What People Are Saying

Jason Gillespie Heashot

Jason Gillespie

REALTOR®

CONTACT

(781) 690-3308
jgillespie@lamacchiarealty.com
Easton Office
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Languages Spoken

English

about

Jason Gillespie believes great real estate service starts with a simple philosophy: Clients Over Transactions. Whether buying your first home, selling a longtime property, or relocating, Jason takes an education-first approach so his clients understand the market, the process, and their options.

For sellers, Jason combines local market knowledge with Lamacchia Realty’s powerful marketing, professional photography, strategic pricing, and extensive exposure. For buyers, he provides hands-on guidance from the first meeting through negotiations and closing. When you work with Jason, you’re not just hiring one agent. You benefit from a strong team and trusted network of lenders, attorneys, inspectors, contractors, and real estate professionals.

Jason proudly serves buyers and sellers throughout the South Shore and Southeastern Massachusetts. For Jason, closing day isn’t the end of the relationship. Clients Over Transactions. Always.

 

What made you want to join Lamacchia Realty? 

“The training is top-notch, and their approach to helping agents grow is unmatched. From the first conversation with leadership, I knew this was the right place for me.”
 

What do you enjoy doing outside of work? 

“I love anything outdoors—skiing in the winter with my daughters, beach trips in the summer, or heading up to Sebago Lake in Maine. I’m also a big fan of North Conway and camping. But what I enjoy most? Watching my daughters play sports—Emma plays soccer year-round, and Riley is a captain on the high school swim team.”
 

What is your favorite thing about your job? 

“Meeting new people and helping them through one of the biggest decisions of their lives. Being part of that journey is incredibly rewarding. The team here is also amazing—everyone’s genuinely supportive and passionate. It feels like a family.”
 

Fun Facts:

  • Big Patriots fan—season ticket holder. He’s been to all the big games (including the Snow Bowl), but still has the Super Bowl on his bucket list.

  • Proud dog dad to Bailey, a high-energy boxer who loves her walks.

 
Diana L.
Jay was so helpful on our home buying journey! He was always responsive, attentive, and working behind the scenes to get us our dream place. His knowledge of the process and area made him a great advocate to have by our side! Anyone would be lucky to have him as a realtor!
Julia L.
Jason went above and beyond as are our realtor. He stuck by our side through the long and challenging home buying process and always had the best intentions for us. He was a great educator and communicator. Jason was honest, supportive, reliable, and trustworthy. At the end of the home buying process not only had we gained a great relationship with a real estate agent and great company but we gained a great friend too.
Heather K.
Every step of the way Jason was there holding my hand, navigating the new waters for me. A huge sigh of relief having his knowledge, advisement, and network of professionals all within reach. It was a huge life change for our family; yet with confidence Jason knew what needed to be done. Without hesitation he was jumping in and literally rolling his sleeves up to make sure we got our goal accomplished. I cant begin express my level of gratitude and will continue celebrate this experience.
Katherine G.
Jason was exceptional! My husband and I were first time homebuyers and right from the start he listened to our laundry list of items. Jason came to every house with us and even gave some pointers to look out for. He would get down on his hands and knees or walk around in socks whatever was needed to make sure we were confident in each home. All while being incredibly courteous and professional. He is very responsive and always checked in with us. I would highly recommend Jason to anyone looking to buy or sell. You will not be disappointed.
Jennifer A.
Jason was beyond amazing. He was eager to answer any questions big or small along the way of my buying process. Not only was he brilliant but also a kind and understanding broker. If you're looking for someone to hustle and get the job done Jason is your guy!

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