Driving Jobs in Winter Park, FL — Apply Today

As of May 2026, there are 40+ open driving positions in Winter Park, FL. Current pay ranges from $840 to $8,500 per year. Most openings are in Delivery Driver. New roles are posted daily — listings on this page are verified and updated regularly.

Urban Pedal Logistics

Work in Winter Park:Independent Contractor Driver-Urban E-bike/scooter

Winter Park, FL

$2,500 - $4,500

Corporate Catering Couriers

Winter Park-based Independent Contractor Driver-Catering Logistics

Winter Park, FL

$3,500 - $6,000

FreshDrop Logistics

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

Winter Park, FL

$3,000 - $5,500

Morning Express Couriers

Weekend Shift:Driver Opportunity-Winter Park

Winter Park, FL

$2,200 - $3,800

Grubhub

Grubhub Large Order Delivery Driver

Winter Park, FL

$3,500 - $6,000

Grubhub

Early Morning Grubhub Driver

Winter Park, FL

$1,870 - $3,230

Heavy Freight Logistics

Winter Park-based Independent Contractor Driver-Cargo Van / Box Truck

Winter Park, FL

$5,000 - $8,500

Final Mile Delivery Co.

Winter Park Career:Independent Contractor Driver-Final Mile Parcel at

Winter Park, FL

$3,000 - $5,500

Secure Document Couriers

Join Team in Winter Park:Independent Contractor Driver-Night Shift

Winter Park, FL

$2,800 - $5,000

Regional Expedite Logistics

Winter Park Contractor Independent Contractor Driver-Long Distance /

Winter Park, FL

$3,500 - $6,000

Suburban Delivery Network

Student Friendly:Driver Opportunity(Winter Park)

Winter Park, FL

$2,800 - $4,800

Local Shopper Partners

Urgent Hire in Winter Park:Courier

Winter Park, FL

$1,900 - $3,325

Driving Jobs in Winter Park — FAQ

How many driving jobs are available in Winter Park, FL right now?
There are currently 40+ open driving positions in Winter Park, 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 Park?
Driving job pay in Winter Park 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 Park?
Yes. Many delivery driver, courier, and DSP positions in Winter Park 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 Park?
Driving jobs in Winter Park 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 Park?
Benefits vary by employer, but many driving positions in Winter Park 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 Park?
Your take-home pay as a driver in Winter Park 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 Park?
Yes, many driving positions in Winter Park 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: May 04, 2026