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Find Health Insurance Agents Near You in Wellesley, MA

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

The top-rated health 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., Happily Insured. This directory lists 12 health insurance agents serving Wellesley.

Showing 12 health 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
4Happily Insured1 Washington St # 105(351) 203-0257
5Shining Insurance LLC277 Linden St(781) 757-1097
6Hoffman Insurance Services, Inc.148 Linden St Suite 300(781) 235-0087
7Sun Life96 Worcester St(781) 237-6030
8Harvard Pilgrim Health Care93 Worcester St(888) 333-4742
9Insurance Services of New England148 Linden St Suite 300(844) 386-8730
10Northwestern Mutual55 William St #100(781) 237-7070
DG
36 Washington St #40
Deland, Gibson Insurance Associates — Wellesley Hills
Health Insurance Agent · Wellesley, MA

Deland, Gibson Insurance Associates – Wellesley Hills serves the greater Wellesley, Massachusetts area as a health insurance agent. The company works with individuals and businesses to find suitable medical coverage plans. It helps clients understand policy options from various insurers available in the region. The office assists with enrolling in plans during open enrollment periods and navigating special enrollment for qualifying life events. Among the specific services handled here are individual health plan comparisons and small business group health insurance setup.

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

Cross Insurance serves residents in Wellesley, Massachusetts with individual health coverage, including plans for families and those transitioning between jobs. The agency also assists local businesses by advising on group commercial health plans to meet employer needs. Serving Wellesley and the surrounding communities, clients receive guidance through enrollment periods and plan selections. After securing a policy, the agent provides follow-up support for claims or plan changes, ensuring consistent service between regular annual reviews.

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

CAV Insurance Agency, Inc. offers a complete range of health insurance agent services to individuals and groups throughout the Wellesley area. Its work includes helping clients understand plan options, guiding them through enrollment periods, and assisting with claims or coverage questions. The agency also provides ongoing plan maintenance, such as reviewing policy changes annually and managing renewal paperwork. CAV Insurance Agency, Inc. services single-family homes, apartments, retail establishments, and restaurants seeking health coverage solutions for themselves or their employees.

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

Happily Insured serves homeowners, families, and small business owners in Wellesley, Massachusetts, as a health insurance agent. The agency helps clients navigate private health plans, Medicare options, and supplemental coverage throughout the annual enrollment period. It focuses on explaining policy details and comparing plans to match individual healthcare needs and budgets. Coverage guidance extends to neighboring communities in the MetroWest region, including the town of Needham.

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

Shining Insurance LLC serves clients in Wellesley, Massachusetts, and the surrounding communities of the greater Boston area. As a health insurance agent, the company handles the selection and enrollment of individual and family health plans, as well as group coverage for local small businesses. It assists clients in comparing available policy options to match their medical needs and financial circumstances. To complete a typical job, the agent reviews each client’s coverage requirements and recommends suitable plans from multiple carriers.

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

As local families in the Wellesley area begin reviewing their coverage for the upcoming year, a common question is how to align healthcare plans with shifting medical needs and household budgets. Hoffman Insurance Services, Inc. serves as a health insurance agent helping residents navigate these decisions. They focus on explaining policy options, including deductibles and provider networks, to ensure individuals understand their choices. The company emphasizes careful plan comparison as part of every initial assessment step. A first appointment typically involves a thorough review of current coverage and personal health priorities.

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

Sun Life specializes in helping individuals and families navigate health insurance options, offering plan comparisons and enrollment assistance. As a health insurance agent in Wellesley, Massachusetts, it provides general guidance on coverage choices and policy details. The agency works to clarify complex health plans, ensuring clients understand deductibles, networks, and out-of-pocket costs. During the annual open enrollment period, it helps residents evaluate changes to their current plans and meet deadlines effectively.

HP
93 Worcester St
Harvard Pilgrim Health Care
Health Insurance Agent · Wellesley, MA

Harvard Pilgrim Health Care, based in Wellesley, MA, offers both one-time consultations for immediate health insurance needs and recurring support for ongoing policy management. The agency assists clients in understanding coverage options, including plan networks and benefits that fit individual or family circumstances. Service can be arranged on a one-time, scheduled, or as-needed basis to accommodate changing healthcare requirements throughout the year.

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

Serving residents in and around Wellesley, Insurance Services of New England helps individuals navigate the complexities of health coverage by explaining plan options and enrollment steps. The agency also assists local businesses, advising on commercial health insurance packages tailored to their workforce needs across the region. Their straightforward guidance supports clients during open enrollment and life changes, with follow-up service available between regular visits to answer questions or adjust plans as circumstances evolve.

NM
55 William St #100
Northwestern Mutual
Health Insurance Agent · Wellesley, MA
AE
93 Worcester St
Aetna
Health Insurance Agent · Wellesley, MA
(800) 872-3862
aetna.com
CP
981 Worcester St
Cochrane & Porter Insurance Agency
Health Insurance Agent · Wellesley, MA
(781) 943-1555
cochraneandporter.com

What Does a a Health Insurance Agent in Wellesley Cost?

Health insurance agent services in Massachusetts are generally free to consumers because agents earn commissions from insurers. Plan premiums vary widely based on age, income, and coverage level. A typical individual plan may cost between 300 and 700 dollars per month before subsidies. This is general information and not insurance advice.

About health insurance agents in Wellesley

A health insurance agent in Wellesley, Massachusetts can help you compare plans from private insurers and the Massachusetts Health Connector. Agents must be licensed by the Massachusetts Division of Insurance. They provide guidance on open enrollment periods and special enrollment qualifying events as defined by state law.

Frequently Asked Questions

What does a health insurance agent in Wellesley do?

A health insurance agent helps individuals and families review plan options, estimate costs, and enroll in coverage. They explain differences between HMO, PPO, and high-deductible plans available in Massachusetts. Agents also assist with subsidy eligibility through the Health Connector.

Do I have to pay a fee to use a health insurance agent in Massachusetts?

In most cases, health insurance agents are paid by the insurance company, not by you. Their commission is built into the plan premium. You should confirm fee arrangements before starting the process.

When can I enroll in a health plan through an agent in Wellesley?

Open enrollment for individual plans typically runs from November 1 to January 23 each year. You may qualify for a special enrollment period after certain life events like marriage, birth, or loss of other coverage. Massachusetts law allows up to 60 days after a qualifying event to enroll.

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.