The Crawley-born 23-year-old started his career at Brighton and follows James Tilley as an ex-Albion youngster at the People's Pension Stadium.
Although never making a first team appearance for the Seagulls, Maguire-Drew got plenty of experience with loan spells at Worthing, Dagenham and Redbridge, Lincoln City, Coventry and Wrexham before joining Orient in 2019 where he has scored 12 goals in 56 appearances.
He joins former teammate Josh Wright at Crawley Town.
Technical Director Erdem Konyar said, “Jordan is another local lad that has a good pedigree and EFL experience.
“He will give us an added boost in the offensive area, and it’s testament to our manager John Yems and Lee Bradbury; as we are building a side that players want to be a part of. This near enough completes our recruitment for January.”
Jordan will be available for Tuesday's game against Stevenage.