How We’re Different

It’s not just our expertise that sets us apart (although not many agents can say they have construction and real estate expertise under one roof), it’s our approach to buying and selling that gives our clients a market advantage. We prioritize quality over quantity and place client satisfaction above all else.

We care about quality—in relationships and in real estate.

Our Background Builds Your Future

Jake spent almost a decade in the trades industry, and while working on custom homes he learned a passion for design and developed a keen eye for detail. Whether buying a dream property or selling a special home, our clients benefit from the specialized knowledge we have about real estate that goes beyond the surface.

Anne—with a background in high-end hospitality, and managing Kingston’s busiest restaurant—helped build Caldwell & Co. to be a well-organized team that never sacrifices service quality. Our clients experience white-glove, comprehensive support from the minute we meet. Nothing is missed, we are proactive with communication, and we work in sync to make sure our clients always end up with the best outcomes.

Glenn has been working in Real Estate since 2013, and brings a deep understanding of the Kingston market and community to the Caldwell & Co. Team. He’s our listings co-ordinator, data analysis guru, and Sunnyside expert. Before real estate Glenn and Anne worked together in the hospitality industry. Their teamwork has always been a hallmark of their incredible attention to what matters most – our clients.

Kayla has perfected the art of working with first time home buyers. She’s great at guiding people through every stage of the process and ensures smooth sailing for all of our clients. Whether working with buyers or sellers, Kayla excels at finding answers, pulling team members together, and getting you across the finish line

The result? A real estate team that works in perfect harmony.

Imagine having A Contractor By Your Side

Someone who knows the value of quality materials, can spot good craftsmanship, and has the vision to show you the potential in any property. Now imagine that contractor is also your realtor—one who knows the Kingston market as well as all the neighbourhoods, and treats your transaction like it’s their own.

That’s exactly what it’s like when you work with Caldwell & Co. You get the benefit of many different experts all in one, no matter who your agent is. Everyone works together, sharing resources and expertise, to make sure each deal runs smoothly.

When we say full service, we really mean it.

Meet The Team

We Don’t Do Cookie Cutter

We are fascinated by Kingston real estate. There is so much character to be found behind the doors of the homes in this city. Our specialty is finding these gems, and representing them well.

We are drawn to the unique, the special, the interesting, the historical, the well designed. Homes that inspire and properties that tell a story as unique as your own.

Featured Listings

We Know Kingston Real Estate

Whether it’s an 1850’s limestone in the heart of Kingston’s Portsmouth Village neighbourhood or a mid-century home surrounded by mature trees in Grenville Park, we know where to find your dream home and how to spot potential in Kingston’s most sought-after communities.

Not stuck in the past or obsessed with the present, we appreciate the older homes that speak to Kingston’s heritage just as much as well-designed newer builds. Our experts are skilled at finding properties that embody emotion, and marketing homes that speak directly to the soul of buyers.

Explore Kingston What’s Your Property Value?

What’s right for our clients is always what’s right for us—rock solid, personalized advice.

Always Building Community

This is about more than real estate for us. We want to partner with people who have the same appreciation for quality and attention to detail as we do. Whether helping a family find a perfectly-designed heritage home, or matching a first time buyer with a thoughtfully-built condo community, we jump at the opportunity to connect great properties with even better people.

We are your collaborators—partners on your journey who are as invested in your success as you are. Our team thinks about how your new community fits with your lifestyle just as much as we consider how your new home matches your needs. And we plan listing strategies completely customized for your specific goals, while respecting your timelines.

Buy With Us Sell With Us

Never Satisfied With Standard

We are relationship-focused, and our team is committed to going the extra mile in every way. We want you to be so happy with the outcome and experience of working with us that when it comes time to sell or buy in the future you wouldn’t even consider going elsewhere—and you’ll tell your friends and family the same thing.

Read Our Reviews

Your Kingston Market & Neighbourhood Guides

Get to know the experts on our team and see how our specialized skill set elevates your real estate experience.

Meet Caldwell & Co.