5 Elevated Hawaiian Estates from Oahu to Maui’s North Shore

Along the water’s edge on Windward Oahu, this modern residence by award-winning architect Jim Schmit was completed in 2017, pairing contemporary European luxury with the natural drama of Kaneohe Bay. A grand 8-foot pivot entry door opens to an expansive, open floor plan with high ceilings and wall-to-wall ceramic tile flooring. The chef’s kitchen is fitted with high-end European-style cabinetry and premium stainless steel appliances, designed for effortless everyday living. Each bedroom is arranged as a private retreat, featuring its own en-suite full bathroom and generous walk-in closet space. Outside, a secluded tropical setting is enhanced by professional landscaping, while direct water access invites kayaking or paddleboarding from the backyard—reaching the world-famous Kaneohe Sandbar in under 10 minutes. A private two-car garage plus additional driveway keeps arrival easy, close to Honolulu conveniences, local shopping, and the Kaneohe Yacht Club.

Beyond a gated entry in Haiku on Maui’s North Shore, this rare 27-acre holding unfolds across three contiguous TMKs, offering exceptional privacy, serenity, and sweeping panoramic views. Multiple vantage points take in the ocean and Haleakala, giving the land a sense of scale that shifts as you move from the upper acreage to the lower. A custom-built 2-bedroom, 1-bath home sits on the upper portion of the property, comfortable for immediate living and well-suited as a guest house while a larger vision takes shape. Up top, flat, usable pasture land invites agricultural or equestrian possibilities, while the lower section transitions to gently rolling terrain. With land that hasn’t been farmed in over 30 years, the setting feels quietly removed—ready to be shaped into a private retreat, estate home, or more.

From its elevated setting on Lower Old Pali Road, this estate unfolds across approximately half an acre of lush tropical grounds, framed by sweeping mountain views. The beautifully remodeled residence pairs soaring wood ceilings and expansive picture windows with rich wood detailing and a newer aluminum roof. A covered porch and tranquil water feature set a calm tone on arrival, while inside, the gourmet kitchen with pantry flows to a dining room that looks out to the mountains and a spacious great room suited to gatherings. The living room adds drama with high ceilings and a fireplace, and the expansive primary suite offers space for a sitting area or home office. Outside, a soothing stream, mature landscaping, and numerous fruit trees deepen the sense of retreat. Three separate rental units add flexibility, with extensive parking, 72 PV panels, and two Tesla batteries supporting everyday ease.

Along the water’s edge in Hakalau, this architecturally distinctive oceanfront residence brings contemporary island living into quiet conversation with timeless Japanese-inspired design. Thoughtfully conceived as a one-of-a-kind retreat, it sits behind a private gated entrance, creating a sense of arrival that feels both intentional and serene. Lush native and ornamental landscaping surrounds the home, softening the lines between structure and shoreline and lending a calm, garden-like atmosphere throughout the property. Here, indoor and outdoor living are designed to exist in perfect harmony, shaping days around open-air ease and the restorative rhythm of the ocean nearby. The overall effect is tranquil and composed—a place where design and setting work together to encourage a slower, more grounded pace of life.

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Along the north side of the Ritz-Carlton Residences in Kapalua, Residential Suite 1221-23 looks toward Honolua Bay and the West Maui mountains, placing Maui’s iconic scenery front and center. Inside, the layout includes two bedrooms and two baths, arranged in a lock-off configuration that allows the one-bedroom and studio to be rented separately—an appealing flexibility for owners who value both privacy and options. Life here is shaped by resort-level amenities: a spa with volcanic stone grottos and private garden showers, a fitness center, restaurants, concierge service, and the Jean-Michel Cousteau Ambassadors of the Environment program. Beyond the residence, Kapalua Resort’s 22,000 acres unfold with championship golf, three white sand beaches, hiking, tennis, and expansive island views that make even everyday routines feel like a getaway.