Koolaupoko Homes for Sale

Welcome to Koolaupoko, a stunning gem nestled on the eastern coast of Oahu, Hawaii. Known for its breathtaking landscapes and vibrant community, Koolaupoko offers a unique blend of natural beauty and suburban charm. This picturesque neighborhood, part of the city of Kailua, is framed by the majestic Ko'olau Mountains and the sparkling waters of Kailua Bay, making it a paradise for outdoor enthusiasts and beach lovers alike.

Koolaupoko is renowned for its friendly atmosphere and tight-knit community, where neighbors become friends and families thrive. With a variety of local shops, cozy cafes, and delicious dining options, residents enjoy a laid-back lifestyle that embodies the spirit of island living. The area is also home to some of the best schools on the island, making it an ideal place for families looking to settle down.

For those seeking their dream home, Koolaupoko offers a diverse range of properties for sale. From charming single-family homes with lush gardens to modern condos with ocean views, there’s something to suit every taste and budget. Many homes boast spacious layouts, inviting outdoor spaces, and proximity to pristine beaches and scenic hiking trails. Whether you’re looking for a serene retreat or a vibrant community, Koolaupoko has it all.

Experience the magic of Koolaupoko and discover why so many are choosing to call this enchanting neighborhood home. Explore the available homes for sale today and take the first step towards your new island lifestyle!

Newest Koolaupoko Homes for Sale

$1,499,000

4 Beds ⋅ 3 Baths ⋅ 202613595 MLS ⋅ FS - Fee Simple Tenure ⋅ 21 DOM

HUGE Price Improvement! Don't miss this incredible opportunity to own a beautiful family home on a quiet, private loop in the heart of Kailua! Ideally located just minutes from Kailua Town and the world-famous Kailua Beach, this low-maintenance single-family home offers the perfect blend of comfort, convenience, and island living. With a spacious and flexible 4-bedroom, 3-bathroom floor plan, there's plenty of room for family, guests, and entertaining. The home also features owned solar panels to help reduce electricity costs and split A/C units throughout to keep you cool and comfortable year-round. Schedule your private showing today and discover all this exceptional home has to offer!

433 Kaimake Loop Unit A, Kailua

$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.