Jason Gillespie

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Jason Gillespie


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After buying his first condo, Jason was disappointed with his real estate agent, and when he had to sell & buy again 7 years later, he knew he needed someone better. Luckily, he found a great REALTOR® and remembers how helpful she was especially knowing how new he was to the process. Ultimately, she inspired Jason to finally take the plunge into real estate after already having a passion for the industry for several years. Jason can’t wait to help other first time home buyers! Jason’s goals are to help and educate first-time homebuyers. Having been in their shoes once before, if he can help them experience the joy of buying their first house, that would be so rewarding to him. Many would describe Jason as hardworking, committed, and outgoing.

Previously, Jason worked in retail for over 25 years, the last 20 of those as a Meat Manager for Stop and Shop. Overall, that is 25 years of customer service where he talked to and dealt with the public at various S&S locations. From this, he learned how to manage different people and he met so many great customers and still interacts with them to this day.

Jason has lived on the South Shore for his entire life. Growing up, he lived in Brockton and Stoughton, bought his first condo in Weymouth, and lived there for 7 years. He bought a house with his wife in Raynham in 2009 where he currently resides.

What made you want to join Lamacchia Realty? 

First in foremost training and seeing how they set their agents up for success. No one markets like Lamacchia Realty. Second was the minute I talked to members of the leadership team I knew it was the right spot for me, and I didn’t need to look anywhere else. I could go on and on to be honest.”

What do you enjoy doing outside of work? 

Anything outdoors. Winter time skiing with my daughters. Summer time going to the beach, and spending time with my family up at Sebago Lake in Maine. Love to go to various islands, camping, North Conway, NH. I love to do all these things but nothing I like more than to watch my daughters in their sports. Emma is a huge into soccer and plays on various teams. Riley is on the high school swim team at Bridgewater High School.”

What is your favorite thing about your job? 

I love to meet and connect with new people. Being able to help and guide people with the biggest purchase of their lives and be by their side while they do it is so inspiring and rewarding. The company culture also, I have never worked with so many people within the same company that are genuinely passionate about what they do, and helping everyone succeed. Total family oriented company.”

Do you have any pets? 

“We have a 7 year old boxer named Bailey. Love taking her for walks to burn all that energy she has.”

What are your favorite sports, and sports teams? 

“Football, 100% Patriots fan, I’ve been a season ticket holder for over 10 years, been to all the big games, snow bowl game, AFC championships, haven’t been to a Super Bowl yet but it’s on my bucket list.”

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