Driving Jobs in Winter Garden, FL — Start This Week

As of October 2026, there are 60+ open driving jobs in Winter Garden, FL. Current pay ranges from $15 to $135,000 per year. Top hiring areas include Delivery Driver, Owner Operator and General. New roles are posted daily — listings on this page are verified and updated regularly.

Levin Furniture and Mattress

Winter Garden:Mattress Delivery Driver-2 Person Team Home Setup

Winter Garden, FL

$21 - $28

Southern Glazer's Wine & Spirits

Join Southern Glazer's Wine & Spirits in Winter Garden as a Wine And

Winter Garden, FL

$25 - $31

FedEx

Start ASAP:Driver Opportunity(Winter Garden)

Winter Garden, FL

$3,500 - $6,500

Corporate Catering Couriers

Independent Contractor Driver - Catering Logistics

Winter Garden, FL

$3,675 - $6,300

Urban Pedal Logistics

Urgent Hire in Winter Garden:Driver Opportunity

Winter Garden, FL

$2,500 - $4,500

Pella Windows and Doors

Glass And Window Delivery Driver-CDL B Flatbed•Winter Garden,FL•Pella

Winter Garden, FL

$22 - $27

Auto Logistics Pros

Driver Opportunity(Part-Time)@ Auto Logistics Pros-Winter Garden

Winter Garden, FL

$2,800 - $4,800

Canteen

Vending Machine Delivery Driver And Route Service•Winter

Winter Garden, FL

$15 - $20

Bimbo Bakeries USA

Join Bimbo Bakeries USA in Winter Garden as a Bakery Product Delivery

Winter Garden, FL

$20 - $28

Urban Pedal Logistics

Independent Contractor Driver - Urban E-Bike/Scooter Courier

Winter Garden, FL

$2,500 - $4,500

Regional Expedite Logistics

[Part-Time] Driver Opportunity-Winter Garden

Winter Garden, FL

$3,500 - $6,000

General Beer Northeast

General Beer Northeast seeks Beer Delivery Driver-CDL A Distributor

Winter Garden, FL

$27 - $34

Driving Jobs in Winter Garden — FAQ

How many driving jobs are available in Winter Garden, FL right now?
There are currently 60+ 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 60+ open routes above and apply directly.

Last updated: October 28, 2026