Skybound Realty, Brokerage

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Perry Staikopoulos

Perry Staikopoulos
VP Business Development

Perry Staikopoulos is a seasoned entrepreneur and real estate leader whose career spans nearly four decades across hospitality, business ownership, and real estate investment.

Perry’s entrepreneurial journey began at age 12 in his family’s restaurant business. By 20, he was leading operations for a new Toronto location, overseeing menu development, customer experience, inventory systems, and lease negotiations. His leadership culminated in the successful sale of the business following a profitable run.

Shortly thereafter, Perry was recruited to manage a high-volume franchised corporate restaurant, overseeing a team of more than 50 employees. This role refined his expertise in large-scale operations, financial performance, and team leadership—skills that naturally transitioned into real estate.

At 29, Perry obtained his real estate license and joined a leading independent brokerage in the GTA, quickly establishing himself as a top-producing agent.

After 18 years with the same real estate brokerage, Perry joined one of the region’s largest independent firms. Within his first year, he was offered a management role after identifying and securing a new office location. Starting with just two agents, Perry successfully grew the office to over 150 professionals, cultivating a culture defined by professionalism, accountability, and performance.

Throughout his career, Perry has completed more than 500 residential and commercial transactions, earned multiple Top Agent Awards, and has been featured in Profiles of Success.

A serial entrepreneur, Perry has partnered in ventures across diverse industries, including private-label consumer products, hospitality, nightclub, transportation and logistics, and a Health Canada–regulated facility requiring rigorous licensing, compliance, and audits.

Perry’s commercial real estate expertise includes business sales, industrial and office sales and leasing, multi-residential assets, land assemblies, and investment strip plazas. He has worked closely with developers, transit authorities, custom home builders, and institutional and private investors—guiding projects from land acquisition through construction and final disposition.

His leadership also extends into condominium and multi-unit development. Perry played a key role in the sales of two major developments and later served five years as President of the Condo Board in one phase and three years as Vice President in another, contributing to governance, strategic planning, and long-term asset value.

Currently, Perry is actively involved in projects aligned with the “Missing Middle” housing initiative, focused on delivering sustainable, community-oriented housing solutions.

Committed to lifelong learning, Perry has completed multiple CNE courses and ongoing professional development in sales, leadership, and personal growth. With over 98% of his business generated through repeat clients and referrals, Perry brings experience, strategic insight, and integrity to every relationship.