Tailored. Transparent. Technology-First. Proven.
FiveCircle Property Management is a modern, technology-enabled property management company built to serve homeowner and condominium associations of all sizes—especially those often overlooked by traditional firms.
With decades of industry experience and a national platform of expert leadership, we deliver scalable solutions that are flexible, transparent, and rooted in service excellence. Whether you’re a 20-unit condo building or a growing community of 100+ homes, FiveCircle provides the structure, service, and support you need—without forcing you into a one-size-fits-all model.
To enhance property values and improve the quality of life for the communities we manage. Every system we build, every team we train, and every service we deliver reflects that purpose.
We are not a legacy firm doing business the same way it’s always been done. FiveCircle was built from the ground up to serve modern HOA and condo communities with:
pay only for the services you need
that enables transparency and ease of access
for faster, more reliable service
trained in EOS (Entrepreneurial Operating System) for strategic consistency and operational discipline
We are committed to delivering exceptional support that enhances the quality of life for every resident.
We leverage advanced technology and modern practices to streamline community management.
We foster trust through open communication and easy access to essential information.
We bring specialized knowledge and proven experience to meet the unique challenges of community management.
We take full responsibility for delivering reliable, measurable, and high-quality results.
We run on the Entrepreneurial Operating System (EOS), a framework that ensures discipline, accountability, and clarity across every department. Combined with a best-in-class tech stack—including Vantaca, STAN AI, Microsoft, and AvidXchange—we deliver a consistently exceptional experience for board members, homeowners, and internal teams.
Whether you’re part of a self-managed HOA, considering a management switch, or looking to scale community services responsibly—FiveCircle is here to help.
Chris is a seasoned entrepreneur with over 34 years of leadership experience and nearly two decades in the property management space. He has grown one of the region’s largest firms and now leads FiveCircle with a strategic vision rooted in accountability, innovation, and care.
Chris is known for his ability to scale teams and deliver measurable results through big-picture thinking and operational excellence.
Outside of work, Chris is dedicated to community involvement, charitable initiatives, and family travel adventures.
Christina D’Annunzio serves as President of Five Circle Property Management, where she provides strategic leadership and operational oversight focused on delivering high-quality, forward-thinking community management services.
With nearly two decades of experience in community association management, Christina brings deep expertise in governance, financial oversight, operational efficiency, and board relations. Her leadership emphasizes building high-performing teams, implementing scalable systems, and leveraging technology to enhance transparency, communication, and service delivery.
Christina holds the industry’s highest professional credential, the Professional Community Association Manager (PCAM®) designation, and is passionate about professional development, innovation, and elevating the overall community management experience for boards, residents, and staff alike.
Lisa brings 25+ years of accounting and financial leadership to FiveCircle, where she drives financial transformation, efficiency, and regulatory compliance. She holds multiple community management certifications and is fluent in both English and Spanish. Lisa’s leadership combines financial expertise with a passion for team development and client success. When not analyzing budgets, Lisa enjoys spending time with her family and supporting industry education initiatives.
Jodi leads operations in the Bethany Beach, DE area with a people-first approach and a background in hospitality and property management. With certifications from Cornell in revenue management and a strong operational toolkit, Jodi excels at building trusted relationships with communities and boards.
In her free time, she explores historical research and cares for her three beloved cats.
After a distinguished 20-year career in law enforcement, Ethan brings a calm, solutions-focused presence to his role at FiveCircle. Based in Delaware, he serves communities with empathy, integrity, and a deep understanding of what it takes to support smooth operations and positive homeowner experiences.
Outside the office, you’ll find Ethan on Delaware’s beaches with his wife and kids, soaking in coastal life.
