A serial shoplifter who has skirted jail time despite dozens of busts was arrested yet again this week — and accused of 27 new heists at Manhattan pharmacies, The Post has learned.

Wilfredo Ocasio, 44, was finally held on bail Tuesday on charges he swiped more than $5,000 in goods from three Duane Reades over several weeks, prosecutors said.

The sticky-fingered recidivist was allegedly caught red-handed at a Duane Reade in the Financial District on Monday and charged for terrorizing that and two other of the chain’s Lower Manhattan outposts for months, police sources said.

Ocasio, who has served two stints in state prison on rape and robbery convictions, already has 33 busts on his resume since mid-August when he was arrested on Nov. 16 for 23 separate thefts from two Duane Reade stores.

But he caught a break when prosecutors with the Manhattan District Attorney’s Office charged him with just two — telling The Post at the time it would have been “a waste of resources” to move forward with all the charges.

“Nobody should be surprised that Mr. Ocasio has been once again arrested — this time on 27 [petit] larceny charges,” said Paul DiGiacomo, president of the NYPD Detective’s Endowment Association. “Why would he stop when there are absolutely no consequences?”

Under state law, Ocasio would only have to serve a maximum of two years behind bars under state law, even if he was charged with and convicted of all the raps, a spokesman for the office explained at the time.

DiGiacomo blasted DA Alvin Bragg’s office for how it handled Ocasio’s cases last month, saying, “The store owners and dedicated detectives know he belongs behind bars.”

On Tuesday, prosecutors from Bragg’s office changed their tune, asking a judge to set bail on Ocasio based on the “harm on harm” clause, which stipulates a repeat offender who gets busted on a class-A misdemeanor or a felony while facing charges in another case can be held on bail if they represent “harm” to a person or property.

Ocasio was arraigned on a third-degree grand larceny charge “which includes 27 incidences of thefts from the three” Duane Reades, Assistant District Attorney Jesse Castaneda said.

“The defendant continuously steals property from the same stores,” Castaneda said. “[He] has demonstrated an unwillingness to abide by the law and all court orders.”

Ocasio is accused of repeatedly hitting Duane Reade outlets on Broadway, Water Street and Wall Street between Nov. 18 and Dec. 26 — stealing more than $5,000 of goods that were never recovered, the prosecutor said.

Police sources said he made off with candy bars, donuts, Monster and Red Bull drinks, and a Whitman chocolate sampler — along with holiday items like gingerbread houses.

The defendant is now well known to the managers of all three of these stores as a regular shoplifter,” Castaneda said, in requesting $25,000 bail.

Judge Rachel Pauley set bail at $5,000 cash or $15,000 bond.

Ocasio’s defense attorney Geoffrey Bickford argued his client was “badly in need of medical help” and that he shouldn’t be sent to languish on problem-plagued Rikers Island as the crimes he is accused of are non-violent.

Ocasio’s name surfaced last month when NYPD Chief of Department Kenneth Corey cited his case as an example of the state’s failed criminal justice reforms.

“Just this past weekend [a] detective squad sergeant down in the First Precinct covering Lower Manhattan, Soho, Tribeca, Financial District reached out to me to express her frustration over an individual that they had arrested and charged with 21 separate crimes,” Corey said during an appearance on NY1 then.

“That’s right, that’s 21 different victims, 21 different dates,” he said. “They thought that the aggregate at least of that — you victimize 21 people on 21 different occasions — would get him held. It didn’t.”