Koolaupoko Real Estate

Welcome to Koolaupoko, a breathtaking gem nestled on the eastern coast of Oahu, Hawaii. This enchanting neighborhood, part of the vibrant city of Kailua, offers a unique blend of natural beauty, rich culture, and a tight-knit community atmosphere that captures the essence of island living.

Koolaupoko is renowned for its stunning landscapes, where the majestic Ko'olau Mountains serve as a dramatic backdrop to the lush, tropical surroundings. Residents and visitors alike are treated to panoramic views that inspire outdoor adventures, from hiking the scenic trails of the mountains to relaxing on the pristine beaches of Kailua and Lanikai. The soft sands and crystal-clear waters invite you to unwind and soak in the sun, while the gentle trade winds provide the perfect setting for windsurfing and kayaking.

The neighborhood is not just about its natural allure; it’s also rich in local culture and community spirit. The vibrant Kailua town center is home to an array of charming boutiques, delightful cafes, and farm-to-table restaurants that showcase the flavors of Hawaii. The community hosts various events throughout the year, fostering connections among neighbors and celebrating the unique heritage of the area.

Families will appreciate the excellent schools and recreational facilities available, making Koolaupoko a wonderful place to raise children. With its friendly atmosphere, breathtaking scenery, and a plethora of activities, Koolaupoko offers a lifestyle that is both relaxed and invigorating. Discover the magic of this coastal paradise and experience the true spirit of aloha in Koolaupoko!

Newest Listings in Koolaupoko

$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

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.