Along Diamond Head Road
The Diamond Head Lighthouse. Designated a National Natural Landmark in 1968, the 300,000 year old crater peaks at 761 feet and encompasses more than 493 acres protected as the Diamond Head (Leahi) State Monument and administered by the Hawaii Department of Land and Natural Resources as a State Park. Photo by Phil Spalding III

The Diamond Head Lighthouse. Designated a National Natural Landmark in 1968, the 300,000 year old crater peaks at 761 feet and encompasses more than 493 acres protected as the Diamond Head (Leahi) State Monument and administered by the Hawaii Department of Land and Natural Resources as a State Park. Photo by Phil Spalding III

Second in a series

The approximately two mile section of Diamond Head Road that skirts the south facing slope of the crater is the site of some of the world’s most sought after and valuable real estate. Historically, both developers and conservationists have focused attention on this unique natural landmark. Fortunately, what was once a conflict of objectives has over time been resolved into a common goal of maintaining the integrity of the site.

In the early 1900s kamaaina families acquired undeveloped land along the road and built both simple beach cottages and grand estates. Many of these parcels have been subdivided and redeveloped both in the form of multiple residences and condominium projects.

One of the first such projects was undertaken by Realtor/ developer Nancy Simmons Schoocraft who represented owner Mildred Tavares Walholm in the sale of her 1910 estate at 3311 Diamond Head Road. “Mrs. Walholm’s home was actually on Beach Road, a spur road on the Waikiki side of the Diamond Head Lighthouse,” Schoocraft said. “It was beyond repair and she had plans to move back to her native Maui. She asked us to develop the property for her, so we formed Diamond Head Beach Venture and subdivided the property into residential parcels where we built two homes designed by architect John Edwards and completed in 1988. We sold them for the full price to the first buyer who came to look. One home was later sold to clothing designer Geoffrey Beene and featured in the New York Times Magazine.

“The Diamond Head area itself really is a showplace that carries the image of Hawaii far beyond our shores, in television series and films as well as magazines. Numerous film industry notables and international business leaders have made their home here. Recognizing this, we launched a beautification project in 1986, Friends for Diamond Head, a non-profit organization set up for a 10 year period.”

Schoocraft served as president and rallied support from numerous individuals and corporations for the extensive landscaping project which focused on a mile long section of Diamond Head just above the road and included new parking areas. In 1991, FFDH received the National “Take Pride in America” Award. Today, the beautification of Diamond Head Road is under the auspices of the Diamond Head State Monument Foundation, headed up by Clark Hatch who serves as both president and volunteer. He noted that the organization had replanted the landscaping from Beach Road to Flanders Park, which was decimated by a rock fall in 2007, with an assist from Diamond Head resident Jay Shidler who donated $10,000 to the project.

Coldwell Banker Pacific Properties Realtor Anne Hogan Perry, a specialist in Diamond Head and the Gold Coast, considers this stretch of Oahu coastline the best in terms of offering opportunities for the full range of water sports. “The water is crystal clear and has an energy of its own…it’s like swimming in a spa with the underwater fresh springs bubbling up to the surface. There is almost always surf breaking. From sunrise to sunset to moonrise it’s a magical setting, whether you’re in the ocean or in your home,” Perry said. She recently listed and sold a half-acre estate at 3222 Diamond Head Road for $10.6 million, the highest recorded MLS off-water sale on Oahu since 1975. Offering a 360 degree view, the property is one of six subdivided from the original Denison estate.

Prudential Locations Realtor and Fine Homes Specialist Glen Fujihara is currently listing one of the rarely available condominium homes at Aina Malu, the former Brown Estate. The two bedroom, three bath residence priced at $5,990,000 is surrounded by gardens and steps from the beach. The gated enclave of 11 one and two story homes developed by Duncan MacNaughton and Richard Gushman and designed by architect Vladimir Ossipoff includes a 40,000 square foot common area of green open space that extends to the beach. “Aina Malu is clearly one of the finest ocean-front communities on Diamond Head Road…it’s private, beautifully landscaped, and perfectly situated on one of the south shore of Oahu’s best beach-es…if you’re an ocean lover, it doesn’t get any better than this,” Fujihara said.

Locations Hawaii
Michael Marks
Sandwich Isles Realty
Kimo Smigielski, Broker-in-Charge
R, ABR, CRS, GRI, e-PRO
Hawaii Life Real Estate Brokers
Emily Garcia
Agent, REALTOR(A), RS-77391
Coldwell Banker
DAY-LUM Properties

Edith Crabb, RB-8195
Coldwell Banker
DAY-LUM Properties

Glenn Takase, RB-18547
Coldwell Banker
DAY-LUM Properties

Misti R. Tyrin, RS-75836
Coldwell Banker
DAY-LUM Properties

David L. Skeele, RB-12882
Kauai Landmark Realty
Phil Fudge, RB-18576
Claire Keaton, RS-73854
Coldwell Banker
DAY-LUM Properties

Shea Miyashiro, RS-64678
Coldwell Banker
DAY-LUM Properties

Atsuko Winston, RS-75899
Coldwell Banker
DAY-LUM Properties

Mark Skeele, RS-77005