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Find Medicare Insurance Agents Near You in Wellesley, MA

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

The top-rated medicare 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 13 medicare insurance agents serving Wellesley.

Showing 13 medicare 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
8Page & Lugton Insurance Agency31 Washington St(781) 444-0853
9Harvard Pilgrim Health Care93 Worcester St(888) 333-4742
10Insurance Services of New England148 Linden St Suite 300(844) 386-8730
DG
36 Washington St #40
Deland, Gibson Insurance Associates — Wellesley Hills
Medicare Insurance Agent · Wellesley, MA

Deland, Gibson Insurance Associates — Wellesley Hills serves residents of Wellesley and the surrounding Norfolk County area with independent Medicare insurance guidance. The agency helps individuals navigate plan options during initial enrollment and annual open enrollment periods. Understanding the shifting landscape of healthcare coverage is central to their client consultations. They assist with plan comparisons for both Parts A and B. Specific services handled in this area include Medicare Supplement plan selection and stand-alone Part D prescription drug plan enrollment.

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

Cross Insurance of Wellesley, Massachusetts, is known for guiding individuals through the complexities of Medicare plans. Its service range includes helping clients compare Medicare Advantage, Supplement, and Part D drug coverage options to match their healthcare needs and budgets. The agency works to explain enrollment periods and plan limitations clearly. For those seeking broader health security, Cross Insurance can add on a specialized Medicare Supplement plan designed to cover out-of-pocket costs not paid by Original Medicare.

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

CAV Insurance Agency, Inc. in Wellesley, MA provides services including plan comparisons, enrollment assistance, and annual coverage reviews for Medicare beneficiaries. It also maintains ongoing support for clients through policy adjustments during open enrollment periods and helps with plan changes when personal health or financial circumstances shift. The agency tailors its guidance to an individual’s specific healthcare needs and budget considerations. It services single-family homes, apartments, retail, and restaurants.

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

Happily Insured serves homeowners and retirees in the Wellesley, MA area who require guidance navigating Medicare plan options. The agency helps clients understand their coverage choices, including Medigap and Medicare Advantage plans, during enrollment periods. It assists beneficiaries in comparing benefits to select a plan suited to their health needs and budget. Annually, the office reviews client policies to note coverage changes. Agents further provide support with plan changes. The agency serves clients as far as neighboring Needham.

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

Shining Insurance LLC serves Wellesley, Massachusetts, and the surrounding communities in the area. It focuses on helping clients navigate their options for Medicare coverage. Each case is approached with a straightforward assessment of individual healthcare needs and available plan details. The agent works to explain the differences between Medicare supplements, Part D drug plans, and Medicare Advantage options. To handle a typical job, the company reviews the client’s current prescriptions and preferred doctors before recommending specific plans from available carriers.

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

As enrollment periods approach in Massachusetts, many seniors in Wellesley seek clarity on their Medicare options. Hoffman Insurance Services, Inc. assists local residents by explaining plan differences and navigating coverage changes. Their work involves reviewing each client’s current health needs and budget considerations. An agent will examine the available Part D and Medigap plans for the coming year. This process concludes with an initial assessment of the client’s existing coverage and prescription usage to determine the most suitable next step.

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

Sun Life offers Medicare plan comparisons and enrollment guidance for residents in and around Wellesley, Massachusetts. The agency helps individuals navigate Original Medicare, Medicare Advantage, and Part D prescription drug plans. Recognizing that coverage needs shift over time, agents assist with annual plan reviews to ensure benefits still meet health and budgetary requirements. This work is especially critical during the Medicare Open Enrollment Period, when clients adjust their plans to avoid gaps or rising out-of-pocket costs.

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

Page & Lugton Insurance Agency provides comprehensive guidance for individuals navigating Medicare options, including assistance with plan selection and enrollment processes. Serving the Wellesley, Massachusetts area, the agency specializes in supplement and Part D prescription drug coverage to address varying healthcare needs and budgets. Its client services extend to supporting those researching both initial enrollment and annual plan changes. The agency’s expertise further covers insurance solutions for commercial sectors including office spaces, warehouses, and food service establishments.

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

Some clients require a one-time consultation to review their current Medicare plan, while others seek ongoing support for annual enrollment changes or claims questions. Harvard Pilgrim Health Care offers guidance on Medicare Advantage and prescription drug coverage options from a Wellesley, Massachusetts office. The agent explains plan benefits, costs, and network choices without pressuring immediate decisions. Service accommodates clients on a one-time, scheduled, or as-needed basis depending on the individual's preference for future assistance.

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

Insurance Services of New England serves residents in and around Wellesley, Massachusetts, helping them navigate their Medicare options for individual health coverage. The agency also assists clients with commercial Medicare plans and related supplemental policies for those who qualify. Service extends throughout Norfolk County and the greater Boston area. The team schedules follow-up appointments after each enrollment period to review any changes in plans or health needs, continuing this support between regular visits to ensure ongoing access to appropriate coverage.

DM
267 Washington St #4
Drislane & Mastroianni Brokerage
Medicare Insurance Agent · Wellesley, MA
(800) 227-1258
dandmbrokerage.com
MM
981 Worcester St
MMA
Medicare Insurance Agent · Wellesley, MA
(781) 235-0708
GI
62 Walnut St
Global Insurance Services Ltd
Medicare Insurance Agent · Wellesley, MA
(781) 997-0670

What Does a a Medicare Insurance Agent in Wellesley Cost?

Medicare insurance agents in Massachusetts are typically paid by insurance companies so you do not pay a fee for their services. Medigap plan premiums in Wellesley can range from about 100 to 300 dollars per month depending on age gender and plan type. Medicare Advantage plans often have low or zero monthly premiums but may have copays and deductibles. This is general information and not insurance advice.

About medicare insurance agents in Wellesley

Medicare insurance agents in Wellesley Massachusetts help residents compare Medicare Advantage and Medigap plans. Massachusetts has a unique annual enrollment period from October 15 to December 7. Agents can explain how state laws affect your coverage options and guide you through plan choices.

Frequently Asked Questions

What does a Medicare insurance agent in Wellesley do?

A Medicare insurance agent helps you review and enroll in Medicare plans such as Part D drug plans Medicare Advantage or Medigap. They work with multiple carriers to show you options that fit your needs and budget.

Do I need a special enrollment period in Massachusetts?

Massachusetts follows federal Medicare enrollment periods. You have an Initial Enrollment Period when you turn 65 and an Annual Enrollment Period from October 15 to December 7. Special Enrollment Periods may apply if you move or lose other coverage.

Can a Medicare agent help me with Medigap plans in Massachusetts?

Yes. Agents can explain Medigap plans A through N which are standardized in Massachusetts. They can help you compare premiums and benefits. Massachusetts does not require guaranteed issue for Medigap outside of certain situations.

Medicare Insurance Agents in Other Massachusetts Cities

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