Driving Jobs in Winter Garden, FL — Now Hiring

As of September 2026, there are 40+ open driving positions in Winter Garden, FL. Current pay ranges from $14 to $115,500 per year. Top hiring areas include Delivery Driver, Cdl Driver and Part Time. New roles are posted daily — listings on this page are verified and updated regularly.

Atlas Van Lines

CDL A Household Goods Mover Truck Driver

Winter Garden, FL

$89,250 - $115,500

Stevens Trucking

CDL A Livestock Hauler Truck Driver - Cattle Transport

Winter Garden, FL

$72,250 - $97,750

AAA Roadside

CDL B Tow Truck Driver - Heavy Duty Recovery

Winter Garden, FL

$28 - $40

Waste Management

CDL B Garbage Truck Driver - Residential Refuse

Winter Garden, FL

$28 - $37

Cersosimo Lumber Company

CDL A Log Truck Driver - Forestry Hauler

Winter Garden, FL

$32 - $41

Heavy Legacy LLC

CDL A Frac Sand Driver - Oilfield West Texas

Winter Garden, FL

$76,500 - $106,250

SCC Concrete

CDL B Truck Driver - Ready Mix Concrete Mixer

Winter Garden, FL

$28 - $36

Staker Parson Companies

CDL A Dump Truck Driver - Local Aggregate Hauling

Winter Garden, FL

$27 - $34

Old Dominion Freight Line

CDL A Truck Driver - LTL Pickup and Delivery

Winter Garden, FL

$80,000 - $95,000

J.B. Hunt Intermodal

CDL A Truck Driver - Intermodal Container Drayage

Winter Garden, FL

$78,750 - $99,750

Regional Expedite Logistics

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

Winter Garden, FL

$3,500 - $6,000

Urban Pedal Logistics

$40.50/hr Driver Opportunity-Winter Garden(PT)

Winter Garden, FL

$2,500 - $4,500

Driving Jobs in Winter Garden — FAQ

How many driving jobs are available in Winter Garden, FL right now?
There are currently 40+ 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 40+ listings above and apply directly.

Last updated: September 09, 2026