Driving Jobs in Winter Garden, FL — Open Positions

As of May 2026, there are 50+ open driving positions in Winter Garden, FL. Current pay ranges from $14 to $85,000 per year. Top hiring areas include Delivery Driver, Cdl Driver and Dsp. New roles are posted daily — listings on this page are verified and updated regularly.

FedEx Ground

Apply Now:Delivery Driver-Package Handler in Winter Garden | Hiring

Winter Garden, FL

$21 - $26

Domino's Pizza

Delivery Driver-Pizza Delivery Tips Plus Wages Needed-Winter Garden

Winter Garden, FL

$14 - $20

Wayfair

Now Hiring in Winter Garden:Delivery Driver-Furniture And Appliance

Winter Garden, FL

$21 - $27

Quest Diagnostics

Winter Garden Full-time Delivery Driver-Medical Courier

Winter Garden, FL

$20 - $26

XPO Logistics

Delivery Driver-Package Handler Box Truck•Winter Garden,FL•XPO

Winter Garden, FL

$22 - $28

Instacart

Winter Garden-based Delivery Driver-Grocery Same Day Service Opening

Winter Garden, FL

$16 - $23

Schneider National

Join Schneider National in Winter Garden as a Delivery Driver-CDL

Winter Garden, FL

$70,000 - $85,000

DoorDash

Delivery Driver-Food Delivery Part Time Evenings-Winter Garden,FL

Winter Garden, FL

$15 - $22

Amazon Flex

Flexible Delivery Driver-Independent Contractor in Winter Garden,FL

Winter Garden, FL

$18 - $25

Express Logistics

Express Logistics Needs Delivery Driver-Full Time Local Routes in

Winter Garden, FL

$19 - $24

Roadie

Box Truck Delivery Driver

Winter Garden, FL

$4,500 - $7,800

Uber Eats

Daily Pay Delivery Driver

Winter Garden, FL

$2,800 - $4,800

Driving Jobs in Winter Garden — FAQ

How many driving jobs are available in Winter Garden, FL right now?
There are currently 50+ open driving positions in Winter Garden, 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 Garden?
Driving job pay in Winter Garden 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 Garden?
Yes. Many delivery driver, courier, and DSP positions in Winter Garden 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 Garden?
Driving jobs in Winter Garden 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 Garden?
Benefits vary by employer, but many driving positions in Winter Garden 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 Garden?
Your take-home pay as a driver in Winter Garden 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 Garden?
Yes, many driving positions in Winter Garden 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 50+ listings above and apply directly.

Last updated: May 10, 2026