Koolaupoko Homes with Waterfront Frontage

Welcome to Koolaupoko, a breathtaking slice of paradise nestled in Kailua, Hawaii. This enchanting neighborhood is renowned for its stunning natural beauty, where the majestic Ko'olau Mountains meet the sparkling waters of the Pacific Ocean. With its lush landscapes and vibrant local culture, Koolaupoko is the perfect place to call home for those seeking a tranquil yet active lifestyle.

One of the standout features of Koolaupoko is its impressive array of homes boasting waterfront frontage. Imagine waking up to the soothing sounds of gentle waves lapping against the shore, with the sun casting a golden glow over the water each morning. These waterfront properties offer not only stunning views but also direct access to some of the best recreational activities Hawaii has to offer, including kayaking, paddleboarding, and swimming in crystal-clear waters.

Kailua is celebrated for its friendly community atmosphere, where neighbors become friends and outdoor adventures await at every turn. Enjoy a leisurely stroll along the pristine beaches, explore the lush hiking trails, or indulge in the local dining scene featuring fresh seafood and farm-to-table delights. Families will appreciate the highly-rated schools and parks, making Koolaupoko an ideal location for raising children.

Whether you’re seeking a serene retreat or an active lifestyle, Koolaupoko offers a unique blend of natural beauty and community spirit. Discover your dream home with waterfront frontage in this captivating neighborhood and experience the magic of living in paradise. Your Hawaiian dream awaits!

Newest Koolaupoko Homes with Waterfront Frontage

$4,900,000

202616097 MLS ⋅ FS - Fee Simple Tenure ⋅ 20 DOM

This rare 27,725 sq. ft. estate property has fabulous mountain views over the wide canal, in a prime Kailua location one street from the beach. Enjoy over 295 ft of direct waterfront canal living! Kayak, SUP right from your yard. The layout gives you incredible flexibility, featuring multiple suites within a spacious compound. The original single-level 3-bedroom/2-bath home opens to a green yard along the waterfront, flanked by two 2-bedroom/1-bath wings with private entrances and ample parking. A breezeway carport connects to another living area with 3 bedrooms/2.5-baths upstairs opening to a gorgeous view lanai. On the ground level is a two-car enclosed garage and workshop plus a 1-bd/1-bath wing. The property has been well-kept and maintained over the years by one family. Everything Kailua has to offer is convenient to this estate including the canal, beach, restaurants and businesses, shopping centers, the Pali and H-3. 117 owned PV panels and EV Charger too! Don’t miss this one-of-a-kind opportunity!

865 N Kalaheo Avenue, Kailua

$4,900,000

11 Beds ⋅ 8 Baths ⋅ 202616094 MLS ⋅ FS - Fee Simple Tenure ⋅ 20 DOM

865 N Kalaheo Avenue, Kailua

$2,500,000

5 Beds ⋅ 5 Baths ⋅ 202612304 MLS ⋅ FS - Fee Simple Tenure ⋅ 91 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 ⋅ 216 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.