Our lives were uprooted, but that became the catalyst to realize our dreams and create our own opportunities.

In 2013 my husband, Jay, lost his job. Everything changed for our family overnight. At the time, we were living in Texas where I was homeschooling our kids, Rock and Duke. I asked my dad if we could move into his extra river house in Kilmarnock, Virginia, to help Jay start a new business. I fully expected my dad to say “no” and to tell us to stay in Potomac, Maryland, where there were more job opportunities. To my surprise, he said “yes.”

We packed up our lives in Texas and moved to the Northern Neck of Virginia, a place most people have never heard of, nestled between the Potomac River, the Chesapeake Bay, and the Rappahannock River. Kilmarnock is a tiny town, part of a cluster of three small towns, each with fewer than a thousand people. It felt like we were moving to the edge of the world, but we fell in love with the close-knit community and incredible landscape.
Launching our first restaurant together in 2013 was a crash course in resilience and resourcefulness. Jay had years of experience in the restaurant industry, but opening a business in a rural area was a completely different challenge. I handled everything I could, from paperwork and logistics to community outreach and all the behind-the-scenes work that comes with starting from scratch. Our family-friendly Burger joint quickly became a gathering spot for the community, filling a real gap in Kilmarnock.

Once our family was established, it was finally time to pursue my own dream. I had always wanted to be a REALTOR® and even earned my license in Texas right before our move. In 2017 I earned my Virginia license, and from the start, I knew I had found my calling. On my first day as a licensed agent, I wrote a ratified offer for a buyer. That’s far from the norm for the first day, I took it as a sign I was on the right path.

My focus quickly became luxury waterfront properties, which are truly unique in this area. There are no cookie-cutter neighborhoods or homes here. My background growing up around the water in Annapolis, Maryland, and my family’s love for sailing, gave me the knowledge and comfort to help clients navigate the ins and outs of buying and selling waterfront homes. I love the treasure hunt aspect of it, driving down a gravel road and discovering a stunning estate with views you cannot find anywhere else. My love for this area, the incredible properties here, and the amazing people I get to work with is what keeps this work so exciting.
Now, we couldn’t imagine living anywhere else. In that challenging time when we took a huge leap of faith, we completely transformed our lives and took control of our future.
My husband went on to open a new restaurant concept in 2023, Small Town Burger. It’s our creative take on casual dining. It started with a food trailer permanently set up on Main Street in Kilmarnock. We offer outdoor seating, fire pits, and a backyard vibe. It was a huge hit, leading us to open two more locations. Now, Rock and Duke are partners with Jay in running Small Town Burger, making it a true family venture. I’m proud of what we’ve built together, and even prouder to see our sons learning firsthand what it takes to create and grow a business and life they love.

Outside of work, a passion is showing horses. In my first year, I was able to win several awards, I give most of the credit to my amazing horse, Gus. I also serve as secretary on the executive board of our local Chamber of Commerce and volunteer at a variety of community events throughout the year. And of course, I love quality time with my family and friends.

Working with Isabell Horsley Real Estate, the leading family-owned brokerage in the Northern Neck and Middle Peninsula, aligns perfectly with my background and values. I grew up in a multi-generational family business and my family and I are proud local business owners today. This shared commitment to integrity, community, and service iscentral to my approach to real estate.
No matter what goals my clients come to me with, I am always ready to jump in and take on the challenge. I’m very resourceful, finding solutions and helping uncover opportunities. My specialty is second homes and waterfront properties, so I bring in-depth knowledge of waterways, docks, water depths, and shorelines, understanding how each of these factors relates to your specific goals and lifestyle. Every home here is unique, and I love showcasing what makes each one special through strategic marketing and listing prep.
One of the things I’m most proud of is that my clients consistently tell me they feel like they’re my only client. My clients feel this level of service because I truly care about each person I work with. I stay organized, remain flexible to their needs, and keep communication consistent throughout the entire process. As someone who lives, works, and plays on the water here.
Sincerely,

Diana Wolfson
