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The Village Guru Team


Jeff O’Leary, Broker & Team Leader

Jeff is an Entrepreneur, University of Toronto graduate, former Canadian Forces member, and devoted husband & father. He is a respected member of his community as the Chair of the Lake Wabukayne Committee, he is an active member of the Rotary Club of Meadowvale and serves on the Board of Directors for the Mississauga Real Estate Board.

Jeff created The Village Guru to provide a higher level of expertise and service that was lacking in the industry. Jeff and his team focus on the client, and tailor their proven systems to each client’s individual goals and needs. Since the inception of the Village Guru, Jeff has received annual Top Producer Sales Awards and is in the top 3% of the GTA market of over 40,000 agents. He regularly speaks at industry events, to teach other agents how to improve their business. And year after year, he receives awards from multiple media outlets, recognizing The Village Guru as one of the Top Real Estate Blogs in Canada. Sharing knowledge and educating prospective clients is the first step to providing better service and getting better results.

Christopher Dacosta, Sales Representative

Chris was hand picked by Jeff for his personality, values and intellect. You can teach anyone a “skill” but you can’t teach attitude. You can’t teach a positive energy and a desire to be the best. Chris has all of these qualities in spades. The cornerstone of The Village Guru is integrity – and we don’t say that lightly. In this industry, it is sorely lacking, and Chris is a perfect compliment to the Village Guru principles of protecting our clients needs & interests above all else. Chris is analytical, a great communicator, and not afraid to ask questions. He never assumes anything about anyone, he takes the time to get to know you and what’s important to you. He is a dedicated professional whom you can count on as part of your buying or selling team.



Stephanie O’Leary, Home Stager & Interior Decorator

Yes, Stephanie and Jeff are partners both personally and professionally. But make no mistake, this isn’t nepotism, she has staged hundreds of homes over the last 12 years and started in the real estate industry even before Jeff.  And now, she is the team’s secret weapon for our listing clients. The Village Guru team is known for setting price records with our house sales, due in large part to how much buyers love her work. Buying is an emotional process and her artistic & strategic ability to hit these emotional notes is second to none. Also included in our services is her warehouse of stylish props, which is an unparalleled advantage.


Photography & Marketing Professionals

We don’t think being a one-man show gets the best results. We focus on what we do best, and hire professionals who are at the top of their craft. We cannot emphasize how critical listing photos are to a successful first impression and we have hired the best artists to showcase your home in its best light. This can also include video tours, floor plans, print marketing and social media marketing. You truly get an entire team of experts all doing their part to give you better service and the best results.

Our clients know that working with true professionals gets them far better results when selling and buying. Click below to see the kind of clients we attract and whom we love to work with:

Contact The Village Guru Today

If you’re looking for real service, better value, and the best results, we’re looking for you.