Enrique Benitez Jr

Rick Benitez Jr. brings a unique and well-rounded background to his role as a Real Estate Consultant with the Sherwood & Company Team at Compass. With a BA in Psychology from The Ohio State University and a career spanning education, leadership, and real estate operations, Rick offers a powerful blend of emotional intelligence, strategic thinking, and deep client focus.

Rick’s real estate practice includes residential sales, rentals, commercial properties, and investment strategy across Greater Boston and the North Shore. Whether assisting a first-time homebuyer, advising a seasoned investor, or managing the details of a multi-unit portfolio, Rick’s approach is rooted in thoughtful problem-solving, personalized service, and authentic relationship-building.

Prior to real estate, Rick served as Dean of Students in the Boston Public Schools, where he developed leadership, crisis management, and communication skills that now allow him to navigate real estate transactions with precision and calm under pressure.

Fluent in Spanish and deeply connected to Greater Boston’s diverse communities, Rick serves a wide range of clients with care and confidence. As part of Sherwood & Company, he leverages the strength of a collaborative, high-performing team to help his clients achieve their goals—whether that means maximizing a sale, sourcing off-market opportunities, or building long-term investment strategies.

In every transaction, Rick leads with integrity, empathy, and a genuine commitment to creating an exceptional client experience.