Thinking About a Second Home in Hawaii? Jon Anderson Says You Should Rent First.

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The Backyard View at 61-753 Papailoa Road
The Backyard View at 61-753 Papailoa Road

Paradises the world over are littered with stories of people who packed up their hum-drum lives and moved to paradise only to discover it was quite different from the post cards.  Certainly a good rule of thumb for any move — “Rent first” — is doubly important when moving to costly locales you’ve not spent enough time in to really understand whether you’d be happy there.

Before I purchased my second home, I’d spent many months over several years renting in the building before the stars aligned and I purchased.  If your second home will ultimately be your post-retirement home, you owe it to yourself to thoroughly investigate.

These cautions bring me to 61-753 Papailoa Road.  Far from a typical rental at $30,000 per month, it’s the most expensive home for lease on the island. But it’s a beachfront single-family home located on the famed North Shore of Oahu … and you pay for that. The home is only available from December through March (when I assume the owners are off elsewhere). It’s also month-to-month, so don’t be pestering the agent (Kimo Smigielski of Sandwich Isles Realty) with your 2-day rental requests.


The 1,957-square-foot home sits on just over a third of a beachfront acre and contains four bedrooms and three full bathrooms.  For sitting back and being captivated by the views, there are 608 square feet of lanais.  As you can see, it’s not an enormous, out-of-place McMansion, it’s all about location, location, location.  It’s also about living a different life … and at that this property excels.


Just entering this property your blood pressure drops.  A large well-maintained front lawn full of tropical vegetation is just what the doctor ordered. You’ll notice there’s no “driveway” but instead the use of open blocks that allow the green to grow through.  It’s a neat trick to extend your yard while still having a car.


But it’s the back of the house you’re all wanting to see.  With beach frontage, it’s no surprise that this home is oriented to the water.  Lots of windows and sliding doors lead out to major deckage.  See the second floor?  That’s the master suite and its private deck.


The inside of the home is just the kind of beach experience you imagine.  Light colors with a bit of blue to remind you you’re right on a tranquil beach.  The windows in the background are of the front of the house.  In back of the photographer is the ocean.  To the right you can see the beginnings of the dining area … it’s all open concept.


The living, dining room and kitchen all flow together and attach you always to the ocean.  It’s a great setting for family gatherings … they’d visit … you know they would. Especially with four bedrooms and a 48” wide Sub Zero fridge.


Just sitting in those deck chairs and watching the world go by is, for many, the definition of heaven.  And while the views will never wear off, renting a home for an extended period near where you want to live is important.  Where’s the grocery store? Healthcare? Restaurants? Movies? The list of day-to-day needs is as endless as it is personal.  Does it all gel together?  Only by living and experiencing a location can you be sure.


The master bedroom is the perfect place to contemplate your second home.  Although truth be told, lying in bed with the sound of the ocean in the background is scientifically the most difficult place to think with a clear head.  Drawing up “pro” and “con” lists will tax your focus here.


The private deck off the master bedroom is an equally terrible place for objective thinking. And while the big reason you’re in paradise is to change your focus, when deciding if it’s right for you in the long term, focus is what you require.

Many people who vacation in Hawaii are surprised that my home is located fairly close to the hubbub of Waikiki and Honolulu.  They think of Hawaii in terms of Maui or Kauai where they spend a week basking in the sun.  For me, long-term, I needed more civilization and a larger local population.  It gets tedious when all the people you meet are leaving on Sunday.  I needed livable vibrancy along with my ocean views.

But that’s me.  What are your requirements in a second home location? Are they the same after you’ve rented for a few months in that ideal location?  There’s only one way to find out.  Do it.

Remember: When I’m not stirring up trouble in Dallas, Texas or Honolulu, Hawaii for and, I’m off scouting interesting locations for a second home.  In 2016, my writing was recognized with Bronze and Silver awards from the National Association of Real Estate Editors. If you’re a Realtor with second home clients who’d like me to feature their journey, shoot me an email