Koolaupoko Homes with Canal Frontage

Welcome to Koolaupoko, a breathtaking neighborhood nestled on the windward side of Oahu, where the lush mountains meet the sparkling waters of the Pacific. Located in the charming city of Kailua, this area is a paradise for those seeking both tranquility and adventure. With its stunning landscapes, vibrant community, and rich cultural heritage, Koolaupoko is a place that truly captures the essence of island living.

One of the standout features of Koolaupoko is its picturesque canal frontage homes. Imagine waking up each morning to the gentle sounds of water lapping at your doorstep, with your very own slice of paradise right outside. These canal-front properties offer unique access to serene waterways, perfect for kayaking, paddleboarding, or simply enjoying a peaceful afternoon by the water. The homes are often designed with open floor plans and large windows, allowing for natural light to flood in and providing stunning views of the lush surroundings.

Kailua is renowned for its beautiful beaches, including the famous Lanikai Beach, known for its soft, white sands and turquoise waters. The neighborhood also boasts a vibrant local scene with charming boutiques, delightful cafes, and farmer’s markets, where you can savor the flavors of the island. With a strong sense of community and a plethora of outdoor activities, Koolaupoko is an ideal destination for families, retirees, and anyone looking to embrace the aloha spirit.

Come explore the enchanting neighborhood of Koolaupoko, where your dream home with canal frontage awaits!

Newest Koolaupoko Homes with Canal 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.