Driving Jobs in Winter Park, FL — Apply Today

As of September 2026, there are 20+ open driving positions in Winter Park, FL. Current pay ranges from $1,200 to $9,775 per year. Top hiring areas include Delivery Driver and Dsp. New roles are posted daily — listings on this page are verified and updated regularly.

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

Amazon DSP

Delivery Driver•Winter Park,FL•Amazon DSP | Hiring

Winter Park, FL

$3,080 - $4,224

Driving Jobs in Winter Park — FAQ

How many driving jobs are available in Winter Park, FL right now?
There are currently 20+ open driving positions in Winter Park, FL. These include delivery drivers, CDL truck drivers, couriers, bus drivers, DSP drivers, and local route positions. New jobs are added daily.
How much do driving jobs pay in Winter Park?
Driving job pay in Winter Park varies by role: Delivery drivers earn $18–$25/hr, CDL truck drivers $55K–$90K+/year, couriers $16–$22/hr, and bus drivers $20–$30/hr. Night and weekend routes often pay premium rates.
Can I get a driving job with no experience in Winter Park?
Yes. Many delivery driver, courier, and DSP positions in Winter Park require no prior experience and provide paid training. Delivery driver positions require a valid driver's license but no CDL. Some carriers offer free CDL training programs.
What schedules do driving jobs offer in Winter Park?
Driving jobs in Winter Park offer flexible schedules: day routes (6 AM–4 PM), evening routes (1 PM–10 PM), overnight/line haul (6 PM–6 AM), and weekend-only schedules (Fri–Sun or Sat–Mon). Part-time and gig-style shifts are also available. Overnight and weekend routes typically pay premium rates.
What benefits do driving jobs offer in Winter Park?
Benefits vary by employer, but many driving positions in Winter Park offer: health, dental, and vision insurance; 401(k) or retirement plans; paid time off; sign-on bonuses; weekly or daily pay; company-provided vehicles for delivery positions; and CDL training assistance from select employers.
How much do drivers take home after taxes in Winter Park?
Your take-home pay as a driver in Winter Park depends on your pay rate, hours worked, and state tax rate. For example, a delivery driver earning $22/hr in a no-tax state like Texas takes home about $750/week, while in California it's closer to $670/week after state tax.
Are driving companies hiring immediately in Winter Park?
Yes, many driving positions in Winter Park are hiring immediately with start dates within 1–2 weeks of applying. Delivery driver and courier roles often offer same-week start dates. Browse the 20+ listings above and apply directly.

Last updated: September 11, 2026