Jason McGuire

Jason McGuire is the Owner and Broker of Clover Property Management, serving Pensacola, Pace, Milton, Gulf Breeze, Navarre, Orlando, and Beachside markets. Licensed as a Realtor since 2005, Jason opened his first property management office in 2008 and has spent nearly two decades building, refining, and scaling real estate and property management operations across Florida.

As a second-generation Realtor, Jason grew up immersed in the industry, benefiting from early guidance while developing his expertise through hands-on experience. His career has been shaped by continuous learning, real-world problem solving, and a commitment to improving systems, standards, and outcomes for both owners and tenants.

In his role at Clover, Jason focuses on strategic growth while maintaining quality, consistency, and a strong customer experience. He works most closely with investor clients who own A- and B-class properties and is responsible for setting the direction, standards, and expectations that guide the entire organization. While he is no longer involved in daily owner or tenant interactions, Jason steps in for high-level problem solving, negotiations, and complex situations that require de-escalation and creative resolution.

Jason’s strongest areas of expertise include negotiation, conflict resolution, and strategic problem solving. He takes pride in finding thoughtful, practical solutions and continually improving processes rather than settling for “good enough.” His leadership philosophy emphasizes progress, accountability, and building systems that scale without sacrificing service quality.

His approach to property management is neutral, fair, and solution-focused. Jason believes good property management means maintaining clear standards, acting with fairness, owning mistakes when they occur, and delivering higher-quality service through experienced, professional teams. He places strong value on transparency, over-communication, and staying current on laws, regulations, and best practices.

Jason believes Clover Property Management stands apart because of its commitment to constant improvement and the strength of its team. Practically speaking, Clover provides more than most—enhanced marketing tools such as video and 3D tours, experienced managers and staff, and a proactive approach to compliance and risk management. These systems are designed to protect owner investments while creating stable, comfortable living environments for residents.

He measures success through financial stability for owners, quality housing for tenants, and the professionalism of the organization as a whole. One of Jason’s proudest accomplishments is the growth and development of the Clover team, including successfully navigating multiple company acquisitions, launching a partner program to expand across Florida, and watching the team rise to every challenge with professionalism and care.

Raised in the Pace and Pensacola area, Jason enjoys anything on the water—kayaking, boating, and beach time—and values travel as a way to recharge and gain perspective. As Owner and Broker, his focus remains on building a company that consistently delivers better outcomes through strong people, clear standards, and thoughtful leadership.