Koolaupoko Homes with Waterfront Frontage

Welcome to Koolaupoko, a picturesque neighborhood nestled on the stunning windward coast of Oahu, Hawaii. Known for its breathtaking natural beauty, Koolaupoko is a haven for those seeking a tranquil lifestyle infused with the spirit of aloha. This charming community is characterized by its lush landscapes, majestic mountains, and pristine beaches, making it an idyllic setting for families, retirees, and nature enthusiasts alike.

One of the standout features of Koolaupoko is its impressive selection of homes with waterfront frontage. Imagine waking up to the soothing sounds of the ocean waves and enjoying panoramic views of the azure waters from your own backyard. These waterfront properties offer a unique opportunity to experience the best of island living, with direct access to the beach for swimming, kayaking, or simply soaking up the sun.

The neighborhood is not just about stunning homes; it boasts a vibrant community atmosphere. Residents can explore local parks, hiking trails, and farmers' markets, fostering a sense of connection and belonging. The nearby Kailua town offers a delightful mix of boutique shops, cafes, and dining options, ensuring that all your needs are just a stone's throw away.

Whether you are looking for a serene retreat or an active lifestyle, Koolaupoko provides the perfect backdrop for your dream home. With its captivating waterfront properties and welcoming community, this neighborhood invites you to experience the magic of island life in one of Hawaii's most beautiful settings. Come discover your slice of paradise in Koolaupoko!

Newest Koolaupoko Homes with Waterfront 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

Start Your Search

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.