Jack Cherry

Sales Representative

Jack is a third generation Realtor who has been involved in the Real Estate industry for over ten years.  The rare opportunity to work with a successful family run brokerage over the past decade has allowed Jack to learn the Real Estate business and gain valuable insight into the value of client relationships to the success of the business.  This influence early in his career has fuelled Jack's passion for continued success with the brokerage and for his valued clients.

While playing competitive baseball growing up, Jack attended Mercyhurst College in Erie Pennsylvania on an athletic scholarship.  Through his athletic background Jack has developed continued relationships in the sporting world that has carried over into the real estate industry and brings a team based philosophy to the table.  Jack has a very strong referral network that provides clients with the best possible service in all areas -- from mortgage professionals to contractors, lawyers, handymen, insurance agents, home inspectors, stagers, interior designers, financial planners and Accountants.

Growing up in Toronto and spending his summers on Lake Simcoe has exposed Jack to different markets, allowing him to learn the intricacies of buying and selling in all market conditions.  Using this experience, Jack has a unique ability to strategically position his clients for the most beneficial outcome while applying his desired low pressure approach. Jack has a successful partnership with fellow representative Jamie Kinnaird.  This strong partnership ensures complete satisfaction to his clients during the transaction and most importantly, nothing is overlooked during the buying/selling process.


“As a first time home buyer I didn’t really know what to expect when I recently began looking at places. Thankfully Jack and Jamie were there to guide me through every step of the process. Something that I have always heard can be very stressful for some, turned out to be a very enjoyable process, and they are without a doubt the biggest reason for that.  You can tell when working with them that they are two people who genuinely enjoy what they do, with their only focus and goal being to find the perfect match between home and buyer. The entire experience was a team effort, they explained everything I needed to know in ways that were easy to understand, they were constantly on the lookout for any potential properties that suited my interests, and were incredible resources for helping me weigh the pros and cons that came with every option.    As someone with a difficult schedule I was blown away by their flexibility and willingness to meet and view properties with me without hesitation. Not once during our search did I ever feel any pressure, nor did they ever try to sell me on something that was not a good fit. They were as honest about the good as they were about the bad, and that enabled me to trust and rely on them as invaluable resources.  They also proved to be shrewd in negotiations as they were able to land my home for well under the asking price, something I was not expecting but was nonetheless thrilled to find. Even after the sale was completed they were eager to help me feel comfortable in my new home in any way they could.  I will always be grateful to them, and I owe both a huge debt of gratitude for not only finding the perfect place for me, but also for making me feel comfortable throughout the entire process and making it a truly enjoyable experience. Anyone I know looking at places will not hear me recommend Jack and Jamie, they will hear me insist on Jack and Jamie. There is no one else I could ever trust more. There is no one better.  ”

- Teddy Ferreira -

“"We want to thank all of the staff at Bernice Whelan Realty for all their hard work in finding the right house for our blended family. Jack Cherry was presented with a challenge to find a home to suit the life style of two generations, at a specific neighborhood, on a tight budget. He was patient and understanding through the entire process and continually offered his services after the purchase was complete. Everyone at the office has shown a vast knowledge of the current real estate market and tireless professionalism. We will continue to look for Jack's help in future real estate sales and purchases.”

- Darlene & Brian Bramhill -

“Jack was very professional, kind and courteous throughout the entire process of selling our house. I highly recommend Jack as a real estate agent and will definitely hire him again should the need arise.”

- Sherri Patrick-Perri -

“Jack - We truly appreciate all the time you've spent with us so far. As we told you before, our past experience with real estate agents has been disappointing so to have you keeping in touch with us with new properties and not pressuring us at all has been great! We will absolutely recommend you to anyone looking for an agent”

- Carol and Kevin Macdonald -
contact details
  • 416-961-9000
  • Toronto, Lake Simcoe
request more information from Jack Cherry
All fields are required

Please Call Me Email

Guess the letters and numbers
(passphrase riddle)
2 chars before small E
1 chars before small L
3 chars before small P,
3 chars before small D