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HomeTruck Insurance AgentsFlorida › Winter Haven

Find Truck Insurance Agents Near You in Winter Haven, FL

Browse truck insurance agents serving Winter Haven, Florida. Updated 2026-07-14.

The top-rated truck insurance agent in Winter Haven, Florida is Rob Semans - State Farm Insurance Agent, rated 4.9 stars across 984 reviews. Other highly rated options include Team Barfield - Barfield Insurance, Acceptance Insurance, Freeway Insurance. This directory lists 18 truck insurance agents serving Winter Haven.

Showing 18 truck insurance agents in Winter Haven, FLListings are displayed in no particular order and are not ranked. Order does not constitute a recommendation or endorsement.

Comparison

Top 10 listings
#NameAddressPhone
1Rob Semans - State Farm Insurance Agent639 1st St S(863) 299-1274
2Team Barfield - Barfield Insurance141 5th St NW #302(863) 662-3134
3Acceptance Insurance910 Havendale Blvd NW #134(863) 733-7006
4Freeway Insurance1136 6th St NW(863) 733-7003
5Direct Auto Insurance5937 Cypress Gardens Blvd Ste 200(863) 969-4916
6Barfield Insurance & Financial Services Inc.110 Spirit Lake Rd Unit 5(863) 293-5400
7Joseph Bullington: Allstate Insurance1900 Havendale Blvd NW ste c(863) 299-6449
8Ryan Gunkel - GEICO Insurance Agent5935 Cypress Gardens Blvd Suite 200(863) 269-4700
9Zinsmeister - Your Home, Boat & Auto Insurance Agency1211 6th St SE(863) 294-1034
10GreatFlorida Insurance: Brock Schnabel5658 Cypress Gardens Blvd(863) 594-2600
RS
639 1st St S
Rob Semans - State Farm Insurance Agent
Truck Insurance Agent · Winter Haven, FL

Rob Semans - State Farm Insurance Agent serves Polk County from its Winter Haven, Florida location. This agency focuses on truck insurance coverage for commercial operators and owner-operators. Their truck insurance agents help local drivers secure the liability protection required for over-the-road operations. The team assists with quotes for physical damage coverage on heavy trucks and trailers. Additional services for this area include connecting clients with local policy options for non-trucking liability and cargo insurance.

TB
141 5th St NW #302
Team Barfield - Barfield Insurance
Truck Insurance Agent · Winter Haven, FL

Team Barfield - Barfield Insurance provides truck insurance agent services to commercial drivers and fleet operators in Winter Haven, Florida. Its offerings typically include liability, physical damage, and cargo coverage for heavy trucks. Service plans often involve policy reviews to ensure adequate protection for changing operational needs. The firm helps clients manage risk associated with local and regional hauling. Its service approach emphasizes clear policy explanations and claims guidance. The agency services single-family homes, apartments, retail, and restaurants.

AI
910 Havendale Blvd NW #134
Acceptance Insurance
Truck Insurance Agent · Winter Haven, FL

Acceptance Insurance specializes in providing tailored truck insurance policies for commercial and local haulers in Winter Haven, Florida. It also handles general vehicle, property, and liability coverage to support business and personal needs. Located in Polk County, this agency assists operators with balancing fleet requirements and individual risks common to regional routes. It helps clients manage insurance adjustments during peak produce shipping seasons, when fleet exposure increases due to higher traffic and fluctuating cargo loads.

FI
1136 6th St NW
Freeway Insurance
Truck Insurance Agent · Winter Haven, FL

As truckers along the I-4 corridor and surrounding citrus groves face busy harvest and holiday shipping seasons, securing reliable coverage becomes an urgent priority. Freeway Insurance, serving the Winter Haven, Florida area, addresses this need by connecting commercial drivers with necessary liability and cargo protection. Their agents work directly with local independent operators and fleet owners to tailor policies that meet state requirements and daily operational risks. The process begins with a straightforward review of driving history, vehicle specifications, and typical hauling routes to determine suitable coverage options.

DA
5937 Cypress Gardens Blvd Ste 200
Direct Auto Insurance
Truck Insurance Agent · Winter Haven, FL

Direct Auto Insurance provides truck insurance coverage for operators in Winter Haven and the surrounding area, specializing in policies designed for commercial vehicles. They offer liability, cargo, and physical damage protections that address the specific needs of truck drivers and fleet owners. This agency works with independent long-haul operators, local delivery services, and businesses that require dependable coverage for their transport vehicles. Clients include those managing offices, warehouses, and food service operations throughout the region.

BI
110 Spirit Lake Rd Unit 5
Barfield Insurance & Financial Services Inc.
Truck Insurance Agent · Winter Haven, FL

Barfield Insurance & Financial Services Inc. serves local trucking and freight businesses in the Winter Haven, FL area, offering commercial truck insurance coverage tailored to the unique risks of the transportation industry. The agency provides protection for truck fleets, owner-operators, and independent haulers, including liability, cargo, and physical damage policies. Their offerings help businesses manage regulatory compliance and unexpected losses on the road. The company also extends its truck insurance services to clients in the neighboring community of Lake Wales and the broader Polk County region.

JB
1900 Havendale Blvd NW ste c
Joseph Bullington: Allstate Insurance
Truck Insurance Agent · Winter Haven, FL

Located in Winter Haven, FL, this agency serves the surrounding communities in Polk County and central Florida. It handles a variety of policies for truck insurance needs. The agency works with clients to evaluate different levels of protection for commercial vehicles. It also addresses issues like cargo liability and physical damage coverage. To handle a typical job, the agent begins with a discussion of the client’s routes and cargo, then recommends appropriate coverage options while explaining the policy terms in plain language.

RG
5935 Cypress Gardens Blvd Suite 200
Ryan Gunkel - GEICO Insurance Agent
Truck Insurance Agent · Winter Haven, FL

Ryan Gunkel - GEICO Insurance Agent in Winter Haven, FL, assists clients in choosing between one-time liability coverage for short hauls and recurring policies for regular trucking operations. The agency provides insurance for delivery vehicles, over-the-road rigs, and local commercial trucks, addressing the distinct needs of the area’s logistics providers. Gunkel focuses on explaining coverage options to ensure fleets meet state requirements. Service is primarily offered on an as-needed basis for policy adjustments and new enrollments, with scheduled support available for renewals or any policy-related questions.

ZY
1211 6th St SE
Zinsmeister - Your Home, Boat & Auto Insurance Agency
Truck Insurance Agent · Winter Haven, FL

Zinsmeister - Your Home, Boat & Auto Insurance Agency in Winter Haven, FL offers specialized truck insurance agent services that address the unique liability and cargo needs of commercial drivers. The agency also works with clients on standard personal auto, home, and boat insurance policies. Understanding Florida’s fluctuating weather patterns, the team helps truck operators adjust their coverage for hurricane season when heavy rain and strong winds increase the risk of roadside accidents and cargo damage.

GI
5658 Cypress Gardens Blvd
GreatFlorida Insurance: Brock Schnabel
Truck Insurance Agent · Winter Haven, FL

As fleet schedules intensify with the citrus harvest and central Florida's peak shipping season, securing adequate coverage for commercial vehicles becomes a practical necessity. GreatFlorida Insurance: Brock Schnabel in Winter Haven addresses this demand by helping truck operators match their policies to local hauling routes and cargo types. The process involves reviewing driver logs, equipment value, and typical mileage within the region. This initial assessment helps ensure that coverage limits are aligned with the specific risks encountered on area highways and agricultural roads.

DM
6380 Cypress Gardens Blvd
Dan Mann - State Farm Insurance Agent
Truck Insurance Agent · Winter Haven, FL
(863) 318-8881
danmanninsurance.com
AI
3610 Havendale Blvd
American Insurance Inc
Truck Insurance Agent · Winter Haven, FL
(863) 965-2886
americaninsuranceinc.com
LM
600 3rd St SW
Lacy McClintock - State Farm Insurance Agent
Truck Insurance Agent · Winter Haven, FL
(863) 294-3580
teamlacy.com
GI
116 W Central Ave
Garland Insurance fka Victory Insurance
Truck Insurance Agent · Winter Haven, FL
(863) 683-9334
CI
3021 Cypress Gardens Rd
Cypress Insurance Management
Truck Insurance Agent · Winter Haven, FL
(863) 326-1885
cypressinsuranceonline.com
SI
3395 Cypress Gardens Rd
Sealy Insurance
Truck Insurance Agent · Winter Haven, FL
(863) 324-3100
CM
205 Ave G SW
Carroll-Marshall Insurance, Inc.
Truck Insurance Agent · Winter Haven, FL
(863) 293-1111
cminsure.com
DI
190 Avenue A NW
Dershimer Insurance Agency
Truck Insurance Agent · Winter Haven, FL
(863) 299-8330
dershimerinsurance.com

What Does a a Truck Insurance Agent in Winter Haven Cost?

Truck insurance costs in Florida vary widely based on driving history, cargo type, and annual mileage. A basic liability policy for a single truck may start around 3 thousand to 5 thousand dollars per year. Full coverage with cargo and physical damage can range from 8 thousand to 15 thousand dollars annually. This is general information and not insurance advice.

About truck insurance agents in Winter Haven

Truck insurance agents in Winter Haven Florida assist owner operators and fleet managers with commercial auto policies. Florida law requires minimum liability coverage of 50 thousand dollars per person and 100 thousand dollars per accident for trucks. Agents can help you meet Florida Department of Transportation filing requirements and obtain cargo or physical damage coverage.

Frequently Asked Questions

What minimum liability coverage do trucks need in Florida?

Florida requires commercial trucks to carry at least 50 thousand dollars in bodily injury liability per person and 100 thousand dollars per accident. Higher limits are often needed for interstate hauling or to comply with broker contracts.

Do I need a specific filing to operate a truck in Winter Haven?

Yes. Florida requires proof of insurance filed with the Department of Highway Safety and Motor Vehicles. Your agent can file the SR 22 or FR 44 form if needed and help you meet the state self-insurance requirements for large fleets.

Can a Winter Haven agent help with cargo insurance for my truck?

Yes. Many agents offer cargo insurance that covers goods being transported. This is often required by shippers and brokers. Typical cargo limits range from 10 thousand to 100 thousand dollars depending on the load value.

Listings are compiled from publicly available information. Inclusion does not constitute endorsement. Verify each truck insurance agent's credentials and current standing with your state Department of Insurance.