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Find Supplemental Insurance Agents Near You in Boston, MA

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

The top-rated supplemental insurance agent in Boston, Massachusetts is Vargas & Vargas Insurance Inc., rated 4.9 stars across 690 reviews. Other highly rated options include Ironside Insurance Group, LLC, Bender Hatch Insurance, Connie Health. This directory lists 14 supplemental insurance agents serving Boston.

Showing 14 supplemental insurance agents in Boston, MAListings are displayed in no particular order and are not ranked. Order does not constitute a recommendation or endorsement.

Comparison

Top 10 listings
#NameAddressPhone
1Vargas & Vargas Insurance Inc.1133 Washington St(617) 298-0655
2Ironside Insurance Group, LLC112 Water St #401(617) 227-2400
3Bender Hatch Insurance87 Wendell St 4th Floor(617) 367-4900
4Connie Health99 High St(888) 984-8825
5State Fund Insurance100 Summer St(617) 956-9999
6Click Insurance131 Dartmouth St Fl 3rd, Suite 82(617) 580-3499
7Flynn Insurance Agency30 Park St APT 2(617) 242-1200
8Point Insurance - Boston1103 Commonwealth Ave(617) 783-1160
9Beacon Hill Insurance Agency200 Portland St(800) 568-4091
10Best Choice Insurance Agency163 Harvard Ave(617) 782-8800
VV
1133 Washington St
Vargas & Vargas Insurance Inc.
Supplemental Insurance Agent · Boston, MA

Vargas & Vargas Insurance Inc. serves the Boston, Massachusetts metro area as a supplemental insurance agent. The company helps clients address out-of-pocket healthcare costs that primary insurance policies often leave uncovered. These supplemental plans provide financial support for expenses like deductibles and copayments. Medicare supplement policies are among the options this agency handles, as are critical illness insurance plans. Both products are designed to fill gaps in standard coverage for local residents.

II
112 Water St #401
Ironside Insurance Group, LLC
Supplemental Insurance Agent · Boston, MA

Ironside Insurance Group, LLC in Boston, MA offers a range of supplemental insurance policies that fill gaps left by standard health coverage, including plans for accident, critical illness, and hospital indemnity. Their service approach involves helping clients select appropriate supplemental plans and providing ongoing support for claims and policy adjustments as needs change. The company primarily assists policyholders who own or manage single-family homes, apartments, retail establishments, and restaurants in the Boston area.

BH
87 Wendell St 4th Floor
Bender Hatch Insurance
Supplemental Insurance Agent · Boston, MA

Bender Hatch Insurance serves Boston homeowners, renters, and small business owners seeking supplemental insurance coverage. It offers gap-filling policies that address deductibles, coinsurance, and loss-of-income scenarios not covered by primary plans. The agency provides guidance on Medigap, critical illness, accident, and hospital indemnity plans. Bender Hatch Insurance clarifies coverage differences and helps clients select appropriate supplemental benefits. Its service area includes the downtown core and also extends throughout the Cambridge metro region, ensuring nearby residents have access to similar supplemental insurance agent support.

CH
99 High St
Connie Health
Supplemental Insurance Agent · Boston, MA

Connie Health serves the Boston area and its surrounding communities, handling supplemental insurance for local residents. As a supplemental insurance agent, the company works with clients to address gaps in their primary health coverage. Its services often include helping individuals navigate options like Medicare supplements or dental and vision plans. The approach typically involves assessing each client’s specific healthcare needs and existing coverage before suggesting suitable supplemental policies, then guiding them through the enrollment process step by step.

SF
100 Summer St
State Fund Insurance
Supplemental Insurance Agent · Boston, MA

Unlike one-time insurance purchases, supplemental insurance operates through ongoing policy agreements that renew regularly. State Fund Insurance, located in Boston, Massachusetts, assists clients by offering supplemental plans designed to fill coverage gaps left by major medical policies. These plans typically address costs such as deductibles and copays for unforeseen hospital stays or critical illnesses. The company’s service model for administering these policies is structured as scheduled renewals, with coverage continuing on a recurring basis as long as the client maintains premiums.

CI
131 Dartmouth St Fl 3rd, Suite 82
Click Insurance
Supplemental Insurance Agent · Boston, MA

As Bostonians prepare for winter’s heavy snow and ice, gaps in standard health coverage can become a real concern. Click Insurance serves the area as a local supplemental insurance agent, helping clients explore policies for unexpected medical costs, accident recovery, or critical illness. They focus on explaining plans that work alongside existing major medical coverage. Each new client starts with a thorough, no-obligation review of their current benefits to identify potential gaps before selecting appropriate supplemental options.

FI
30 Park St APT 2
Flynn Insurance Agency
Supplemental Insurance Agent · Boston, MA

Flynn Insurance Agency specializes in connecting individuals and families with supplemental insurance policies tailored to their needs. It also offers general agent services, assisting clients in navigating their coverage options to fill gaps left by primary health insurance. The agency frequently helps residents of the Boston area address coverage concerns during open enrollment periods, ensuring they have additional financial protection for unexpected medical costs like deductibles and copayments.

PI
1103 Commonwealth Ave
Point Insurance - Boston
Supplemental Insurance Agent · Boston, MA

Point Insurance in Boston, Massachusetts assists individuals and businesses in securing core insurance coverage while addressing gaps with supplemental insurance options. These specialty add-ons often provide extra financial protection for accidents, critical illness, or hospital stays. The agency works with clients in a variety of commercial sectors, including office environments, warehouses, and food service operations, to recommend policies that align with specific operational needs and employee benefit strategies.

BH
200 Portland St
Beacon Hill Insurance Agency
Supplemental Insurance Agent · Boston, MA

Beacon Hill Insurance Agency serves the Boston, Massachusetts metro area as a local Supplemental Insurance Agent. The company helps clients navigate policies that fill gaps left by major medical coverage. These supplemental plans address needs such as accident, critical illness, and hospital indemnity. The agency assists individuals in tailoring coverage for specific life events and health concerns. Residents can seek guidance on specialized products including dental and vision insurance plans.

BC
163 Harvard Ave
Best Choice Insurance Agency
Supplemental Insurance Agent · Boston, MA

Best Choice Insurance Agency in Boston, MA assists residents with supplemental coverage designed to fill gaps in primary health plans. For commercial clients, they offer similar gap-filling policies to protect small businesses from unexpected medical costs. Their service area covers Boston and the greater metropolitan region. After an initial policy is placed, the agency follows up to adjust coverage as needs change and provides ongoing support between regular insurance renewal cycles.

AI
60 Brighton Ave
ALD Insurance
Supplemental Insurance Agent · Boston, MA
(617) 787-7877
aldinsurance.com
UL
23 Essex St
Uni Life Insurance Agency
Supplemental Insurance Agent · Boston, MA
(857) 576-3957
leomadelnero756483.wixsite.com/uni-life-insurance-a
KD
4 Copley Pl Suite 120
K D Hicks Insurance Agency
Supplemental Insurance Agent · Boston, MA
(617) 442-1300
kdhicksinsurance.com
SI
123 Beach St
Sterling Insurance Group of Boston
Supplemental Insurance Agent · Boston, MA
(508) 687-2750
insurewithsterling.com

What Does a a Supplemental Insurance Agent in Boston Cost?

Supplemental insurance agent services in Massachusetts are typically free to consumers because agents earn commissions from insurance carriers. Medigap plan premiums in Boston range from about 100 to 300 dollars per month depending on age gender and plan type. Medicare Advantage plans often have 0 dollar premiums but may have copays and network limits. Costs vary by case and insurer. This is general information and not insurance advice.

About supplemental insurance agents in Boston

Supplemental insurance agents in Boston help residents fill gaps in Medicare coverage. Massachusetts requires standardized Medigap plans for most seniors. Agents can explain options like Plan G or Plan N and compare costs for your needs.

Frequently Asked Questions

What is the best time to buy a Medigap plan in Massachusetts?

The Medigap Open Enrollment Period starts when you are 65 and enrolled in Medicare Part B. During this six-month window you can buy any Medigap plan without medical underwriting. Massachusetts law also provides a guaranteed issue right for certain situations.

Can a supplemental insurance agent help with Medicare Advantage plans in Boston?

Yes many agents are licensed to sell both Medigap and Medicare Advantage plans. They can compare the costs benefits and provider networks for plans available in Suffolk County. Massachusetts has specific rules about plan availability and enrollment periods.

Are there state-specific rules for Medicare supplements in Massachusetts?

Massachusetts uses a unique Medigap system with only three standardized plans: Core Supplement 1 and Supplement 1A. The state also requires insurers to offer a guaranteed issue period for certain plan changes. An agent can explain how these rules affect your choices.

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.