Cailey Heaps

^{Contact Information}

Office: 416.424.4910

Email: cailey@heapsestrin.com

^{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.

White Spacer

Cailey and Sandra, You folks do everything right, and we could not have felt in better hands over the past several months. Thank you again for such service and support - your generous gift is just more icing on the cake (that was already as “iced” as we could ever expect it to be!!). Thank you both so much again.

Timothy J. Fallis on Working With Cailey Heaps

What a pleasure it was to work again with Heaps Estrin and too great success. A big thank you to both Cailey and Aman for their exceptional service and attention to detail. My family and I were very pleased to be in such good hands throughout the experience of selling my mother's condominium. Once again, thank you and best wishes to you both.

Jeremy Aykroyd on Working With Cailey Heaps

It's been so good working with Cailey, Jeannine and The Whole Crew. It's a rare thing to feel so confident and supported by a professional team of any nature. When it's such a loaded and personal moment as we prepare to release this house and continue to say our goodbyes to our parents, that support and confidence have meant a great deal.

Simone on Working With Cailey Heaps

Cailey and the Heaps Estrin Team were nothing short of fantastic during our recent house sale experience in Toronto. Their professionalism, responsiveness, and depth of knowledge inspired total confidence. This team has the drive and resources to get things done on time and to the highest standards, and we never had any doubt that our best interests were at the forefront. We were very satisfied with the results, which exceeded our expectations. Patrick and I recommend Heaps Estrin 100%. Anyone looking to buy or sell a property need not look further- these guys are the best of the best!!!

Lee Murphy Nobbs on Working With Cailey Heaps

Working with Cailey Heaps and her team at Heaps Estrin was the easiest process I have ever experienced in selling a house. And I have sold several. They made it stress-free; everything was taken care while we were out of town. Every question was answered immediately. They are wonderful.

Sarah Hampson on Working With Cailey Heaps

Cailey and Jeannine, I would like to thank you both for your extremely efficient and professional care in selling Jane’s condo. Throughout the whole sale, you were on top of the process. I have always recommended your services before but now I can give my recommendation based on first hand knowledge. Best of all , the proceeds will allow Jane to have the care that she needs now. I will see her tomorrow and tell her how well everything happened thanks to you.

Peter on Working With Cailey Heaps

I was fortunate enough to successfully work with the Heaps Estrin team for both the selling of my home and the purchase of a new one during a very "hot" market this spring. I don't think there can be a finer firm to work with than Heaps Estrin. Cailey has built a fabulous team that delivers outstanding results, exudes a high degree of professionalism and, importantly, displays empathy and support for the needs of their client under trying circumstances. I feel fortunate to have been able to count fully on Cailey and Jessica during this process and to have arrived at a very happy outcome!

Jan on Working With Cailey Heaps

We chose Heaps Estrin to list our home after considering several Realtors. We chose them because their highly professional yet personal approach to marketing the property provided, in our opinion, the best strategy and formula for a successful outcome. Cailey Heaps Estrin and Christina Pinelli were focused, articulate and decisive in their planning and the process was smooth and far less stressful than anticipated. Our house sold in a week. We would highly recommend their services.

Chris on Working With Cailey Heaps

Listing my condo with the Heaps Estrin Team was a very positive experience. From my initial meeting with Cailey, I was impressed by the professionalism, attention to detail & personal warmth that characterized the entire team. Their marketing strategy was highly effective resulting in a quick sale. I would recommend them with enthusiasm.

Marsha on Working With Cailey Heaps

Thank you, Cailey, for handling the sale of our parent's home. You were great, and we are so happy we chose you to help us during this difficult time. I know my sisters & I will miss 127 Bessborough Drive, but we will cherish our wonderful memories we all shared there with our sweet parents. Thank you again

Lorrie on Working With Cailey Heaps

When we thought about selling our home in Lawrence Park, we knew we needed to work with Cailey Heaps and The Heaps Estrin Team. We felt we were in good hands from the way they approach the selling process to their unrivalled marketing strategies. Cailey and Megan made the process of preparing our home less daunting, and when we went to market, our home sold quickly - exceeding our own (high) expectations! Cailey and Megan brilliantly managed the multiple offers to achieve the best outcome. It is without hesitation that I would recommend working with The Heaps Estrin Team.

Karalee on Working With Cailey Heaps

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