Koolaupoko Homes with Waterfront Frontage

Welcome to Koolaupoko, a hidden gem nestled on the stunning windward coast of Oahu, Hawaii. This enchanting neighborhood of Kailua captures the essence of island living, offering a blend of natural beauty, vibrant community, and tranquil waterfront access. Imagine waking up to the gentle sounds of waves lapping against the shore, with breathtaking views of the majestic Ko'olau Mountains as your backdrop.

Koolaupoko is renowned for its picturesque beaches, including the world-famous Kailua Beach and Lanikai Beach, both of which boast soft white sands and crystal-clear turquoise waters. Whether you’re an avid surfer, paddleboarder, or simply love to soak up the sun, this neighborhood provides endless opportunities for outdoor adventures.

For those seeking a home with waterfront frontage, Koolaupoko presents an exceptional selection of properties that offer direct access to the ocean. Picture yourself sipping your morning coffee on a spacious lanai, watching the sunrise over the water, or hosting sunset barbecues with friends and family. These homes not only provide stunning views but also a lifestyle that embraces the beauty of nature.

The community of Koolaupoko is vibrant and welcoming, with a rich cultural history and a strong sense of togetherness. Enjoy local farmers' markets, charming boutiques, and delightful eateries that showcase the best of Hawaiian cuisine. With its perfect blend of relaxation and recreation, Koolaupoko is not just a place to live; it’s a lifestyle waiting to be embraced. Discover your dream home in this idyllic neighborhood and experience the true spirit of island living!

Newest Koolaupoko Homes with Waterfront Frontage

$2,500,000

5 Beds ⋅ 5 Baths ⋅ 202612304 MLS ⋅ FS - Fee Simple Tenure ⋅ 42 DOM

Rare opportunity to own a canal front home on a nearly 10,000 sq. ft. R-5 zoned lot with a legal ‘ohana unit, each with its own utility meters, complete with pool & spa. Tucked along the peaceful cul-de-sac end of Kainui Drive, locally known as “Duck Road.” The spacious single-level main home features three generously sized bedrooms with new carpeting, three bathrooms, a dedicated study and bright living and dining areas that flow seamlessly into an enclosed lanai. A large recreation room or studio complete with a kitchenette, bathroom, private entrance, and its own courtyard provides additional flexibility for guests, home office or extended family. Upstairs, the 800 sq ft 'ohana unit (823 Kainui Dr) features two bedrooms, one bathroom, and a covered lanai. Recent upgrades include a new roof on the main home and a freshly re-plastered pool. Take in stunning sunsets over the Ko'olau Mountains from the multiple outdoor areas, relax in the pool and spa, or enjoy a paddle or boat out to Kailua Bay. This unique property offers flexibility and is ideal for multigenerational living, generating rental income, or both. The possibilities are truly endless.

821 Kainui Drive, Kailua

$4,350,000

6 Beds ⋅ 4 Baths ⋅ 202525771 MLS ⋅ FS - Fee Simple Tenure ⋅ 167 DOM

Discover the perfect blend of lifestyle, comfort, and value at 1251 Kainui Drive—an exceptional canal-front retreat situated along an established, palm tree-lined street in North Kailua. Fully renovated in 2026 & move-in ready, the spacious single-level main residence offers 4 beds, 3 baths, and over 3000 SF of beautifully designed living space with soaring ceilings, high-end finishes, and an effortless flow. New standing seam roof, net-metered PV & split AC. The kitchen is the heart of the home, featuring a grand island and luxurious, durable Taj Mahal quartzite countertops, ceiling-high cabinetry, premium appliances, a butler’s pantry, dedicated dining area and a charming breakfast nook. Covered and open lanais connect the living areas to landscaped grounds and a peaceful canal with ocean access—perfect for paddling from your backyard. Room to build your dream pool! A dedicated laundry room, 2-car garage, & ample storage provide everyday ease. The 2-bed, 1-bath ADU adds ~800 SF for multi-generational living, guests or rental flexibility. This desirable location is just two blocks from the beach and provides easy access to Kailua Town, top schools, and freeways for easy commuting.

1251 Kainui Drive, Kailua

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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.