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Find Supplemental Insurance Agents Near You in Winchester, MA

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

The top-rated supplemental 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 12 supplemental insurance agents serving Winchester.

Showing 12 supplemental 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
8Barry & McHugh Insurance Inc10 Skillings Rd(781) 729-6600
9BARRY FREEMAN895 Main St(781) 368-9029
10Jay M Finn Insurance10 Skillings Rd(781) 729-5724
SI
19 Mt Vernon St
Scotti Insurance Agency
Supplemental Insurance Agent · Winchester, MA

Scotti Insurance Agency serves the Winchester, Massachusetts area as a local supplemental insurance agent. The agency helps residents fill gaps in their primary health coverage by providing access to specialized policies. These plans address specific needs that major medical insurance often leaves uncovered. Common offerings include policies for accident-related expenses, critical illness events, and hospital indemnity benefits. By working as a local broker, the agency assists clients in navigating the selection of these additional coverages. It handles accident insurance plans and hospital indemnity policies in this region.

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

Saltmarsh Insurance Agency provides a comprehensive range of supplemental insurance solutions for residents and businesses in Winchester, MA. Their service plans include tailored Medicare supplements, accident and critical illness coverage, and hospital indemnity policies designed to fill gaps in primary health plans. They support clients through the claims process and offer periodic policy reviews to adjust coverage for changing health needs or budgets. Their maintenance approach includes annual consultations and direct customer support for billing questions. The agency services major properties, including single-family homes, apartments, retail locations, and local restaurants.

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

Serving Winchester and the surrounding communities, Admiralty Insurance Agency Inc is a supplemental insurance agent that helps clients fill coverage gaps left by primary health plans. It specializes in policies addressing specific needs such as accident, critical illness, or hospital indemnity. To handle a typical job, it assesses individual circumstances to recommend appropriate limited-benefit plans that align with each client’s budget and personal risk factors.

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

Homeowners in Winchester, Massachusetts often turn to John A Pierce Insurance Inc for guidance on supplemental insurance options. The agency helps clients fill gaps in standard policies by offering tailored coverage solutions. As a local supplemental insurance agent, the firm focuses on providing personalized service and clear explanations of available plans. Residents seeking to protect their assets frequently rely on this office for advice on additional protection. The agency also serves clients in nearby communities throughout the Middlesex County area.

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

W Allan Wilde & Son Insurance Agency, Inc. in Winchester, MA provides services for supplemental coverage needs, distinguishing between one-time policy enrollments and recurring benefit options that adjust to changing client circumstances. Supplemental insurance agents in this area help individuals fill gaps left by primary health plans, such as with accident or critical illness policies. Their approach involves reviewing existing coverage to recommend appropriate supplemental plans for local residents. Their service runs on an as-needed basis, initiated whenever a client requests a consultation or policy review.

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

Horace Mann Insurance Co is based in Winchester, Massachusetts, serving that town and neighboring communities throughout the area. As a supplemental insurance agent, the firm helps clients address coverage gaps not fulfilled by primary health or life policies, typically offering options for accident, hospital, or critical illness protection. To handle each job, the agent begins with a thorough review of an individual’s existing benefits and personal needs. It then presents clearly explained plan choices to ensure informed decisions are made before any enrollment.

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

Furey Insurance in Winchester, Massachusetts, specializes in supplemental insurance products designed to cover gaps in primary health plans. Its general service work includes helping individuals and families evaluate policies for dental, vision, disability, and accident-related expenses that standard medical insurance often leaves unmet. For those approaching the winter season in New England, the agency assists clients in reviewing coverage for potential hospital stays or outpatient procedures that could arise from seasonal slips or illnesses.

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

Barry & McHugh Insurance Inc, based in Winchester, MA, provides supplemental insurance policies designed to fill gaps left by standard health or property coverage. Its specialty add-ons include plans for specific medical events or income protection that many primary policies exclude. The agency assists local clients in customizing their coverage to address unique, out-of-pocket expenses. It can serve commercial sectors such as offices needing extended benefits for employees, warehouses requiring supplementary liability options, and food service establishments seeking tailored loss-of-income protections.

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

As winter weather often brings unexpected slips and falls in Winchester, residents look for reliable protection against out-of-pocket medical costs. Barry Freeman serves this area as a supplemental insurance agent, helping clients bridge gaps left by primary health plans. The company guides individuals through plan options for accident, critical illness, or hospital indemnity coverage tailored to local needs. A no-obligation initial consultation is scheduled to review personal circumstances and assess which policy structures best fit the client's budget and daily life.

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

Jay M Finn Insurance provides supplemental insurance to residents of Winchester, Massachusetts. Their residential services help clients cover costs not paid by standard health policies, including dental, vision, and accident plans. They also offer supplemental coverage for area businesses, assisting employers with group disability, critical illness, and hospital indemnity plans. The company serves the local community exclusively. Agents regularly follow up with policyholders and coordinate benefits between visits, ensuring coverage remains up to date and claims are addressed promptly.

BH
175 Washington St # C24
Black Horse Insurance
Supplemental Insurance Agent · Winchester, MA
(781) 729-1164
blackhorseinsurance.com
DI
10 Skillings Rd
Ducey Insurance Agency
Supplemental Insurance Agent · Winchester, MA
(781) 235-6795

What Does a a Supplemental Insurance Agent in Winchester Cost?

Supplemental insurance costs in Massachusetts vary by plan type, age, and insurer. Medigap Plan G premiums for a 65-year-old in Winchester typically range from $120 to $250 per month. Medicare Advantage plans may have $0 premiums but include out-of-pocket costs. Costs can change annually. This is general information, not insurance advice.

About supplemental insurance agents in Winchester

Supplemental insurance agents in Winchester, Massachusetts help residents navigate Medicare Supplement plans, Medicare Advantage, and other gap coverage. Massachusetts has a unique Medigap open enrollment period that starts when you turn 65 and enroll in Medicare Part B. Local agents can explain how state regulations like the guaranteed issue rules apply to your situation.

Frequently Asked Questions

What is a supplemental insurance agent in Winchester?

A supplemental insurance agent in Winchester helps you find policies that cover costs not paid by Original Medicare, such as copayments and deductibles. They are licensed in Massachusetts and can explain Medigap plans standardized by the state.

When can I enroll in a Medigap plan in Massachusetts?

In Massachusetts, you have a six-month Medigap open enrollment period that begins the month you are 65 and enrolled in Medicare Part B. During this time, insurers cannot deny you coverage or charge higher premiums due to pre-existing conditions.

What types of supplemental insurance are available in Winchester?

Common supplemental options include Medicare Supplement plans (Medigap), Medicare Advantage plans, and standalone prescription drug plans. Massachusetts also offers a Medicare Supplement plan called the Core plan and the Supplement 1 plan.

Supplemental Insurance Agents in Other Massachusetts Cities

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