Driving Jobs in Winter Garden, FL — Hiring Now

As of May 2026, there are 180+ 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.

XPO Logistics

Winter Garden Contract:Local City Driver

Winter Garden, FL

$5,000 - $8,000

Ferguson HVAC

Part-Time Job in Winter Garden – HVAC Parts Delivery Driver And

Winter Garden, FL

$19 - $26

Postmates

Work in Winter Garden:Same-day Delivery Driver | Hiring

Winter Garden, FL

$3,679 - $6,209

Amazon Delivery Service Partners

Winter Garden Contract:Amazon DSP Delivery Van Driver

Winter Garden, FL

$3,400 - $4,800

Roadie

Box Truck Delivery Driver

Winter Garden, FL

$4,095 - $7,098

US Postal Service Contractors

Highway Contract Route (HCR) Driver

Winter Garden, FL

$4,200 - $7,350

United States Postal Service

Neighborhood Postal Carrier

Winter Garden, FL

$3,600 - $5,500

Staker Parson Companies

Student Friendly:Driver Opportunity(Winter Garden)

Winter Garden, FL

$27 - $34

Schneider National

Winter Garden-based Delivery Driver-CDL Class A Regional Routes

Winter Garden, FL

$70,000 - $85,000

Quantix

CDL A Truck Driver - Regional Liquid Tanker Hazmat

Winter Garden, FL

$97,200 - $118,800

Walmart Spark

Walmart Spark Delivery Driver

Winter Garden, FL

$2,940 - $4,725

Medline Industries

Medline Medical Supply Delivery Driver

Winter Garden, FL

$18 - $23

Driving Jobs in Winter Garden — FAQ

How many driving jobs are available in Winter Garden, FL right now?
There are currently 180+ 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 180+ listings above and apply directly.

Last updated: May 14, 2026