Your Ultimate Guide to May 2026 Canadian Real Estate Events, Conferences, and Networking Opportunities

The Canadian real estate market is constantly evolving, presenting new challenges and opportunities for professionals across the country. To stay ahead of the curve, it’s essential to engage in continuous learning, build a strong professional network, and keep a pulse on the latest industry trends. This May, a diverse lineup of conferences, summits, and meetups offers invaluable platforms for growth, collaboration, and strategic insight. Whether you’re an experienced investor, a new agent, a commercial real estate executive, or an entrepreneur, there is an event tailored to your professional goals. From high-profile keynotes by global figures to intimate local meetups, this guide details the must-attend real estate events happening across Canada. Explore this curated list to find the perfect opportunity to enhance your skills, expand your network, and elevate your real estate business this spring.

Kickstart Your Month with the Toronto Real Estate Investor Meetup

For those in the Greater Toronto Area, May begins with a fantastic opportunity for informal networking and knowledge sharing. The Canadian Real Estate Investor Podcast is hosting its highly anticipated Toronto Meetup on Tuesday, May 12, from 6:00 p.m. to 8:00 p.m. The event will take place at the relaxed and welcoming Madison Avenue Pub, conveniently located near the bustling intersection of Bloor and Spadina.

This evening is specifically designed to be an inclusive gathering, welcoming real estate professionals of all experience levels. Whether you’re just starting your journey or are a seasoned veteran, you’ll find immense value in connecting with a diverse group of agents, investors, and entrepreneurs. The agenda is fluid, encouraging open discussions on today’s most pressing topics, including navigating current mortgage landscapes, optimizing property management techniques, and developing resilient investment strategies. It’s a prime environment to ask questions, share your own experiences, and forge meaningful connections that can lead to future partnerships and collaborations. Proudly sponsored by Sherwin-Williams, this meetup is the perfect way to build momentum for the month ahead.

Find more details and RSVP for this valuable networking event here.

Michelle Obama to Headline TRREB Realtor Quest 2026: ‘Igniting Real Connections’

Prepare for the industry’s most significant event of the year as the Toronto Regional Real Estate Board (TRREB) presents its 19th annual Realtor Quest. As Canada’s largest real estate conference and trade show, this event is a cornerstone of the industry calendar, and this year promises to be more inspiring than ever. Mark your calendars for Wednesday, May 13, and Thursday, May 14, at the expansive Toronto Congress Centre.

This year’s theme, Beyond Business: Igniting Real Connections, underscores the fundamental importance of human connection in an increasingly digital world. Headlining this extraordinary event is Michelle Obama, the former First Lady of the United States, a bestselling author, and a global advocate for leadership and community building. Her keynote address is expected to offer profound insights into resilience, purpose, and the power of authentic engagement—principles that are directly applicable to building a successful and fulfilling career in real estate.

The inspiration doesn’t stop there. The two-day conference will also feature powerful sessions from renowned Canadian speakers. Darci Lang, a celebrated member of the Speaking Hall of Fame, will present Lead the 90%, a talk focused on fostering a positive mindset through acceptance, compassion, and effective leadership. Additionally, Rebecca Mountain, a bestselling author and dynamic keynote speaker, will equip attendees with practical tools for building unshakeable confidence and transforming knowledge into decisive action.

Beyond the main stage, TRREB Realtor Quest 2026 offers an immersive experience. Attendees can explore an expanded trade show floor featuring the latest technologies and services shaping the industry. A comprehensive schedule of practical learning sessions will cover a wide range of topics, providing actionable strategies to implement in your business immediately. Above all, the event provides unparalleled networking opportunities, allowing you to connect with thousands of peers and industry leaders from every corner of the country. This event is complimentary for all TRREB members, making it an unmissable opportunity for professional growth.

Gain a Competitive Edge at the 2026 Edmonton Real Estate Forum

On Wednesday, May 13, the Edmonton Real Estate Forum will convene at the Edmonton Convention Centre, assembling the region’s most influential leaders in commercial real estate. This full-day event is a critical gathering for senior executives, developers, investors, lenders, and civic officials who are shaping the future of Edmonton’s property market. The forum is renowned for delivering high-level market intelligence and fostering top-tier networking.

The day will commence with a crucial economic outlook presentation by Michael Gregory, Deputy Chief Economist and Managing Director at BMO Capital Markets. He will provide a detailed analysis of key economic indicators, including GDP growth projections, employment trends, interest rate forecasts, immigration patterns, and the fiscal trajectory of Alberta. This session will provide the essential macroeconomic context needed for strategic decision-making in the year ahead. Following this, a keynote fireside chat will feature an insightful conversation between Edmonton Mayor Andrew Knack and Doug Griffiths, President and CEO of the Edmonton Chamber of Commerce, offering a unique perspective on the city’s growth and development plans.

The forum’s agenda is packed with specialized sessions designed to provide a deep dive into every major sector of the commercial market. Expert panels will dissect the current state and future prospects of the industrial, office, and retail sectors. Other critical discussions will focus on pressing topics such as managing climate risk in commercial real estate, navigating the complexities of new development and redevelopment projects, and understanding the evolving conditions in the lending market. The day will culminate in a closing roundtable discussion with a panel of senior executives, who will share their candid perspectives on Edmonton’s investment outlook for the next 12 to 18 months, offering invaluable foresight for attendees.

View the complete agenda and secure your registration here.

OREA Brings Professional Development to Your Doorstep with New ‘Re-Connect’ Summit Series

The Ontario Real Estate Association (OREA) is making professional development more accessible and convenient than ever with the launch of its new Re-Connect series. This innovative initiative consists of one-day regional conferences specifically designed to bring high-quality education and valuable networking opportunities directly to Realtors in their local communities across the province, reducing the need for extensive travel and time away from their business.

The inaugural summit in this exciting series is set to take place on Thursday, May 21, at the prestigious Caesar Windsor Hotel in Windsor, Ontario. The event promises a full day of impactful learning focused on some of the most relevant topics for modern real estate professionals. Sessions will cover essential strategies for building a powerful personal brand, proven methods for accelerating business growth, and a critical exploration of the role of Artificial Intelligence (AI) in the future of real estate. For an accessible price of just $99, attendees will receive a full day of expert-led content, along with included breakfast and lunch, providing an excellent return on investment. Following the Windsor event, OREA plans to host additional Re-Connect summits later in 2026 in Sudbury and Kingston, extending this valuable opportunity to more members across Ontario.

For any inquiries regarding the summit series, please reach out to the events team at [email protected].

Registration for the Windsor summit is now open.

Empowering Women in Business: The Exclusive Queen Bee Female Founders Summit

An exclusive and empowering event for women entrepreneurs is set to take place in west Toronto this month. The Queen Bee Female Founders Network summit is an intimate gathering designed to foster connection, collaboration, and inspiration among female leaders in business. This special event will be held on Thursday, May 28, from 11:00 a.m. to 2:30 p.m. at the elegant Edenbridge on the Kingsway in Etobicoke.

Presented by The Buzz Conference in a landmark collaboration with Tridel, this summit is intentionally designed to be an intimate affair, with seating strictly limited to 100 attendees. This ensures a high-quality networking environment where every participant has the opportunity to engage in meaningful conversations and build genuine relationships. The event is tailored for female founders and entrepreneurs who are looking to connect with a powerful network of peers, share challenges and successes, and gain fresh perspectives to fuel their professional and personal growth. Don’t miss this unique opportunity to join a community of influential women shaping the future of business.

Pre-register here to secure your limited spot.

Can’t-Miss Virtual Events in May

For those who prefer the convenience of virtual learning, May also offers excellent online events that you can attend from anywhere. These webinars provide targeted expertise on crucial aspects of the real estate business, from negotiation to long-term career planning.

Master Real-World Negotiations in a Free Webinar with Suze Cumming

Sharpen your most critical skill in a dynamic and interactive online session. Renowned negotiation expert Suze Cumming is hosting a free live webinar on Friday, May 15, at 1:00 p.m. EST. Titled Negotiation in the real world: What would you do?, this session goes beyond theory to tackle the practical, real-life scenarios that agents face every day. Suze and a panel of top-performing agents will work through complex and messy situations—the kind that don’t have simple, textbook answers. This is your chance to learn how experts navigate difficult clients, competitive offers, and unexpected challenges. Attendees are encouraged to bring their toughest negotiation problems, as there will be dedicated time for a live Q&A session.

Planning Your Future: REM Mastermind Tackles Buying and Selling a Book of Business

The monthly REM Mastermind series continues with a timely and increasingly relevant topic for agents at every stage of their career. Join the conversation on Wednesday, May 27, at 2:00 p.m. EST to explore the intricacies of buying and selling a book of business. As more real estate professionals consider retirement, forming partnerships, or developing a succession plan, understanding the valuation, process, and legalities of transferring a client base has become essential knowledge. This session will provide a comprehensive overview of how to prepare your business for sale or how to strategically acquire another agent’s book to accelerate your growth. The session will be expertly moderated by REM’s Andrew Fogliato, with a panel of industry experts to be announced soon. The REM Mastermind series is always free for all to attend, thanks to the generous support of official series sponsor Re/max.

Coming in June: The Future is Now at the ‘AI Meets Real Estate’ Conference

Get ready for a deep dive into the technology that is reshaping our industry. Following a completely sold-out event in 2025, the AI Meets Real Estate conference is returning on Thursday, June 4, to Catalyst Commons in Kitchener, Ontario, from 1:00 p.m. to 5:00 p.m. This focused afternoon is meticulously designed for real estate professionals, mortgage brokers, builders, and technology operators who want to move beyond the hype and understand the practical applications of artificial intelligence.

The conference will explore how AI is revolutionizing core business functions, including sales processes, marketing automation, client experience, and the future of lending. With attendance capped at 150 to ensure an interactive and engaging experience, this event provides a unique opportunity to learn from the pioneers who are actively implementing AI in their operations. The speaker lineup features a host of industry thought leaders, including REM Publisher Andrew Fogliato, Valery CRO and REM columnist Daniel Foch, Carrie Soave, Tom Storey, Ron Butler, and Tracy Valko, among other distinguished experts. This is your chance to gain a significant competitive advantage by learning how to leverage AI to work smarter, not harder.

Tickets and complete event details are available here.