Koolaupoko Homes with Fee Simple Land tenure

Welcome to Koolaupoko, a stunning gem nestled on the windward coast of Oahu, Hawaii. This picturesque neighborhood, known for its lush landscapes and breathtaking views, offers residents a unique blend of natural beauty and vibrant community life. With the majestic Ko'olau Mountains as your backdrop and the sparkling waters of Kailua Bay just a stone's throw away, Koolaupoko is a paradise for outdoor enthusiasts and those seeking tranquility.

Kailua, the heart of Koolaupoko, boasts a charming small-town vibe, where friendly locals and a strong sense of community create an inviting atmosphere. The area is dotted with quaint shops, delightful cafes, and local eateries that serve up the freshest island flavors. Residents enjoy easy access to pristine beaches, including the renowned Kailua and Lanikai beaches, perfect for sunbathing, swimming, and water sports.

One of the standout features of homes in Koolaupoko is the availability of Fee Simple land tenure. This means that homeowners have full ownership of both the property and the land it sits on, providing a sense of security and investment value that is hard to beat. Whether you're looking for a cozy beach cottage or a luxurious estate, the diverse real estate options in Koolaupoko cater to a variety of lifestyles and budgets.

In Koolaupoko, you’re not just purchasing a home; you’re investing in a lifestyle filled with adventure, relaxation, and the spirit of Aloha. Experience the beauty of island living in this idyllic neighborhood, where every day feels like a vacation. Come discover your dream home in Koolaupoko today!

Newest Koolaupoko Homes with Fee Simple Land tenure

$1,625,000

4 Beds ⋅ 3 Baths ⋅ 202613595 MLS ⋅ FS - Fee Simple Tenure ⋅ 10 DOM

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

$2,625,000

5 Beds ⋅ 5 Baths ⋅ 202612304 MLS ⋅ FS - Fee Simple Tenure ⋅ 20 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

$1,649,000

6 Beds ⋅ 3 Baths ⋅ 202605034 MLS ⋅ FS - Fee Simple Tenure ⋅ 139 DOM

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

$4,350,000

6 Beds ⋅ 4 Baths ⋅ 202525771 MLS ⋅ FS - Fee Simple Tenure ⋅ 145 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.