Service Areas
Haiku, HIKahului, HIKihei, HIKula, HILahaina, HIMakawao, HIPaia, HIPukalani, HIPuunene, HIWailuku, HI
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About Roger Pleski
With over 45 years of real estate experience and deep roots in the South Maui community, I bring unmatched local knowledge, negotiation skills, and integrity to every transaction. Whether you're buying a beachfront condo in Kihei or selling a luxury home in Wailea, my team and I are here to guide you with honesty, professionalism, and results-driven strategy. I specialize in helping clients navigate Maui's unique market--including vacation rentals, 1031 exchanges, and oceanfront properties--while ensuring every detail is handled with care. If you're looking for a trusted Maui real estate agent who delivers, I'd be honored to help you make your next move.
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Specialties
- Buyers
- Sellers
Awards
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2026
TOP AGENT
Kihei, HI
2026
TOP AGENT
Lahaina, HI
2026
TOP AGENT
Haiku, HI
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FAQ
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.
Contact Information
Location
3750 Wailea Alanui B-35 #2777 Wailea, HI, 96753
Social Media
Available Listings View All
Active
$899,900
1bds | 2ba 1039 Acres
2777 S Kihei Rd APT F103 Kihei, HI 96753,USA
Active
$799,900
1bds | 1ba 777 Acres
4365 Lower Honoapiilani Rd #709 Lahaina, HI 96761,USA
Active
$599,900
1bds | 1ba 960 Acres
2661 Kekaa Dr #E204 Lahaina, HI 96761,USA
Active
$950,000
2bds | 2ba 1112 Acres
2737 S Kihei Rd #336 Kihei, HI 96753,USA
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Trusted Pro
Roger Pleski is a Trusted Pro with a network of verified professionals.
Lisa Pleski
Real Estate Agent
Greg Beddor
Digital Marketing
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