Koolaupoko Homes with Waterfront Frontage

Welcome to Koolaupoko, a picturesque neighborhood nestled on the windward side of Oahu, Hawaii. Known for its breathtaking landscapes and serene coastal beauty, Koolaupoko offers a unique blend of lush mountains, sparkling ocean views, and a vibrant community spirit. This charming area is perfect for those seeking a tranquil lifestyle, surrounded by nature’s splendor.

Kailua, the heart of Koolaupoko, is celebrated for its pristine beaches, including the famous Kailua Beach and Lanikai Beach, both offering soft white sands and crystal-clear waters ideal for swimming, kayaking, and paddleboarding. The neighborhood is also home to a variety of local shops, cafes, and restaurants, where you can savor delicious Hawaiian cuisine and fresh local produce. The community is tight-knit, with numerous events and activities that foster a welcoming atmosphere.

For those dreaming of a home with a view, Koolaupoko boasts an array of stunning properties with waterfront frontage. Imagine waking up to the soothing sounds of the ocean and enjoying panoramic views of the turquoise waters right from your doorstep. These homes offer not just a place to live, but a lifestyle defined by relaxation and outdoor adventure. Whether you’re looking for a cozy beach cottage or a luxurious estate, Koolaupoko has something for everyone.

With its idyllic setting, rich culture, and exceptional quality of life, Koolaupoko is more than just a neighborhood; it’s a sanctuary where you can truly embrace the beauty of island living. Come explore the charm of Koolaupoko and discover your dream home by the water!

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.