 6, 13-15) mentions the building of the sheep-gate, the fish-gate, the old gate, or gate of the old city, the valley-gate, the dung-gate, the gate of the fountain; but not these.