Kawailoa North Shore Homes with Fee Simple Land tenure

Welcome to Kawailoa, a hidden gem nestled within the stunning North Shore of Oahu, Hawaii. Known for its breathtaking landscapes, vibrant local culture, and laid-back lifestyle, Kawailoa offers a unique blend of tranquility and adventure. This charming neighborhood is the perfect escape for those seeking a slice of paradise while still being close to the vibrant town of Haleiwa.

Kawailoa's picturesque surroundings feature pristine beaches, lush greenery, and stunning ocean views, making it a haven for outdoor enthusiasts. Residents enjoy a plethora of activities, from surfing the world-renowned waves of Waimea Bay to hiking along scenic trails that showcase the island's natural beauty. The area is also home to a diverse array of wildlife, offering opportunities for birdwatching and exploring the rich ecosystems that thrive here.

One of the standout features of Kawailoa is its real estate offerings, particularly homes with Fee Simple land tenure. This means homeowners enjoy full ownership of their property, providing peace of mind and long-term investment potential. Many properties in Kawailoa boast spacious lots, allowing for gardens, outdoor living spaces, and the ability to embrace the island lifestyle fully.

The community is welcoming and friendly, with a strong emphasis on local culture and sustainability. Farmers' markets, art festivals, and community events are common, fostering a sense of belonging among residents. Whether you're looking for a permanent residence or a vacation retreat, Kawailoa on the North Shore is a captivating destination that promises a lifestyle filled with sunshine, surf, and serenity. Discover your dream home in this enchanting neighborhood today!

Newest Kawailoa North Shore Homes with Fee Simple Land tenure

$3,500,000

4 Beds ⋅ 5 Baths ⋅ 202606358 MLS ⋅ FS - Fee Simple Tenure ⋅ 151 DOM

Your slice of paradise on O?ahu’s North Shore. This stunning 4-bedroom, 4.5-bath home offers incredible ocean views, a private home gym that also doubles as a two-car garage, a 10-person sauna, solar power with Tesla batteries, and a massive primary suite with an oversized balcony and sweeping views. Set in one of the newest and quietest neighborhoods in the area, this modern residence features clean architectural finishes and thoughtful attention to detail throughout. Enjoy easy access to world-class surf and beaches, with Hale?iwa just a short drive away for shopping, dining, and daily essentials.

61-1010 Tutu Place, Haleiwa

$5,995,000

4 Beds ⋅ 3 Baths ⋅ 202606359 MLS ⋅ FS - Fee Simple Tenure ⋅ 151 DOM

An exceptionally rare offering on Oahu’s North Shore, this legal NUC-permitted vacation rental is one of the last few fully permitted vacation rentals in the entire zip code. With annual income exceeding $500,000, it represents a compelling blend of established performance, long-term rarity, and an elegantly configured coastal property designed to support multiple private guest experiences. In a market defined by strict limitations and enduring demand, this is a true legacy-caliber STR asset.

61-104 Iliohu Way, Haleiwa

$5,000,000

5 Beds ⋅ 4 Baths ⋅ 202521091 MLS ⋅ FS - Fee Simple Tenure ⋅ 345 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

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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.