Koolaupoko Homes with Waterfront Frontage

Welcome to Koolaupoko, a picturesque neighborhood nestled in the heart of Kailua, Oahu. This enchanting area is renowned for its stunning natural beauty, offering a harmonious blend of lush landscapes and breathtaking waterfront views. With the majestic Ko'olau Mountains as a backdrop and the sparkling waters of the Pacific Ocean at your doorstep, Koolaupoko is a slice of paradise that promises a lifestyle like no other.

One of the most appealing aspects of Koolaupoko is its waterfront properties, where homes with direct access to the water are a common sight. Imagine waking up each morning to the gentle sound of waves lapping at the shore and enjoying your morning coffee with panoramic ocean views. These waterfront homes are ideal for those who appreciate the finer things in life, including kayaking, paddleboarding, or simply soaking in the sun on your private beach.

The neighborhood is not just about the stunning properties but also about the vibrant community. Koolaupoko boasts a rich cultural heritage, with friendly neighbors and a strong sense of belonging. Residents enjoy easy access to local amenities, including charming shops, delicious dining options, and picturesque parks, making it an ideal place for families and individuals alike.

Whether you are looking for a serene retreat or an active lifestyle filled with outdoor adventures, Koolaupoko offers it all. With its captivating waterfront homes and welcoming atmosphere, this neighborhood truly embodies the essence of island living. Come experience the magic of Koolaupoko and discover your dream home in this tropical haven!

Newest Koolaupoko Homes with Waterfront Frontage

$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.