Driving Jobs in Winter Park, FL — See Openings

As of May 2026, there are 20+ open driving positions in Winter Park, FL. Current pay ranges from $14 to $85,000 per year. Top hiring areas include Delivery Driver and Cdl Driver. New roles are posted daily — listings on this page are verified and updated regularly.

FedEx Ground

Winter Park:Delivery Driver-Package Handler(Full-time,$21-$26/hr)

Winter Park, FL

$21 - $26

Domino's Pizza

Winter Park-based Delivery Driver-Pizza Delivery Tips Plus Wages

Winter Park, FL

$14 - $20

Wayfair

Wayfair(Winter Park)Hiring:Delivery Driver-Furniture And Appliance

Winter Park, FL

$21 - $27

Quest Diagnostics

Quest Diagnostics seeks Delivery Driver-Medical Courier

Winter Park, FL

$20 - $26

XPO Logistics

Winter Park,FL:Delivery Driver-Package Handler Box Truck at XPO

Winter Park, FL

$22 - $28

Instacart

Immediate Opening in Winter Park for a Delivery Driver-Grocery Same

Winter Park, FL

$16 - $23

Schneider National

Winter Park Delivery Driver-CDL Class A Regional Routes

Winter Park, FL

$70,000 - $85,000

DoorDash

Winter Park Delivery Driver-Food Delivery Part Time

Winter Park, FL

$15 - $22

Amazon Flex

Immediate Opening in Winter Park for a Delivery Driver-Independent

Winter Park, FL

$18 - $25

Express Logistics

Winter Park Career:Delivery Driver-Full Time Local Routes at Express

Winter Park, FL

$19 - $24

Grubhub

Winter Park-based Suburban Delivery Driver Opening | Hiring

Winter Park, FL

$3,360 - $5,488

DoorDash

Work in Winter Park:Morning Shift Delivery Driver | Hiring

Winter Park, FL

$2,700 - $4,600

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: May 10, 2026