Opener Toby Albert had retired hurt after he had extended his knee when taking a quick single on the second evening, but his return was short-lived as Gregory had him leg-before.
Ben Mayes was bowled through the gate by Archie Vaughan, but Somerset wrestled back the advantage with the second new ball.
Vaughan tempted Liam Dawson into a loose leg side shot, before Gregory brought himself on, found good movement and four more wickets.
Ben Brown was the latest candidate to break the century curse, but was stopped on 66 by an inswinger.
Kyle Abbott and Eddie Jack were also bowled, before Sonny Baker was lbw – Gregory returning from a pectoral injury that had ruled him out of the opening two rounds in style.
This was his first five-wicket haul against Hampshire, despite taking more wickets against the opponent than any other in first-class matches.
In his six overs with the second new ball, during which he swapped ends, he took four wickets for five runs, with overall figures of 5-42.
Vaughan saw the 287 target as one to attack, despite there being plenty of time left in the match. The opener got the chase against Essex done and dusted in quick time, and struck six boundaries in a 30 before taking on a Baker short ball and losing for the second time in the match.
Baker swapped ends and removed the rest of the Somerset top order. Josh Thomas was plumb in front and then Tom Lammonby hooked straight to deep square leg.
Not for the first time in the match, or the season, Somerset looked to Rew and Tom Abell to build an important partnership – they once again answered with runs.
The pair put on 87, after 101 in the first innings, with Rew doing the majority of the run scoring.
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