Koolaupoko Homes with Waterfront Frontage

Welcome to Koolaupoko, a hidden gem nestled on the eastern shores of Oahu, Hawaii. This enchanting neighborhood, part of the vibrant city of Kailua, offers a unique blend of breathtaking natural beauty and a warm, welcoming community atmosphere. With its lush landscapes, stunning mountain backdrops, and pristine beaches, Koolaupoko is a paradise for those seeking a tranquil lifestyle infused with the spirit of Aloha.

One of the standout features of Koolaupoko is its remarkable waterfront properties. Imagine waking up to the soothing sounds of the ocean, with panoramic views of the turquoise waters right from your backyard. Homes with waterfront frontage in this area provide not only a picturesque living experience but also direct access to some of the most beautiful beaches in Hawaii. Whether you enjoy kayaking, paddleboarding, or simply soaking up the sun, living by the water opens up a world of outdoor adventures.

Kailua town, just a stone's throw away, boasts a vibrant local scene with charming boutiques, delightful cafes, and a variety of dining options. The community is known for its friendly residents and active lifestyle, making it an ideal place for families and individuals alike. With excellent schools nearby and a strong sense of community, Koolaupoko is a place where you can truly feel at home.

If you're dreaming of a life where ocean waves meet mountain breezes, Koolaupoko is waiting for you. Explore the waterfront homes available and discover the perfect blend of serenity and adventure that this remarkable neighborhood has to offer. Your slice of paradise awaits!

Newest Koolaupoko Homes with Waterfront Frontage

$2,625,000

5 Beds ⋅ 5 Baths ⋅ 202612304 MLS ⋅ FS - Fee Simple Tenure ⋅ 24 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 ⋅ 149 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.