Some mornings I get up, push aside my trash bag full of dirty clothes, ignore the alarming number of ants crawling on my bathroom wall, put on one of the seven outfits I managed to squeeze into my suitcase for the foreseeable future, check my email for more student loan payment reminders and ride the bus to work thinking about how different my life might be if I were living in Oprah’s multi-million dollar Upcountry Maui house (with access to her bank account, of course). Pretty different, I think.

Well, last month I was lucky enough to be invited to something in between a backyard kegger and a grand ball, a Hawaii Life real estate event called WorthShop #3, and got to see exactly how the other half lives in paradise.

Our first stop was a tour of the Ho’olei Properties, a complex of high-end, multi-level townhomes that sits directly across from one of the fanciest resorts on the island, where residents can use the amenities at no extra charge and can even have restaurant items charged to their townhome on a monthly billing system. Maui realtor Dano Sayles showed us around the Ho’olei pool area, which looks like a resort in and of itself, and also offers poolside massages. Say what?! The only thing my last apartment complex offered poolside was the possibility of tetanus.

the other half

We were given a tour of two different properties, which each cost around 2 to 4 million dollars, and got a nice slice of what life is like in one of the fanciest townhomes on the island. Each unit faces west for optimal sunset-gazin’, has a nice balcony and bath water that pours from the CEILING.

maui million dollar homes

We then headed over to the location of the actual WorthShop event, the Four Seasons Resort in Wailea. And snap! It turns out I do like extraordinarily fancy places. I mean, hole-in-the-wall dive bars and restaurants are charming as hell and always have a special place in my heart, but I can still sip a martini and make up things about investment opportunities when needed.

maui's best resorts

For the final stop of the evening, we headed to a private party at a 9 million dollar house in the Maui Meadows hood, which sits on a beautiful property with an herb garden and is surrounded by several kinds of fruit trees. That view is killer!

maui meadows real estate

maui properties for sale

The saddest part of the evening was returning home, where there were sadly no complimentary cocktails, lounge chairs by the pool or trees throwing delicious fruit at you. Bummertown. If anyone has 9 million dollars and would like to purchase this house, I can put you in touch with Lucas Woodford, the listing agent on the property. Then you can share with me why I never knew you had 9 million dollars.

P.S. I like boats.