Driving Jobs in Winter Garden, FL — Apply Today

As of September 2026, there are 30+ open driving jobs in Winter Garden, FL. Current pay ranges from $14 to $90,000 per year. Top hiring areas include Delivery Driver, Cdl B and Box Truck. New roles are posted daily — listings on this page are verified and updated regularly.

Mobile Tool Networks

Immediate Opening in Winter Garden for a Mobile Tool Sales Route

Winter Garden, FL

$5,175 - $9,200

AquaDrop Delivery

FL Career:Home Delivery Route Driver in Winter Garden | Hiring

Winter Garden, FL

$3,080 - $4,400

City Waste Solutions

City Waste Solutions is hiring a Residential Waste & Recycling Route

Winter Garden, FL

$4,095 - $5,915

Textile Transit Co.

Textile Transit Co.(Winter Garden)Hiring:Industrial Linen & Laundry

Winter Garden, FL

$4,000 - $5,800

Morning Crust Logistics

Morning Crust Logistics Needs Bakery & Bread Route Driver in Winter

Winter Garden, FL

$3,200 - $4,800

Prime Beverage Distributors

Urgent Hire:Beverage Distribution Route Driver in Winter Garden,FL

Winter Garden, FL

$4,400 - $7,040

SecureShred Logistics

Secureshred Logistics seeks Secure Document Destruction Route Driver

Winter Garden, FL

$3,496 - $4,784

BioSafe Transit

Immediate Opening in Winter Garden for a Medical Waste & Sharps Route

Winter Garden, FL

$4,480 - $6,160

SnackRoute Solutions

Apply Today:Vending & Micro-market Route Driver in Winter Garden,FL

Winter Garden, FL

$2,730 - $4,095

ProWear Logistics

Uniform & Apparel Route Driver Needed-Winter Garden Area | Hiring

Winter Garden, FL

$3,220 - $5,060

Transportation Concepts

Part-Time Non-cdl Box Truck Delivery Driver at Transportation

Winter Garden, FL

$20 - $26

Performance Foodservice

Part-Time CDL Class A Route Delivery Driver(Winter Garden) | Part

Winter Garden, FL

$70,000 - $90,000

Driving Jobs in Winter Garden — FAQ

How many driving jobs are available in Winter Garden, FL right now?
There are currently 30+ open driving jobs in Winter Garden, FL. They range from CDL-A truck driving and local home-daily routes to delivery, box truck, bus and non-CDL driving work. New routes are added daily.
How much do driving jobs pay in Winter Garden?
Pay in Winter Garden depends on the licence and the type of driving: delivery and non-CDL routes usually run $18–$26/hr, local CDL work $22–$32/hr, and CDL-A regional or OTR seats $1,200–$1,900 a week. Night runs and specialised freight such as flatbed or tanker pay more.
Are there driving jobs in Winter Garden with no experience?
Yes. Many employers in Winter Garden run paid CDL training or hire recent CDL school graduates, and non-CDL delivery, shuttle and rideshare work needs only a regular licence and a clean record.
Can I get a driving job in Winter Garden that is home every night?
Local routes in Winter Garden are home daily, including delivery, box truck, yard, dump truck and local CDL-A work. Regional runs get you home weekly, and OTR means longer stretches away for higher weekly pay.
Do I need a CDL to drive in Winter Garden?
Not for every job. Cargo van, sprinter, courier, shuttle and most 26' box truck routes need only a regular driver's licence. A CDL-B is needed for heavier straight trucks and buses, and a CDL-A for tractor-trailers.
What do employers check before hiring a driver in Winter Garden?
Your driving record for the last 3–5 years, a background check, and for commercial roles a DOT physical and drug test. Most insurers require drivers to be at least 21 for interstate work.
Which companies are hiring drivers immediately in Winter Garden?
Many carriers, delivery firms and local fleets in Winter Garden hire on a rolling basis, with start dates often within one to two weeks of applying. Browse the 30+ open routes above and apply directly.

Last updated: September 28, 2026