Roger Pleski

Take the time to understand the market—and partner with someone who understands it even better. South Maui’s real estate landscape moves quickly, especially in places like Wailea, Kihei, and Makena. I advise buyers to get pre-approved for financing early, be ready to act fast when the right opportunity arises, and don’t underestimate the long-term value of location. My role is to guide you every step of the way with honest advice, sharp negotiation skills, and deep insight into local trends.

Preparation is everything. The South Maui market is competitive, but the homes that stand out are the ones that show well, are priced right, and are marketed strategically. I work closely with my sellers to make sure their property is presented in its best light—using professional photography, targeted marketing, and decades of local experience. Whether you’re selling a vacation condo in Kihei or a luxury estate in Wailea, timing and presentation can make all the difference.

Over the past 45+ years, I’ve worked with a wide range of clients—from first-time homebuyers and investors to retirees, second-home buyers, and military families relocating to Maui. Many of my clients are from the mainland or overseas and rely on me for local knowledge, honest feedback, and seamless transactions. Whether you're buying your dream condo near the beach or selling a family estate, I’m committed to making your Maui real estate experience smooth and successful.

One recent transaction that stands out involved helping a couple from California purchase their dream oceanfront condo in Wailea. They had been searching for the right place for over a year with other agents but hadn’t found the right fit. I listened carefully to what they truly wanted—location, privacy, and unobstructed views—and matched them with an off-market opportunity I had been tracking. We closed smoothly under asking price, and today, they call it their forever home. Transactions like that remind me why I love this business.

I got my start in real estate in the late 1970s, initially drawn to the industry by my fascination with architecture and property development. After moving to Maui, I quickly realized how much opportunity there was to help others navigate this unique and ever-changing market. Over the past 45+ years, I’ve built my business around referrals, relationships, and a reputation for integrity and results. Real estate on Maui isn’t just about buying and selling—it’s about building a lifestyle.

Yes—along with decades of hands-on experience, I’ve consistently pursued continuing education in real estate contracts, investment analysis, and market forecasting. I also have deep familiarity with the ins and outs of vacation rental zoning, leasehold vs. fee simple properties, and 1031 exchanges—critical topics for many Maui buyers and sellers. This ongoing learning allows me to offer expert-level guidance and protect my clients from common pitfalls in Hawaii’s complex real estate landscape.