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Find Truck Insurance Agents Near You in Winchester, MA

Browse truck insurance agents serving Winchester, Massachusetts. Updated 2026-07-14.

The top-rated truck insurance agent in Winchester, Massachusetts is Scotti Insurance Agency, rated 4.3 stars across 14 reviews. Other highly rated options include Saltmarsh Insurance Agency, Admiralty Insurance Agency Inc, John A Pierce Insurance Inc. This directory lists 13 truck insurance agents serving Winchester.

Showing 13 truck insurance agents in Winchester, MAListings are displayed in no particular order and are not ranked. Order does not constitute a recommendation or endorsement.

Comparison

Top 10 listings
#NameAddressPhone
1Scotti Insurance Agency19 Mt Vernon St(781) 729-9200
2Saltmarsh Insurance Agency751 Main St(781) 729-4615
3Admiralty Insurance Agency Inc2 Central St(781) 721-5500
4John A Pierce Insurance Inc934 Main St(781) 729-8770
5W Allan Wilde & Son Insurance Agency, Inc.887 Main St #1911(781) 729-1400
6Horace Mann Insurance Co895 Main St(781) 368-9029
7Furey Insurance28 Church St #8(781) 721-5758
8Northeast Adjustment Bureau24 River St(781) 721-3300
9Barry & McHugh Insurance Inc10 Skillings Rd(781) 729-6600
10BARRY FREEMAN895 Main St(781) 368-9029
SI
19 Mt Vernon St
Scotti Insurance Agency
Truck Insurance Agent · Winchester, MA

Scotti Insurance Agency serves the greater Winchester, Massachusetts area as a truck insurance agent. This agency helps local truck operators secure essential commercial coverage to meet the specific demands of transporting freight. Policies for liability, cargo protection, and physical damage are tailored to the unique risks of working on regional roadways and highways. The agency also assists with compliance documents that carriers need to legally operate across state and local routes, handling both owner-operator and fleet requirements. Scotti Insurance Agency specifically manages liability coverage and cargo insurance for trucks.

SI
751 Main St
Saltmarsh Insurance Agency
Truck Insurance Agent · Winchester, MA

Saltmarsh Insurance Agency provides truck insurance coverage for operators in the Winchester area, offering policies tailored to local commercial driving needs and industry compliance requirements. The agency works with drivers to maintain proper protection for their vehicles through standard coverage options and periodic policy reviews. It services a range of commercial properties, including the small retail stores, restaurants, and single-family homes that often require additional fleet policy management for delivery or service trucks.

AI
2 Central St
Admiralty Insurance Agency Inc
Truck Insurance Agent · Winchester, MA

Serving Winchester, Massachusetts, and the surrounding communities, Admiralty Insurance Agency Inc handles truck insurance for commercial vehicle operators. The firm manages coverage needs including liability, physical damage, and cargo protection for local and regional fleets. It assists clients in evaluating policy options that meet regulatory requirements and operational demands. To handle a typical job, the agency first reviews the client’s driving routes and fleet size, then identifies suitable insurers offering tailored protection and competitive terms.

JP
934 Main St
John A Pierce Insurance Inc
Truck Insurance Agent · Winchester, MA

John A Pierce Insurance Inc serves professional trucking companies, owner-operators, and independent haulers operating throughout Winchester and the broader Middlesex County area. The agency focuses on securing commercial auto and cargo liability policies tailored to regional freight routes. Protection extends across fleet vehicles, non-trucking liability, and physical damage coverage customarily required by local regulations. Every policy is structured to address unique transit risks typical of this zone. It also covers adjacent communities within the Greater Boston metropolitan region, including Woburn and Lexington.

WA
887 Main St #1911
W Allan Wilde & Son Insurance Agency, Inc.
Truck Insurance Agent · Winchester, MA

W Allan Wilde & Son Insurance Agency, Inc. in Winchester provides specialized truck insurance coverage tailored for commercial vehicles operating in the Boston area. It also offers broader business and personal insurance services to meet the varied needs of local clients. Given the harsh New England winters, the agency helps trucking clients secure policies that address increased risks of icy roads and collision-related cargo damage.

HM
895 Main St
Horace Mann Insurance Co
Truck Insurance Agent · Winchester, MA

As spring thaws bring road construction and increased traffic through the Winchester area, trucking operators in Middlesex County need reliable protection for their commercial fleets. Horace Mann Insurance Co serves as a truck insurance agent, helping local businesses secure coverage for liability, physical damage, and cargo during the busy shipping season. Agents here assess each operator’s specific routes, vehicle types, and cargo risk. The process typically begins with a detailed review of the fleet’s safety records and a walk-around inspection of the trucks to verify their condition.

FI
28 Church St #8
Furey Insurance
Truck Insurance Agent · Winchester, MA

Furey Insurance provides truck insurance coverage for operators in the Winchester area, placing emphasis on both standard liability and physical damage policies to protect vehicles and cargo. Specialty add-ons commonly include bobtail insurance for non-business use and coverage for hazardous materials hauling. The agency serves a range of commercial sectors that require reliable vehicle and fleet protection, including local businesses running trucking operations to support small offices, nearby warehouses, and food service distribution companies.

NA
24 River St
Northeast Adjustment Bureau
Truck Insurance Agent · Winchester, MA

Northeast Adjustment Bureau offers both one-time policy reviews and ongoing service options for truck insurance clients. As a local agent in Winchester, MA, the agency helps commercial truck operators select coverage that protects their vehicles, cargo, and liability exposures on the road. Regular policy adjustments may be necessary as routes or fleet sizes change. Service runs on either a scheduled or as-needed basis depending on client preference.

BM
10 Skillings Rd
Barry & McHugh Insurance Inc
Truck Insurance Agent · Winchester, MA

Barry & McHugh Insurance Inc, based in Winchester, MA, serves local trucking businesses by securing liability and physical damage coverage for commercial fleets and owner-operators. The agency helps operators evaluate risks unique to this region, matching policies to cargo type and route frequency. They provide hands-on guidance through filing and claim processes, ensuring timely resolution of vehicle repairs or loss events. For added protection, the firm can arrange coverage for non-trucking liability when the vehicle is used for personal trips.

BF
895 Main St
BARRY FREEMAN
Truck Insurance Agent · Winchester, MA

Barry Freeman operates as a truck insurance agent in Winchester, focusing on residential service for private owners of commercial vehicles. He assists local operators with the necessary coverage for their trucks in the Winchester area and surrounding communities. Clients benefit from regular consultations to review changing protection requirements for their cargo and equipment. He adjusts policies as needed to match new routes or updated vehicle specs, and he remains available for follow-up assistance in between those scheduled visits.

JM
10 Skillings Rd
Jay M Finn Insurance
Truck Insurance Agent · Winchester, MA
(781) 729-5724
barryfinn.com
DI
10 Skillings Rd
Ducey Insurance Agency
Truck Insurance Agent · Winchester, MA
(781) 235-6795
BH
175 Washington St # C24
Black Horse Insurance
Truck Insurance Agent · Winchester, MA
(781) 729-1164
blackhorseinsurance.com

What Does a a Truck Insurance Agent in Winchester Cost?

Typical annual premiums for truck insurance in Massachusetts range from 8000 to 15000 dollars for a single owner-operator with a clean record. Fleet policies can cost 25000 dollars or more depending on vehicle count and cargo type. Factors like driving history vehicle value and coverage limits affect the final price. This is general information not insurance advice.

About truck insurance agents in Winchester

Truck insurance agents in Winchester Massachusetts help owner-operators and fleet managers secure the right commercial auto coverage. Massachusetts requires all commercial trucks to carry liability insurance with minimum limits of 750000 dollars for bodily injury per accident. Local agents understand the specific filing requirements of the Massachusetts Division of Insurance and can guide you through the process.

Frequently Asked Questions

What types of truck insurance do agents in Winchester offer?

Agents typically offer liability coverage physical damage coverage cargo insurance and non-trucking liability. They also provide coverage for hired and non-owned trucks as needed for Massachusetts-based operations.

Do I need a specific license to drive a commercial truck in Massachusetts?

Yes Massachusetts requires a Commercial Drivers License (CDL) for vehicles over 26000 pounds gross vehicle weight rating or those carrying hazardous materials. Your insurance agent can help ensure your policy matches your CDL class.

How does Massachusetts law affect my truck insurance rates?

Massachusetts is a fault state meaning the at-fault driver pays for damages. This can increase rates for drivers with accidents. The state also mandates uninsured motorist coverage which adds to premium costs.

Truck Insurance Agents in Other Massachusetts Cities

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.