Category: Hawaii Real Estate by Jason Wong

Buying the land under your own home in Hawaii is expensive, but not buying it could cost you even more. If you are navigating Hawaii’s complex real estate market, understanding the difference between Leasehold and Fee Simple ownership is critical to protecting your investment. In this video, I break down the brutal truth about “Fee…

Looking past the beach to Hawaii’s spectacular hillside and ridge estates? While coastal properties navigate shoreline setbacks and sea-level rise disclosures, elevated luxury homes face a relentlessly unsentimental force: gravity. Whether you are a local homeowner aiming to maximize your property’s value, or an international investor seeking a premium Honolulu retreat, understanding Hawaii’s strict geotechnical…

Everyone loves the romantic idea of owning a registered historic home in Hawaii—especially when discovering the massive property tax exemptions available from the county. But is the architectural pedigree worth the highly expensive set of handcuffs? In this deep dive into Hawaii’s luxury historic real estate market, we uncover the reality behind the state’s most…

Suppose your Hawaii commercial building needs a $200,000 roof. Most sellers reach the same conclusion: deduct $200,000 from the price and the deal is solved. Commercial buyers do not underwrite it that way. In this segment I walk through why deferred maintenance on an Oʻahu or neighbor-island commercial asset almost never trades at repair cost.…

Are you an investor or homeowner on the Big Island of Hawaii? Recent legislative shifts have significantly changed the carrying costs for luxury properties, and understanding these new tiers is crucial for your real estate portfolio. In this breakdown, I analyze the precise financial impact of Hawaii County’s Bill 128 and Resolution 574-26. We look…

Rates shown are FY2026–27 (July 1, 2026 – June 30, 2027). Every county resets rates each July 1 — verify before you act. Four islands. One identical $4 million assessed value. Four completely different annual property tax bills — and the most expensive one is not where almost anyone would guess. I ran the same…

Are you buying or selling a condo in Hawaii? Don’t let hidden insurance deductibles jeopardize your real estate investment. Understanding your condo association’s master policy is more critical than ever. In this comprehensive update, we break down the complex layers of Hawaii condo insurance, exploring how the latest 2026 Fannie Mae and Freddie Mac guidelines…

“Triple net.” Two words that make a Hawaii commercial property sound effortless — the tenant pays everything, the owner collects a cheque. Sometimes that is exactly true. Sometimes it is not remotely true. And the difference is not decided by the acronym printed on the offering memorandum. It is decided by the lease. I am…

Are Honolulu office buildings the next big real estate investment, or a financial misstep? For years, office real estate has been treated as the unwanted sector of commercial property, but recent market data and groundbreaking zoning laws are rapidly changing the landscape in Hawaii. In this video, Jason Wong, Principal Broker at Island Dragonfly, analyzes…

Everyone in Hawaii heard the headline: the state now requires counties to allow two accessory dwelling units on residential lots. Almost nobody heard the three sentences that follow it in the statute. In this segment I go through what Act 39 actually reaches — and what it quietly leaves out. What this covers: UPDATE, September…