A True Gem in Diamond Head: Historic Hawaiian Cottage

Not every standout listing is grand or flashy—some are simply timeless. One of my favorite listings this year is a modest, yet iconic Hawaiian-style cottage tucked in the heart of Diamond Head. Listed by my colleague Doug Shanefield and just steps from one of my longtime surf spots, this 2-bedroom, 2-bath home at 3030 Kalakaua Avenue is a rare treasure. I got a first look before it hit the market, and had a hunch it wouldn’t last long. I was right—it went under contract in just three days, listed at $3.5M.

What makes this home truly special is its history. It was the original residence of Charles W. Dickey, one of Hawaii’s most influential architects, known for pioneering a distinct “Hawaiian style” of architecture. Dickey’s signature double-pitched hip roof, now famously known as the Dickey roof, graces this cottage, which is listed on the National Register of Historic Places. Built in 1926, the home features board-and-batten siding, acid-stained concrete floors, and a backyard oasis that feels worlds away from the city bustle.

This listing is more than a home. It’s a piece of Hawaii’s architectural legacy. It’s a reminder that charm, history, and location can come together beautifully in a home that feels like an authentic island treasure.