About Us

Robert Dell’Osso has been involved in real estate and property management for most of his life. Having grown up in the industry, he understands both the owner’s perspective and the property manager’s perspective. As the founder of MasterKey Property Management, he has successfully grown the company while establishing himself as a knowledgeable resource on investment properties in the Triangle. Robert has resided in the area since 2000, holds a North Carolina Real Estate Broker’s License, and is the Broker-in-Charge of MasterKey Property Management.

Robert is actively involved in the National Association of Residential Property Managers (NARPM) and holds the Residential Management Professional (RMP) designation. He currently serves as President-Elect for the Triangle NARPM Chapter (2025) and is the Government Affairs Committee Chairman for the chapter. At the national level, he is a 2025 NARPM National Government Affairs Committee Member and will serve as Vice Chair for the NARPM Capitol Summit in 2026.

Cheryl Dell’Osso, a licensed North Carolina real estate broker, serves as Chief Operating Officer for MasterKey Property Management. She leads the company’s operations, marketing, and strategic growth efforts, with a strong focus on optimizing internal systems and streamlining cross-team collaboration.

Ligia serves as MasterKey’s Operations Manager, overseeing the systems, workflows, and daily coordination that keep our portfolio running smoothly. She leads process execution across pods, supports team performance, and ensures consistency in communication, documentation, and service delivery. With a deep understanding of property operations, Ligia plays a central role in aligning field activity, maintenance coordination, and internal workflows to maintain efficiency and high operational standards.

Sierra is MasterKey’s Business Development Manager. After many successful years supporting clients and properties on the operations side, Sierra now leads our growth and relationship development efforts. She works closely with prospective owners, referral partners, and investors — guiding new clients through discovery, setting clear expectations, and ensuring a smooth onboarding experience. Her firsthand operational knowledge allows her to communicate MasterKey’s services with clarity, confidence, and practical insight.

Mykaelyn is one of our Assistant Property Managers, bringing years of prior property management experience to MasterKey. She supports properties through inspections, turnover coordination, vendor follow-up, and make-ready workflows. Known for her strong organization and attention to detail, Mykaelyn helps ensure each property is carefully evaluated, properly documented, and prepared for successful marketing and resident placement.

Hugo plays a key role in supporting daily operations through organized communication and consistent follow-through. He coordinates tenant and vendor interactions, tracks maintenance and turnover workflows, and ensures documentation and system updates remain accurate. Hugo’s structured, detail-focused approach helps keep processes moving efficiently while supporting both residents and owners.

Frank Best is one of our dedicated Assistant Property Managers. A North Carolina native and proud graduate of the University of North Carolina at Chapel Hill, Frank brings a strong sense of local knowledge and community connection to his work. Known for his attention to detail and commitment to operational efficiency, Frank plays a key role in ensuring the properties we manage are well-maintained and consistently meet our high standards.

Antonio keeps daily operations running smoothly with organized communication and steady follow-through. He supports residents during move-ins, coordinates maintenance needs, and works closely with owners and vendors to ensure every detail is handled the right way. Known for his calm, reliable approach, Antonio helps make the entire process feel seamless for everyone involved.

Rita is often the first friendly voice you hear when you call MasterKey. She supports our team by directing calls, organizing communication, handling HOA notices, and keeping documentation on track. Her warm, steady approach helps owners and residents get the answers they need quickly and ensures our operations run smoothly behind the scenes.

Marcos is the point person for all maintenance and repair coordination. He reviews incoming requests, works with trusted vendors, and keeps owners and residents updated every step of the way. With a practical, solution-focused mindset and clear communication, Marcos ensures repairs are completed efficiently and to MasterKey’s quality standards.