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Find Supplemental Insurance Agents Near You in Wellesley, MA

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

The top-rated supplemental insurance agent in Wellesley, Massachusetts is Deland, Gibson Insurance Associates — Wellesley Hills, rated 4.9 stars across 50 reviews. Other highly rated options include Cross Insurance, CAV Insurance Agency, Inc., Shining Insurance LLC. This directory lists 11 supplemental insurance agents serving Wellesley.

Showing 11 supplemental insurance agents in Wellesley, MAListings are displayed in no particular order and are not ranked. Order does not constitute a recommendation or endorsement.

Comparison

Top 10 listings
#NameAddressPhone
1Deland, Gibson Insurance Associates — Wellesley Hills36 Washington St #40(781) 237-1515
2Cross Insurance287 Linden St(781) 235-3100
3CAV Insurance Agency, Inc.40 Grove St #260(781) 237-4107
4Shining Insurance LLC277 Linden St(781) 757-1097
5Happily Insured1 Washington St # 105(351) 203-0257
6Hoffman Insurance Services, Inc.148 Linden St Suite 300(781) 235-0087
7Sun Life96 Worcester St(781) 237-6030
8Page & Lugton Insurance Agency31 Washington St(781) 444-0853
9Insurance Services of New England148 Linden St Suite 300(844) 386-8730
10Drislane & Mastroianni Brokerage267 Washington St #4(800) 227-1258
DG
36 Washington St #40
Deland, Gibson Insurance Associates — Wellesley Hills
Supplemental Insurance Agent · Wellesley, MA

Deland, Gibson Insurance Associates — Wellesley Hills serves the greater Wellesley area and surrounding Middlesex County. As a supplemental insurance agent, this company offers policies that cover expenses beyond primary health plans. These financial protection options often help with out-of-pocket costs from accidents, critical illnesses, hospital stays, or medical gaps in basic coverage. Residents commonly use these products to reduce financial risk during unexpected health events. This local agency handles clients seeking short-term medical coverage and hospital indemnity plans for added security.

CI
287 Linden St
Cross Insurance
Supplemental Insurance Agent · Wellesley, MA

Cross Insurance serves Wellesley and the surrounding Middlesex County area as a supplemental insurance agent. The agency helps clients fill coverage gaps in their primary health plans. It offers policies designed to manage out-of-pocket medical expenses and provide income protection during illness or injury. Such supplemental plans can address deductibles, copayments, and other costs not covered by major medical insurance. The office in Wellesley works with local residents to evaluate accident insurance options and to secure critical illness coverage that pays a lump-sum benefit upon diagnosis.

CI
40 Grove St #260
CAV Insurance Agency, Inc.
Supplemental Insurance Agent · Wellesley, MA

CAV Insurance Agency, Inc. in Wellesley, MA provides a range of supplemental insurance products designed to fill gaps not covered by primary health or property policies. Its service approach typically includes personalized policy reviews and recommendations, with ongoing support to help clients adjust coverage as their needs change. The agency also offers options for managing claims and policy maintenance through direct agent consultation. It serves a variety of local properties, including single-family homes, apartments, retail establishments, and restaurants.

SI
277 Linden St
Shining Insurance LLC
Supplemental Insurance Agent · Wellesley, MA

Shining Insurance LLC serves homeowners and renters in Wellesley, Massachusetts who seek coverage gaps not addressed by major medical plans, offering supplemental policies that help with deductible costs and copayments. The agency assists clients in understanding their choices for accident, critical illness, and hospital indemnity plans. It provides personalized guidance through the enrollment process and policy selection to match individual needs. The company also extends its services to neighboring Natick.

HI
1 Washington St # 105
Happily Insured
Supplemental Insurance Agent · Wellesley, MA

Located in Wellesley, Massachusetts, and serving clients throughout the surrounding communities of Norfolk County, Happily Insured provides supplemental insurance policies that help cover gaps left by major medical plans. This agency handles a range of products including accident, critical illness, hospital indemnity, and dental coverage. The typical job for a local client begins with a complimentary needs assessment, followed by a straightforward comparison of available plans and a personalized recommendation tailored to the individual’s specific health and financial situation.

HI
148 Linden St Suite 300
Hoffman Insurance Services, Inc.
Supplemental Insurance Agent · Wellesley, MA

Hoffman Insurance Services, Inc. specializes in supplemental insurance policies that fill coverage gaps left by major medical plans. It also offers guidance on how to coordinate these extra benefits with a client’s existing health coverage. Based in Wellesley, MA, the agency works with individuals and families in the surrounding area to review their protection needs. It helps address financial exposure from unexpected out-of-pocket medical costs, such as those arising during the unpredictable flu and cold season.

SL
96 Worcester St
Sun Life
Supplemental Insurance Agent · Wellesley, MA

Sun Life offers both one-time consultations and ongoing service arrangements for supplemental insurance needs in Wellesley, Massachusetts. One-time appointments focus on reviewing specific coverage gaps, while recurring service provides periodic policy adjustments. Coverage includes accident, critical illness, hospital indemnity, and disability insurance to supplement primary health plans. Service runs on an as-needed basis, allowing clients to schedule appointments based on changing life events or policy renewal cycles without a fixed calendar commitment.

PL
31 Washington St
Page & Lugton Insurance Agency
Supplemental Insurance Agent · Wellesley, MA

As the leaves turn in Wellesley, homeowners often reassess their financial protections, and Page & Lugton Insurance Agency meets this need as a supplemental insurance agent. These plans help cover gaps in primary health coverage for local families and retirees. The agency focuses on identifying potential out-of-pocket expenses that major medical policies might not fully address. An initial assessment begins with them, where a representative reviews existing coverage to pinpoint specific vulnerabilities or new options. This review involves a straightforward inspection of current policies and budget limits for the prospective client.

IS
148 Linden St Suite 300
Insurance Services of New England
Supplemental Insurance Agent · Wellesley, MA

Insurance Services of New England, based in Wellesley, Massachusetts, provides primary insurance coverage and specializes in supplemental insurance products designed to address gaps in standard policies. These add-ons help policyholders manage unexpected out-of-pocket costs. The agency serves commercial clients operating in office environments, warehouse and distribution facilities, and food service establishments. Businesses in each sector can receive guidance on selecting appropriate supplemental enhancements to their existing coverage.

DM
267 Washington St #4
Drislane & Mastroianni Brokerage
Supplemental Insurance Agent · Wellesley, MA

Serving residences in Wellesley and the surrounding area, Drislane & Mastroianni Brokerage helps clients fill gaps in their existing health coverage. The firm also provides supplemental insurance plans for commercial businesses, addressing broader needs across the local region. These policies can cover benefits such as accident, critical illness, or hospital indemnity that standard medical insurance may leave out. After enrolling new clients, the agency schedules periodic reviews to adjust coverage as needs change, typically following up directly before each renewal cycle to ensure continued alignment with policyholder priorities.

CP
981 Worcester St
Cochrane & Porter Insurance Agency
Supplemental Insurance Agent · Wellesley, MA
(781) 943-1555
cochraneandporter.com

What Does a a Supplemental Insurance Agent in Wellesley Cost?

Supplemental insurance agent services in Massachusetts are typically free to you because the agent earns a commission from the insurance company. Medigap plan premiums in Wellesley can range from about 100 to 300 dollars per month depending on your age health and the plan type. Costs vary by carrier and plan level. This is general information not insurance advice.

About supplemental insurance agents in Wellesley

Supplemental insurance agents in Wellesley Massachusetts help residents find Medigap plans and other health coverage options. Massachusetts state law provides a six-month open enrollment period for Medicare Supplement plans when you first turn 65. Local agents can guide you through the specific rules and plan choices available in Wellesley and the surrounding area.

Frequently Asked Questions

What is a supplemental insurance agent in Wellesley?

A supplemental insurance agent in Wellesley helps you compare and enroll in Medicare Supplement plans also called Medigap. These agents are licensed in Massachusetts and understand local insurance carriers and plan options.

When can I enroll in a Medigap plan in Massachusetts?

In Massachusetts you have a six-month open enrollment period that starts when you are both 65 and enrolled in Medicare Part B. During this time you can buy any Medigap policy without medical underwriting. After this period you may face health questions or higher rates.

How do I choose a supplemental insurance agent in Wellesley?

Look for an agent licensed in Massachusetts with experience in Medicare Supplement plans. Ask about the carriers they represent and whether they offer free consultations. You can verify an agents license through the Massachusetts Division of Insurance website.

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.