Delivery Driver Jobs in Winter Park, FL — See Openings

As of September 2026, there are 19 delivery driver openings in Winter Park, FL. Local pay ranges from $1,200 to $9,775/year. Listings are updated daily — benefits start Day 1 for most positions.

Regional Expedite Logistics

Independent Contractor Driver - Long Distance / Regional Courier

Winter Park, FL

$3,500 - $6,000

Urban Pedal Logistics

Independent Contractor Driver - Urban E-Bike/Scooter Courier

Winter Park, FL

$2,300 - $4,140

On-Demand Tasks Network

Independent Contractor Driver - On-Demand Errands (TaskRabbit/Roadie)

Winter Park, FL

$2,240 - $4,480

Heavy Freight Logistics

Independent Contractor Driver - Cargo Van / Box Truck Specialist

Winter Park, FL

$5,750 - $9,775

Secure Document Couriers

Independent Contractor Driver - Night Shift Legal/Document Courier

Winter Park, FL

$2,940 - $5,250

Local Merchant Delivery Network

Independent Contractor Driver - Early Morning Bakery/Floral

Winter Park, FL

$2,640 - $4,620

Corporate Catering Couriers

Independent Contractor Driver - Catering Logistics

Winter Park, FL

$3,185 - $5,460

Final Mile Delivery Co.

Independent Contractor Driver - Final Mile Parcel

Winter Park, FL

$2,730 - $5,005

Auto Logistics Pros

Independent Contractor Driver - Auto Parts Courier

Winter Park, FL

$2,464 - $4,224

United Parcel Service (UPS)

UPS Package Delivery Driver

Winter Park, FL

$4,480 - $8,400

Domino's Pizza

Domino's Pizza(Winter Park)Hiring:Pizza Delivery Driver | Apply Now

Winter Park, FL

$2,625 - $4,410

FedEx Ground

Winter Park Career:Delivery Driver at Fedex Ground | Hiring

Winter Park, FL

$4,256 - $5,824

Delivery Driver Jobs in Winter Park — FAQ

How many delivery driver jobs are open in Winter Park, FL?
There are currently 19+ 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 19+ 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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1 open positions

Last updated: September 11, 2026