Robert Chestnut in

Robert Chestnut

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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

Communication Style
Decision Approach
Work Preference

Behavioral traits and communication patterns that shape how this person evaluates opportunities, builds trust, and makes decisions in professional settings.

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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.
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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

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Education
Bachelor of Arts
Stonehill College
Social presence
in
Behavioral profile

DISC profile (public)

DISC behavioral profile

Dominance, influence, steadiness, and calculativeness scores with guidance on how this person prefers to communicate and decide.

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