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Diamond Head: From Estate Views To Crashing Waves


Tour the beautiful homes and estates that surround Diamond Head, and you can catch glimpses of the people who helped to shape the cultural history of the island.

Originally settled by Hawaii’s elite, the slopes of Diamond Head today reflect both their interests and their legacy. Today, Diamond Head is one of Oahu’s most exclusive addresses, known for multimillion-dollar properties.

Diamond Head was undeveloped until the early 20th century, when some of the old kama’aina families built some of the first homes on the hillside.

In 1910, Walter F. Dillingham, son of Oahu Railway and Land founder Benjamin Dillingham, married Louise Gaylord at Villa La Pietra, a magnificent 600-year-old villa in Florence, Italy belonging to Louise’s aunt. When the newlyweds returned to Oahu to build their dream home, the Italian villa where they married became their inspiration. That estate now serves as La Pietra – Hawaii’s School for Girls.

In 1929, Dillingham’s grandson, Harold Erdman and his bride built the first home on Noela Drive, uphill from La Pietra. The story goes that it was given to them as a wedding gift.

As living beneath Diamond Head’s shadow became vogue, estates there were sought after by notable people of the time. The architect Charles Dickey built a house on Makalei Place. In the 1920s, Henry Waterhouse Trust Co. created Diamond Head Terrace, a subdivision of 100 relatively small lots, most without views.

In 1937, Doris Duke built Shangri La, her famed mansion on the cliff overlooking the surf break where she enjoyed swimming and surfing with the Kahanamoku brothers and others. Today that surf break is still known as Cromwells, after her husband James.

Duke’s mansion created interest in the Eastern side of Diamond Head, but it wasn’t until the late 1950s and early 1960s that much of what is on Diamond Head today was built.

Today, the different areas of Diamond Head afford different lifestyles and each has a unique, distinct character. They range from being able to wake up and jump in the water to large, quiet, view-oriented estates.

I talked with three Fine Homes Premier Specialists at Prudential Locations to learn more about the special charms of the Diamond Head neighborhoods: “The Noela area, first settled by the Dillinghams, is now characterized by large, beautiful and private estate properties, running up to 20,000 square feet of land. These remain some of the most expensive properties on the island,” says Dolores Bediones (R).

On the other side of Diamond Head, where Doris Duke found paradise, you can find luxurious beach-style living on and above the water. Donna Yamagishi (RA) explains, “These lovely homes are more expensive and clustered closer together, with a focus on the water. The homes with beach front or deeded access to the ocean carry more value.”

Many people are surprised to learn that the gated community of Black Point was originally started in the 1960s as an artsy, bohemian community. Says Julie Meier (R), “One of its charms is a beautiful, naturally formed black rock saltwater pool fed by the ocean, with the ocean as a backdrop.”

Meier says Black Point is highly desirable with very low turnover “in part due to the limited number of properties in the Black Point community. Currently there is one active listing (for $6.349 million) and two sales have closed in the last six months.”

Moving uphill from the ocean are the neighborhoods of Poka and Hakaka. “There are many original owners here,” Yamagishi says. “Everybody knows everybody. Everybody knows each other’s dogs. At open houses, people will chat for a half-hour or more, enjoying catching up on each other’s lives.”

Yamagishi recently held an open house on Hakaka Street to large buyer interest. “Over 80 individual groups came to the open house, which was the same weekend as the marathon when most people were focused on that event.”

Yamagishi says the Hakaka property is a perfect example of what many buyers are seeking as an entry into the area: “A lot over 12,000 square feet, a single-level, mid-century home with fabulous potential, listed at $1.78 million. If a property is $2 million or under these days, it’s getting snapped up.”

In all Diamond Head neighborhoods, the inventory is low. There are just 23 properties currently listed for sale, ranging from $1.26 million to $8.5 million.

The sales of single-family home sales in Diamond Head for 2012 year-to-date (27 sales) have exceeded the annual sales of every year since 2007 (39 sales). The median sales price for the past 12 months is $2.15 million. The months of remaining inventory are 9.1 months.

For more information on properties in Diamond Head and Black Point, you can consult with a Fine Homes Specialist. Contact the Fine Homes division at Prudential Locations at (808) 377-4646.

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