My path to real estate was shaped by market crashes, bold career pivots, and a lifelong discipline that taught me to keep going even when it’s tough.

I’ll share a secret with you: I love numbers, but I don’t love staring at spreadsheets all day. That realization is what made the decision to get my real estate license easier—I was craving more human connection, and my personality was simply a better fit for a people-centered career.

Before real estate, I was deeply immersed in finance. I originally pursued a math degree in college—since numbers have always come naturally to me—but back then, a math degree meant learning to program at the very beginning of the computer age. I realized that wasn’t how I wanted to spend my future. I pivoted to business with a concentration in finance, which felt like the right balance.

I began my career in the accounting department of a nonprofit in the financial services space. I stayed there for 12 years, working my way up the ranks. During that time, I married my husband, Coburn (this year we celebrate 30 years together).

A pivotal moment came in 1997 when I became Vice President of Finance and Administration for a tech startup during the height of the dot-com boom. It was an exhilarating time to be in tech. For three intense years, we worked behind the scenes preparing to go public. I helped build the red herring prospectus and worked around the clock, fueled by big dreams of success.

 At the last minute, everything changed. The stock market crashed, we pulled the filing, and our plans to go public were canceled. Shortly after, the company was sold. I received a nice payout—but suddenly, I found myself with no clear, predictable path forward.

At the time, I was a mother to two boys, Sean and Kyle, and I wanted more flexibility. I also knew I was ready for a career with more human interaction. Real estate had always been in the back of my mind—I had even considered studying architecture at one point—so I decided this was the moment to take the leap.

That decision launched a chapter of pure hustle. I got my license during a market crash—not exactly ideal timing for a rookie agent. To make it work, I took on other jobs to support myself. Another challenge was the lack of mentorship; real estate can be a surprisingly secretive industry. Fortunately, I was also working as a headhunter for a staffing firm, recruiting high-performing accountants. That role gave me solid sales training, which turned out to be invaluable in real estate. I kept going, learning as I went.

That discipline was actually shaped early on through my years in the 27th Lancers Drum and Bugle Corps. I started at age 8, practicing through the winters and competing in the summers. It was incredibly disciplined—almost military-like. At sixteen, I performed in the opening and closing ceremonies of the 1980 Winter Olympics in Lake Placid! By the time I retired from the corps at 20, grit and tenacity were part of who I was.

I brought that same mindset into real estate. I put my head down and did the work. A commission-only career was nerve-wracking at first, but I’m grateful I took the risk.

 Today, my sons are grown—Sean is an architect, and Kyle is a photographer. I love skiing, hiking, going to the beach, and traveling, especially to places rich in historical architecture. I served on the planning board in Merrimac and feel incredibly lucky to live in Merrimac and serve greater Newburyport, a community that offers beaches, rivers, hiking, arts, and something for everyone.

Looking back, real estate became the place where my analytical mind and my heart finally met, where data supports decisions but people remain at the center of every outcome. I don’t see homes as transactions; I see them as turning points in people’s lives, much like the moments that shaped my own.

With over 20 years of experience, I bring a thoughtful, client-centered approach to real estate, treating every client like family and genuinely wanting what’s best for them. From the very first meeting, I focus on understanding not just what my clients want, but why they want it. That insight is key to matching them with the right home. I ask detailed questions early on to ensure clarity and alignment throughout the process. 

My strong analytical background allows me to dig deeply into market data and assess a property’s true value within its local context. I approach pricing the way an appraiser would, conducting thorough research and evaluating the full picture to arrive at an accurate, realistic valuation. This careful analysis carries through to negotiations, where I pride myself on being fair, objective, and well-prepared. While not every agent takes the time to fully analyze the numbers, I do, ensuring that offers are grounded in data rather than emotion. My goal is always to protect my clients’ interests with integrity.

Sincerely, 

 

Karol Flannery