Driving Jobs in Winter Park, FL — Start This Week - Page 4

40+ driving jobs in Winter Park, FL hiring now — CDL, delivery driver, courier & more. $18–$90K+, many with benefits. See what's open in Winter Park.

Heavy Freight Logistics

Heavy Freight Logistics Needs Independent Contractor Driver-Cargo Van

Winter Park, FL

$5,000 - $8,500

On-Demand Tasks Network

Winter Park Contractor Independent Contractor Driver-On-demand Errands

Winter Park, FL

$2,000 - $4,000

Urban Pedal Logistics

FL Career:Independent Contractor Driver-Urban E-bike/scooter Courier

Winter Park, FL

$2,500 - $4,500

Regional Expedite Logistics

Regional Expedite Logistics seeks Independent Contractor Driver-Long

Winter Park, FL

$3,500 - $6,000

Last updated: May 11, 2026