A Historic Diamond Head Estate Hits the Market for the First Time

Some rich buyer will have the chance to live like Makalapua’s noteworthy former owner.
3229 Diamond Head Road House
Photos: Courtesy of Andy Landgraf – 360 Property Videos


Makalapua, a sprawling oceanfront estate at the foot of Diamond Head overlooking a very private slice of white sand beach, was just listed for sale. Not only is it a beautiful property, it also has a famous former owner: Sanford Dole, justice of the Supreme Court of the Kingdom of Hawai‘i, president of the Republic of Hawai‘i following the overthrow of the monarchy, and first governor of the territory of Hawai‘i.

  3229 Diamond Head Road Pool

  3229 Diamond Head Road Lawn

  3229 Diamond Head Road Lanai


The 3,926-square-foot two-bedroom, two-and-a-half-bath home could easily be reconfigured into more bedrooms, and there’s a separate one-bedroom guesthouse by the pool. The second-floor master suite overlooks an expansive yard and the ocean; the estate, more than 13,000 square feet, has 75 feet of linear ocean frontage. The floors are local ‘ōhi‘a wood, and the walls throughout are Venetian plaster. The living areas all open directly to the lawn, allowing for indoor-outdoor living and alfresco dining.

  3229 Diamond Head Road Living Room

  3229 Diamond Head Road Dining Room

  3229 Diamond Head Road


Off the beach lies a channel in the reef, making it an ideal place for swimming, snorkeling and paddling. The pool and waterfall, located just beyond the Mediterranean-esque entry to the home, are covered in Bisazza Italian glass and 24-karat-gold tile. The hot tub is situated in the oceanfront garden and offers unparalleled views of the ocean and sunsets.

  3229 Diamond Head Road Bedroom

  3229 Diamond Head Road

  3229 Diamond Head Road

  3229 Diamond Head Road


Located at 3229 Diamond Head Road, the estate is listed for $22 million by Anne Hogan Perry of Coldwell Banker Pacific Properties. 


3229 Diamond Head Road


Read more stories by Rachel Ross Bradley