Robert Chestnut in

Robert Chestnut

Doer · DISC type ds
Health Insurance Agent at South Shore Medicare and Health Insurance Advisors
📍 Greater Boston, United States

Robert Chestnut is a dual-career professional with over 25 years of experience as a Broker Associate at Keller Williams Realty and as a Health Insurance Agent. He specializes in guiding Massachusetts retirees through significant life transitions, including real estate transactions and navigating Medicare. People who have worked with him describe him as professional, dedicated, and top-notch.

Outside of work, Robert is a family man, married with two children, Anthony and Ava. His personal posts suggest he is guided by his faith. He has a varied background, having lived in Hollywood in his twenties before settling in Massachusetts. His interest in Under Armour suggests a potential focus on fitness.

Interesting fact: Before his long-standing career in real estate and insurance in Massachusetts, Robert lived in Hollywood, California during his twenties.

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Experience
1 Years
Current Role
Health Insurance Agent
Location
Greater Boston, United States
Personality Overview

How Robert shows up

Fast-paced
Strategic Planner
Long-term Focused

They exhibit a rare combination of being result-oriented but patient at the same time. Reading between the lines and seeing beyond your words comes naturally to them. They are very professional in their approach and can weigh multiple perspectives together.

Priorities

Topics Robert cares about

Real Estate Transitions
With 25+ years of experience, he helps clients with buying, selling, downsizing, and investment properties, focusing on major life changes.
Medicare Guidance
As a health insurance agent, he is passionate about helping Massachusetts seniors understand their Medicare options and avoid common, costly mistakes.
+5 more topics Login to view topics
Career

Work history

4-2025
Health Insurance Agent
South Shore Medicare and Health Insurance Advisors
Broker Associate
Keller Williams Realty
Broker Associate
RE/Max Advanced
Sales Associate
Coldwell Banker Hunneman
In the press

Media appearances

No media yetWe could not find public media appearances for this person.
Education
Bachelor of Arts
Stonehill College
Social presence
in
Behavioral profile

DISC profile (public)

d

Dominance (D)

Dominance (D) reflects how goal and task oriented a person is, and their ability to accomplish results irrespective of how demanding the circumstances might be. Those scoring high tend to be motivated by winning, competition, and success.

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