Koolaupoko Homes with Waterfront Frontage

Welcome to Koolaupoko, a picturesque neighborhood nestled on the windward side of Oahu, Hawaii. Known for its stunning natural beauty and vibrant community, Koolaupoko boasts breathtaking views of the Ko'olau mountain range and is just a stone's throw away from the pristine shores of Kailua and Lanikai beaches. This idyllic area is perfect for those seeking a serene lifestyle infused with the spirit of Aloha.

Koolaupoko is characterized by its lush landscapes, charming streets, and friendly neighbors. The neighborhood offers a blend of residential options, but it’s the homes with waterfront frontage that truly capture attention. Imagine waking up to the gentle sound of waves lapping against the shore, with the sun rising over the horizon just outside your window. These waterfront properties provide not only stunning views but also direct access to the ocean, making them perfect for water enthusiasts and those who appreciate the tranquility that comes with living by the sea.

In Koolaupoko, outdoor activities abound. Residents can enjoy kayaking, paddleboarding, and swimming in the crystal-clear waters, or simply relax on the soft sandy beaches. The area is also home to lush parks and hiking trails, offering plenty of opportunities to explore the breathtaking natural surroundings.

With a strong sense of community, excellent schools, and convenient access to local shops and dining, Koolaupoko is more than just a neighborhood; it's a place where you can create lasting memories. Discover the charm of Koolaupoko and find your dream home with waterfront frontage today!

Newest Koolaupoko Homes with Waterfront Frontage

$2,625,000

5 Beds ⋅ 5 Baths ⋅ 202612304 MLS ⋅ FS - Fee Simple Tenure ⋅ 20 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 ⋅ 145 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.