The history of Kaneohe Ranch and the history of the town of Kailua have been intertwined for almost the past 100 years.

Harold K.L. Castle, the only child of James B. Castle owned most of the ahupuaa of Kaneohe and Kailua in the early 1900s. The Ranch was started back in 1894, ran cattle and leased land to others for growing vegetables and rice. By the end of World War II, ranching was no longer economically viable and the company became primarily a landlord to other farmers.

Oahu grew substantially in the 1950s and 1960s. The growth that occurred on Oahu during that period spilled over into the windward side with the opening of the Wilson Tunnel and the Pali Highway. Due to very high tax rates on real estate sales most old-time Hawaii landowners chose to lease their land to residential developers rather then sell on a fee-simple basis. Kaneohe Ranch at one time had leased their land for over 5,000 single family residential lots in Kailua and Kaneohe. The vast majority of those leaseholds have now been sold to the lessees.

In addition to residential holding, Kaneohe Ranch owns around 40 acres, or roughly half, of downtown Kailua. The holdings are mostly contiguous and are most of the commercial lands south of Kailua Road and makai of Hamakua Drive.

The commercial and industrial properties were also developed leasehold 40 to 50 years ago. Many of those leases have either expired or will be expiring by the end of this decade.

Kaneohe Ranch is now taking a more active role in re-developing and managing its own real estate and the real estate of its sister company, the Harold K.L. Castle Foundation.

The Castle family has made a personal and financial commitment to re-developing its Kailua properties in a sensible manner that is appropriate for Kailua.