When buying a house in Hawaii, you might own the land (fee simple) or just the building (leasehold), with fee simple being full ownership (land + structure), common for single-family homes, while leasehold means you lease the land from an owner (like the state or a trust) for a set term, often for condos or Hawaiian Homelands, requiring lease payments and potentially reverting the land to the owner at lease end.
Larry Ellison, the co-founder of Oracle, owns about 98% of the Hawaiian island of Lānaʻi, having purchased it in 2012, making him the primary landowner of Hawaii's sixth-largest island. His holdings include most of the island's land, two resorts, much of the housing, and commercial properties, affecting the daily lives of the island's few thousand residents.
Oprah Winfrey (Maui)
Oprah owns more than 1,000 acres on Maui, mostly in the upcountry Kula area and in Hana. In addition to the land, it is said that Oprah owns an 11-bedroom ranch home, which was meticulously remodeled and designed. Was Oprah's home destroyed by the 2023 Maui fires?
The states where $100 is worth the least are the District of Columbia ($84.60), Hawaii ($85.32), New York ($86.66), New Jersey ($87.64), and California ($88.57). That same money goes the furthest in Mississippi ($115.74), Arkansas ($114.16), Missouri ($113.51), Alabama (113.51), and South Dakota ($113.38).
Between 2022 and 2023, she reportedly purchased four parcels of land, totaling 870 acres, for $6.6 million. In March 2023, Maui Now reported that Winfrey spent $6.6 million on 870 acres of land in Kula. First, two parcels of 10 acres each were sold in December 2022 to Winfrey's Los Angeles-based company Harpo Inc.
Pros of Investing in Hawaii Real Estate
Hawaii is known for having notable appreciation rates, helping to offset the higher initial purchase costs. This, paired with strong rent increases over time, is beneficial for long-term investors over short-term investors.
Hawaii's "Big Five" refers to five powerful, interconnected corporations (Castle & Cooke, Alexander & Baldwin, C. Brewer & Co., Theo H. Davies & Co., and American Factors (Amfac)) that controlled much of Hawaii's economy, particularly sugar plantations, from the late 19th to mid-20th centuries, stemming from missionary families and wielding significant political influence. While the original oligarchy faded, the term can also refer to modern powerful landholders like the Kamehameha Schools or Robinson family (Parker Ranch), but the historical Big Five remain key to understanding Hawaii's past.
Yes, Matthew McConaughey owns a significant home on the Big Island (Hawaii Island) in the exclusive Kukio Golf & Beach Club in Kailua-Kona and is a frequent visitor, though he also maintains homes in Texas and elsewhere. He purchased the luxury property in late 2020, a custom-built home with extensive amenities like infinity pools, multiple fire pits, and high-end finishes, designed as a retreat for his family.
Richest billionaires in Hawaii
Amazon founder Jeff Bezos just bought a remote $78 million 14-acre estate surrounded by dormant lava fields on La Perouse Bay in Maui, adding to his $500 million real estate portfolio.
Since their arrival in 2011, Zuckerberg and his wife, Priscilla Chan have acquired 11 homes in Palo Alto's serene neighbourhood of Crescent Park, spending over $110 million. Zuckerberg and Chan expanded their real estate portfolio by buying properties at double or triple the market value.
You can typically inherit a very large amount from your parents without paying federal tax, as the federal estate tax exemption is around $15 million per person for 2026, meaning only estates larger than that pay tax, not you directly. While you generally don't pay income tax on inheritances (except for pre-tax retirement funds like IRAs/401(k)s, which are taxed as income when withdrawn), some states have their own estate or inheritance taxes with much lower thresholds, affecting a smaller portion of wealth.
Hawaii exempts certain income like Social Security, U.S. government bond interest, and some military pay, while offering deductions for specific items like Individual Housing Account contributions or exceptional tree maintenance; however, Hawaii taxes some income federally exempt (like certain student loan interest) and has personal exemptions ($1,144 each) plus extra for seniors (65+). Specific income from Qualified High-Technology Businesses (QHTB) is also exempt.