Cheryl Thompson

Background

About Cheryl Thompson

I help discerning Baby Boomers and Seniors with expert real estate guidance to navigate their next chapter in style. Downsizing isn’t about doing less. It’s about living more intentionally. As a luxury real estate advisor with Sotheby’s International Realty Canada, I specialize in guiding accomplished baby boomers and seniors through the complexities of selling the family home and transitioning into a new lifestyle, whether that means a bespoke pied-à-terre in the city, a serene retreat elsewhere, or something entirely new. My clients are discerning individuals who value expert guidance, personal attention, and the highest standards of professionalism. Many have lived in their homes for decades and are ready for change, but are unsure where to begin. That’s where I come in. I bring a refined, concierge-level approach to real estate that’s rooted in trust, discretion, and results. From pre-listing planning and home preparation to sourcing ideal properties and coordinating every step in between, I offer a seamless experience tailored to your life and vision. My goal is to make the process not only manageable but deeply rewarding. Before real estate, I built and led several successful businesses across North America, including a consulting firm focused on retirement planning, a multi-location automotive distribution company, and a celebrated restaurant in Toronto’s Rosedale neighbourhood. These experiences sharpened my business acumen, marketing savvy, and deep respect for client relationships, all of which I bring into every real estate transaction. I’m also a passionate foodie and wine enthusiast, and I believe that how we live and where we live should reflect what we truly love. If you're beginning to think about a transition, or simply want to explore what’s possible, I’d be delighted to offer guidance and insight, with no pressure, just conversation. Let’s talk about what your next chapter could look like — beautifully.