Matt Waddington

Realtor

Hi, I’m Matt Waddington — a real estate agent helping buyers and sellers in Bennington, Manchester, and Southern Vermont navigate the market with clarity, expert guidance, and a stress-free process.

With nearly 20 years of success as a top-performing Realtor on Cape Cod and more than 225 homes sold in my career, I bring seasoned expertise to home buyers and sellers in Southwestern Vermont and Western Massachusetts. What matters most to me is using that experience to protect your interests, reduce stress, and help you achieve the best possible result.

How I Support Home Buyers & Sellers in Bennington County

Whether you’re relocating, upsizing, downsizing, investing, or purchasing a second home, you deserve an agent who listens carefully and advocates for you at every step. Clients value my ability to:

• Offer knowledgeable guidance in both Vermont and Massachusetts markets

• Break down complex decisions with clarity

• Spot issues early and troubleshoot before they become problems

• Negotiate strategically to help you reach your goals

• Keep the process organized, predictable, and on track

For home sellers, I provide honest pricing advice, effective marketing, and hands-on help preparing your home to shine. For home buyers, I help you evaluate properties with confidence and understand which homes will truly fit your lifestyle and long-term plans.

Why People Choose Me as Their Realtor

You’ll never feel like “just another transaction.” I’m accessible, responsive, and fully invested in my clients’ success. That often means going further than what most agents consider normal.

In one recent example, a seller I represented had a buyer using a VA loan — but the peeling paint on the exterior meant the deal couldn’t move forward. Rather than let the buyer lose the home and my seller lose the sale, I spent a Saturday repainting the house so the appraisal would pass. The deal closed on time, and years later that new homeowner hired me to sell it for them

My commitment to people goes beyond the closing table. Sometimes clients become true friends — one couple I met at an open house even asked me to officiate their wedding. It’s still one of my favorite stories.

Local Life & Community Connection

My family relocated from Cape Cod when my wife joined Surgical Services at Southwestern Vermont Medical Center, and we quickly fell in love with this community. Our son, Jude, is a three-season athlete at MAU, Class of 2026, and you’ll often find me cheering on the track and cross-country teams or hosting team dinners.

When I’m not with clients, I’m connecting with friends at Union South or the Eagles Club, enjoying Vermont’s great outdoors (kayaking, fishing, hiking) or finding humor in everyday life through comedic writing — a creative outlet that has earned quite a following. I’m also a lover of history, Beatles music (we had a dog named Rigby and you’ve already heard about Jude!), and exploring antique shops around Southern Vermont.

Let’s Make Your Move a Great One

Buying or selling a home is a major transition — and you deserve an agent who’s fully in your corner. If you’re moving to, from, or within Southwestern Vermont or Massachusetts, I’d be honored to guide you with experience, energy, and genuine care.

I look forward to guiding you through your next move with the same care, dedication, and problem-solving that my clients rely on every day.