Real Realty: A seaside sit-down with the Compass agent

Hanging Ten with Kevin Flaherty

Independent/Ty Wenzel

For Kevin Flaherty, there’s more to living on the East End than catching waves and rays in the summer months. This born and bred Hamptonite, and rising star on the Compass team alongside Diane Shifman, has an eye for all corners of the market, from new constructions to the booming rental market, and everything in between.

You’re a real local. What was it like to grow up on the East End?

The East End is a very special place, and I am privileged enough to be born and raised here. I am surrounded by some of the best golfing, surfing, and fishing on the east coast. I couldn’t have picked a better place to grow up.

How do you think this gives you an edge?

I know the ins and outs of every neighborhood, restaurant, and beach. My local contacts are extremely valuable to me in this business.

Did you always know you had a knack for real estate?

I didn’t, but six years ago when I started, I immediately realized that I had found my calling.

You also specialize in rentals. How was that added into your portfolio?

Through my local contacts, I was able to rack up rental listings and learn the business from the bottom up. Renters often become buyers, and landlords or sellers. My extensive knowledge in the rental market helps me advise buyers looking for investment properties and guide them through the rental season.

How and why did you and Diane Shifman begin to work together as a team?

We were both overwhelmed with work and realized that by working together, we can be more productive. Two heads are always better than one.

Do you and Diane split up the various parts of the buying/selling process?

Our personalities are so different that we click with people in our own style. Plus, having different points of views helps us work through the process.

Do you ever take time for projects outside of real estate, including remodeling or new constructions?

Coming from a family with a construction background, I sense that in my near future.

What are some marketing tools that you use?

There’s a very long answer to this question, and I will spare the readers. The short answer is that Compass has a suite of proprietary tools that allows me to make better and more data-backed decisions. This innovative technology has given me the knowledge I need to find the right audience and market a property efficiently.

Have you noticed any trends or up-and-coming locations on the East End that you’re excited about?

Springs is taking off. With the beautiful bay beaches and the emergence of trendy restaurants, Millennials are following the artists and are moving in.

We hear you’re an avid surfer. Where are your favorite spots?

The Surf Lodge — just kidding! It varies depending on the swell direction, wind direction, and sand bar set up. You can find me in the water anywhere from Georgica to Montauk.

To learn more about Kevin Flaherty or Compass call 631-905-9410 or email