Caleb Roy is an accomplished Realtor with over eight years of experience, known for his integrity, professionalism, and exceptional service. Based in Waterloo, Ontario, Caleb specializes in residential properties, income properties, pre-construction, and commercial real estate. Fluent in English, Hindi, and Punjabi, he provides personalized, client-focused support to families, investors, and businesses across Ontario, including Niagara, Toronto, Mississauga, Burlington, and Woodstock. His ability to negotiate effectively and communicate clearly has earned him multiple accolades, including three awards for excellence in real estate and a Diversity Award for his community contributions.
Caleb has lived in Waterloo for 38 years and is deeply connected to the community. He supports local charities, has previously served as a director on various boards and actively participates in cultural and arts initiatives. Outside of work, Caleb enjoys golfing, biking, playing soccer and tennis, and spending quality time with his family, which he considers his greatest joy.
Caleb’s approach to real estate is straightforward: treat clients with honesty, ensure their needs are met, and make the process as smooth as possible. Whether guiding first-time buyers or seasoned investors, Caleb’s commitment to excellence and community sets him apart as one of the most trusted Realtors in the region.
What Made You Want to Do the Work You Do?
I became a Realtor because I’ve always loved helping people make big, positive changes in their lives. Real estate felt like the perfect fit for me—it’s about making a difference by guiding clients through life-changing decisions. Helping someone find their dream home or make a smart investment is incredibly rewarding. I also enjoy solving problems and negotiating deals, which are areas where I thrive. Every day in this career brings a new challenge, and seeing the excitement on my clients’ faces makes all the hard work worthwhile.
Tell us 3 surprisingly easy and 3 surprisingly difficult things about your job.
Easy:
Connecting with clients: Listening to people and building trust comes naturally to me. Years of working in the community have taught me how to communicate effectively and genuinely.
Understanding the market: I love numbers and trends, so analyzing the real estate market feels more like a fun puzzle than a chore.
Staying organized: I’m naturally detail-oriented, so managing contracts, timelines, and schedules is something I handle well.
Difficult:
Managing emotions: Real estate can be emotional for clients. Helping someone stay calm during stressful moments takes patience and empathy.
Balancing work and life: The job doesn’t stop at 5 PM, so it’s hard to switch off sometimes. Finding time for family is something I prioritize but continually work on.
Handling surprises: Every deal is unique, and unexpected issues—like legal hiccups or last-minute buyer changes—can be tricky to navigate.
What are the 3 things you like best about your work and why?
First, I love helping people. Whether it’s finding the perfect home or negotiating a great deal, making a difference in someone’s life is incredibly fulfilling. Second, I enjoy the variety. No two days are the same in real estate, and every client brings a new challenge or opportunity. Third, I appreciate the relationships I build. I often stay in touch with my clients long after a deal is done, and many of them become friends. These personal connections make my work feel meaningful. Plus, seeing the joy on someone’s face when they step into their new home is unbeatable.
What do you think are your 3 biggest weaknesses and how are you overcoming them?
One weakness is that I sometimes take on too much because I hate saying no. I’m learning to set boundaries and delegate tasks when needed. Another is being a perfectionist. I’ve realized that while details are important, overthinking can slow me down, so I focus on prioritizing what really matters. Lastly, I’m not naturally tech-savvy. I’ve been working on improving my tech skills by taking courses and staying open to learning new tools. These improvements have helped me be more efficient and keep up with industry changes.
Tell us about a time where you saw a surprising outcome that you did not expect.
One time, a deal I thought was solid fell apart at the last minute because of financing issues. It was a shock to both me and my client. We regrouped quickly, explored new options, and ended up finding an even better property within a week. The experience taught me to always have a backup plan and to keep a positive mindset. Challenges often lead to unexpected opportunities, and that’s a lesson I carry with me every day.
Have you ever moved for a new job? Tell us about that experience.
I haven’t moved for a job, but my transition from law enforcement to real estate felt like a big move in itself. Shifting from a structured career to a more flexible one was a challenge, but it also brought a lot of freedom and excitement. It was like starting a new chapter, and I embraced the chance to learn and grow. While the adjustment took time, the support from my family and the Waterloo community made all the difference.
What do you value most and why?
I value integrity the most. It’s the foundation of everything I do, both personally and professionally. I’ve learned that being honest and treating people with respect builds trust and lasting relationships. I also value family, because they’re my support system and my motivation to work hard. Lastly, I value giving back. Supporting my community is a way of showing gratitude for all the opportunities I’ve had.
How do you celebrate your victories?
I keep it simple. When I close a big deal or accomplish a goal, I celebrate by spending time with my family. We might go out for dinner or just enjoy a quiet evening together. Sometimes, I treat myself to a round of golf or a bike ride to unwind. For me, the best celebrations are about appreciating the little things and reflecting on what went well.
What is your favorite movie and why?
My favorite movie is The Pursuit of Happyness. It’s a powerful story about perseverance and the importance of never giving up. The film reminds me that even in tough times, there’s always hope and a chance to turn things around. It’s inspiring and humbling, and it motivates me to keep striving for my goals while staying grounded.
What advice would you give to your younger self and why?
I’d tell my younger self to worry less and trust the process. Things have a way of working out, even if they don’t go as planned. I’d also remind myself to take more risks and not be afraid of failure—it’s how you grow. Lastly, I’d say to enjoy the journey and spend more time with the people who matter most.
Are you willing to be a mentor? If yes, what is the best way to reach you?
Yes, I’d be happy to mentor. Real estate has given me so much, and I’d love to help others succeed in this field. The best way to reach me is through email at calroy667@gmail.com. I believe in sharing knowledge and helping others avoid the pitfalls I’ve encountered.
Just for fun, what is your favorite dessert?
I have a sweet tooth for apple pie. There’s something comforting about a warm slice with a scoop of vanilla ice cream. It reminds me of family gatherings and the simple joys in life. Whether homemade or from a local bakery, it’s my go-to treat when I want something indulgent but classic.