Koolaupoko Homes with Canal View

Welcome to Koolaupoko, a hidden gem nestled on the windward side of Oahu, where the breathtaking beauty of Hawaii comes alive in every sunrise and sunset. This enchanting neighborhood in Kailua is renowned for its stunning landscapes, lush greenery, and the tranquil waters of the Koolau Mountains that cradle the area. Koolaupoko offers a unique blend of island living and vibrant community spirit, making it an ideal place to call home.

One of the standout features of Koolaupoko is its exceptional homes with canal views. Imagine waking up each morning to the soothing sounds of water gently lapping against the shore, with stunning vistas right outside your window. These properties not only offer picturesque views but also provide easy access to the serene canals, perfect for kayaking, paddleboarding, or simply enjoying a peaceful afternoon by the water.

The neighborhood is rich in recreational opportunities, with nearby beaches such as Kailua and Lanikai, known for their soft sands and crystal-clear waters. Nature lovers will appreciate the nearby hiking trails that lead to breathtaking viewpoints, while families can take advantage of the excellent schools and community parks.

Koolaupoko is more than just a place to live; it’s a lifestyle. With its welcoming atmosphere, friendly neighbors, and a plethora of outdoor activities, you’ll find that this captivating neighborhood truly embodies the spirit of aloha. Whether you’re looking for a tranquil retreat or an active lifestyle, Koolaupoko offers the perfect backdrop for your dream home. Come discover the magic of canal-view living in this idyllic Hawaiian paradise!

Newest Koolaupoko Homes with Canal View

$2,625,000

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

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

Listing courtesy of Arquette Properties Inc.

$4,350,000

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

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

Listing courtesy of Compass.

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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.