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$3,195,000
5 Beds ⋅ 3 Baths ⋅ 202616719 MLS ⋅ FS - Fee Simple Tenure ⋅ 2 DOM
Rare oceanfront legal duplex on Oahu’s legendary North Shore. Set on a spacious 7,786 sq ft beachfront parcel in Haleiwa’s “Fresh Airs” community, this coastal sanctuary captures sweeping ocean, mountain, and sunset views, with world-class surf just beyond the lawn. Fully updated with permitted improvements throughout, the property features two legal residences with separate addresses—ideal for multi-generational living or a luxury rental/investment opportunity. The main home (66-471 Pikai) offers 3 bedrooms, 2 full baths, open-concept living, and expansive dual oceanfront lanais for effortless indoor/outdoor island living. The attached second home (66-469 Pikai) features 2 bedrooms, 1 bath, complete privacy, and its own entrance. Upgrades include a new pitched roof, dual-meter electrical enclosure with new subpanels, EV charger, refreshed plumbing, rebuilt oceanfront lanai decking, premium Pella 250 Series impact-rated windows and sliders, designer appliances, and fresh coastal paint. A turnkey beachfront trophy offering rare dual-residence versatility and pure North Shore magic.

66-471 Pikai Street, Haleiwa
$1,200,000
5 Beds ⋅ 2 Baths ⋅ 202612612 MLS ⋅ FS - Fee Simple Tenure ⋅ 73 DOM
Fantastic opportunity for redevelopment of very desirable Haleiwa property that's been in the family for decades. Two original homes (top house built in 1958 is a raised 3BR/1BA; bottom house in back built in 1938 is a single story 2BR/1BA) sit on a huge 10,575 square foot lot that is zoned R-5! Create a multi-gen, multi-family compound in the country on this downward, but gently sloped terrain. Mature tropical plants include plumeria, hibiscus, crown flower, and more! Excellent proximity to Haleiwa Town restaurants, food trucks, shops, and services. Short drive to Paalaa Kai Market and Bakery and the Old Waialua Sugar Mill and Town offerings. Enjoy gardening, hiking, all manner of water sports, and sea life while savoring gorgeous sunsets along beautiful Haleiwa Beach Park and Kaiaka Bay. This could be a peaceful retreat or home base with easy access to world class surfing competitions and festivals. Call your Realtor today and make your North Shore dreams come true! Please do not enter property without appointment. Sold strictly AS IS. Buyers to do their own due diligence.

66-413 Paalaa Road, Haleiwa
$5,800,000
5 Beds ⋅ 5 Baths ⋅ 202611319 MLS ⋅ FS - Fee Simple Tenure ⋅ 92 DOM
RARE North Shore luxury retreat with panoramic ocean views to Kaena Point! Elevated approx. 85 ft above sea level and outside the flood zone, enjoy peace of mind, cooling trade winds, and seasonal whale watching from your own property. Ideally located near the world-famous "7 Mile Miracle" surf breaks, Haleiwa, and Turtle Bay Resort. The expansive 5 bedroom, 4 bath main home offers open-concept living, seamless indoor-outdoor flow, and a grand porte-cochere entry. Resort-style grounds feature a pool, jacuzzi, covered outdoor grill, cabana, and hotel quality turf lawn--perfect for entertaining. A detached guest house with full bath plus an attached apartment WITHIN the main home (separate entry + kitchenette) creates strong multi-generational living or income potential. Opportunities like this are limited-- secure your piece of North Shore paradise before it's gone.

59-011 Kamehameha Highway Unit B, Haleiwa
$5,000,000
5 Beds ⋅ 4 Baths ⋅ 202521091 MLS ⋅ FS - Fee Simple Tenure ⋅ 344 DOM
Experience exceptional beachfront living on coveted Papailoa Road along Oahu's world-famous North Shore. This private 5-bedroom, 3.5-bath residence boasts 119 feet of sandy ocean frontage with panoramic views from Ka?ena Point to Waimea Bay. Lush tropical landscaping, a wraparound lawn, and meandering garden paths create a peaceful island retreat. Step from your lanai onto the beach to swim with sea turtles, enjoy breathtaking sunsets, or dine under the stars. Designed for flexibility, the home features two interconnected living areas, each with its own kitchen, making it ideal for multi-generational living, guests, or rental opportunities. Enjoy direct access to renowned surf breaks including Laniakea and Himalayas, with surfing, snorkeling, kayaking, paddleboarding, kite surfing, and wing foiling just outside your door. A gated electric entry and fenced perimeter provide privacy, while historic Hale?iwa Town's shops, cafés, art galleries, and restaurants are just a scenic one-mile stroll along the shoreline. This rare legacy property offers the perfect blend of tranquility, adventure, and timeless island elegance in one of Oahu's most sought-after beachfront communities.

61-707 Papailoa Road, Haleiwa

Based on information from the Multiple Listing Service of Hicentral MLS, Ltd. Listings last updated on . Information is deemed reliable but not guaranteed. Copyright: 2026 by HiCentral MLS, Ltd. IDX information is provided exclusively for consumers' personal, non-commercial use. It may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.