We're delighted to welcome home Phillip Chiesa to Island Sotheby's International Realty, where he continues to bring dedication to every client relationship. For Phillip, real estate is about much more than buying and selling homes. It's about understanding each client's goals, solving complex challenges, and helping people make confident decisions during one of life's biggest milestones. When he's not working with clients, you'll likely find him exploring Maui's incredible landscapes, climbing at the local rock gym, or enjoying the peaceful beauty of ʻĪao Valley.

Get to know Phillip as he shares more about his journey, what he loves most about Maui, and the philosophy that guides his approach to real estate.

What led you to where you are today?

I started my real estate career at 24 with, frankly, a limited understanding of what the role would entail. I quickly learned firsthand how fun and rewarding it is to help clients achieve their goals. It's a perfect blend of relationship and network building, analytical, data-driven work, and creative problem-solving, and that combination is what's kept me engaged ever since.

What's your favorite part about living on Maui and why?

The sheer diversity of natural beauty in such a compact place. ʻĪao Valley, Mākena, Haleakalā Crater, and the waterfalls on the North and East Shore. Few places on earth offer that kind of variety on one small island.

What's your favorite part about being a REALTOR?

The most intrinsically rewarding part of being an agent is helping first-time homebuyers. It's a process that's equally exciting and intimidating for them. Helping a client reach the peace of mind that comes with homeownership is a genuinely enriching experience.

Why did you choose to return to Island Sotheby's International Realty?

In my eight years as a full-time real estate agent, ISIR is the only brokerage I've ever been with. The leadership, marketing, and administrative support are unparalleled, and I've never felt the need to explore other brokerages. From day one, I felt at home here.

Where can we find you on the weekends?

ʻĪao Valley and Aloha Rock Gym. I love nature and I love rock climbing. ʻĪao Valley is a core part of my life, whether it's spending time by the river reading a book, swimming, or simply enjoying the surroundings. Aloha Rock Gym is a full-size climbing gym that's cultivated an amazing community of both new and experienced climbers.

What local spot is a must-visit?

I can't give away all my secret spots, but on a serious note, ʻĪao Valley. It's accessible for most people, centrally located, and outrageously beautiful. Whether you drive in and enjoy the views from the parking lot or hike miles into the forest, it's always worth the stop.

What's your favorite thing about the town your office is located in, Makawao?

Silk Sky Tea Shop, an eclectic tea house on Makawao Avenue just before you reach Makawao town. Beyond serving top-notch tea, they host community events and have managed to create an authentic hub for artists, musicians, and tea drinkers.

What should clients know about you? What sets you apart?

I'm not a salesperson at heart. I enjoy understanding people's goals and helping them achieve those goals. I never get attached to the outcome of a transaction. My satisfaction comes from providing genuine value to my clients and advocating effectively on their behalf.

Whether you're purchasing your first home, searching for your next investment, or simply exploring your options on Maui, Phillip is ready to provide thoughtful guidance, honest advice, and unwavering advocacy throughout the process. Reach out to Phillip today to begin your Maui real estate journey.