Jake Caldwell

Hi, I'm Jake Caldwell

Working in real estate since 2014, I eventually set out to create Caldwell & Co. to combine diverse expertise, providing buyers and sellers with a one-stop-shop solution. Intertwining custom building services, financial expertise, and Kingston real estate intelligence, we provide full service support to clients at any stage in the real estate life cycle.

Hi, I'm Jake Caldwell

Working in real estate since 2014, I eventually set out to create Caldwell & Co. to combine diverse expertise, providing buyers and sellers with a one-stop-shop solution. Intertwining custom building services, financial expertise, and Kingston real estate intelligence, we provide full service support to clients at any stage in the real estate life cycle.

The best part about real estate is providing buyers with clarity to make easy, smart decisions, and making a seller’s home shine to get top dollar in any market.

All I do is think about houses. It’s a bit of an obsession. My bookshelves are filled with design, building, and of course, real estate books. I get up in the morning and I work with blueprints (because it’s fun), I spend my days going through houses with clients or setting up listings, and at night I’ll read about real estate trends. I just can’t help myself!

When asked what I wanted to be when I grew up, I’d have said “architect” (of course this was after my “garbage truck driver” phase). “Architect” morphed into “builder” and that’s where I found myself for just under a decade. 

I loved my work, crafting timber frames or reading about natural building techniques. A wonky back eventually pushed me out of the profession, and after a brief stint with marketing and in the family business doing financial planning (where I learned what it meant to provide advice, and guide people through large financial decisions) I couldn’t help but be drawn back to what I love.

Sharing my expertise, protecting you from a bad buying decision, or helping your listing shine are all a part of what you can expect when you work with me. Ultimately, real estate is more than bricks and mortar (and maybe that’s why I love it so much). It’s about families, life, stories, and memories. 

Put me to work for you, and I’ll help bring together the bricks and mortar of your story.

I’m an all or nothing kind of guy. This works in your favour, big time. What you get when you mix my wild obsession with housing, design, and real estate with my job as your Realtor® is someone who loves what they do, and it shows.

Everyone at Caldwell & Co. is encouraged to be themselves. We all have our own unique abilities, insights and skillsets and we build on each other’s strengths to create a well-rounded team of experts. No matter who our clients work with, they have the support of everyone on our team, because we work collaboratively for the benefit of all our clients.

Outside Of Real Estate

On the days I have to myself, I like to go deep—whether it’s mountain biking, downhill skiing, coffee, home design, or another interest. When I get into something, it’s all about the details!

My Awards

"Jake was incredible! We're so happy with our home. His insights and advice were always bang-on, his previous experience as a builder invaluable, and he really understood what we wanted and needed."

— Malumir Beavis

"Helpful, polite, never pushy. I hadn't dealt with real estate in 15 years; Jake guided and brought me up to date. He asked what I was looking for, about my needs and set me up on the real estate mailing list. Moving from Toronto to Kingston, Jake set up virtual walk throughs. His home construction and area knowledge was a great help. He wasn't just looking to make a sale, he was looking to make a match. Jake found me a great home. Even after moving in, he was more than willing to help out. I'm very fortunate!"

— Norman Baccari

"Excellent experience with Jake and his team! It was a short-deadline, no-fail move and not a buyer's market. Jake and the team rallied to find exactly the house we wanted in Strathcona Park, within our tight timeline. Beyond the normal realtor services you'd expect, Jake is an ex-contractor and can size up a house and talk about renovations like a pro!"

— Andrew Pohran

What Your Neighbours Are Saying

See what buyers and sellers throughout Kingston have to say about working with Caldwell & Co.