Delivery Driver Jobs in Winter Garden, FL — Start This Week

As of May 2026, there are 113 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.

Wayfair

$21-$27/hr Delivery Driver-Furniture And Appliance Home Installation

Winter Garden, FL

$21 - $27

Grubhub

Restaurant Delivery Driver•Winter Garden,FL•Grubhub | Hiring

Winter Garden, FL

$3,300 - $5,400

Quest Diagnostics

Medical Courier Delivery Driver

Winter Garden, FL

$2,940 - $4,410

FedEx Custom Critical

Winter Garden Career:Expedited Sprinter Van Driver-Time Critical Cargo

Winter Garden, FL

$82,500 - $148,500

SCC Concrete

$32.00/hr Driver Opportunity-Winter Garden(PT)

Winter Garden, FL

$28 - $36

Amazon Flex

Package Delivery Driver•Winter Garden,FL•Amazon Flex | Hiring

Winter Garden, FL

$3,600 - $5,800

Quest Diagnostics

Medical Courier Delivery Driver|Flexible|Winter Garden

Winter Garden, FL

$15 - $22

Corporate Catering Couriers

Independent Contractor Driver-Catering Logistics Position in Winter

Winter Garden, FL

$3,500 - $6,000

Curri

Weekend Shift:Driver Opportunity-Winter Garden

Winter Garden, FL

$21 - $36

Corporate Catering Couriers

Independent Contractor Driver - Catering Logistics

Winter Garden, FL

$3,500 - $6,000

Sherwin-Williams

Part-Time Paint Store Delivery Driver-Commercial Accounts –

Winter Garden, FL

$18 - $24

DoorDash

Weekend Delivery Driver•Winter Garden,FL•Doordash | Hiring

Winter Garden, FL

$2,200 - $3,800

Delivery Driver Jobs in Winter Garden — FAQ

How many delivery driver jobs are open in Winter Garden, FL?
There are currently 113+ 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 113+ 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 13, 2026