Image: Oprah Winfrey's Hawaiian home
Will Binns  /  Celebrityhomephotos
Oprah Winfrey has invested in a number of properties on the beautiful island of Maui, one of which is this fabulous estate in Kula. The ranch sits on 60 acres of land and the main house, which features first and second floor porches, offers sweeping views of the Pacific.
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updated 9/11/2007 4:10:47 PM ET 2007-09-11T20:10:47

A few weeks ago, real estate agent Dave Jackson took advantage of one of the many perks of Hawaiian living — he and his wife went surfing at their favorite break off Kauai. They had to share the waves with four other people (Matt Damon, his wife Luciana Barroso, Ben Affleck and Jennifer Garner) but by all accounts, the surf was superb.

“And the best part is … there were no shutterbugs anywhere, which was great.” says Jackson. “I don’t think the locals here would tolerate the paparazzi. They would be asked in not so friendly terms to leave the island … and I think the celebrities know that.”

Hawaii has perennially attracted second home buyers who also happen to be world famous. Ben Stiller, Pierce Brosnan, Michael Crichton, Natalie Merchant and Bette Midler (a native islander) own homes in Kauai. High-profile Maui dwellers include Kelsey Grammar, Oprah Winfrey and Woody Harrelson. Roseanne Barr recently purchased a former macadamia farm on the Big Island. And then there’s the cast of a certain popular television program.

Over the last several years, Kauai has become a particularly big draw. With a population of only 60,000 people, the island has about 7 percent the population of Oahu, with roughly the same size land mass. The result is a cozy, small-town community, where famous faces don’t cause commotion.

“The locals that live here on Kauai just don’t seem to be as star struck as you would imagine,” said Jackson. “I see Pierce in the Kilauea Fish Market all the time, waiting in line like everyone else. No one seems to give him a second look.”

And while the islands have an inherent quality of life appeal, purchasing high-end real estate in Hawaii is also a sound investment. According to local agent Ric Rocker, while the market in the $1 to 3 million range is relatively stagnant (“basically speculators are out of the market, and there are a lot fewer end users”), anything over $5 million is bound to appreciate.

As in most competitive markets involving finite shorelines, geography comes into play. According to Anne Hogan Perry, a vice president at Coldwell Banker, the largest real estate firm in Hawaii, the limited number of prime beachfront properties has helped fuel this boom at the top.

For example, last November Donald Trump’s latest hotel-condo venture in Waikiki sold seven hundred million dollar’s worth of real estate in a matter of hours—and the building won’t be finished until mid-2009. When it does, some of its tenants will include several NBA stars and professional golfers, as well as the landlord’s daughter, Ivanka.

To some A-list names, a good investment isn’t the only appeal to buying in Hawaii — some are getting outright discounts in exchange for their star appeal. “Some of the new developments have offered incentives to celebrities, both entertainment or business leaders, to buy within their developments to enhance demand and image,” says Hogan Perry. And many celebs are just as dollar-savvy as the CEO neighbors; country crooner Randy Travis rents out his estate on Maui for $1,250 a night.

Though the high-end real estate agents we talked to wouldn’t reveal the names of their celebrity clients (citing something about confidentiality agreements), they did mention a number of private resort areas that have proved particularly attractive to some of their more conspicuous clients. These properties are usually focused around a five star hotel and a golf course, and feature a number of residential options such as condominiums, townhouses, or secluded homes.

Favorites in this category include the Kuki’o Resort, Waikoloa Beach Resort, and the Mauna Lani Resort on the Big Island. On Maui, the exclusive neighborhoods include Kapalua, Wailea and Koele. Several of these communities boast blueblood roots. The Mauna Kea Resort in South Kohala (currently recovering from the October 2006 earthquake) was originally developed by Lawrence Rockefeller.

The islands are also blessed with a thriving entertainment industry, which frequently brings big productions to the islands, and tends to create fond memories for stars. The "Jurassic Park" trilogy, "South Pacific", "Blue Hawaii", "Six Days Seven Nights", and parts of "Raiders of the Lost Ark" were all filmed on Kauai.

Lately, the man with the fedora and the bullwhip has returned to his Hawaiian stomping grounds. Harrison Ford recently celebrated his 65th birthday along with Steven Spielberg, John Hurt and Cate Blanchett on the Hamakua Coast of the Big Island. The reason for the location? They were all in town making the fourth Indiana Jones film.

Read on to see the Hawaiian hideaways of some of Hollywood’s biggest stars.

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