Contact Information
Office: 416.424.4910
Email: cailey@heapsestrin.com
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President & CEO, Broker of Record, BComm
Cailey Heaps
Cailey Heaps is a forward-thinking real estate entrepreneur and business leader at the helm of one of the most successful real estate teams in the country. Known for her innovative mindset and bold strategic vision, she has built a reputation for challenging traditional industry models and identifying new opportunities for growth. Under her leadership, the Heaps Estrin Team consistently ranks among the top 1% of realtors in North America year after year.
With more than two decades of experience in the industry, Cailey’s role has evolved from practitioner to visionary leader. As President and CEO, she focuses on shaping the long-term strategy, culture and direction of the business while driving innovation across marketing, client experience and operations. Her entrepreneurial approach and willingness to embrace calculated risk have positioned the Heaps Estrin Team as a leader in Toronto’s highly competitive luxury real estate market.
Cailey began her career in advertising after earning a Bachelor of Commerce with a major in Marketing. The experience provided a strong foundation in branding, strategy and consumer insight—skills she later brought to the residential real estate industry when she joined her mother, Heather Heaps’ successful real estate business in the 1990s. Over the years, Cailey has played a central role in evolving the company into one of Toronto’s most respected and high-performing real estate teams, recognized for its innovation, collaboration and sustained growth.
Widely regarded as a trailblazer in the Toronto real estate market, Cailey is also recognized as an industry thought leader. She is frequently invited to share her perspective with local and national media and to speak at events across the country, offering insight on leadership, entrepreneurship and the future of real estate. She is also a member of the Young Presidents’ Organization (YPO), the global leadership community of chief executives and business leaders.
Cailey’s entrepreneurial success has been recognized by the Women of Influence+ organization and the prestigious RBC Canadian Women Entrepreneur Awards, as well as through her 2023 induction into the Royal LePage® National Chairman’s Club™ Hall of Fame. She is also a committed supporter of charitable initiatives and community causes.