Driving Jobs in Winter Garden, FL — Start This Week

As of October 2026, there are 250+ open driving positions in Winter Garden, FL. Current pay ranges from $12 to $382,200 per year. Top hiring areas include Delivery Driver, Cdl Driver and General. New roles are posted daily — listings on this page are verified and updated regularly.

First Student

School Bus Driver - CDL B with Passenger and S Endorsements

Winter Garden, FL

$21 - $30

Heavy Freight Logistics

Driver Opportunity(Part-Time)@ Heavy Freight Logistics-Winter Garden

Winter Garden, FL

$4,750 - $8,075

Health Transit Logistics

Flexible Hours:Medical & Pharmacy Package Courier-Winter Garden

Winter Garden, FL

$3,200 - $4,500

Sysco

Part-Time Role in Winter Garden:Foodservice Delivery Driver-CDL A

Winter Garden, FL

$72,250 - $89,250

E-Comm Transit Solutions

Courier needed in Winter Garden(Apply Now)

Winter Garden, FL

$3,200 - $4,800

Regional Expedite Logistics

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

Winter Garden, FL

$3,500 - $6,000

Local Merchant Delivery Network

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

Winter Garden, FL

$2,400 - $4,200

AquaDrop Delivery

Winter Garden Job:Home & Office Beverage Step Van Driver(Full-time)

Winter Garden, FL

$3,780 - $5,460

Gopuff

Gopuff Winter Garden:Part-Time Delivery Driver-On-demand Essentials

Winter Garden, FL

$12 - $18

The Home Depot

Winter Garden Part-Time Opening:Home Depot Pro Delivery Driver-CDL

Winter Garden, FL

$23 - $31

Coach USA

Charter Bus Driver - CDL B with Passenger Endorsement

Winter Garden, FL

$22 - $32

Amazon Flex

Driver Opportunity needed in Winter Garden(Apply Now)

Winter Garden, FL

$18 - $25

Driving Jobs in Winter Garden — FAQ

How many driving jobs are available in Winter Garden, FL right now?
There are currently 250+ 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 250+ listings above and apply directly.

Last updated: October 03, 2026