Delivery Driver Jobs in Winter Park, FL — Apply Today

As of May 2026, there are 40 delivery driver openings in Winter Park, FL. Local pay ranges from $840 to $8,500/year. Listings are updated daily — benefits start Day 1 for most positions.

Urban Pedal Logistics

Work in Winter Park:Independent Contractor Driver-Urban E-bike/scooter

Winter Park, FL

$2,500 - $4,500

Corporate Catering Couriers

Winter Park-based Independent Contractor Driver-Catering Logistics

Winter Park, FL

$3,500 - $6,000

FreshDrop Logistics

Hiring in Winter Park:Driver Opportunity(Part-Time)

Winter Park, FL

$3,000 - $5,500

Morning Express Couriers

Weekend Shift:Driver Opportunity-Winter Park

Winter Park, FL

$2,200 - $3,800

Grubhub

Grubhub Large Order Delivery Driver

Winter Park, FL

$3,500 - $6,000

Grubhub

Early Morning Grubhub Driver

Winter Park, FL

$1,870 - $3,230

Heavy Freight Logistics

Winter Park-based Independent Contractor Driver-Cargo Van / Box Truck

Winter Park, FL

$5,000 - $8,500

Final Mile Delivery Co.

Winter Park Career:Independent Contractor Driver-Final Mile Parcel at

Winter Park, FL

$3,000 - $5,500

Secure Document Couriers

Join Team in Winter Park:Independent Contractor Driver-Night Shift

Winter Park, FL

$2,800 - $5,000

Regional Expedite Logistics

Winter Park Contractor Independent Contractor Driver-Long Distance /

Winter Park, FL

$3,500 - $6,000

Suburban Delivery Network

Student Friendly:Driver Opportunity(Winter Park)

Winter Park, FL

$2,800 - $4,800

Local Shopper Partners

Urgent Hire in Winter Park:Courier

Winter Park, FL

$1,900 - $3,325

Delivery Driver Jobs in Winter Park — FAQ

How many delivery driver jobs are open in Winter Park, FL?
There are currently 40+ delivery driver positions in Winter Park, FL. New delivery driver roles are added regularly — check this page for the latest openings.
How much do delivery driver jobs pay in Winter Park?
Delivery Driver pay in Winter Park varies by employer, route type, and experience level. Many positions offer shift differentials, mileage bonuses, and sign-on bonuses. Browse the listings above to see pay details for each opening.
Do delivery driver jobs in Winter Park require experience?
Many delivery driver positions in Winter Park welcome entry-level applicants. Employers like Amazon, FedEx, and UPS often provide paid training. CDL positions may require a valid commercial license — check individual listings for specific requirements.
How do I apply for delivery driver jobs in Winter Park?
Browse the 40+ delivery driver listings above, click on any position for full details including pay, schedule, and requirements, then follow the application link. Most driving positions have a simple online application.

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Last updated: May 04, 2026