It happened early Wednesday just after 4:30 a.m. at David Harvey Jewelers on Post Road.
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Authorities arrived to the store and found the front door was smashed and jewelry was scattered on the sidewalk.
Inside, several display cases were smashed with jewelry strewn across the floor.
Surveillance video showed four suspects in masks and gloves break into the store with a garbage can before ransacking the displays with a sledgehammer.
The value of what was stolen is unclear.
The smash-and-grab burglary comes just a week after another robbery at Lux, Bond, and Green in Westport that was even more brazen.
In that case, it happened n the middle of the day while customers and employees were inside.
Police are investigating a possible connection.
"It could very well be connected because they're completely covered in terms of face masks, they're all wearing gloves, they're being careful about this so it's clear these thieves know what they're doing," said Darien First Selectman Jon Zagrodzky
Anyone with information is urged to contact the Darien Detective Division at 203-662-5330
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