The ultimate redemption will usher in a profound physical and spiritual transformation across the Land of Israel, fundamentally reshaping its landscape to highlight the glory of the holy city. The mountain ranges that currently surround Jerusalem will be leveled, transforming into a vast, flat plain. [מלבי״ם] specifies that this expansive flatland will emerge from the valley created by the splitting of the Mount of Olives. This topographical shift carries a deep spiritual purpose. According to [אהבת יהונתן], mountains currently act as barriers to the spread of prophecy and the Holy Spirit. Leveling them will allow the divine light to radiate outward without any obstruction.
This smooth plain will stretch across regions like Geba and Rimmon, transforming areas that are currently rocky and mountainous to resemble the naturally flat southern desert [רש״י]. Nearby, the new Jerusalem envisioned by the prophets will eventually stand [מלבי״ם]. As the surrounding landscape is lowered, Jerusalem itself will be left towering above the rest of the land, visibly prominent and magnificent [רש״י, מצודת דוד, רד״ק, צאינה וראינה]. This physical height mirrors a profound spiritual elevation, as the city and its inhabitants will achieve the highest levels of wisdom and understanding of God [אהבת יהונתן].
In this exalted state, Jerusalem will return exactly to its original, historical foundations. Unlike the era of the Second Temple, when the city was not rebuilt precisely on its initial site, the future city will be perfectly restored to its ancient roots [מצודת דוד]. It will expand significantly in all directions [רד״ק], becoming a place where the Israelites will dwell securely, with absolute stability, never to face exile again [צאינה וראינה, ביאור שטיינזלץ].
The newly expanded city will encompass familiar historical landmarks, stretching out to include the Gate of Benjamin, the First Gate, the Corner Gate—which is situated at an angle [מצודת ציון]—and the Tower of Hananel, all marking its vast new perimeter [מצודת דוד, ביאור שטיינזלץ]. The boundary will reach as far as the royal winepresses, which were historically carved pits outside the city used to collect grape juice [רש״י, מצודת ציון, רד״ק]. This final boundary holds deeper significance as well. A midrashic approach suggests that these royal pits represent the oceans carved out by the King of Kings, indicating that Jerusalem's influence will ultimately expand to the very ends of the earth [רש״י]. Alternatively, from a spiritual perspective, [אהבת יהונתן] explains that because consuming wine can interfere with attaining the Holy Spirit, the winepresses mark the outermost edge of the city's intense sanctity. Within those borders, the future inhabitants will distance themselves from wine in their pure devotion to God.