Matt Waddington

Realtor

I was born and raised in Falmouth, MA,where I spent 18 years as a top-performing Realtor. Over the years, I sold over 225 homes and ranked in the top 1% of Realtors on the Cape for the number of units sold for 5 years in a row.  I am still a member of the Cape Cod and Islands Association of Realtors, serving clients on the Cape, as well as a member of MLSPIN for Western Massachusetts.  

My family and I relocated to Vermont when my wife accepted a job offer from Surgical Services at Southwestern Vermont Medical Center (SVMC). Since moving here, I've embraced the local lifestyle, enjoying kayaking, fishing, and hiking. Our amazing son, Jude, is on the Principal’s Honors list and a 3-season athlete at MAU, class of 2026.

I have a passion for comedic writing, turning everyday events into humorous stories. These have garnered a large following and even attracted the interest of literary agents. I love talking to people and making them laugh, often turning brief encounters into memorable moments.

As a huge Beatles fan, my love for music is reflected in my son's name, Jude, and our dog, Rigby. I have a deep fascination with history. I enjoy documentaries, museums, and antique stores. I often feel like I have an old soul, with a deep appreciation for the past.

Generosity is a core part of who I am. Every year, I organized benefits to support families in need. Since moving here, I continue to help locals in Bennington and look forward to making new connections.

I tend to become good friends with my clients.  Mainly because I go above and beyond what most agents are willing to do.  As an example, I had a listing under contract with a U.S. veteran using a VA loan.  The entire back of the house had chipping and peeling paint, which is a dealbreaker for government-backed loans.  My seller couldn’t afford to hire a professional painter, so I rolled up my sleeves and took care of it myself one Saturday afternoon… even paid for the paint.  My efforts satisfied the appraiser and the deal closed!  The buyers were so appreciative that when they went to sell it five years later they called me – instead of their buyer's agent.

Then there was a couple that I sold a house to in 2008.  They were strangers I had met at an open house.  We got along so well that they actually asked me to perform their marriage ceremony.  I applied to be a Justice of the Peace for a day and officiated their union.  True story!

I bring dedication, expertise, and care to your real estate deal, whether you're buying or selling a home. I will ensure a smooth and enjoyable experience... and possibly write about it in the future!