5 Spectacular Hawaii Oceanfront Estates in Lanikai and Maui

Along the water’s edge in Lanikai, The Mokulua Estate is an oceanfront sanctuary with unobstructed views of the Mokulua Islands from nearly every vantage point. More than 150 linear feet of ocean frontage sets the tone, while a private gated entrance brings a sense of seclusion and security. Designed by award-winning architect Jim Jennings, this state-of-the-art residence is conceived for refined indoor/outdoor living, with dramatic ocean and mountain vistas woven throughout. A guest house and caretaker’s quarters provide generous flexibility for hosting and day-to-day ease. From the backyard, direct ocean access turns the shoreline into a daily ritual—swimming, snorkeling, kayaking, surfing, or fishing—balanced by quiet afternoons spent relaxing by the pool in a tropical setting.

Along Keawakapu Beach in Kihei, this one-of-a-kind beachfront estate pairs irreplaceable beach proximity with modern structural integrity and refined island design. Completely rebuilt from the foundation up and completed in 2013—retaining only the original pool and foundation to preserve its rare, grandfathered beachfront setback—the wood-framed residence is reinforced with structural steel beams for expansive open spans and a modern layout. A spacious main residence, separate guest home, and three-car garage create a private compound suited to multigenerational living or effortless hosting. Multiple indoor and outdoor living spaces spill to a resort-style pool with slide, hot tub, waterfalls, and a dramatic rock grotto. Below, a distinctive basement retreat adds a game room with custom Koa wood bar, in-home gym, craft room, and an additional guest suite with full bath—while lush tropical landscaping, sauna, and outdoor showers complete the experience.

Along the water’s edge in Waimanalo, this extraordinary Pahonu Beach estate brings Hawaii’s natural drama into daily life. Nearly one acre of oceanfront land offers 152 linear feet along the Pacific and a private, gated sense of seclusion. The two-lot compound spans a main house, guest house, cottage, and studio, with expansive lawns framing views across the ocean to Manama (Rabbit) Island and out to the Koolau Mountains. Completed in 2022, the main house showcases quality craftsmanship and premium materials, with floor-to-ceiling sliding glass doors lining the oceanfront side to draw in lush landscaping and sea views. The gourmet kitchen continues the sleek, modern design with top-of-the-line appliances, custom walnut cabinetry, and a disappearing pantry. With a 3BR oceanfront guest house and 2BR cottage next door, it’s a setting made for effortless time together.

Along the water’s edge in Maalaea, this private, pastoral gated oceanfront estate spans a lot just under one acre with 127 feet of lineal ocean frontage. Set amid tropical landscaping, the plantation-style two-bedroom main home is joined by a respectfully situated studio ohana, creating a classic retreat with a distinct Hawaiian ambiance. Built in 1942 and carefully upgraded in 2011, the residence remains casually elegant, with a spacious single-level interior where beamed ceilings lead out to a large, covered oceanfront lanai designed for outdoor dining, relaxing, and entertaining. A rooftop lanai adds another open-air vantage point, while the ohana’s in-deck spa offers a quiet place to unwind. Dramatic ocean views include the Freight Trains surf break, plus whale watching in season, all close to Haycraft Beach Park. Turnkey, and ready to be lived in.

Along the water’s edge in Lanikai, this waterfront estate reads as a tropical, serene oasis designed for seamless indoor-outdoor living. Multiple outdoor areas invite long, unhurried days—lounge by the pool, or settle in on the expansive veranda with an ocean breeze, the sound of lapping waves, and regular turtle visits. Inside, a solidly built residence opens to an open floor plan where breathtaking panoramic Pacific views take over from nearly every room. The second level offers four bedrooms with vaulted ceilings, including a primary suite where expansive windows frame sunrise over turquoise waters. A wraparound lanai extends the experience, with two additional rooms also oriented to sunrise views. Privacy feels central here, with a calm sense of seclusion—yet you’re moments from Lanikai Beach, Kailua Beach, and Mid-Pac.