Kill Two Birds: Winter Escape and Second Home Evaluation On Oahu’s North Shore

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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.

Pop over to SecondShelters.com for the rest.

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Jon Anderson

Jon Anderson is CandysDirt.com's condo/HOA and developer columnist, but also covers second home trends on SecondShelters.com. An award-winning columnist, Jon has earned silver and bronze awards for his columns from the National Association of Real Estate Editors in both 2016, 2017 and 2018. When he isn't in Hawaii, Jon enjoys life in the sky in Dallas.

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