Koolaupoko Homes with Waterfront Frontage

Welcome to Koolaupoko, a stunning gem nestled on the windward side of Oahu, where the lush green mountains meet the sparkling blue waters of the Pacific Ocean. This picturesque neighborhood in Kailua is renowned for its breathtaking natural beauty, vibrant community, and unparalleled outdoor lifestyle. Imagine waking up to the sound of gentle waves lapping at the shore and the scent of salt in the air—this is the everyday reality for residents of Koolaupoko.

Koolaupoko is characterized by its serene atmosphere, making it an ideal retreat for families, retirees, and anyone seeking a tranquil lifestyle. The area boasts a variety of parks, hiking trails, and beautiful beaches, including the famous Kailua Beach and Lanikai Beach, both perfect for swimming, kayaking, and paddleboarding. The lush landscapes and stunning views of the Ko’olau Mountain Range provide a picturesque backdrop for outdoor adventures and leisurely strolls.

For those seeking homes with waterfront frontage, Koolaupoko offers a selection of exquisite properties that allow you to embrace the island lifestyle fully. Imagine sipping your morning coffee on your private lanai, overlooking the tranquil waters of the bay, or hosting sunset gatherings with friends and family as the sun dips below the horizon. These waterfront homes provide not just a place to live, but a lifestyle filled with relaxation, recreation, and connection to nature.

With its unique blend of natural beauty, community spirit, and waterfront living, Koolaupoko is more than just a neighborhood—it's a paradise waiting to be discovered. Come explore the opportunities that await you in this idyllic corner of Kailua!

Newest Koolaupoko Homes with Waterfront Frontage

$2,500,000

5 Beds ⋅ 5 Baths ⋅ 202612304 MLS ⋅ FS - Fee Simple Tenure ⋅ 31 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 ⋅ 156 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.