Koolaupoko Homes with Fee Simple Land tenure

Welcome to Koolaupoko, a picturesque gem nestled on the eastern coast of Oahu, where the lush beauty of Hawaii meets the vibrant community spirit of Kailua. This charming neighborhood is renowned for its stunning landscapes, pristine beaches, and a welcoming atmosphere that invites both residents and visitors to embrace the island lifestyle.

Koolaupoko boasts a unique blend of natural wonders and modern conveniences. With the majestic Ko’olau Mountains as a backdrop, outdoor enthusiasts will find endless opportunities for hiking, biking, and water sports. The nearby Kailua Beach, often ranked among the best in the world, offers soft sands and crystal-clear waters perfect for swimming, paddleboarding, and sunbathing.

The community vibe in Koolaupoko is warm and inviting, with local farmers' markets, boutique shops, and a variety of dining options that celebrate the flavors of Hawaii. Families and individuals alike appreciate the close-knit feel of the neighborhood, where friendly faces and community events foster a strong sense of belonging.

For those seeking to make Koolaupoko their home, the availability of homes with Fee Simple land tenure is a significant advantage. This means you own the land outright, providing stability and a true sense of ownership that is often sought after in real estate. Whether you’re looking for a cozy bungalow or a luxurious oceanfront property, Koolaupoko offers a diverse range of homes that cater to various lifestyles and preferences.

Discover the enchanting allure of Koolaupoko, where every day feels like a vacation, and your dream home awaits amidst the breathtaking beauty of Kailua.

Newest Koolaupoko Homes with Fee Simple Land tenure

$1,499,000

4 Beds ⋅ 3 Baths ⋅ 202613595 MLS ⋅ FS - Fee Simple Tenure ⋅ 32 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 ⋅ 42 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 ⋅ 167 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.