Delivery Driver Jobs in Winter Garden, FL — Immediate Openings

As of May 2026, there are 133 delivery driver openings in Winter Garden, FL. Local pay ranges from $12 to $148,500/year. Listings are updated daily — benefits start Day 1 for most positions.

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

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

Staker Parson Companies

Student Friendly:Driver Opportunity(Winter Garden)

Winter Garden, FL

$27 - $34

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

Uber Eats

Night Shift Delivery Driver Needed-Winter Garden Area | Hiring

Winter Garden, FL

$3,100 - $5,300

FedEx Ground Independent Service Provider

Fedex Ground Route Delivery Driver(Contract)|Winter Garden

Winter Garden, FL

$3,500 - $5,500

Levin Furniture and Mattress

Part-Time Mattress Delivery Driver-2 Person Team Home Setup –

Winter Garden, FL

$19 - $25

DHL Express

Winter Garden Contract:Courier Driver

Winter Garden, FL

$3,600 - $5,200

Delivery Driver Jobs in Winter Garden — FAQ

How many delivery driver jobs are open in Winter Garden, FL?
There are currently 133+ delivery driver positions in Winter Garden, FL. New delivery driver roles are added regularly — check this page for the latest openings.
How much do delivery driver jobs pay in Winter Garden?
Delivery Driver pay in Winter Garden varies by employer, route type, and experience level. Many positions offer shift differentials, mileage bonuses, and sign-on bonuses. Browse the listings above to see pay details for each opening.
Do delivery driver jobs in Winter Garden require experience?
Many delivery driver positions in Winter Garden welcome entry-level applicants. Employers like Amazon, FedEx, and UPS often provide paid training. CDL positions may require a valid commercial license — check individual listings for specific requirements.
How do I apply for delivery driver jobs in Winter Garden?
Browse the 133+ delivery driver listings above, click on any position for full details including pay, schedule, and requirements, then follow the application link. Most driving positions have a simple online application.

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Other Driving Jobs in Winter Garden

Cdl Driver Jobs in Winter Garden

28 open positions

Other Driving Jobs in Winter Garden

12 open positions

DSP Driver Jobs in Winter Garden

3 open positions

Warehouse Jobs in Winter Garden

2 open positions

Yard Jockey Jobs in Winter Garden

1 open positions

Grocery Jobs in Winter Garden

1 open positions

Last updated: May 14, 2026