Koolaupoko Homes with Fee Simple Land tenure

Welcome to Koolaupoko, a hidden gem nestled on the breathtaking windward coast of Oahu, Hawaii. This enchanting neighborhood, located primarily in Kailua, offers a unique blend of natural beauty and vibrant community living. With its stunning vistas of the Ko'olau Mountains and pristine beaches, Koolaupoko is a paradise for those who appreciate the great outdoors. Residents here enjoy a laid-back lifestyle, with ample opportunities for hiking, kayaking, and beachcombing just moments from their doorsteps.

Koolaupoko is not just about its picturesque landscapes; it also boasts a rich cultural heritage, with charming local shops, farmers' markets, and eclectic dining options that celebrate the flavors of Hawaii. The community is known for its welcoming atmosphere, making it an ideal place for families, retirees, and anyone seeking a serene yet engaging environment.

One of the standout features of Koolaupoko is the availability of homes with 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 stability and investment in this desirable area. Whether you are looking for a cozy single-family home, a modern condo, or a sprawling estate, Koolaupoko offers a diverse range of real estate options to suit every lifestyle and budget.

Experience the magic of Koolaupoko, where the beauty of nature meets the warmth of community. Discover your dream home in this idyllic neighborhood and enjoy all that Oahu has to offer!

Newest Koolaupoko Homes with Fee Simple Land tenure

$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.