Exclusive Pics: Inside Obama's Hawaiian Hideaway

55, 57 and 57A Kailuana Place, Kailua, Hawaii, 96734. Those digits are what President and Mrs. Obama, their children and entourage are once again calling home for the next several days.

Seven years ago, my cousin Brendan Lane Larson lived in 55 Kailuana Place when it was on the market for about $3 million and the only structure on a historic piece of prime Oahu beachfront. The pad sold for $9 million, after a major spiff-up but before the president vacationed there. (That's a 183% increase over seven years.) The Obama connection has now brought all three homes on windward Oahu into the limelight, and the appraisals will likely spike--especially if the President signs on the dotted line to buy one of them.

Kailua, or "two waters," is a Honolulu bedroom community filled with families, artists and Hawaiian culture. And talk about presidential perfection: The homes are on a cul de sac overlooking the Pacific ocean about three miles from a marine corps base -- and I know cul de sacs are the Secret Service's security dream when it comes to presidential pads.

But Brendan tells me the home he leased has a pre-Obama past intimately tied to Hawaiian history.

The lure of the Obama's Winter White House is its amazing location, which inspired the name chosen by its current owner and developer, Dave Zimel: Paradise Point Estates. For centuries these sands have been choice five-star digs for vacationing Hawaiian kings and emperors. It's on this stretch that the former owners, the Castle family, once owned ten lineal miles of prime Kailuana beach. This is where Harold K. L. Castle, grandson of New England missionary Samuel Castle, built the family compound around the 1940s, the home my cousin leased more than seven years ago. The Castles were one of three prominent land-owning kama'aina families/developers who staked out huge Hawaiian land fortunes as far back as the 1800s. (The Castles also happen to be one of the nation's oldest real estate developers through their firm, Castle & Cooke.) In 1917, Harold K.L. Castle purchased title to 9,500 acres of pineapple plantation in the Kailua ahupua'a, which he developed into home sites following World War II, building his own compound on the most choice acreage.

By the time my cousin Brendan and his roomies lived at 55 Kailuana, from 1999 to 2002, it had become an elegant but not over-the-top property -- a comfortable Hawaiian estate whose best asset was its proximity to the beach and breathtaking views of the Pacific and the Mokulua Islands. That and the biggest sliding glass doors he has ever seen -- two giant sets you really had to lean on to open. Harold's grandson, Chris Castle, once told him they pulled both sets open during hurricanes, including powerful Hurricane Iniki in 1992, to let the Pacific Trade winds pass through.

"There were four bedrooms in a line," says Brendan, "but you could walk right out of your bedroom, put on your flip flops and be outside."

And if you had your surfboard or kayak, you could could just pop into the water. No need for air conditioning: Brendan preferred to leave his bedroom windows open at night to hear the waves crashing on Castle Point.

The original kitchen sported no granite or state-of-the-art appliances, but was roomy enough for house workers and caterers. (Brendan says he and his roomies threw an awesome millennium party on December 31, 1999. They also cooked four turkeys Imu style -- an in-the-ground Hawaiian oven using hot stones.)

The home had a round swimming pool on the side opposite the beach when Brendan lived there, not the lagoon-style water park the First Girls are enjoying. And Brendan warns the Obamas to beware of the coconut rats who scamper up the trees. (A couple of trained Secret Service cats should keep them literally at bay.) First Pup Bo should also have a fine time; he misbehaves, the home Brendan leased has special on-premises dog kennels.

One of the best stories surrounding this home is how, following the attack on Pearl Harbor, when many Japanese living in the U.S. were detained, the Castles hid a Japanese woman who worked for them on the property, later building her a special bungalow.

After Castle's death, his heirs sold the approximately four-acre estate in 2003 to a man who had been eying the property for years, Paul Sullivan. Hawaiian real estate values were heading for the moon. A Dallas developer told me so many major players like Michael Dell and Silicon Valley billionaires were building mega homes on Hawaii's Big Island there was barely enough room to park their private jets. Sullivan sub-divided and shaved off parcels of Castles' original four acres to a team of developers who began construction on two new homes, completing them in 2006. All along, says Zimel, Sullivan's eye was on the original Harold Castle property at 55 Kailuana, which he sank at least $500,000 into remodeling. But guess what, there is always a Texas connection: According to reports, Sullivan sold the Castle home to a Houston portfolio manager, Kevin Comcowich, for $9 million on January 18, 2007. Comcowich drove a hard bargain: Sullivan had originally listed it for $11.9 million.

As the hot Hawaii real estate market cooled, Portland, Oregon-based Zimel bought out the developers and became owner of the two parcels. Thus what had been 55 Kailuana Place expanded to 55, 57 and 57A, according to Zimel. While the Obamas have leased all three properties for their winter holiday at about $4000 per day, or $56,000 for a ten-day vaca, the Plantation Estate, 57A, is the one reportedly occupied by the First Family. We hope they like their companions because 57, the Balinese Estate, is within shouting distance. That home sold last year for about $7 million, or $1005 per square foot, about par for the 'hood. (Chad Castle's home down the street was recently on the market and listed at $12.8 million.) The new owners are a Chinese couple from Shanghai. Which means that should the Obamas buy Plantation Estate, currently listed at $8.9 million, not only will POTUS finally own a home near the waters where he first learned to swim, he will live among international neighbor -- and that includes a Texan!
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