Jake Windsor

Jake Windsor

Sales Representative
Property.ca Inc., Brokerage
About Jake Windsor

Whether you're buying your first home, upsizing for your growing family, relocating to Ottawa, or expanding your investment portfolio, I’m here to help make the process smooth, informed, and even enjoyable. With years of experience helping all kinds of clients—from first-time buyers to seasoned investors—I bring a hands-on, honest, and strategic approach to every transaction. Before real estate, I worked in professional sports sales and client relations with top-tier organizations like the Toronto Maple Leafs, Raptors, and Ottawa RedBlacks. That fast-paced, high-stakes environment taught me how to deliver results under pressure, communicate clearly, and always put the client first—skills I use every day in real estate. Based in Stittsville with my wife, our two young boys, and our spirited little Morkie, I know what it’s like to balance a busy life while making big decisions. I’m committed to providing guidance you can trust, quick response times, and real local insight. Outside of work, you’ll find me in the gym, on the golf course, cheering on local teams, or exploring Ottawa’s restaurants and events. I’m passionate about this city and the people who call it home. If you're thinking about making a move, let’s talk. I’d love the chance to earn your trust and help you reach your goals.

Testimonials
(1/4)

We just completed our purchase of our new home in Barrhaven today and I wanted to personally thank Jake for helping us find the home that was the right fit for us. We've dealt with different agents in the past, but we felt that Jake really stood out to us. He was very genuine, open and honest with us throughout the entire process and we felt that he always made sure we had the information we needed to make the right decisions along the way. He never made us feel pressured, which was a breath of fresh air for us. Jake helped us choose a winning strategy which ended up getting us a great home in a really nice neighbourhood. We're very grateful and would definitely recommend Jake to anyone looking for a new home. Thank you again!

-Ben Simpson

I had the pleasure of working with Jake Windsor for one of my recent real estate transactions & I couldn’t be more satisfied with his exceptional service! Jake’s extensive knowledge of the market & attention to detail made the entire process smooth & successful. From our initial meeting, it was evident that Jake was a true professional. He took the time to understand my specific needs & preferences & ensured all of my requirements were met. His responsiveness was outstanding, he promptly addressed all of my queries & concerns, providing timely updates throughout the process. What impressed me the most about Jake was his unwavering commitment to always putting my best interests first. I wholeheartedly recommend him to anyone in need of a reliable & trustworthy real estate agent in Ottawa.

-Dr. Robert Taylor

Our experience with Jake was exceptional! He made the process painless by truly understanding what we were looking for. Jake is nothing but professional and very knowledgeable of his craft which made it easy on our end. He knows when to be patient and when to be persistent, which in a very difficult market, makes it ideal to have him on your team.

-Cameron J.

I recently had the pleasure of working with Jake Windsor as my real estate sales representative, and I couldn't be happier with the experience! Jake was professional, knowledgeable, and incredibly responsive throughout the entire process. He took the time to understand my needs and preferences, ensuring that I found the perfect home for my family. What stood out the most was Jake's attention to detail and his commitment to client satisfaction. He guided me through every step, providing valuable insights and advice that made my decision-making much easier. His friendly demeanor made the process enjoyable, and I always felt supported. I highly recommend Jake Windsor to anyone looking to buy or sell a home. His expertise and dedication truly make him a standout in the real estate field. Thank you Jake!

-Kelly MacLeod