Gabriella (“Gabby”) Chakkos is a certified paralegal with over five years of experience in real estate insurance and risk management. She advises commercial real estate owners and lenders on master property and casualty programs, renewals, and insurance coordination for acquisitions and loan closings.

Starting her career as a paralegal at a multi-state law firm, Gabby supported attorneys in corporate formation, real estate-related matters, medical malpractice, employment litigation, and franchise disputes. Working in a growing satellite office, she assisted multiple attorneys across practice areas and gained early exposure to contractual analysis, risk allocation, and litigation support. That legal foundation informs her disciplined approach to contract review and risk evaluation.

Gabby transitioned into risk management in 2021, joining a national real estate risk advisory practice where she supported large portfolio-wide master renewals, schedule of values management, underwriting submissions, and quote and policy review. She worked closely with lenders and borrower teams to confirm insurance compliance for financings and refinancings, helping transactions close smoothly and on schedule.

At Custom House, Gabby supports clients across stabilized portfolios and transactional matters, assisting with renewal strategy, policy analysis, underwriting coordination, and lender compliance. She brings a structured, detail-oriented approach and clear client communication style to every engagement.

Education & Certifications

• Paralegal Certificate, Boston University
• Bachelor of Arts in International Relations and Affairs, University of San Diego
• Licensed Insurance Advisor, Commonwealth of Massachusetts