Nestled below the dramatic peak of Mount Olomana, the lush and luxurious valley of Maunawili offers sweet seclusion. Although within the boundaries of Kailua—a vast, highly desirable Windward Oahu community that stretches from mountain to sea—Maunawili’s hidden upland setting has preserved its tranquility and authenticity as a real Hawaii-style neighborhood. And yet, Maunawili residents are only a short drive from Kailua Town’s charming shops and cafés, plus enjoy an especially easy commute over the Pali to Honolulu.

Maunawili—which means “twisted mountain” in Hawaiian—is rich in history and lore. According to legend, the 1,643-foot-high mountain, Olomana, is the shoulder of an enormous warrior-chief who was killed here in battle long ago. Archeological research suggests that Hawaiians were farming this once stream-streaked valley as early as 1200 AD and, with its abundant freshwater springs, eventually settled here. They may have also managed to lure mullet upstream from Kailua’s wetland fishponds, enhancing Maunawili’s potential to support a large population. Hawaiian temple sites, or heiau, dotted the landscape into the 20th century.

By the late 1800s, Maunawili’s most prominent structure was Maunawili Ranch, one of the largest cattle ranches in the region. Agricultural ventures also flourished in the valley into the mid-1900s, including coffee, cacao, papaya and rice, and the valley’s plentiful water resources were harnessed to feed coastal plantations.

Only a handful of homes marked this verdant valley until the mid-20th century. One Maunawili homeowner writes, “When we bought our home on Maunawili Road in 1957, there was no mail delivery in the valley and no house numbers. There were only a few houses, and no subdivisions.” By the mid-1960s, however, in keeping with home development island-wide as Oahu’s population grew, the neighborhood had transformed into peaceful, winding streets lined with executive-style homes. Today these expansive homes are in particularly high demand for their beautiful architectural designs and large lots.

Despite the growth of Kailua Town, Maunawili remains a peaceful residential neighborhood of about 2,000 people, softly edged by golf courses, the Honolulu Watershed Forest Reserve, an Air Force station and Kawainui Marsh. In addition to its reputation as one of Oahu’s most exclusive enclaves, Maunawili has also become renowned for its tropical-jungle trails.

Key attractions in and around Maunawili include:

+ The Maunawili Falls Trail, Maunawili Demonstration Trail and Olomana Trail
+ The 8.2-acre Maunawili Park, with a playing field, picnic area and tennis courts
+ Golf clubs and courses, including the Royal Hawaiian Golf Club, Pali Golf Course, Koolau Golf Club, Olomana Golf Club and Mid-Pacific Country Club
+ Castle Medical Center, a full-service hospital
+ Kailua Town, featuring shops, restaurants and services, plus a 2-mile-long beach
+ Maunawili Elementary School and the prestigious Le Jardin Academy

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