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Find Health Insurance Agents Near You in Winchester, MA

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

The top-rated health insurance agent in Winchester, Massachusetts is Scotti Insurance Agency, rated 4.3 stars across 14 reviews. Other highly rated options include Saltmarsh Insurance Agency, John A Pierce Insurance Inc, W Allan Wilde & Son Insurance Agency, Inc.. This directory lists 11 health insurance agents serving Winchester.

Showing 11 health 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
3John A Pierce Insurance Inc934 Main St(781) 729-8770
4W Allan Wilde & Son Insurance Agency, Inc.887 Main St #1911(781) 729-1400
5Horace Mann Insurance Co895 Main St(781) 368-9029
6Furey Insurance28 Church St #8(781) 721-5758
7Barry & McHugh Insurance Inc10 Skillings Rd(781) 729-6600
8BARRY FREEMAN895 Main St(781) 368-9029
9Jay M Finn Insurance10 Skillings Rd(781) 729-5724
10Black Horse Insurance175 Washington St # C24(781) 729-1164
SI
19 Mt Vernon St
Scotti Insurance Agency
Health Insurance Agent · Winchester, MA

Scotti Insurance Agency serves the Winchester, Massachusetts area as a local health insurance agent. This agency assists residents and businesses with navigating the complex health insurance marketplace. They offer guidance on selecting appropriate medical coverage and help clients understand plan options and benefits. Scotti Insurance Agency handles individual health plans and family coverage enrollments during open enrollment periods.

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

Saltmarsh Insurance Agency offers a range of health insurance services for individuals and families in Winchester, MA, including plan selection guidance and enrollment assistance. Its service offerings help clients review coverage options and manage ongoing policy needs, with maintenance support for updates and claims questions throughout the year. The agency assists with insurance solutions tailored for various properties, such as single-family homes, apartments, retail spaces, and restaurants.

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

John A Pierce Insurance Inc works with homeowners, families, and small business owners in Winchester to secure individual and group health insurance plans. The agency helps clients evaluate coverage options, compare plan benefits, and navigate enrollment periods each year. This health insurance agent focuses on matching each customer’s medical needs with a suitable policy from major carriers. The company also serves residents and business owners seeking coverage in the neighboring communities of Woburn and Medford.

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

Serving Winchester and the surrounding communities of Greater Boston, W Allan Wilde & Son Insurance Agency, Inc. specializes in health insurance coverage for individuals and families. It handles plan selection for private insurance, Medicare options, and group health benefits for local small businesses. The agency reviews each client’s medical needs and budget to compare available policies from multiple carriers. To handle a typical job, it first gathers the client’s current coverage details and health priorities before presenting tailored plan options that match their specific situation.

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

Horace Mann Insurance Co serves Winchester, Massachusetts, and the surrounding communities in the area. The company handles health insurance policies for individuals and families, addressing coverage needs for medical care and preventive services. It assists clients in comparing plan options from available carriers to match their budgets and healthcare requirements. Each typical job is managed by assessing the client’s current coverage and personal circumstances before recommending suitable plans and supporting the enrollment process.

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

A health insurance agent in Winchester such as Furey Insurance can help clients compare one-time enrollment options through the individual marketplace or employer-sponsored plans, while also offering recurring services for annual open enrollment and ongoing policy adjustments. Coverage needs, including preventive care, prescription drugs, and specialist referrals, are addressed through plan comparisons. Service runs on a scheduled annual review basis, with additional as-needed support for life changes that require plan updates.

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

With the open enrollment period approaching each year, many Winchester residents seek guidance to navigate their health insurance options. Barry & McHugh Insurance Inc serves local individuals and families by helping them compare major medical plans and evaluate coverage details for their unique circumstances. As health insurance agents, they clarify policy differences regarding deductibles and provider networks. An initial consultation typically begins with a review of the client's current coverage and any anticipated medical needs, followed by a simplified assessment of available plan options for their consideration.

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

BARRY FREEMAN provides dedicated guidance for Medicare supplement plans and helps individuals navigate the complexities of individual health insurance coverage. As a health insurance agent serving the Winchester, MA area, it connects clients with suitable plans from major carriers and explains the differences between policy options. The agency also assists families in reviewing and selecting dental and vision coverage. With the annual open enrollment period approaching, it helps residents evaluate their current plans and make changes before the December 7th deadline.

JM
10 Skillings Rd
Jay M Finn Insurance
Health Insurance Agent · Winchester, MA

Jay M Finn Insurance in Winchester, MA helps individuals and businesses evaluate and select health coverage options. As a health insurance agent, the company focuses on guiding clients through plan comparisons and enrollment processes in the local area. It can assist with both individual policies and group benefit plans tailored to different operational needs. Commercial sectors that may be served include offices requiring employee packages, warehouses needing flexible workforce health solutions, and food service businesses with varied staff schedules.

BH
175 Washington St # C24
Black Horse Insurance
Health Insurance Agent · Winchester, MA

Black Horse Insurance serves as a residential health insurance agent in Winchester, helping individuals and families select appropriate medical coverage. The company also structures commercial health plans for local businesses needing group benefits. Their office provides assistance to clients throughout the Winchester area and surrounding communities. Agents guide customers through annual enrollment periods and help match policies to current healthcare needs. They offer follow-up support to address any billing or coverage questions that arise between regular visits, ensuring continued service throughout the policy year.

DI
10 Skillings Rd
Ducey Insurance Agency
Health Insurance Agent · Winchester, MA
(781) 235-6795

What Does a a Health Insurance Agent in Winchester Cost?

Health insurance agents in Massachusetts do not charge you directly for their services. Their compensation comes from the insurance carrier. The cost of a health insurance plan varies widely based on age, income, and metal tier. A bronze plan for a 40-year-old in Winchester might cost around 450 to 600 dollars per month before subsidies. Subsidies from the Massachusetts Health Connector can lower that cost significantly. This is general information, not insurance advice.

About health insurance agents in Winchester

Health insurance agents in Winchester Massachusetts help individuals and families compare plans on the Massachusetts Health Connector. They also assist with Medicare options and employer-sponsored coverage. Massachusetts law requires most residents to have health insurance or pay a penalty on their state tax return.

Frequently Asked Questions

What does a health insurance agent in Winchester do?

A health insurance agent helps you review plan options from carriers like Blue Cross Blue Shield and Harvard Pilgrim. They explain deductibles, copays, and provider networks. They do not charge you a fee because they earn a commission from the insurance company.

When can I enroll in a health insurance plan in Massachusetts?

Open enrollment for individual plans typically runs from November 1 to January 23 each year. If you lose other coverage, move, or have a qualifying life event, you may qualify for a special enrollment period. You have 60 days from the event to enroll.

Do I need health insurance in Massachusetts?

Yes, Massachusetts has a health insurance mandate. If you go without qualifying coverage for more than three consecutive months, you may face a tax penalty. An agent can help you find a plan that meets the minimum creditable coverage standard.

Health Insurance Agents in Other Massachusetts Cities

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