5 Resort-Style Hawaiian Estates with Ocean Views and Island Living

Beyond the gates of Hokuliʻa, this brand new ocean-view estate sits on 1.1 acres in a quiet cul-de-sac, pairing modern Hawaiian luxury with a sense of retreat. Wide plank white oak floors and bespoke cabinetry set a refined tone, while seamless indoor–outdoor living keeps the focus on panoramic ocean vistas throughout. Resort-style outdoor spaces extend the daily rhythm outdoors, with a shimmering pool, a firepit for lingering evenings, and a full outdoor kitchen for effortless hosting. Inside, the private Primary Wing is positioned as a spa-like escape, and a separate guest wing offers comfort and privacy for visitors. Ownership also includes access to Hokuliʻa’s world-class golf, clubhouse, fitness, and dining amenities—an easy shift from serene home life to resort-caliber experiences.

Along the water’s edge in Kailua, this Aalapapa Drive estate pairs ocean views with a rare, expansive level lot and over 5,300 square feet designed for flexible, multi-generational living. Configured to function as one refined residence or as up to three independent homes, it offers separate entrances and parking for guests or extended family. The main residence spans over 3,000 square feet with five bedrooms and four baths, high ceilings, hardwood floors, and granite finishes, plus two expansive decks that frame island and ocean vistas. A light-filled studio adds its own deck, while a separate lower residence includes two bedrooms, generous living areas, and seamless indoor-outdoor flow. Solid concrete construction, updated landscaping, 33 solar panels, and a full second-floor remodel completed in 2025 round out a setting made for unhurried days.

Perched high above Kauai’s iconic Secrets (Kauapea) Beach, this north shore parcel on Kauapea Road offers a rare canvas for a custom estate with sweeping panoramic views. Sightlines stretch across the sparkling Anini Reef, framed by the dramatic Wainiha Mountain Range and Bali Hai (Makana Peak) in the distance. Nearby, the historic Kilauea Lighthouse anchors the setting, with the town of Kilauea close at hand for boutique shopping and fine dining, plus easy access to outdoor adventures. With ample space to design a luxurious private compound—whether envisioned as a contemporary coastal retreat, a tranquil wellness sanctuary, or a legacy estate—the land invites a lifestyle shaped by privacy, serenity, and ever-changing light over the Pacific. Each day here would begin and end with an unmatched perspective on Kauai’s natural beauty.

Size: 1.72 acres

Commanding views from high above Kauai’s iconic Secrets (Kauapea) Beach, this north shore parcel on Kauapea Road offers a rare canvas for a custom estate. Sweeping panoramas stretch across the turquoise waters of Anini Reef, framed by the dramatic Wainiha Mountain Range and the unmistakable silhouette of Bali Hai (Makana Peak). Set in Kilauea near the historic Kilauea Lighthouse and the vibrant town center, the location balances seclusion with easy access to boutique shopping, fine dining, and outdoor pursuits. With 1.808 acres described as expansive and dramatic, Lot 3 provides ample space to envision anything from a contemporary coastal retreat to a tranquil wellness sanctuary or a legacy compound. Positioned at the heart of the property with its own access off Kilauea Road, it’s a setting made for long horizons and quiet, intentional living.

Size: – acres

Commanding ocean views from its forward-most position, Ho’olei 21-4 is an elegant Plumeria floor plan townhome in the heart of Wailea, Maui. Offered tastefully furnished and totally turnkey, this Hotel Zoned residence is active and successful in the Grand Wailea’s exclusive vacation rental program. Inside, new upgraded bedroom flooring pairs with a chef’s kitchen appointed with Wolf and Sub-Zero appliances. Pocketing Fleetwood glass sliders erase the boundary between indoors and out, extending daily living onto the widest lanai—complete with a built-in BBQ and refrigerator for effortless entertaining. Practical comforts include an attached garage and a private elevator. Beyond the front door, Ho’olei’s resort-style pool and spas, state-of-the-art workout facility, and saunas complement lush landscaping and gated 24-hour security, creating an easy rhythm to life in Wailea.

Price: Contact for pricing