Driving Jobs in Winter Garden, FL — Apply Today

As of May 2026, there are 160+ open driving positions in Winter Garden, FL. Current pay ranges from $12 to $331,240 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.

Wayfair

$21-$27/hr Delivery Driver-Furniture And Appliance Home Installation

Winter Garden, FL

$21 - $27

Jack Cooper Transport

CDL A Truck Driver - Auto Hauler Car Transport

Winter Garden, FL

$106,400 - $151,200

Grubhub

Restaurant Delivery Driver•Winter Garden,FL•Grubhub | Hiring

Winter Garden, FL

$3,300 - $5,400

Quest Diagnostics

Medical Courier Delivery Driver

Winter Garden, FL

$2,940 - $4,410

Foremost Transport

Immediate Opening in Winter Garden for a Mobile Home Transport

Winter Garden, FL

$97,200 - $129,600

FedEx Custom Critical

Winter Garden Career:Expedited Sprinter Van Driver-Time Critical Cargo

Winter Garden, FL

$82,500 - $148,500

SCC Concrete

$32.00/hr Driver Opportunity-Winter Garden(PT)

Winter Garden, FL

$28 - $36

Amazon Flex

Package Delivery Driver•Winter Garden,FL•Amazon Flex | Hiring

Winter Garden, FL

$3,600 - $5,800

Quest Diagnostics

Medical Courier Delivery Driver|Flexible|Winter Garden

Winter Garden, FL

$15 - $22

Corporate Catering Couriers

Independent Contractor Driver-Catering Logistics Position in Winter

Winter Garden, FL

$3,500 - $6,000

Curri

Weekend Shift:Driver Opportunity-Winter Garden

Winter Garden, FL

$21 - $36

Corporate Catering Couriers

Independent Contractor Driver - Catering Logistics

Winter Garden, FL

$3,500 - $6,000

Driving Jobs in Winter Garden — FAQ

How many driving jobs are available in Winter Garden, FL right now?
There are currently 160+ 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 160+ listings above and apply directly.

Last updated: May 13, 2026