Driving Jobs in Winter Park, FL — Hiring Now

As of October 2026, there are 50+ open driving positions in Winter Park, FL. Current pay ranges from $14 to $85,000 per year. Top hiring areas include Delivery Driver, General and Dsp. New roles are posted daily — listings on this page are verified and updated regularly.

Local Merchant Delivery Network

Independent Contractor Driver - Early Morning Bakery/Floral

Winter Park, FL

$2,640 - $4,620

United States Postal Service

United States Postal Service Needs Rural Carrier Associate(RCA)in

Winter Park, FL

$3,400 - $4,800

Walmart Spark

Winter Park:Delivery Driver(Contractor,$2.6k-$4.1k/Month) | Hiring

Winter Park, FL

$2,576 - $4,140

Instacart

Start ASAP:Driver Opportunity(Winter Park)

Winter Park, FL

$2,900 - $4,800

United Parcel Service (UPS)

UPS Package Delivery Driver

Winter Park, FL

$4,480 - $8,400

Quest Diagnostics

$23.00/hr Driver Opportunity-Winter Park(PT)

Winter Park, FL

$20 - $26

Schneider National

Driver Opportunity needed in Winter Park(Apply Now)

Winter Park, FL

$70,000 - $85,000

Auto Logistics Pros

Independent Contractor Driver - Auto Parts Courier

Winter Park, FL

$2,464 - $4,224

DoorDash

Driver Opportunity needed in Winter Park(Apply Now)

Winter Park, FL

$2,400 - $4,200

Final Mile Delivery Co.

Independent Contractor Driver - Final Mile Parcel

Winter Park, FL

$2,730 - $5,005

Amazon DSP

Delivery Driver•Winter Park,FL•Amazon DSP | Hiring

Winter Park, FL

$3,080 - $4,224

Amazon Flex

Winter Park Needs:Driver Opportunity(Part-Time)

Winter Park, FL

$4,500 - $7,500

Driving Jobs in Winter Park — FAQ

How many driving jobs are available in Winter Park, FL right now?
There are currently 50+ 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 50+ listings above and apply directly.

Last updated: October 03, 2026