Koolaupoko Homes with Canal Frontage

Welcome to Koolaupoko, a captivating neighborhood nestled in the heart of Kailua, on the stunning island of Oahu, Hawaii. Renowned for its breathtaking natural beauty and vibrant community, Koolaupoko offers a unique blend of tranquil living and access to a wealth of outdoor activities. With the majestic Ko'olau Mountains as a backdrop and the sparkling waters of Kailua Bay just moments away, this area is a paradise for nature lovers and adventure seekers alike.

One of the standout features of Koolaupoko is its charming homes with canal frontage. Imagine waking up each morning to the gentle sounds of water lapping against your private dock, with the opportunity to enjoy kayaking, paddleboarding, or simply relaxing by the water’s edge. These homes offer not just a residence, but a lifestyle filled with serenity and connection to nature.

The neighborhood is also known for its strong sense of community, with friendly neighbors and local events that foster a welcoming atmosphere. Families will appreciate the nearby top-rated schools, parks, and recreational areas, making it an ideal place to raise children. Additionally, the vibrant town of Kailua is just a short drive away, offering an array of shops, restaurants, and cultural experiences.

Whether you’re seeking a peaceful retreat or an active lifestyle, Koolaupoko's canal-front homes provide the perfect setting. Embrace the beauty of island living and make Koolaupoko your new home, where every day feels like a vacation in paradise.

Newest Koolaupoko Homes with Canal 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.