5 Spectacular Hawaii Oceanfront and Resort Homes in Kailua and Wailea

Along the ocean’s edge in Kailua’s prestigious Lanikai neighborhood, the Mokulua Estate pairs seclusion with a vivid sense of place. More than 150 linear feet of ocean frontage frames unobstructed views of the Mokulua Islands from nearly every vantage point, while a private gated entrance adds security and privacy. Designed by Maybeck award winning architect Jim Jennings, this state-of-the-art residence unfolds across more than 10,000 square feet of refined indoor/outdoor living, with dramatic ocean, mountain, and island vistas woven throughout. A guest house and caretaker’s quarters provide flexible accommodation for family and guests. From the backyard, direct ocean access invites days shaped by swimming, snorkeling, kayaking, surfing, and fishing—then a slower rhythm poolside, surrounded by the estate’s natural harmony.

Along the pristine shores of Kailua Beach, 376 Dune Circle sits on one of Kailua’s most coveted beachside streets, offering a true beachfront living experience with azure ocean views as its daily backdrop. This single-story 4-bedroom, 4-bath retreat blends timeless elegance with modern comfort, set within a warm, earthy palette inspired by sand and native hardwoods including koa, monkeypod, and ohia. Inside, an open, light-filled interior is framed by high peaked ceilings and terrazzo tile floors, balancing casual sophistication with low-maintenance island living. Rich wood and stone accents carry through the well-designed layout, while spacious living areas flow easily for quiet mornings or easy entertaining. The meticulously appointed kitchen features high-end appliances and a clear commitment to quality. Thoughtfully designed by Jaime Jackson and architect Mark Eyler, it’s a sanctuary tuned to the laid-back spirit of the islands.

Along the water’s edge in Lanikai, this waterfront estate unfolds as a tropical, serene oasis designed for seamless indoor-outdoor living. Multiple outdoor areas invite long afternoons—lounge by the pool or gather on the expansive veranda as the ocean breeze drifts through, accompanied by lapping waves and regular turtle visits. Inside, a solidly built home opens to an open floor plan where breathtaking panoramic views of the Pacific command attention from nearly every room. The second level offers four bedrooms with vaulted ceilings, including a primary suite whose expansive windows frame sunrise over turquoise waters. Step onto the wraparound lanai, where two additional rooms share those early-morning views. Privacy is treated as a true amenity, with a calm, secluded feel throughout. Just half a block from Lanikai Beach, one block from Kailua Beach, and two blocks from Mid-Pac, days here begin and end with the shoreline.

Along the water’s edge in Kaupulehu on the Kona Coast, this rare homesite is an exceptional canvas for a dream estate, set within one of the Big Island’s most exclusive coastal enclaves. The setting is defined by endless ocean views, dramatic lava rock shores, and sunsets that anchor daily life in the rhythms of the coastline. With unmatched privacy and direct proximity to the water, the property also overlooks a 214-acre Cultural Reserve—preserving forever-unobstructed ocean vistas and a deep sense of Hawaiian heritage. Ownership includes access to the Kaupulehu Beach Club, with a dining lanai, bar and fire pit, a two-tiered pool, an expansive event lawn, and a pathway to a secluded black sands beach. Within the 24-hour access-controlled community, invitation-only opportunities extend to Kukio Golf and Beach Club and its array of amenities.

Size: 1.15 acres

From its elevated setting at the top of Wailea, this thoughtfully designed single-level custom home, built in 2020 by Buddy L & Sons, pairs practical elegance with an easy sense of retreat. Set within The Ridge at Wailea—an intimate, coveted neighborhood of just nine lots—it frames magnificent, expansive ocean views while keeping daily living effortless. Open living spaces flow seamlessly to the pool and outdoor entertaining area, underscoring Maui’s signature indoor-outdoor lifestyle. The layout includes four bedrooms, three baths, and a separate home office, balancing comfort and functionality. Owned photovoltaic and central air conditioning support modern convenience, while a generous garage adds workspace and extra storage. Outside, a gated driveway leads to a spacious yard with mature landscaping, citrus trees, and a garden bed—an inviting backdrop for slow mornings and sunset evenings.