Koolaupoko Homes with Waterfront Frontage

Welcome to Koolaupoko, a serene slice of paradise nestled in the heart of Oahu, Hawaii. This enchanting neighborhood, located in the vibrant city of Kailua, boasts breathtaking views and a lifestyle that many dream of. Known for its stunning landscapes, Koolaupoko is bordered by the majestic Ko'olau Mountains to the west and the sparkling waters of the Pacific Ocean to the east, creating a picturesque backdrop that is simply unmatched.

One of the most alluring features of Koolaupoko is its collection of homes with waterfront frontage. Imagine waking up to the gentle sound of waves lapping against the shore, with the sun rising over the horizon, painting the sky in hues of orange and pink. These waterfront properties not only offer direct access to the beach but also provide a unique opportunity for outdoor enthusiasts to indulge in kayaking, paddleboarding, or simply enjoying a sunset stroll along the shore.

The community here is as vibrant as the natural beauty surrounding it. With a blend of local shops, delightful eateries, and lush parks, residents enjoy a relaxed, island lifestyle that fosters a strong sense of community. Families and individuals alike appreciate the excellent schools and recreational facilities, making Koolaupoko an ideal place to call home.

Whether you're looking for a cozy beachfront cottage or a luxurious estate with panoramic ocean views, Koolaupoko offers an array of real estate options tailored to suit every lifestyle. Embrace the tranquility and beauty of this idyllic neighborhood, where every day feels like a vacation. Discover your dream home in Koolaupoko today!

Newest Koolaupoko Homes with Waterfront Frontage

$2,500,000

5 Beds ⋅ 5 Baths ⋅ 202612304 MLS ⋅ FS - Fee Simple Tenure ⋅ 66 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 ⋅ 191 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.