Koolaupoko Real Estate

Welcome to Koolaupoko, a stunning gem nestled on the windward side of Oahu, Hawaii. Known for its breathtaking natural beauty and vibrant community, Koolaupoko offers a unique blend of serene landscapes and lively local culture. This enchanting neighborhood encompasses the charming town of Kailua, where residents enjoy a laid-back lifestyle surrounded by lush mountains and pristine beaches.

Koolaupoko is a paradise for outdoor enthusiasts. With the majestic Ko'olau Mountains as a backdrop, the area offers countless hiking trails, including the popular Lanikai Pillbox hike, which rewards trekkers with panoramic views of the turquoise ocean and the neighboring Mokulua Islands. The region is also home to Kailua Beach, often regarded as one of the best beaches in the world, where residents can soak up the sun, paddleboard, or simply enjoy a leisurely stroll along the soft sands.

The community spirit in Koolaupoko is palpable, with local farmers' markets, art festivals, and cultural events that showcase the rich heritage of the area. Residents take pride in supporting local businesses, from charming boutiques to delightful eateries serving up fresh, island-inspired cuisine.

Families will appreciate the excellent schools and safe environment, making Koolaupoko a perfect place to raise children. With its welcoming atmosphere, stunning scenery, and a plethora of recreational activities, Koolaupoko is not just a place to live; it’s a lifestyle. Discover the magic of this remarkable neighborhood and experience the true essence of island living!

Newest Listings in Koolaupoko

$1,625,000

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

Well-maintained single-family home located on a quiet private loop in one of Kailua's most desirable neighborhoods, offering a welcoming, family-friendly atmosphere. Ideally situated just minutes from Kalaheo Park, Kailua Bay, and the world-famous beaches of Kailua. This home features an open-concept floor plan with four bedrooms and two bathrooms in the main residence, plus an attached studio with its own full bathroom-perfect for visiting guests, extended family, or a private home office.

433 Kaimake Loop Unit A, Kailua

Listing courtesy of Corcoran Pacific Properties.

$2,625,000

5 Beds ⋅ 5 Baths ⋅ 202612304 MLS ⋅ FS - Fee Simple Tenure

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

Listing courtesy of Arquette Properties Inc.

$1,649,000

6 Beds ⋅ 3 Baths ⋅ 202605034 MLS ⋅ FS - Fee Simple Tenure

Spacious 6-bedroom, 3-bath home located in the heart of Kailua. This versatile property offers a flexible layout that is ideal for extended family and multi-generational living. With generous interior space and multiple bedrooms, the home provides comfort and functionality for a variety of living arrangements. Conveniently situated just minutes from Kailua’s beautiful beaches, parks, shopping centers, restaurants, and local markets. Enjoy the relaxed island lifestyle while still having quick access to major roads for an easy commute to town or nearby communities.

837 Oneawa Street, Kailua

Listing courtesy of Five Star Realty, Inc..

$4,350,000

6 Beds ⋅ 4 Baths ⋅ 202525771 MLS ⋅ FS - Fee Simple Tenure

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

Listing courtesy of Compass.

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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.