Oprah Vs. Howard Stern: Latest Rich/Famous Hawaii Land Grabs

When Oprah does anything, people notice, including Howard Stern. And so, following nearly two decades of part-time living in upcountry Maui, the TV mogul made news for purchasing another 870 acres of land. For this ag land acquisition, she reportedly paid $6.6 million. She also did two other small land purchases last year, bringing her total ownership to about 1k acres on Maui.

Today, unrelated to Oprah, another spectacular nearly 3,000 Hawaii acre property also traded. See more on that below.

The debate about whether it’s a good thing or a bad thing? It depends on who you ask.

Residents, officials, and others are all questioning whether Oprah acquiring more precious Maui land is beneficial or does it displace residents, including native Hawaiians. And we welcome your thoughts in the comments.

For one, Maui councilmember Yuki Lei Sugimura said that Oprah should be commended for keeping most of her Maui land holdings undeveloped and hiring residents to do work. On the other hand, the council member pointed out that too many invasive wild pigs and axis deer are present on the property, which will need to be addressed by Oprah.

Another official, Hawaii senator Lynn DeCoite said, “I wish we had more people like her.” That comment was in relation to the fact that Maui has been swamped with overdevelopment and tourism.

Another talk show host, Howard Stern, however, outspokenly criticized Oprah and accused her of being braggadocious:

I make a good living and have trouble watching Oprah. I go, wow. Look what’s going on over there. Her estate is unbelievable. When she goes shopping, she goes shopping in her backyard, cause everything is growing back there. — Howard Stern.

Oprah Maui

Is a much bigger Oprah land grab in the works?

A massive property, the most significant currently for sale in Hawaii, sits next to Oprah’s current Maui land holdings. It is offered for $75 million, which, while expensive to us, is probably nothing to Oprah. It leaves us wondering why Oprah hasn’t picked that up yet. Could it be related to political correctness and timing, or is she simply disinterested?

The 3,600-acre Hana Ranch (featured image) came on the market last year and appears still for sale. It is adjacent to Oprah’s property.

Currently a working ranch with more than 1k cattle, it is owned by a Denver capital company that purchased it eight years ago for a paltry $9 million before investing $17 million more to upgrade it. According to the owner, the land is used for regenerative technique experiments in Maui’s tropical climate.

As it stands now, it would theoretically be possible for up to 37 homes to be built on the developable portion of that property. On the other hand, the current buildings are minimal, with a 1,800 sq. ft house, offices, and stables. It features private walking trails, which would seemingly be right up Oprah’s hiking passion alley, and fruit orchards.

The seller said that for any sale, approximately 125 acres would be gifted to Maui County for affordable housing development.

Zuckerberg, Ellison, and Bezos are other Hawaii landowner stars.

Among other notable property acquisitions in Hawaii, these three stand out for their notoriety, scope, and expense. They include:

1. Zuckerberg’s 1,500 acres on Kauai set Facebook’s founder back some $170 million.

2. Larry Ellison’s ownership of nearly the entire island of Lanai. Almost three years ago, the Oracle kingpin bought it from Castle & Cook at about one-half billion dollars. That included two world-class Hawaii resorts with 30 miles of paved roads and 141 square miles of land. Ellison is in the process of turning Lanai into an eco-friendly agricultural island.

3. Jeff Bezos’s small but fantastic property is one of the most beautiful spots on Maui. The Amazon founder purchased his La Perouse Bay property near Wailea two years ago to make Maui his part-time home. It cost Bezos some $78 million.

Today’s news includes a $36.5 million Hawaii land sale.

It is being reported today that North Shore Oahu’s 2,740-acre Dillingham Ranch has just been sold after being on the market for some time. We aren’t yet aware of who the buyer is. That piece, which has been used for filming movies and TV, also features a 19-acre oceanfront parcel with more than 1,100 feet being directly oceanfront. It is vast and goes all the way to the ridge of the Waianae Mountains.

Do you have a take on rich and famous Hawaii’s latest property buys?

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23 thoughts on “Oprah Vs. Howard Stern: Latest Rich/Famous Hawaii Land Grabs”

  1. It’s exasperating that the ultra rich can buy up exorbitant amounts of land in Hawaii just so they can get a tax write off. I remember when the Kohala coast was beautiful and Hapuna beach on the Big Island was public until they built fancy hotels. There should be a law to monitor how much acreage can be sold before greed ruins the islands.

    1. “… here should be a law to monitor how much acreage can be sold before greed ruins the islands.” That shipped sailed a long time ago.

  2. Jeff Bezos has made some very generous donations to benefit the Maui community. It would be nice if Oprah would put some cash towards homelessness and hunger on Maui.

  3. Well, it’s the ‘rich get richer’ syndrone again. Oprah, with her mega-bucks, buys another big chunk of land on Maui so she can enjoy a lot of ‘privacy’ (that’s what it’s really all about, it’s not about ‘preserving the land’, etc.). So local folks, you will gradually see the available land become ‘unavailable’, the rich/mega-rich will be happy in their Private enclaves, and you will get to pitch a tent at the beach as your new, stylish mega-mansion. Congratualtions.

    As an additional note, if Oprah was the ‘mega-goddess of goodness’ that so many folks think she is, why wouldn’t she buy the 3,600 acres and Donate it to the State of HI for the purpose of building real affordable housing??? She can afford it!

    1. Why doesn’t the state of Hawaii by the land and build affordable housing? And why doesn’t the state of Hawaii build affordable housing on land the state already owns?
      I’d like you to explain That one?

  4. It’s very easy to understand where the animosity comes from in Hawaii for tourism and non locals. It tends to make things pricey.

  5. I’m not crazy about all the rich and famous (not to mention powerful) buying up Hawaii one way or another, but isn’t that the way it’s always been? King Kamehameha the Great wouldn’t have united the islands without power, including some killing with that power.

    Bad land use decisions are made by anyone, not just kamaainas and haoles. Plenty of locals, some well intending and some not, have squandered the land, the Aina, for a quick buck or some perceived power!
    That’s what zoning ordinances are for. If the zoning needs updating then do it. As long as someone abides by the land use ordinances on their acreage, I say to let them be.

  6. Are you seriously wondering what the risk/reward analysis is when billionaires purchase parts of an island? Nobody should be able to own that much of anything. If I didn’t know any better – that is, if I hadn’t paid attention to any classes from 1st grade through grad school, I’d still know it’s not a good idea. I get needing to keep real estate agents working, but selling out to the 1% perpetuates the very complaints that has led to them owning/controlling everything.

    Limit ownership and let the people thrive. Or else.

    1. Land is an incredibly valuable and sacred resource in Hawaii. I agree with you completely – there should be a limit to how much land one person can buy. What will become of Oprah’s large holdings, and Ellison’s, when they die? If they would go the right thing and make them available to the people of Hawaii at affordable prices, or better yet, donate the land for affordable housing, that would be one thing – but I highly doubt either will do that. Considering their age, we should know relatively soon what the answer to this will be. Zuckerberg is a completely different, and scarier, issue. I don’t trust him as far as I could throw him, which worries me for Kauai. At least Bezos only bought 14acres!

    2. “…Nobody should be able to own that much of anything.” And who decides how much is to much? You? Me? Maybe people should be limited to only owning one car? Or only traveling so much in a year?

  7. Aloha, what happened to the resettlement of native Hawaiians? The list waiting to get land must be in the tens of thousands by now. I why are the rich non-islanders given preference over the Hawaiians who were promised that they would get a piece of their heritage back? Once again, I believe, the tradition of Haolies using fake promises to get elected.

  8. It is really Ironic How Much Tourists are vilified but it is A OK for Rich Billionaires to buy up your Land!! How about extending the same Aloha to us Tourists who Actually Give Back and Spend a Lot of our money in Hawaii when we visit, Just a Thought!

  9. 7,600 per acre for any land in HI, let alone Maui?? There’s something behind this story. No commoner could buy it for that price.

    1. I am a real estate agent on the big island. I can show you tons of land (all 1 acre properties) that are priced under $10,000.

        1. Parking millions on desireible
          properties is a better bet than stocks, bonds, banks, or gold. maybe even better than an NFL team. Im pleased when US citizens own US property.

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