Category: Hawaii Real Estate by Jason Wong

Every week, buyers from the mainland call asking about gorgeous Hawaii houses priced at a mere fraction of the surrounding market value. But there is a catch. In this video, we break down the massive, fundamental difference between standard fee-simple real estate and properties sitting on Hawaiian Home Lands. Governed by the Hawaiian Homes Commission…

Selling your property in Hawaii? You could be losing thousands of dollars at the closing table if you don’t fully understand the Hawaii Conveyance Tax. In this market update, we break down exactly why Hawaii’s tax system is a “cliff” rather than a marginal rate, and what that critical difference means for your net proceeds.…

Leaving a house doesn’t mean living small. If you’re ready to trade maintenance for ease—but not give up space—this rare ground-floor end residence at gated Kalele Kai delivers nearly 2,000 sq ft of single-level living, 3 bedrooms, 2.5 baths and an extraordinary 589 sq ft wraparound garden patio. Bring the furniture: generous living and dining…

Are you buying or selling a condominium in Hawaii? Understanding where your building’s master insurance policy ends and your personal liability begins is one of the most crucial steps in protecting your island investment. In this video, I break down exactly how Hawaii condominium association master policies interact with HO-6 unit owner policies. Many buyers…

Are you planning to sell commercial real estate in Hawaii? Don’t let hidden environmental liabilities kill your transaction. When dealing with commercial properties in Hawaii, buyers and lenders face decades of historical land use that could flag a Recognized Environmental Condition (REC) during a Phase I Environmental Site Assessment (ASTM E1527-21). In this video, I…

Are you planning to buy or sell a home in Hawaii with an existing cesspool? The state’s 2050 mandate (Act 125) is already reshaping the local real estate landscape, and ignoring the regulatory details could cost you tens of thousands of dollars at the negotiating table. In this video, we uncover the reality of Hawaii’s…

A 1% difference in cap rate can move the indicated value of a commercial property by millions of dollars. That is why “just use a five cap” is not commercial real estate analysis. In this video, I break down one of the most misunderstood tools in Hawaii commercial real estate: the capitalization rate, or cap…

Are you dreaming of waking up to ocean views in a beautiful Hawaii condo? Before you buy your slice of paradise, there is one critical step you cannot skip: reading the condominium’s Reserve Study. Welcome to my channel! I am Jason Wong, MBA and Principal Broker at Island Dragonfly. In this video, I break down…

Maui’s housing market is experiencing a profound transformation, and if you own or are looking to invest in Hawaii real estate, you need to understand the latest legislative shifts. On December 15, 2025, the Maui County Council passed Ordinance 5909, marking the largest short-term rental phase-out in American history. But what does this actually mean…

Are you dreaming of waking up to the sound of crashing waves in Hawaii? Oceanfront living is spectacular, but not all coastal properties are created equal. In this video, we break down the critical differences between buying a sandy beachfront home and a cliffside oceanfront estate in Hawaii. Whether you are a local resident upgrading…